Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII (540 views)
Curr Med Chem (ISSN: 0929-8673, 1875-533x, 1875-533xelectronic), 2010; 17(15): 1516-1526.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 4.63, 5-year impact factor: 4.961
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-77953521863&partnerID=40&md5=7866b9c40b5fa96c23eb5c7737ab6214
Keywords: Antibody, Ca Ix, Ca Xii, Carbonic Anhydrase (ca), Coumarin, Enzyme Selective Inhibition, Hypoxia, Phenol, Sulfonamides, Tumor Acidification, Tumor Imaging, Tumorigenesis, X-Ray Crystallography, Acetazolamide, Carbonate Dehydratase Inhibitor, Carbonate Dehydratase Xii, Clioquinol, Coumarin Derivative, Imatinib, Nilotinib, Thiocoumarin, Unclassified Drug, Article, Cancer Cell, Carcinogenesis, Cell Growth, Diagnostic Procedure, Drug Design, Drug Inhibition, Drug Targeting, Enzyme Inhibition, Enzyme Structure, Protein Expression, Antigens, Neoplasm, Antineoplastic Agents, Carbonic Anhydrase Inhibitors, Humans,
Affiliations:
*** IBB - CNR ***
Balikesir University Science and Art Faculty Department of Chemistry/Biochemistry division, Cagis yerleskesi /Kampus, Balikesir, Turkey
Istituto di Biostrutture e Bioimmagini-CNR, via Mezzocannone 16, 80134 Naples, Italy
Polo Scientifico, Laboratorio di Chimica Bioinorganica, Università degli Studi di Firenze, 188, Via della Lastruccia 3, 50019 Sesto Fiorentino, Florence, Italy
References:
Supuran, C.T., Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators (2008) Nat. Rev. Drug Discov, 7, pp. 168-18
Supuran, C.T., Scozzafava, A., Conway, J., (2004) Carbonic Anhydrase-Its Inhibitors and Activators, pp. 1-363. , CRC Press: Boca Raton, New York, London
Cecchi, A., Supuran, C.T., Fluorescence and spin-labeled carbonic anhydrase inhibitors (2008) Curr. Pharm. Des, 14, pp. 699-707
Scozzafava, A., Mastrolorenzo, A., Supuran, C.T., Modulation of carbonic anhydrase activity and its applications in therapy (2004) Expert Opin. Ther. Pat, 14, pp. 667-702
Pastorekova, P.S., Pastorek, J., Supuran, C.T., Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects (2004) J. Enz. Inhib. Med. Chem, 19, pp. 199-229
Hilvo, M., Baranauskiene, L., Salzano, A.M., Scaloni, A., Matulis, D., Innocenti, A., Scozzafava, A., Parkkila, S., Biochemical characterization of CA IX: One of the most active carbonic anhydrase isozymes (2008) J. Biol. Chem, 283, pp. 27799-27809
Kivelä, A.J., Parkkila, S., Saarnio, J., Karttunen, T.J., Kivelä, J., Parkkila, A.K., Pastoreková, S., Rajaniemi, H., Expression of the membrane-associated carbonic anhydrase isozyme XII in the human kidney and renal tumors (2000) Histochem. Cell Biol, 114, pp. 197-204
Wykoff, C.C., Beasley, N.J., Watson, P.H., Turner, K.J., Pastorek, J., Sibtain, A., Wilson, G.D., Talks, K.L., (2000) Maxwell,.P.H.
Harris, A.L. Hypoxia-inducible Expression of Tumor-associated Carbonic Anhydrases. Cancer Res, 60, pp. 7075-7083
Brahimi-Horn, M.C., Pouysségur, J., Hypoxia in cancer cell metabolism and pH regulation (2007) Essays Biochem, 43, pp. 165-178
Bartosova, M., Parkkila, S., Pohlodek, K., Karttunen, T.J., Galbavy, S., Mucha, V., Harris, A.L., Pastorekova, S., Expression of carbonic anhydrase IX in breast is associated with malignant tissues and is related to overexpression of c-erbB2 (2002) J. Pathol, 197, pp. 1-8
Kaelin Jr., W.G., Ratcliffe, P.J., Oxygen sensing by metazoans: The central role of the HIF hydroxylase pathway (2008) Mol. Cell, 30, pp. 393-402
Vastová, E., Huliková, A., Rafajová, M., Zat'ovičová, M., Gibadulinová, A., Casini, A., Cecchi, A., Pastorek, J., Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH (2004) FEBS Lett, 577, pp. 439-445
Tureci, O., Sahin, U., Vollmar, E., Siemer, S., Gottert, E., Seitz, G., Parkkila, S., Sly, W.S., Human carbonic anhydrase XII: CDNA cloning, expression, and chromosomal localization of a carbonic anhydrase gene that is overexpressed in some renal cell cancers (1998) Proc. Natl. Acad. Sci. USA, 95, pp. 7608-7613
Ivanov, S.V., Kuzmin, I., Wei, M.H., Pack, S., Geil, L., Johnson, B.E., Stanbridge, E.J., Lerman, M.I., Down-regulation of transmembrane carbonic anhydrases in renal cell carcinoma cell lines by wild-type von Hippel-Lindau transgenes (1998) Proc. Natl. Acad. Sci. USA, 95, pp. 12596-12601
Ulmasov, B., Waheed, A., Shah, G.N., Grubb, J.H., Sly, W.S., Tu, C., Silverman, D.N., Purification and kinetic analysis of recombinant CA XII, a membrane carbonic anhydrase overexpressed in certain cancers (2000) Proc. Natl. Acad. Sci. USA, 97, pp. 14212-14217
Whittington, D.A., Grubb, J.H., Waheed, A., Shah, G.N., Sly, W.S., Christianson, D.W., Crystal structure of the dimeric extracellular domain of human carbonic anhydrase XII, a bitopic membrane protein overexpressed in certain cancer tumor cells (2001) Proc. Natl. Acad. Sci. USA, 98, pp. 9545-9559
Alterio, V., Hilvo, M., Di Fiore, A., Supuran, C.T., Pan, P., Parkkila, S., Scaloni, A., de Simone, G., Crystal structure of the extracellular catalytic domain of the tumor-associated human carbonic anhydrase IX (2009) Proc. Natl. Acad. Sci. USA, 106, pp. 16233-16238
Innocenti, A., Pastorekova, S., Pastorek, J., Scozzafava, A., de Simone, G., Supuran, C.T., The proteoglycan region of the tumor-associated carbonic anhydrase isoform IX acts as an intrinsic buffer optimizing CO2 hydration at acidic pH values characteristic of solid tumors (2009) Bioorg. Med. Chem. Lett, 19, pp. 5825-5828
Supuran, C.T., Briganti, F., Tilli, S., Chegwidden, W.R., Scozzafava, A., Carbonic anhydrase inhibitors: Sulfonamides as antitumor agents? (2001) Bioorg. Med. Chem, 9, pp. 703-714
Swietach, P., Wigfield, S., Cobden, P., Supuran, C.T., Harris, A.L., Vaughan-Jones, R.D., Tumor-associated carbonic anhydrase 9 spatially coordinates intracellular pH in three-dimensional multicellular growth (2008) J. Biol. Chem, 283, pp. 20473-20483
Pastorekova, S., Casini, A., Scozzafava, A., Vullo, D., Pastorek, J., Supuran, C.T., Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX (2004) Bioorg. Med. Chem. Lett, 14, pp. 869-873
Supuran, C.T., Indisulaman anticancer sulfonamide in clinical development (2003) Expert Opin. Investig. Drugs, 12, pp. 283-287
Cecchi, A., Hulikova, A., Pastorek, J., Pastoreková, S., Scozzafava, A., Winum, J.-Y., Montero, J.-L., Supuran, C.T., Carbonic anhydrase inhibitors. Sulfonamides inhibit isozyme IX mediated acidification of hypoxic tumors. Fluorescent sulfonamides design as probes of membrane-bound carbonic anhydrase isozymes involvement in tumorigenesis (2005) J. Med. Chem, 48, pp. 4834-4841
