Octreotide labeled aggregates containing platinum complexes as nanovectors for drug delivery(408 views) Accardo A, Mangiapia G, Paduano L, Morelli G, Tesauro D
Keywords: Doxorubicin, Drug Delivery, Octreotide, Platinum Complexes, Sans, Supramolecular Aggregates, Amphophile, Liposome, Macrogol, Nanocarrier, Article, Drug Delivery System, Drug Formulation, Drug Synthesis, Light Scattering, Nanoencapsulation, Neutron Scattering, Priority Journal, Thickness, Antibiotics, Antineoplastic, Antineoplastic Agents, Hormonal, Cisplatin, Receptors, Somatostatin,
Affiliations: *** IBB - CNR ***
CIRPeB, Department of Biological Sciences and IBB CNR, University of Naples 'Federico II', Via Mezzocannone, Napoli, 16-80134, Italy
Department of Chemical Sciences, University of Naples 'Federico II', Via Cynthia, Napoli, 80126, Italy
References: Lippert, B., (1999) Cisplatin. Chemistry and Biochemistry of a Leading Anticancer Drug, , Wiley-VCH: Weinhei
Burger, K.N.J., Staffhorst, R.W.H.M., de Kruijff, B., Interaction of the anti-cancer drug cisplatin with phosphatidylserine in intact and semi-intact cells (1999) Biochim. Biophys. Acta, 1419, pp. 43-54
Reedijk, J., Why does cisplatin reach guanine-N7 with competing S-donor ligands available in the cell (1999) Chem. Rev., 99, pp. 2499-2510
binding to biological molecules (1980) Metal Ions in Biological Systems, pp. 63-125. , In, Vol. XI, Sigel H (ed.). M. Dekker: New York
Long, D.F., Repta, A.J., Cisplatin: chemistry, distribution and biotransformation (1981) Biopharm. Drug Dispos., 2, pp. 1-16
Herman, E.H., Rahman, A., Ferrans, V.J., Vick, J.A., Schein, P.S., Prevention of chronic doxorubicin cardiotoxicity in beagles by liposomal encapsulation (1983) Cancer Res., 43, pp. 5427-5432
Newman, M.S., Colbern, G.T., Working, P.K., Engbers, C., Amantea, M.A., Comparative pharmacokinetics, tissue distribution, and therapeutic effectiveness of cisplatin encapsulated in long-circulating, pegylated liposomes (SPI-077) in tumor-bearing mice (1999) Cancer Chemother. Pharmacol., 43, pp. 1-7
Sur, B., Ray, R.R., Sur, P., Roy, D.K., Effect of liposomal encapsulation of cis-platinum diamminodichloride in the treatment of Ehrlich ascites carcinoma (1983) Oncology, 40, pp. 372-376
Steerenberg, P.A., Storm, G., de Groot, G., Claessen, A., Bergers, J.J., Franken, M.A.M., van Hoesel, Q.G.C.M., de Jong, W.H., Liposomes as drug carrier system for cis-diamminedichloroplatinum (II) (1988) Cancer Chemother. Pharmacol., 21, pp. 299-307
Perez-Soler, R., Shin, D.M., Siddik, Z.H., Murphy, W.K., Huber, M., Lee, S.J., Khokhar, A.R., Hong, W.K., Phase I clinical and pharmacological study of liposome-entrapped NDDP administered intrapleurally in patients with malignant pleural effusions (1997) Clin. Cancer Res., 3, pp. 373-379
Lu, C., Perez-Soler, R., Piperdi, B., Walsh, G.L., Swisher, S.G., Smythe, W.R., Shin, H.J., Shin, D.M., Phase II study of a liposome-entrapped cisplatin analog (L-NDDP) administered intrapleurally and pathologic response rates in patients with malignant pleural mesothelioma (2005) J. Clin. Oncol., 23, pp. 3495-3501