Thiry, A., Dogné, J.-M., Masereel, B., Supuran, C.T., Targeting tumor-associated carbonic anhydrase IX in cancer therapy (2006) Trends Pharmacol. Sci, 27, pp. 566-573
Dubois, L., Douma, K., Supuran, C.T., Chiu, R.K., van Zandvoort, M.A.M.J., Pastoreková, S., Scozzafava, A., Lambin, P., Imaging the hypoxia surrogate marker CA IX requires expression and catalytic activity for binding fluorescent sulfonamide inhibitors (2007) Radiother. Oncol, 83, pp. 367-373
Winum, J.Y., Rami, M., Scozzafava, A., Montero, J.L., Supuran, C., Carbonic Anhydrase IX: A new druggable target for the design of antitumor agents (2008) Med. Res. Rev, 28, pp. 445-463
Özensoy, O., Puccetti, L., Fasolis, G., Arslan, O., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of the tumor associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamide (2005) Bioorg. Med. Chem. Lett, 15, pp. 4862-4866
Wilkinson, B.L., Bornaghi, L.F., Houston, T.A., Innocenti, A., Supuran, C.T., Poulsen, S.-A., A novel class of carbonic anhydrase inhibitors: Glycoconjugate benzene sulfonamides prepared by "click-tailing" (2006) J. Med. Chem, 49, pp. 6539-6548
Ilies, M.A., Vullo, D., Pastorek, J., Scozzafava, A., Ilies, M., Caproiu, M.T., Pastorekova, S., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX with halogenosulfanilamide and halogenophenylaminobenzolamide derivatives (2003) J. Med. Chem, 46, pp. 2187-2196
Winum, J.-Y., Vullo, D., Casini, A., Montero, J.-L., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: Inhibition of cytosolic isozymes I and II and the transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors (2003) J. Med. Chem, 46, pp. 2197-2204
Vullo, D., Innocenti, A., Nishimori, I., Pastorek, J., Scozzafava, A., Pastorekova, S., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-A new target for the design of antitumor and antiglaucoma drugs? (2005) Bioorg. Med. Chem. Lett, 15, pp. 963-969
Pastorekova, S., Vullo, D., Casini, A., Scozzafava, A., Pastorek, J., Nishimori, I., Supuran, C.T., Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozymes IX and XII with polyfluorinated aromatic/heterocyclic sulfonamides (2005) J. Enz. Inhib. Med. Chem, 20, pp. 211-217
Di Fiore, A., de Simone, G., Menchise, V., Pedone, C., Casini, A., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: X-Ray crystal structure of a benzenesulfonamide strong CA II and CA IX inhibitor bearing a pentafluorophenylaminothioureido tail in complex with isozyme II (2005) Bioorg. Med. Chem. Lett, 15, pp. 1937-1942
Menchise, V., de Simone, G., Alterio, V., Di Fiore, A., Pedone, C., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: Stacking with Phe131 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II (2005) J. Med. Chem, 48, pp. 5721-5727
Alterio, V., Vitale, R.M., Monti, S.M., Pedone, C., Scozzafava, A., Cecchi, A., de Simone, G., Supuran, C.T., Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX (2006) J. Am. Chem. Soc, 128, pp. 8329-8335
Garaj, V., Pucetti, L., Fasolis, G., Winum, J.-Y., Montero, J.-L., Scozzafava, A., Vullo, D., Supuran, C.T., Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II and IX with sulfonamides incorporating 1,2,4-triazine moieties (2004) Bioorg. Med. Chem. Lett, 14, pp. 5427-5433
Supuran, C.T., Development of small molecule carbonic anhydrase IX inhibitors (2008) BJU Int, 101, pp. 39-40
Maresca, A., Temperini, C., Vu, H., Pham, N.B., Poulsen, S.A., Scozzafava, A., Quinn, R.J., Supuran, C.T., Non-zinc mediated inhibition of carbonic anhydrases: Coumarins are a new class of suicide inhibitors (2009) J. Am. Chem. Soc, 131, pp. 3057-3062
Parkkila, S., Innocenti, A., Kallio, H., Hilvo, M., Scozzafava, A., Supuran, C.T., The protein tyrosine kinase inhibitors imatinib and nilotinib strongly inhibit several mammalian-carbonic anhydrase isoforms (2009) Bioorg. Med. Chem. Lett, 19, pp. 4102-4106
Dubois, L., Lieuwes, N.G., Maresca, A., Thiry, A., Supuran, C.T., Scozzafava, A., Wouters, B.G., Lambin, P., Imaging of CA IX with fluorescent labelled sulfonamides distinguishes hypoxic and (re)oxygenated cells in a xenograft tumour model (2009) Radiother. Oncol, 92, pp. 423-428
de Simone, G., Vitale, R.M., Di Fiore, A., Pedone, C., Scozzafava, A., Montero, J.L., Winum, J.Y., Supuran, C.T., Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX (2006) J. Med. Chem, 49, pp. 5544-5551
Winum, J.Y., Temperini, C., El Cheikh, K., Innocenti, A., Vullo, D., Ciattini, S., Montero, J.L., Supuran, C.T., Carbonic anhydrase inhibitors: Clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue (2006) J. Med. Chem, 49, pp. 7024-7031
Colinas, P.A., Bravo, R.D., Vullo, D., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of cytosolic isoforms I and II, and extracellular isoforms IV, IX and XII with sulfamides incorporating sugar moieties (2007) Bioorg. Med. Chem. Lett, 17, pp. 5086-5090
Bayram, E., Senturk, M., Kufrevioglu, O.I., Supuran, C.T., In vitro effects of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II (2008) Bioorg. Med. Chem, 16, pp. 9101-9105
Chiche, J., Ilc, K., Laferrière, J., Trottier, E., Dayan, F., Mazure, N.M., Brahimi-Horn, M.C., Pouysségur, J., Hypoxia-inducible carbonic anhydrase IX and XII promote tumor cell growth by counteracting acidosis through the regulation of the intracellular pH (2009) Cancer Res, 69, pp. 358-368
Ahlskog, J.K.J., Dumelin, C.E., Trüssel, S., Marlind, J., Neri, D., In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives (2009) Bioorg. Med. Chem. Lett, 19, pp. 4851-4856
Ahlskog, J.K., Schliemann, C., Mårlind, J., Qureshi, U., Ammar, A., Pedleym, R.B., Neri, D., Human monoclonal antibodies targeting carbonic anhydrase IX for the molecular imaging of hypoxic regions in solid tumours (2009) Br. J. Cancer, 101, pp. 645-657
Supuran, C. T., Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators (2008) Nat. Rev. Drug Discov, 7, pp. 168-18
Supuran, C. T., Scozzafava, A., Conway, J., (2004) Carbonic Anhydrase-Its Inhibitors and Activators, pp. 1-363. , CRC Press: Boca Raton, New York, London
Pastorekova, P. S., Pastorek, J., Supuran, C. T., Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects (2004) J. Enz. Inhib. Med. Chem, 19, pp. 199-229
Kivel, A. J., Parkkila, S., Saarnio, J., Karttunen, T. J., Kivel, J., Parkkila, A. K., Pastorekov, S., Rajaniemi, H., Expression of the membrane-associated carbonic anhydrase isozyme XII in the human kidney and renal tumors (2000) Histochem. Cell Biol, 114, pp. 197-204
Wykoff, C. C., Beasley, N. J., Watson, P. H., Turner, K. J., Pastorek, J., Sibtain, A., Wilson, G. D., Talks, K. L., (2000) Maxwell,. P. H.
Harris, A. L. Hypoxia-inducible Expression of Tumor-associated Carbonic Anhydrases. Cancer Res, 60, pp. 7075-7083
Brahimi-Horn, M. C., Pouyss gur, J., Hypoxia in cancer cell metabolism and pH regulation (2007) Essays Biochem, 43, pp. 165-178
Kaelin Jr., W. G., Ratcliffe, P. J., Oxygen sensing by metazoans: The central role of the HIF hydroxylase pathway (2008) Mol. Cell, 30, pp. 393-402
Vastov, E., Hulikov, A., Rafajov, M., Zat'Ovi ov, M., Gibadulinov, A., Casini, A., Cecchi, A., Pastorek, J., Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH (2004) FEBS Lett, 577, pp. 439-445
Ivanov, S. V., Kuzmin, I., Wei, M. H., Pack, S., Geil, L., Johnson, B. E., Stanbridge, E. J., Lerman, M. I., Down-regulation of transmembrane carbonic anhydrases in renal cell carcinoma cell lines by wild-type von Hippel-Lindau transgenes (1998) Proc. Natl. Acad. Sci. USA, 95, pp. 12596-12601
Whittington, D. A., Grubb, J. H., Waheed, A., Shah, G. N., Sly, W. S., Christianson, D. W., Crystal structure of the dimeric extracellular domain of human carbonic anhydrase XII, a bitopic membrane protein overexpressed in certain cancer tumor cells (2001) Proc. Natl. Acad. Sci. USA, 98, pp. 9545-9559
Supuran, C. T., Briganti, F., Tilli, S., Chegwidden, W. R., Scozzafava, A., Carbonic anhydrase inhibitors: Sulfonamides as antitumor agents? (2001) Bioorg. Med. Chem, 9, pp. 703-714
Supuran, C. T., Indisulaman anticancer sulfonamide in clinical development (2003) Expert Opin. Investig. Drugs, 12, pp. 283-287
Thiry, A., Dogn, J. -M., Masereel, B., Supuran, C. T., Targeting tumor-associated carbonic anhydrase IX in cancer therapy (2006) Trends Pharmacol. Sci, 27, pp. 566-573
Winum, J. Y., Rami, M., Scozzafava, A., Montero, J. L., Supuran, C., Carbonic Anhydrase IX: A new druggable target for the design of antitumor agents (2008) Med. Res. Rev, 28, pp. 445-463
zensoy, O., Puccetti, L., Fasolis, G., Arslan, O., Scozzafava, A., Supuran, C. T., Carbonic anhydrase inhibitors. Inhibition of the tumor associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamide (2005) Bioorg. Med. Chem. Lett, 15, pp. 4862-4866
Wilkinson, B. L., Bornaghi, L. F., Houston, T. A., Innocenti, A., Supuran, C. T., Poulsen, S. -A., A novel class of carbonic anhydrase inhibitors: Glycoconjugate benzene sulfonamides prepared by "click-tailing" (2006) J. Med. Chem, 49, pp. 6539-6548
Ilies, M. A., Vullo, D., Pastorek, J., Scozzafava, A., Ilies, M., Caproiu, M. T., Pastorekova, S., Supuran, C. T., Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX with halogenosulfanilamide and halogenophenylaminobenzolamide derivatives (2003) J. Med. Chem, 46, pp. 2187-2196
Winum, J. -Y., Vullo, D., Casini, A., Montero, J. -L., Scozzafava, A., Supuran, C. T., Carbonic anhydrase inhibitors: Inhibition of cytosolic isozymes I and II and the transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors (2003) J. Med. Chem, 46, pp. 2197-2204
Supuran, C. T., Development of small molecule carbonic anhydrase IX inhibitors (2008) BJU Int, 101, pp. 39-40
Winum, J. Y., Temperini, C., El Cheikh, K., Innocenti, A., Vullo, D., Ciattini, S., Montero, J. L., Supuran, C. T., Carbonic anhydrase inhibitors: Clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue (2006) J. Med. Chem, 49, pp. 7024-7031
Colinas, P. A., Bravo, R. D., Vullo, D., Scozzafava, A., Supuran, C. T., Carbonic anhydrase inhibitors. Inhibition of cytosolic isoforms I and II, and extracellular isoforms IV, IX and XII with sulfamides incorporating sugar moieties (2007) Bioorg. Med. Chem. Lett, 17, pp. 5086-5090
Ahlskog, J. K. J., Dumelin, C. E., Tr ssel, S., Marlind, J., Neri, D., In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives (2009) Bioorg. Med. Chem. Lett, 19, pp. 4851-4856
Ahlskog, J. K., Schliemann, C., M rlind, J., Qureshi, U., Ammar, A., Pedleym, R. B., Neri, D., Human monoclonal antibodies targeting carbonic anhydrase IX for the molecular imaging of hypoxic regions in solid tumours (2009) Br. J. Cancer, 101, pp. 645-657
Curr Med Chem (ISSN: 0929-8673, 1875-533x, 1875-533xelectronic), 2010; 17(15): 1516-1526.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 4.63, 5-year impact factor: 4.961
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-77953521863&partnerID=40&md5=7866b9c40b5fa96c23eb5c7737ab6214
Keywords: Antibody, Ca Ix, Ca Xii, Carbonic Anhydrase (ca), Coumarin, Enzyme Selective Inhibition, Hypoxia, Phenol, Sulfonamides, Tumor Acidification, Tumor Imaging, Tumorigenesis, X-Ray Crystallography, Acetazolamide, Carbonate Dehydratase Inhibitor, Carbonate Dehydratase Xii, Clioquinol, Coumarin Derivative, Imatinib, Nilotinib, Thiocoumarin, Unclassified Drug, Article, Cancer Cell, Carcinogenesis, Cell Growth, Diagnostic Procedure, Drug Design, Drug Inhibition, Drug Targeting, Enzyme Inhibition, Enzyme Structure, Protein Expression, Antigens, Neoplasm, Antineoplastic Agents, Carbonic Anhydrase Inhibitors, Humans,
Affiliations:
*** IBB - CNR ***
Balikesir University Science and Art Faculty Department of Chemistry/Biochemistry division, Cagis yerleskesi /Kampus, Balikesir, Turkey
Istituto di Biostrutture e Bioimmagini-CNR, via Mezzocannone 16, 80134 Naples, Italy
Polo Scientifico, Laboratorio di Chimica Bioinorganica, Università degli Studi di Firenze, 188, Via della Lastruccia 3, 50019 Sesto Fiorentino, Florence, Italy
References:
Supuran, C.T., Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators (2008) Nat. Rev. Drug Discov, 7, pp. 168-18
Supuran, C.T., Scozzafava, A., Conway, J., (2004) Carbonic Anhydrase-Its Inhibitors and Activators, pp. 1-363. , CRC Press: Boca Raton, New York, London
Cecchi, A., Supuran, C.T., Fluorescence and spin-labeled carbonic anhydrase inhibitors (2008) Curr. Pharm. Des, 14, pp. 699-707
Scozzafava, A., Mastrolorenzo, A., Supuran, C.T., Modulation of carbonic anhydrase activity and its applications in therapy (2004) Expert Opin. Ther. Pat, 14, pp. 667-702
Pastorekova, P.S., Pastorek, J., Supuran, C.T., Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects (2004) J. Enz. Inhib. Med. Chem, 19, pp. 199-229
Hilvo, M., Baranauskiene, L., Salzano, A.M., Scaloni, A., Matulis, D., Innocenti, A., Scozzafava, A., Parkkila, S., Biochemical characterization of CA IX: One of the most active carbonic anhydrase isozymes (2008) J. Biol. Chem, 283, pp. 27799-27809
Kivelä, A.J., Parkkila, S., Saarnio, J., Karttunen, T.J., Kivelä, J., Parkkila, A.K., Pastoreková, S., Rajaniemi, H., Expression of the membrane-associated carbonic anhydrase isozyme XII in the human kidney and renal tumors (2000) Histochem. Cell Biol, 114, pp. 197-204
Wykoff, C.C., Beasley, N.J., Watson, P.H., Turner, K.J., Pastorek, J., Sibtain, A., Wilson, G.D., Talks, K.L., (2000) Maxwell,.P.H.