Insook, H., Khokhar, A.R., Perez-Soler, R., Intraliposomal conversion of lipophilic cis-bis-carboxylato-trans-R,R-1,2-diaminocyclohexane-platinum (II) complexes into cis-bis-dichloro-trans-R,R -1,2-diaminocyclohexane-platinum (II) (1996) Cancer Chemother. Pharmacol., 39, pp. 17-24
Kim, D.K., Gam, J., Kim, H.T., Kim, K.H., Synthesis and in vitro cytotoxicity of cis-(glycolato-O,O′)-[2-substituted-(4R,5R)-4,5-bis(aminomethyl)-1,3-dioxolane]platinum(II) (1996) Bioorg. Med. Chem. Lett., 6, pp. 771-774
Liu, W.P., Ye, Q.S., Yu, Y., Chen, X.Z., Hou, S.Q., Lou, L.G., Yang, Y.P., Su, Q., Novel lipophilic Platinum(II) compounds of salicylate derivatives (2008) Platinum Metals Rev., 52, pp. 163-170
Stathopoulos, G.P., Boulikas, T., Lipoplatinum formulation review articles (2012) J. Drug Deliv., pp. 1-10
Sharma, A., Sharma, U.S., Liposomes in drug delivery: progress and limitations (1997) Int. J. Pharm., 154, pp. 123-140
Harrington, K.J., Lewanski, C.R., Northcote, A.D., Whittaker, J., Wellbank, H., Vile, R.G., Peters, A.M., Stewart, J.S., Phase I-II study of pegylated liposomal ciplastin (SPI-077) in patients with inoperable head and neck cancer (2001) Ann. Oncol., 12, pp. 493-496
Bandak, S., Goren, D., Horowitz, A., Tzemach, D., Gabizon, A., Pharmacological studies of cisplatin encapsulated in long-circulating liposomes in mouse tumor models (1999) Anti Canc. Drugs, 10, pp. 911-920
Velinova, M.J., Staffhorst, R.W.H.M., Mulder, W.J.M., Dries, A.S., Jansen, B.A.J., de Kruijff, B., de Kroon, A.I.P.M., Preparation and stability of lipid-coated nanocapsules of cisplatin: anionic phospholipid specificity (2004) Biochim. Biophys. Acta, 1663, pp. 135-142
Zamboni, W.C., Gervais, A.C., Egorin, M.J., Schellens, J.H., Zuhowski, E.G., Pluim, D., Joseph, E., Eiseman, J.L., Systemic and tumor disposition of platinum after administration of cisplatin or STEALTH liposomal-cisplatin formulations (SPI-077 and SPI-077 B103) in a preclinical tumor model of melanoma (2004) Cancer Chemother. Pharmacol., 53, pp. 329-336
White, S.C., Lorigan, P., Margison, G.P., Margison, J.M., Martin, F., Thatcher, N., Anderson, H., Ranson, M., Phase II study of SPI-77 (sterically stabilized liposomal cisplatin) in advanced NSCLC (2006) Br. J. Cancer, 95, pp. 822-828
Rosenthal, D.I., Yom, S.S., Liu, L., Machtay, M., Algazy, K., Weber, R.S., Weinstein, G.S., Hershock, D., A Phase I study of SPI-77 (stealth liposomal cisplatin) concurrent with radiation therapy for locally advanced head and neck cancer (2002) Invest. New Drugs, 20, pp. 343-349
Meerum Terwogt, J.M., Groenewegen, G., Pluim, D., Maliepaard, M., Tibben Matthijs, M., Huisman, A., ten Bokkel Huinink, W.W., Schellens, J.H., Phase I and pharmacokinetic study of SPI-77, a liposomal encapsulated dosage form of cisplatin (2002) Cancer Chemother. Pharmacol., 49, pp. 201-210
Lazarioti, F., Boulikas, T., Diagnostic and therapeutic efficacy of imaging modalities in non-small cell lung cancer (NSCLC): experience from a Phase III clinical study using tumor targeted lipoplatin nanoparticles (2008) Canc. Ther., 6, pp. 629-646
Boulikas, T., Pantos, A., Bellis, E., Christofis, P., Designing platinum compounds in cancer: structures and mechanisms (2007) Canc. Ther., 5, pp. 537-583
Chen, H., Pazicni, S., Krett, N.L., Ahn, R.W., Penner-Hahn, J.E., Rosen, S.T., Halloran, T.V.O., Coencapsulation of arsenic- and platinum based drugs for targeted cancer treatment (2009) Angew. Chem. Int. Ed., 48, pp. 9295-9299
Accardo, A., Morisco, A., Tesauro, D., Pedone, C., Morelli, G., Naposomes: a new class of peptide derivatized target selective multimodal nanoparticles for imaging and therapeutic applications (2011) Ther. Deliv., 2, pp. 235-257
Accardo, A., Tesauro, D., Morelli, G., Gianolio, E., Aime, S., Vaccaro, M., Mangiapia, G., Schillen, K., High-relaxivity supramolecular aggregates containing peptide and Gd complexes agents in MRI (2007) J. Biol. Inorg. Chem., 12, pp. 267-276
Tesauro, D., Accardo, A., Gianolio, E., Paduano, L., Teixeira, J., Schillén, K., Aime, S., Morelli, G., Peptide derivatized lamellar aggregates as target-specific MRI contrast agents (2007) Chembiochem, 8, pp. 950-955
Accardo, A., Mansi, R., Morisco, A., Mangiapia, G., Paduano, L., Tesauro, D., Radulescu, A., Morelli, G., Peptide modified nanocarriers for selective targeting of bombesin receptors (2010) Mol. Biosyst., 6, pp. 878-887
Anelli, P.L., Lattuada, L., Lorusso, V., Schneider, M., Tournier, H., Uggeri, F., Mixed micelles containing lipophilic gadolinium complexes as MRA contrast agents (2001) Magn. Res. Mater Phys. Biol. Med., 12, pp. 114-120
Torchilin, V.P., Omelyanenko, V.G., Papisov, M.I., Bogdanov, A.J., Trubetskoy, V.S., Herron, J.N., Gentry, C.A., Poly(ethylene glycol) on the liposome surface: on the mechanism of polymer-coated liposome longevity (1994) Biochim. Biophys. Acta, 119, pp. 11-20
Robillard, M.S., van Alphen, S., Meeuwenoord, N.J., Jansen, B.A.J., van der Marel, G.A., van Boomw, J.H., Reedjiak, J., Solid-phase synthesis of peptide-platinum complexes using platinum-chelating building blocks derived from amino acids (2004) New J. Chem., 29, pp. 220-225
Edelhoch, H., Spectroscopic determination of tryptophan and tyrosine in proteins (1967) Biochemistry, 6, pp. 1948-1954
Vergara, A., Paduano, L., Sartorio, R., Multicomponent diffusion in solutions containing solutes of different molecular size. 4. Ternary system Tetra(ethyleneglycol)-Di(etyleneglycol)-water (2001) J. Phys. Chem. B, 105, pp. 328-334
Ma, G., Barlow, D.J., Lawrence, M.J., Heenan, R.K., Timmins, P., Small-angle neutron-scattering studies of nonionic surfactant vesicles (2000) J. Phys. Chem. B, 104, pp. 9081-9085
Tardi, P.G., Boman, N.L., Cullis, P.R., Liposomal doxorubicin (1996) J. Drug Target., 4, pp. 129-140
Gabizon, A.A., The quest for the magic bullet stealth liposomes and tumor targeting: one step further in the quest for the magic bullet (2001) Clin. Cancer Res., 7, pp. 223-225
Borrelli, A., Schiattarella, A., Musella, A., Mancini, R., Capasso, C., De Luca, V., Carginale, V., Mancini, A., A molecular carrier to transport and deliver cisplatin into endometrial cancer cells (2012) Chem. Biol. Drug Des., pp. 1-8
Pujade-Lauraine, E., Wagner, U., Aavall-Lundqvist, E., Gebski, V., Heywood, M., Vasey, P.A., Volgger, B., du Bois, A., Pegylated liposomal Doxorubicin and Carboplatin compared with Paclitaxel and Carboplatin for patients with platinum-sensitive ovarian cancer in late relapse (2010) J. Clin. Oncol., 28, pp. 3323-3329