Harris, A.L. Hypoxia-inducible Expression of Tumor-associated Carbonic Anhydrases. Cancer Res, 60, pp. 7075-7083
Brahimi-Horn, M.C., Pouysségur, J., Hypoxia in cancer cell metabolism and pH regulation (2007) Essays Biochem, 43, pp. 165-178
Bartosova, M., Parkkila, S., Pohlodek, K., Karttunen, T.J., Galbavy, S., Mucha, V., Harris, A.L., Pastorekova, S., Expression of carbonic anhydrase IX in breast is associated with malignant tissues and is related to overexpression of c-erbB2 (2002) J. Pathol, 197, pp. 1-8
Kaelin Jr., W.G., Ratcliffe, P.J., Oxygen sensing by metazoans: The central role of the HIF hydroxylase pathway (2008) Mol. Cell, 30, pp. 393-402
Vastová, E., Huliková, A., Rafajová, M., Zat'ovičová, M., Gibadulinová, A., Casini, A., Cecchi, A., Pastorek, J., Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH (2004) FEBS Lett, 577, pp. 439-445
Tureci, O., Sahin, U., Vollmar, E., Siemer, S., Gottert, E., Seitz, G., Parkkila, S., Sly, W.S., Human carbonic anhydrase XII: CDNA cloning, expression, and chromosomal localization of a carbonic anhydrase gene that is overexpressed in some renal cell cancers (1998) Proc. Natl. Acad. Sci. USA, 95, pp. 7608-7613
Ivanov, S.V., Kuzmin, I., Wei, M.H., Pack, S., Geil, L., Johnson, B.E., Stanbridge, E.J., Lerman, M.I., Down-regulation of transmembrane carbonic anhydrases in renal cell carcinoma cell lines by wild-type von Hippel-Lindau transgenes (1998) Proc. Natl. Acad. Sci. USA, 95, pp. 12596-12601
Ulmasov, B., Waheed, A., Shah, G.N., Grubb, J.H., Sly, W.S., Tu, C., Silverman, D.N., Purification and kinetic analysis of recombinant CA XII, a membrane carbonic anhydrase overexpressed in certain cancers (2000) Proc. Natl. Acad. Sci. USA, 97, pp. 14212-14217
Whittington, D.A., Grubb, J.H., Waheed, A., Shah, G.N., Sly, W.S., Christianson, D.W., Crystal structure of the dimeric extracellular domain of human carbonic anhydrase XII, a bitopic membrane protein overexpressed in certain cancer tumor cells (2001) Proc. Natl. Acad. Sci. USA, 98, pp. 9545-9559
Alterio, V., Hilvo, M., Di Fiore, A., Supuran, C.T., Pan, P., Parkkila, S., Scaloni, A., de Simone, G., Crystal structure of the extracellular catalytic domain of the tumor-associated human carbonic anhydrase IX (2009) Proc. Natl. Acad. Sci. USA, 106, pp. 16233-16238
Innocenti, A., Pastorekova, S., Pastorek, J., Scozzafava, A., de Simone, G., Supuran, C.T., The proteoglycan region of the tumor-associated carbonic anhydrase isoform IX acts as an intrinsic buffer optimizing CO2 hydration at acidic pH values characteristic of solid tumors (2009) Bioorg. Med. Chem. Lett, 19, pp. 5825-5828
Supuran, C.T., Briganti, F., Tilli, S., Chegwidden, W.R., Scozzafava, A., Carbonic anhydrase inhibitors: Sulfonamides as antitumor agents? (2001) Bioorg. Med. Chem, 9, pp. 703-714
Swietach, P., Wigfield, S., Cobden, P., Supuran, C.T., Harris, A.L., Vaughan-Jones, R.D., Tumor-associated carbonic anhydrase 9 spatially coordinates intracellular pH in three-dimensional multicellular growth (2008) J. Biol. Chem, 283, pp. 20473-20483
Pastorekova, S., Casini, A., Scozzafava, A., Vullo, D., Pastorek, J., Supuran, C.T., Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX (2004) Bioorg. Med. Chem. Lett, 14, pp. 869-873
Supuran, C.T., Indisulaman anticancer sulfonamide in clinical development (2003) Expert Opin. Investig. Drugs, 12, pp. 283-287
Cecchi, A., Hulikova, A., Pastorek, J., Pastoreková, S., Scozzafava, A., Winum, J.-Y., Montero, J.-L., Supuran, C.T., Carbonic anhydrase inhibitors. Sulfonamides inhibit isozyme IX mediated acidification of hypoxic tumors. Fluorescent sulfonamides design as probes of membrane-bound carbonic anhydrase isozymes involvement in tumorigenesis (2005) J. Med. Chem, 48, pp. 4834-4841
Thiry, A., Dogné, J.-M., Masereel, B., Supuran, C.T., Targeting tumor-associated carbonic anhydrase IX in cancer therapy (2006) Trends Pharmacol. Sci, 27, pp. 566-573
Dubois, L., Douma, K., Supuran, C.T., Chiu, R.K., van Zandvoort, M.A.M.J., Pastoreková, S., Scozzafava, A., Lambin, P., Imaging the hypoxia surrogate marker CA IX requires expression and catalytic activity for binding fluorescent sulfonamide inhibitors (2007) Radiother. Oncol, 83, pp. 367-373
Winum, J.Y., Rami, M., Scozzafava, A., Montero, J.L., Supuran, C., Carbonic Anhydrase IX: A new druggable target for the design of antitumor agents (2008) Med. Res. Rev, 28, pp. 445-463
Özensoy, O., Puccetti, L., Fasolis, G., Arslan, O., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of the tumor associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamide (2005) Bioorg. Med. Chem. Lett, 15, pp. 4862-4866
Wilkinson, B.L., Bornaghi, L.F., Houston, T.A., Innocenti, A., Supuran, C.T., Poulsen, S.-A., A novel class of carbonic anhydrase inhibitors: Glycoconjugate benzene sulfonamides prepared by "click-tailing" (2006) J. Med. Chem, 49, pp. 6539-6548
Ilies, M.A., Vullo, D., Pastorek, J., Scozzafava, A., Ilies, M., Caproiu, M.T., Pastorekova, S., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX with halogenosulfanilamide and halogenophenylaminobenzolamide derivatives (2003) J. Med. Chem, 46, pp. 2187-2196