Schmitt, L., Dietrich, C., Tampe, R., Synthesis and characterization of chelator-lipids for reversible immobilization of engineered proteins at self-assembled lipid interfaces (1994) J. Am. Chem. Soc., 116, pp. 8485-8491
Chang, W.C., White, P.D., (2000) Fmoc Solid Phase Peptide Synthesis, , Oxford University Press: New York, USA
Brehm, G.A., Bloomfield, V.A., Analysis of polydispersity in polymer solutions by inelastic laser light scattering (1975) Macromolecules, 8, pp. 663-665
Russell, T.P., Lin, J.S., Spooner, S., Wignall, G.D., Intercalibration of small-angle X-ray and neutron scattering data (1988) J. Appl. Crystallogr., 21, pp. 629-638
Wignall, G.D., Bates, F.S., Absolute calibration of small-angle neutron scattering data (1987) J. Appl. Crystallogr., 20, pp. 28-40
Burger, K. N. J., Staffhorst, R. W. H. M., de Kruijff, B., Interaction of the anti-cancer drug cisplatin with phosphatidylserine in intact and semi-intact cells (1999) Biochim. Biophys. Acta, 1419, pp. 43-54
Howe-Grant, M. E., Lippard, S. J., Aqueous platinum (II) chemistry
Long, D. F., Repta, A. J., Cisplatin: chemistry, distribution and biotransformation (1981) Biopharm. Drug Dispos., 2, pp. 1-16
Herman, E. H., Rahman, A., Ferrans, V. J., Vick, J. A., Schein, P. S., Prevention of chronic doxorubicin cardiotoxicity in beagles by liposomal encapsulation (1983) Cancer Res., 43, pp. 5427-5432
Newman, M. S., Colbern, G. T., Working, P. K., Engbers, C., Amantea, M. A., Comparative pharmacokinetics, tissue distribution, and therapeutic effectiveness of cisplatin encapsulated in long-circulating, pegylated liposomes (SPI-077) in tumor-bearing mice (1999) Cancer Chemother. Pharmacol., 43, pp. 1-7
Sur, B., Ray, R. R., Sur, P., Roy, D. K., Effect of liposomal encapsulation of cis-platinum diamminodichloride in the treatment of Ehrlich ascites carcinoma (1983) Oncology, 40, pp. 372-376
Steerenberg, P. A., Storm, G., de Groot, G., Claessen, A., Bergers, J. J., Franken, M. A. M., van Hoesel, Q. G. C. M., de Jong, W. H., Liposomes as drug carrier system for cis-diamminedichloroplatinum (II) (1988) Cancer Chemother. Pharmacol., 21, pp. 299-307
Kim, D. K., Gam, J., Kim, H. T., Kim, K. H., Synthesis and in vitro cytotoxicity of cis- (glycolato-O, O) - [2-substituted- (4R, 5R) -4, 5-bis (aminomethyl) -1, 3-dioxolane] platinum (II) (1996) Bioorg. Med. Chem. Lett., 6, pp. 771-774
Liu, W. P., Ye, Q. S., Yu, Y., Chen, X. Z., Hou, S. Q., Lou, L. G., Yang, Y. P., Su, Q., Novel lipophilic Platinum (II) compounds of salicylate derivatives (2008) Platinum Metals Rev., 52, pp. 163-170
Stathopoulos, G. P., Boulikas, T., Lipoplatinum formulation review articles (2012) J. Drug Deliv., pp. 1-10
Harrington, K. J., Lewanski, C. R., Northcote, A. D., Whittaker, J., Wellbank, H., Vile, R. G., Peters, A. M., Stewart, J. S., Phase I-II study of pegylated liposomal ciplastin (SPI-077) in patients with inoperable head and neck cancer (2001) Ann. Oncol., 12, pp. 493-496
Velinova, M. J., Staffhorst, R. W. H. M., Mulder, W. J. M., Dries, A. S., Jansen, B. A. J., de Kruijff, B., de Kroon, A. I. P. M., Preparation and stability of lipid-coated nanocapsules of cisplatin: anionic phospholipid specificity (2004) Biochim. Biophys. Acta, 1663, pp. 135-142
Zamboni, W. C., Gervais, A. C., Egorin, M. J., Schellens, J. H., Zuhowski, E. G., Pluim, D., Joseph, E., Eiseman, J. L., Systemic and tumor disposition of platinum after administration of cisplatin or STEALTH liposomal-cisplatin formulations (SPI-077 and SPI-077 B103) in a preclinical tumor model of melanoma (2004) Cancer Chemother. Pharmacol., 53, pp. 329-336
White, S. C., Lorigan, P., Margison, G. P., Margison, J. M., Martin, F., Thatcher, N., Anderson, H., Ranson, M., Phase II study of SPI-77 (sterically stabilized liposomal cisplatin) in advanced NSCLC (2006) Br. J. Cancer, 95, pp. 822-828
Rosenthal, D. I., Yom, S. S., Liu, L., Machtay, M., Algazy, K., Weber, R. S., Weinstein, G. S., Hershock, D., A Phase I study of SPI-77 (stealth liposomal cisplatin) concurrent with radiation therapy for locally advanced head and neck cancer (2002) Invest. New Drugs, 20, pp. 343-349
Meerum Terwogt, J. M., Groenewegen, G., Pluim, D., Maliepaard, M., Tibben Matthijs, M., Huisman, A., ten Bokkel Huinink, W. W., Schellens, J. H., Phase I and pharmacokinetic study of SPI-77, a liposomal encapsulated dosage form of cisplatin (2002) Cancer Chemother. Pharmacol., 49, pp. 201-210
Anelli, P. L., Lattuada, L., Lorusso, V., Schneider, M., Tournier, H., Uggeri, F., Mixed micelles containing lipophilic gadolinium complexes as MRA contrast agents (2001) Magn. Res. Mater Phys. Biol. Med., 12, pp. 114-120
Torchilin, V. P., Omelyanenko, V. G., Papisov, M. I., Bogdanov, A. J., Trubetskoy, V. S., Herron, J. N., Gentry, C. A., Poly (ethylene glycol) on the liposome surface: on the mechanism of polymer-coated liposome longevity (1994) Biochim. Biophys. Acta, 119, pp. 11-20
Robillard, M. S., van Alphen, S., Meeuwenoord, N. J., Jansen, B. A. J., van der Marel, G. A., van Boomw, J. H., Reedjiak, J., Solid-phase synthesis of peptide-platinum complexes using platinum-chelating building blocks derived from amino acids (2004) New J. Chem., 29, pp. 220-225
Ma, G., Barlow, D. J., Lawrence, M. J., Heenan, R. K., Timmins, P., Small-angle neutron-scattering studies of nonionic surfactant vesicles (2000) J. Phys. Chem. B, 104, pp. 9081-9085
Tardi, P. G., Boman, N. L., Cullis, P. R., Liposomal doxorubicin (1996) J. Drug Target., 4, pp. 129-140
Gabizon, A. A., The quest for the magic bullet stealth liposomes and tumor targeting: one step further in the quest for the magic bullet (2001) Clin. Cancer Res., 7, pp. 223-225
Chang, W. C., White, P. D., (2000) Fmoc Solid Phase Peptide Synthesis, , Oxford University Press: New York, USA
Brehm, G. A., Bloomfield, V. A., Analysis of polydispersity in polymer solutions by inelastic laser light scattering (1975) Macromolecules, 8, pp. 663-665
Russell, T. P., Lin, J. S., Spooner, S., Wignall, G. D., Intercalibration of small-angle X-ray and neutron scattering data (1988) J. Appl. Crystallogr., 21, pp. 629-638
Wignall, G. D., Bates, F. S., Absolute calibration of small-angle neutron scattering data (1987) J. Appl. Crystallogr., 20, pp. 28-40
Octreotide labeled aggregates containing platinum complexes as nanovectors for drug delivery