Winum, J.-Y., Vullo, D., Casini, A., Montero, J.-L., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: Inhibition of cytosolic isozymes I and II and the transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors (2003) J. Med. Chem, 46, pp. 2197-2204
Vullo, D., Innocenti, A., Nishimori, I., Pastorek, J., Scozzafava, A., Pastorekova, S., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-A new target for the design of antitumor and antiglaucoma drugs? (2005) Bioorg. Med. Chem. Lett, 15, pp. 963-969
Pastorekova, S., Vullo, D., Casini, A., Scozzafava, A., Pastorek, J., Nishimori, I., Supuran, C.T., Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozymes IX and XII with polyfluorinated aromatic/heterocyclic sulfonamides (2005) J. Enz. Inhib. Med. Chem, 20, pp. 211-217
Di Fiore, A., de Simone, G., Menchise, V., Pedone, C., Casini, A., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: X-Ray crystal structure of a benzenesulfonamide strong CA II and CA IX inhibitor bearing a pentafluorophenylaminothioureido tail in complex with isozyme II (2005) Bioorg. Med. Chem. Lett, 15, pp. 1937-1942
Menchise, V., de Simone, G., Alterio, V., Di Fiore, A., Pedone, C., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors: Stacking with Phe131 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II (2005) J. Med. Chem, 48, pp. 5721-5727
Alterio, V., Vitale, R.M., Monti, S.M., Pedone, C., Scozzafava, A., Cecchi, A., de Simone, G., Supuran, C.T., Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX (2006) J. Am. Chem. Soc, 128, pp. 8329-8335
Garaj, V., Pucetti, L., Fasolis, G., Winum, J.-Y., Montero, J.-L., Scozzafava, A., Vullo, D., Supuran, C.T., Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II and IX with sulfonamides incorporating 1,2,4-triazine moieties (2004) Bioorg. Med. Chem. Lett, 14, pp. 5427-5433
Supuran, C.T., Development of small molecule carbonic anhydrase IX inhibitors (2008) BJU Int, 101, pp. 39-40
Maresca, A., Temperini, C., Vu, H., Pham, N.B., Poulsen, S.A., Scozzafava, A., Quinn, R.J., Supuran, C.T., Non-zinc mediated inhibition of carbonic anhydrases: Coumarins are a new class of suicide inhibitors (2009) J. Am. Chem. Soc, 131, pp. 3057-3062
Parkkila, S., Innocenti, A., Kallio, H., Hilvo, M., Scozzafava, A., Supuran, C.T., The protein tyrosine kinase inhibitors imatinib and nilotinib strongly inhibit several mammalian-carbonic anhydrase isoforms (2009) Bioorg. Med. Chem. Lett, 19, pp. 4102-4106
Dubois, L., Lieuwes, N.G., Maresca, A., Thiry, A., Supuran, C.T., Scozzafava, A., Wouters, B.G., Lambin, P., Imaging of CA IX with fluorescent labelled sulfonamides distinguishes hypoxic and (re)oxygenated cells in a xenograft tumour model (2009) Radiother. Oncol, 92, pp. 423-428
de Simone, G., Vitale, R.M., Di Fiore, A., Pedone, C., Scozzafava, A., Montero, J.L., Winum, J.Y., Supuran, C.T., Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX (2006) J. Med. Chem, 49, pp. 5544-5551
Winum, J.Y., Temperini, C., El Cheikh, K., Innocenti, A., Vullo, D., Ciattini, S., Montero, J.L., Supuran, C.T., Carbonic anhydrase inhibitors: Clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue (2006) J. Med. Chem, 49, pp. 7024-7031
Colinas, P.A., Bravo, R.D., Vullo, D., Scozzafava, A., Supuran, C.T., Carbonic anhydrase inhibitors. Inhibition of cytosolic isoforms I and II, and extracellular isoforms IV, IX and XII with sulfamides incorporating sugar moieties (2007) Bioorg. Med. Chem. Lett, 17, pp. 5086-5090
Bayram, E., Senturk, M., Kufrevioglu, O.I., Supuran, C.T., In vitro effects of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II (2008) Bioorg. Med. Chem, 16, pp. 9101-9105
Chiche, J., Ilc, K., Laferrière, J., Trottier, E., Dayan, F., Mazure, N.M., Brahimi-Horn, M.C., Pouysségur, J., Hypoxia-inducible carbonic anhydrase IX and XII promote tumor cell growth by counteracting acidosis through the regulation of the intracellular pH (2009) Cancer Res, 69, pp. 358-368
Ahlskog, J.K.J., Dumelin, C.E., Trüssel, S., Marlind, J., Neri, D., In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives (2009) Bioorg. Med. Chem. Lett, 19, pp. 4851-4856
Ahlskog, J.K., Schliemann, C., Mårlind, J., Qureshi, U., Ammar, A., Pedleym, R.B., Neri, D., Human monoclonal antibodies targeting carbonic anhydrase IX for the molecular imaging of hypoxic regions in solid tumours (2009) Br. J. Cancer, 101, pp. 645-657
Supuran, C. T., Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators (2008) Nat. Rev. Drug Discov, 7, pp. 168-18
Supuran, C. T., Scozzafava, A., Conway, J., (2004) Carbonic Anhydrase-Its Inhibitors and Activators, pp. 1-363. , CRC Press: Boca Raton, New York, London
Pastorekova, P. S., Pastorek, J., Supuran, C. T., Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects (2004) J. Enz. Inhib. Med. Chem, 19, pp. 199-229
Kivel, A. J., Parkkila, S., Saarnio, J., Karttunen, T. J., Kivel, J., Parkkila, A. K., Pastorekov, S., Rajaniemi, H., Expression of the membrane-associated carbonic anhydrase isozyme XII in the human kidney and renal tumors (2000) Histochem. Cell Biol, 114, pp. 197-204
Wykoff, C. C., Beasley, N. J., Watson, P. H., Turner, K. J., Pastorek, J., Sibtain, A., Wilson, G. D., Talks, K. L., (2000) Maxwell,. P. H.
Harris, A. L. Hypoxia-inducible Expression of Tumor-associated Carbonic Anhydrases. Cancer Res, 60, pp. 7075-7083
Brahimi-Horn, M. C., Pouyss gur, J., Hypoxia in cancer cell metabolism and pH regulation (2007) Essays Biochem, 43, pp. 165-178
Kaelin Jr., W. G., Ratcliffe, P. J., Oxygen sensing by metazoans: The central role of the HIF hydroxylase pathway (2008) Mol. Cell, 30, pp. 393-402
Vastov, E., Hulikov, A., Rafajov, M., Zat'Ovi ov, M., Gibadulinov, A., Casini, A., Cecchi, A., Pastorek, J., Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH (2004) FEBS Lett, 577, pp. 439-445
Ivanov, S. V., Kuzmin, I., Wei, M. H., Pack, S., Geil, L., Johnson, B. E., Stanbridge, E. J., Lerman, M. I., Down-regulation of transmembrane carbonic anhydrases in renal cell carcinoma cell lines by wild-type von Hippel-Lindau transgenes (1998) Proc. Natl. Acad. Sci. USA, 95, pp. 12596-12601
Whittington, D. A., Grubb, J. H., Waheed, A., Shah, G. N., Sly, W. S., Christianson, D. W., Crystal structure of the dimeric extracellular domain of human carbonic anhydrase XII, a bitopic membrane protein overexpressed in certain cancer tumor cells (2001) Proc. Natl. Acad. Sci. USA, 98, pp. 9545-9559
Supuran, C. T., Briganti, F., Tilli, S., Chegwidden, W. R., Scozzafava, A., Carbonic anhydrase inhibitors: Sulfonamides as antitumor agents? (2001) Bioorg. Med. Chem, 9, pp. 703-714
Supuran, C. T., Indisulaman anticancer sulfonamide in clinical development (2003) Expert Opin. Investig. Drugs, 12, pp. 283-287
Thiry, A., Dogn, J. -M., Masereel, B., Supuran, C. T., Targeting tumor-associated carbonic anhydrase IX in cancer therapy (2006) Trends Pharmacol. Sci, 27, pp. 566-573
Winum, J. Y., Rami, M., Scozzafava, A., Montero, J. L., Supuran, C., Carbonic Anhydrase IX: A new druggable target for the design of antitumor agents (2008) Med. Res. Rev, 28, pp. 445-463
zensoy, O., Puccetti, L., Fasolis, G., Arslan, O., Scozzafava, A., Supuran, C. T., Carbonic anhydrase inhibitors. Inhibition of the tumor associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamide (2005) Bioorg. Med. Chem. Lett, 15, pp. 4862-4866
Wilkinson, B. L., Bornaghi, L. F., Houston, T. A., Innocenti, A., Supuran, C. T., Poulsen, S. -A., A novel class of carbonic anhydrase inhibitors: Glycoconjugate benzene sulfonamides prepared by "click-tailing" (2006) J. Med. Chem, 49, pp. 6539-6548
Ilies, M. A., Vullo, D., Pastorek, J., Scozzafava, A., Ilies, M., Caproiu, M. T., Pastorekova, S., Supuran, C. T., Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX with halogenosulfanilamide and halogenophenylaminobenzolamide derivatives (2003) J. Med. Chem, 46, pp. 2187-2196
Winum, J. -Y., Vullo, D., Casini, A., Montero, J. -L., Scozzafava, A., Supuran, C. T., Carbonic anhydrase inhibitors: Inhibition of cytosolic isozymes I and II and the transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors (2003) J. Med. Chem, 46, pp. 2197-2204
Supuran, C. T., Development of small molecule carbonic anhydrase IX inhibitors (2008) BJU Int, 101, pp. 39-40
Winum, J. Y., Temperini, C., El Cheikh, K., Innocenti, A., Vullo, D., Ciattini, S., Montero, J. L., Supuran, C. T., Carbonic anhydrase inhibitors: Clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue (2006) J. Med. Chem, 49, pp. 7024-7031
Colinas, P. A., Bravo, R. D., Vullo, D., Scozzafava, A., Supuran, C. T., Carbonic anhydrase inhibitors. Inhibition of cytosolic isoforms I and II, and extracellular isoforms IV, IX and XII with sulfamides incorporating sugar moieties (2007) Bioorg. Med. Chem. Lett, 17, pp. 5086-5090
Ahlskog, J. K. J., Dumelin, C. E., Tr ssel, S., Marlind, J., Neri, D., In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives (2009) Bioorg. Med. Chem. Lett, 19, pp. 4851-4856
Ahlskog, J. K., Schliemann, C., M rlind, J., Qureshi, U., Ammar, A., Pedleym, R. B., Neri, D., Human monoclonal antibodies targeting carbonic anhydrase IX for the molecular imaging of hypoxic regions in solid tumours (2009) Br. J. Cancer, 101, pp. 645-657
Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII
The carbonic anhydrase (CA, EC 4.2.1.1) isozymes IX and XII are predominantly found in tumor cells and show a restricted expression in normal tissues. By efficiently hydrating carbon dioxide to protons and bicarbonate, these CAs contribute significantly to the extracellular acidification of solid tumors. CA IX and XII are overexpressed in many such tumors in response to the hypoxia inducible factor (HIF) pathway, and research on the involvement of these isozymes in cancer has progressed in recent years. The report of the X-ray crystal structure of CA IX, which is a dimeric protein with a quaternary structure not evidenced earlier for this family of enzymes, allows for structure-based drug design campaigns of inhibitors against this novel antitumor target. Indeed, it has been known for some time that aro- matic/heterocyclic sulfonamides and sulfamates have good affinity for this isoform, but generally they do not show speci- ficity for the inhibition of the tumor-associated isoform versus the remaining CA isozymes (CA I-VII, and XII-XV) found in mammals. Recently, we reported several classes of compounds with good selectivity for the tumor-associated CAs, be- ing shown that CA IX/XII inhibition reverses the effect of tumor acidification, leading to inhibition of the cancer cells growth. CA IX/XII are now proposed as novel therapeutic antitumor targets. Furthermore, as some types of CA inhibitors (CAIs), such as the fluorescent sulfonamides accumulate only in hypoxic tumor cells overexpressing these enzymes, CAIs may be also used as diagnostic tools for imaging of hypoxic cancer cells. Work from several laboratories recently reported the proof-of-concept studies for the use of CA IX/XII inhibitors as well as antibodies both in the therapy and imaging of hypoxic tumors. © 2010 Bentham Science Publishers Ltd.
The carbonic anhydrase (CA, EC 4.2.1.1) isozymes IX and XII are predominantly found in tumor cells and show a restricted expression in normal tissues. By efficiently hydrating carbon dioxide to protons and bicarbonate, these CAs contribute significantly to the extracellular acidification of solid tumors. CA IX and XII are overexpressed in many such tumors in response to the hypoxia inducible factor (HIF) pathway, and research on the involvement of these isozymes in cancer has progressed in recent years. The report of the X-ray crystal structure of CA IX, which is a dimeric protein with a quaternary structure not evidenced earlier for this family of enzymes, allows for structure-based drug design campaigns of inhibitors against this novel antitumor target. Indeed, it has been known for some time that aro- matic/heterocyclic sulfonamides and sulfamates have good affinity for this isoform, but generally they do not show speci- ficity for the inhibition of the tumor-associated isoform versus the remaining CA isozymes (CA I-VII, and XII-XV) found in mammals. Recently, we reported several classes of compounds with good selectivity for the tumor-associated CAs, be- ing shown that CA IX/XII inhibition reverses the effect of tumor acidification, leading to inhibition of the cancer cells growth. CA IX/XII are now proposed as novel therapeutic antitumor targets. Furthermore, as some types of CA inhibitors (CAIs), such as the fluorescent sulfonamides accumulate only in hypoxic tumor cells overexpressing these enzymes, CAIs may be also used as diagnostic tools for imaging of hypoxic cancer cells. Work from several laboratories recently reported the proof-of-concept studies for the use of CA IX/XII inhibitors as well as antibodies both in the therapy and imaging of hypoxic tumors. © 2010 Bentham Science Publishers Ltd.
Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII
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Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII
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Impact Factor: 6.169
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De Simone G, Scozzafava A, Supuran CT
* Which Carbonic Anhydrases are Targeted by the Antiepileptic Sulfonamides and Sulfamates? (352 views)
Chem Biol Drug Des (ISSN: 1747-0277, 1747-0285), 2009 Sep; 74(3): 317-321.
Impact Factor: 2.473
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D'Ambrosio K, Vitale R, Dogne J, Masereel B, Innocenti A, Scozzafava A, De Simone G, Supuran CT
* Ccarbonic Anhydrase Inhibitors: Bioreductive Nitro-Containing Sulfonamides With Selectivity For Targeting The Tumor Associated Isoforms Ix And Xii (823 views)
J Med Chem (ISSN: 1520-4804, 0022-2623, 0022-2623print), 2008 Jun 12; 51(11): 3230-3237.
Impact Factor: 4.898
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D'Ambrosio K, Masereel B, Thiry A, Scozzafava A, Supuran CT, De Simone G
* Carbonic anhydrase inhibitors: Binding of indanesulfonamides to the human isoform II (378 views)
Chemmedchem (ISSN: 1860-7179, 1860-7187, 1860-7187electronic), 2008 Mar; 3(3): 473-477.
Impact Factor: 3.15
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Alterio V, De Simone G, Monti SM, Scozzafava A, Supuran CT
* Carbonic anhydrase inhibitors: Inhibition of human, bacterial, and archaeal isozymes with benzene-1, 3-disulfonamides-Solution and crystallographic studies (329 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2007 Sep 1; 17(15): 4201-4207.
Impact Factor: 2.604
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Ntziachristos V, Cuénod CA, Fournier L, Balvay D, Pradel C, Siauve N, Clement O, Jouannot E, Lucidarme O, Vecchio SD, Salvatore M, Law B, Tung C-H, Jain RK, Fukumura D, Munn LL, Brown EB, Schellenberger E, Montet X, Weissleder R, Clerck ND, Postnov A
* Tumor Imaging (350 views)
Textbook Of In Vivo Imaging In Vertebrates (ISSN: 9780-4700), 2007 Jul 16; 1: 277-309.
Impact Factor: 1.148
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De Simone G, Vitale RM, Di Fiore A, Pedone C, Scozzafava A, Montero JL, Winum JY, Supuran CT
* Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX (474 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2006 Sep 7; 49(18): 5544-5551.
Impact Factor: 5.115
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Alterio V, Vitale RM, Monti SM, Pedone C, Scozzafava A, Cecchi A, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX (484 views)
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2006 Jun 28; 128(25): 8329-8335.
Impact Factor: 7.696
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Grasso G, D'Agata R, Rizzarelli E, Spoto G, D'Andrea LD, Pedone C, Picardi A, Romanelli A, Fragai M, Yeo KJ
* Activity of anchored human matrix metalloproteinase-1 catalytic domain on Au(111) surfaces monitored by ESI-MS (575 views)
J Mass Spectrom (ISSN: 1076-5174, 1096-9888), 2005 Dec; 40(12): 1565-1571.
Impact Factor: 3.574
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* Inhibition of carbonic anhydrases IX/XII by SLC-0111 boosts cisplatin effects in hampering head and neck squamous carcinoma cell growth and invasion (22 views)
J Exp Clin Cancer Res (ISSN: 0392-9078linking), 2022 Apr 2; 41(1): 122-122.
Impact Factor: 12.658
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Urbański LJ, Angeli A, Hytönen VP, Di Fiore A, De Simone G, Parkkila S, Supuran CT
* Inhibition of the β-carbonic anhydrase from the protozoan pathogen Trichomonas vaginalis with sulphonamides (148 views)
J Enzym Inhib Med Ch (ISSN: 1475-6366linking, 1475-6374electronic), 2021 Dec; 36(1): 329-334.
Impact Factor: 4.673
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Mancuso F, Di Fiore A, De Luca L, Angeli A, De Simone G, Supuran CT, Gitto R
* Design, synthesis and biochemical evaluation of novel carbonic anhydrase inhibitors triggered by structural knowledge on hCA VII (27 views)
Bioorg Med Chem (ISSN: 0968-0896linking, 1464-3391), 2021 Aug 15; 44: 116279-116279.
Impact Factor: 3.641
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Nocentini A, Alterio V, Bua S, Micheli L, Esposito D, Buonanno M, Bartolucci G, Osman SM, Alothman ZA, Cirilli R, Pierini M, Monti SM, Di Cesare Mannelli L, Gratteri P, Ghelardini C, De Simone G, Supuran CT
* Phenyl(thio)phosphon(amid)ate Benzenesulfonamides as Potent and Selective Inhibitors of Human Carbonic Anhydrases II and VII Counteract Allodynia in a Mouse Model of Oxaliplatin-Induced Neuropathy (111 views)
J Med Chem (ISSN: 0022-2623linking, 0022-2623print), 2020 May 28; 63(10): 5185-5200.
Impact Factor: 6.205
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Buemi MR, Di Fiore A, De Luca L, Angeli A, Mancuso F, Ferro S, Monti SM, Buonanno M, Russo E, De Sarro G, De Simone G, Supuran CT, Gitto R
* Exploring structural properties of potent human carbonic anhydrase inhibitors bearing a 4-(cycloalkylamino-1-carbonyl)benzenesulfonamide moiety (323 views)
Eur J Med Chem (ISSN: 1768-3254electronic, 0223-5234linking), 2019 Feb 1; 163: 443-452.
Impact Factor: 4.833
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Alterio V, Esposito D, Monti SM, Supuran CT, De Simone G
* Crystal structure of the human carbonic anhydrase II adduct with 1-(4-sulfamoylphenyl-ethyl)-2, 4, 6-triphenylpyridinium perchlorate, a membrane-impermeant, isoform selective inhibitor (533 views)
J Enzym Inhib Med Ch (ISSN: 1475-6374electronic, 1475-6366linking), 2018 Dec; 33(1): 151-157.
Impact Factor: 4.293
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Monti SM, Meccariello A, Ceruso M, Szafranski K, Slawinski J, Supuran CT
* Inhibition studies of Brucella suis beta-carbonic anhydrases with a series of 4-substituted pyridine-3-sulphonamides (369 views)
J Enzym Inhib Med Ch (ISSN: 1475-6374electronic, 1475-6366linking), 2018 Dec; 33(1): 255-259.
Impact Factor: 2.332
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Mishra CB, Kumari S, Angeli A, Bua S, Buonanno M, Monti SM, Tiwari M, Supuran CT
* Discovery of potent anti-convulsant carbonic anhydrase inhibitors: Design, synthesis, in vitro and in vivo appraisal (234 views)
Eur J Med Chem (ISSN: 0223-5234linking, 1768-3254electronic), 2018 Aug 5; 156: 430-443.
Impact Factor: 4.816
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Marchiori MF, Riul TB, Oliveira Bortot L, Andrade P, Junqueira GG, Foca G, Doti N, Ruvo M, Dias-baruffi M, Carvalho I, Campo VL
* Binding of triazole-linked galactosyl arylsulfonamides to galectin-3 affects Trypanosoma cruzi cell invasion (1019 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2017 Nov 1; 25(21): 6049-6059.
Impact Factor: 2.881
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Brunò E, Buemi MR, Di Fiore A, De LucaL, Ferro S, Angeli A, Cirilli R, Sadutto D, Alterio V, Monti SM, Supuran CT, De Simone G, Gitto R
* Probing Molecular Interactions between Human Carbonic Anhydrases (hCAs) and a Novel Class of Benzenesulfonamides (386 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2017 May 25; 60(10): 4316-4326.
Impact Factor: 6.253
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Mishra CB, Kumari S, Angeli A, Monti SM, Buonanno M, Tiwari M, Supuran CT
* Discovery of Benzenesulfonamides with Potent Human Carbonic Anhydrase Inhibitory and Effective Anticonvulsant Action: Design, Synthesis, and Pharmacological Assessment (830 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2017 Mar 23; 60(6): 2456-2469.
Impact Factor: 6.253
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Altug C, Gunes H, Nocentini A, Monti SM, Buonanno M, Supuran CT
* Synthesis of isoxazole-containing sulfonamides with potent carbonic anhydrase II and VII inhibitory properties (301 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2017 Feb 15; 25(4): 1456-1464.
Impact Factor: 2.881
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Longo DL, Moustaghfir FZ, Zerbo A, Consolino L, Anemone A, Bracesco M, Aime S
* EXCI-CEST: Exploiting pharmaceutical excipients as MRI-CEST contrast agents for tumor imaging (454 views)
Int J Pharm (ISSN: 0378-5173, 1873-3476), 2017; 525(1): 275-281.
Impact Factor: 3.862
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Vullo D, Supuran CT, Scozzafava A, De Simone G, Monti SM, Alterio V, Carta F
* Kinetic and X-ray crystallographic investigations of substituted 2-thio-6-oxo-1, 6-dihydropyrimidine-benzenesulfonamides acting as carbonic anhydrase inhibitors (254 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2016 Aug 15; 24(16): 3643-3648.
Impact Factor: 2.93
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Mishra CB, Kumari S, Angeli A, Monti SM, Buonanno M, Prakash A, Tiwari M, Supuran CT
* Design, synthesis and biological evaluation of N-(5-methyl-isoxazol-3-yl/1, 3, 4-thiadiazol-2-yl)-4-(3-substitutedphenylureido) benzenesulfonamides as human carbonic anhydrase isoenzymes I, II, VII and XII inhibitors (292 views)
J Enzyme Inhib Med Chem, 2016; 17: 1-6.
Impact Factor: 3.428
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La Regina G, Coluccia A, Famiglini V, Pelliccia S, Monti L, Vullo D, Nuti E, Alterio V, De Simone G, Monti SM, Pan P, Parkkila S, Supuran CT, Rossello A, Silvestri R
* Discovery of 1, 1'-Biphenyl-4-sulfonamides as a New Class of Potent and Selective Carbonic Anhydrase XIV Inhibitors (335 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2015 Nov 12; 58(21): 8564-8572.
Impact Factor: 5.589
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Rami M, Dubois L, Parvathaneni NK, Alterio V, van Kuijk SJ, Monti SM, Lambin P, De Simone G, Supuran CT, Winum JY
* Hypoxia-targeting carbonic anhydrase IX inhibitors by a new series of nitroimidazole-sulfonamides/sulfamides/sulfamates (546 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2013 Nov 14; 56(21): 8512-8520.
Impact Factor: 5.48
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Zannetti A, Iommelli F, Speranza A, Salvatore M, Del Vecchio S
* 3'-deoxy-3'-18F-fluorothymidine (FLT) PET/CT to guide therapy with epidermal growth factor receptor (EGFR) antagonists and Bcl-xL inhibitors in non-small cell lung cancer (614 views)
J Nucl Med (ISSN: 0161-5505, 1535-5667, 1535-5667electronic), 2012 Mar 1; 53(3): 443-450.
Impact Factor: 5.774
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Zannetti A, Iommelli F, Speranza A, Salvatore M, Del Vecchio S
* 3'-deoxy-3'-18F-fluorothymidine PET/CT to guide therapy with epidermal growth factor receptor antagonists and Bcl-xL inhibitors in non-small cell lung cancer (525 views)
J Nucl Med (ISSN: 1535-5667, 0161-5505, 1535-5667electronic), 2012 Mar 1; 53(3): 443-450.
Impact Factor: 5.774
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Caraci F, Molinaro G, Battaglia G, Giuffrida ML, Riozzi B, Traficante A, Bruno V, Cannella M, Merlo S, Wang X, Heinz BA, Nisenbaum ES, Britton TC, Drago F, Sortino MA, Copani A, Nicoletti F
* Targeting group II Metabotropic Glutamate (mGlu) receptors for the treatment of psychosis associated with alzheimer's disease: Selective activation of mGlu2 receptors amplifies β-amyloid toxicity in cultured neurons, whereas dual activation of mGlu2 and mGlu3 receptors is neuroprotective (748 views)
Mol Pharmacol (ISSN: 0026-895x), 2011 Mar; 79(3): 618-626.
Impact Factor: 4.883
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Di Fiore A, Maresca A, Alterio V, Supuran CT, De Simone G
* Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of N-substituted benzenesulfonamides to human isoform II (338 views)
Chem Commun (ISSN: 1359-7345, 1364-548x, 1364-548xelectronic), 2011; 47(42): 11636-11638.
Impact Factor: 6.169
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De Simone G, Scozzafava A, Supuran CT
* Which Carbonic Anhydrases are Targeted by the Antiepileptic Sulfonamides and Sulfamates? (352 views)
Chem Biol Drug Des (ISSN: 1747-0277, 1747-0285), 2009 Sep; 74(3): 317-321.
Impact Factor: 2.473
View Export to BibTeX Export to EndNote
D'Ambrosio K, Vitale R, Dogne J, Masereel B, Innocenti A, Scozzafava A, De Simone G, Supuran CT
* Ccarbonic Anhydrase Inhibitors: Bioreductive Nitro-Containing Sulfonamides With Selectivity For Targeting The Tumor Associated Isoforms Ix And Xii (823 views)
J Med Chem (ISSN: 1520-4804, 0022-2623, 0022-2623print), 2008 Jun 12; 51(11): 3230-3237.
Impact Factor: 4.898
View Export to BibTeX Export to EndNote
D'Ambrosio K, Masereel B, Thiry A, Scozzafava A, Supuran CT, De Simone G
* Carbonic anhydrase inhibitors: Binding of indanesulfonamides to the human isoform II (378 views)
Chemmedchem (ISSN: 1860-7179, 1860-7187, 1860-7187electronic), 2008 Mar; 3(3): 473-477.
Impact Factor: 3.15
View Export to BibTeX Export to EndNote
Alterio V, De Simone G, Monti SM, Scozzafava A, Supuran CT
* Carbonic anhydrase inhibitors: Inhibition of human, bacterial, and archaeal isozymes with benzene-1, 3-disulfonamides-Solution and crystallographic studies (329 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2007 Sep 1; 17(15): 4201-4207.
Impact Factor: 2.604
View Export to BibTeX Export to EndNote
Ntziachristos V, Cuénod CA, Fournier L, Balvay D, Pradel C, Siauve N, Clement O, Jouannot E, Lucidarme O, Vecchio SD, Salvatore M, Law B, Tung C-H, Jain RK, Fukumura D, Munn LL, Brown EB, Schellenberger E, Montet X, Weissleder R, Clerck ND, Postnov A
* Tumor Imaging (350 views)
Textbook Of In Vivo Imaging In Vertebrates (ISSN: 9780-4700), 2007 Jul 16; 1: 277-309.
Impact Factor: 1.148
View Export to BibTeX Export to EndNote
De Simone G, Vitale RM, Di Fiore A, Pedone C, Scozzafava A, Montero JL, Winum JY, Supuran CT
* Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX (474 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2006 Sep 7; 49(18): 5544-5551.
Impact Factor: 5.115
View Export to BibTeX Export to EndNote
Alterio V, Vitale RM, Monti SM, Pedone C, Scozzafava A, Cecchi A, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX (484 views)
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2006 Jun 28; 128(25): 8329-8335.
Impact Factor: 7.696
View Export to BibTeX Export to EndNote
Grasso G, D'Agata R, Rizzarelli E, Spoto G, D'Andrea LD, Pedone C, Picardi A, Romanelli A, Fragai M, Yeo KJ
* Activity of anchored human matrix metalloproteinase-1 catalytic domain on Au(111) surfaces monitored by ESI-MS (575 views)
J Mass Spectrom (ISSN: 1076-5174, 1096-9888), 2005 Dec; 40(12): 1565-1571.
Impact Factor: 3.574
View Export to BibTeX Export to EndNote
29 Records (29 excluding Abstracts).
Total impact factor: 136.266 (136.266 excluding Abstracts).
Total 5 year impact factor: 123.416 (123.416 excluding Abstracts).
Total impact factor: 136.266 (136.266 excluding Abstracts).
Total 5 year impact factor: 123.416 (123.416 excluding Abstracts).
540 views. Last view on Wednesday 08 February 2023, 7:28:53
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