Influence of the N-terminus acetylation of Semax, a synthetic analog of ACTH(4-10), on copper(II) and zinc(II) coordination and biological properties (291 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2016 Aug 27; 164: 59-69.
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Paper type: Journal Article,
Impact factor: 3.348, 5-year impact factor: 3.207
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Keywords: Biological Activity, Copper, Oxidation, Stability Constants, Voltammetry, Zinc,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini, Consiglio Nazionale delle Ricerche (CNR), Via P. Gaifami 18, 95126 Catania, Italy., Istituto di Biostrutture e Bioimmagini, Consiglio Nazionale delle Ricerche (CNR), Via P. Gaifami 18, 95126 Catania, Italy. Electronic address: giovanni.tabbi@cnr.it., Dipartimento di Scienze Chimiche, Universita degli Studi di Catania, Viale A. Doria 6, 95125 Catania, Italy., Dipartimento di Scienze Biomediche, Universita degli Studi di Catania, Viale A. Doria 6, 95125 Catania, Italy; Consorzio Interuniversitario C.I.R.C.S.M.B., Via C. Ulpiani 27, 70125 Bari, Italy., Dipartimento di Scienze Biomediche, Universita degli Studi di Catania, Viale A. Doria 6, 95125 Catania, Italy., Istituto di Biostrutture e Bioimmagini, Consiglio Nazionale delle Ricerche (CNR), Via P. Gaifami 18, 95126 Catania, Italy. Electronic address: francesco.attanasio@cnr.it.,
References:
Not available.
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2016 Aug 27; 164: 59-69.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 3.348, 5-year impact factor: 3.207
Url: Not available.
Keywords: Biological Activity, Copper, Oxidation, Stability Constants, Voltammetry, Zinc,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini, Consiglio Nazionale delle Ricerche (CNR), Via P. Gaifami 18, 95126 Catania, Italy., Istituto di Biostrutture e Bioimmagini, Consiglio Nazionale delle Ricerche (CNR), Via P. Gaifami 18, 95126 Catania, Italy. Electronic address: giovanni.tabbi@cnr.it., Dipartimento di Scienze Chimiche, Universita degli Studi di Catania, Viale A. Doria 6, 95125 Catania, Italy., Dipartimento di Scienze Biomediche, Universita degli Studi di Catania, Viale A. Doria 6, 95125 Catania, Italy; Consorzio Interuniversitario C.I.R.C.S.M.B., Via C. Ulpiani 27, 70125 Bari, Italy., Dipartimento di Scienze Biomediche, Universita degli Studi di Catania, Viale A. Doria 6, 95125 Catania, Italy., Istituto di Biostrutture e Bioimmagini, Consiglio Nazionale delle Ricerche (CNR), Via P. Gaifami 18, 95126 Catania, Italy. Electronic address: francesco.attanasio@cnr.it.,
References:
Not available.
Influence of the N-terminus acetylation of Semax, a synthetic analog of ACTH(4-10), on copper(II) and zinc(II) coordination and biological properties
Semax is a heptapeptide (Met-Glu-His-Phe-Pro-Gly-Pro) that encompasses the sequence 4-7 of N-terminal domain of the adrenocorticotropic hormone and a C-terminal Pro-Gly-Pro tripeptide. N-terminal amino group acetylation (Ac-Semax) modulates the chemical and biological properties of parental peptide, modifying the ability of Semax to form complex species with Cu(II) ion. At physiological pH, the main complex species formed by Ac-Semax, [CuLH-2]2-, consists in a distorted CuN3O chromophore with a weak apical interaction of the methionine sulphur. Such a complex differs from the Cu(II)-Semax complex system, which exhibits a CuN4 chromophore. The reduced ligand field affects the [CuLH-2]2- formal redox potential, which is more positive than that of Cu(II)-Semax corresponding species. In the amino-free form, the resulting complex species is redox-stable and unreactive against ascorbic acid, unlike the acetylated form. Semax acetylation did not protect from Cu(II) induced toxicity on a SH-SY5Y neuroblastoma cell line, thus demonstrating the crucial role played by the free NH2 terminus in the cell protection. Since several brain diseases are associated either to Cu(II) or Zn(II) dyshomeostasis, here we characterized also the complex species formed by Zn(II) with Semax and Ac-Semax. Both peptides were able to form Zn(II) complex species with comparable strength. Confocal microscopy imaging confirmed that peptide group acetylation does not affect the Zn(II) influx in neuroblastoma cells. Moreover, a punctuate distribution of Zn(II) within the cells suggests a preferred subcellular localization that might explain the zinc toxic effect. A future perspective can be the use of Ac-Semax as ionophore in antibody drug conjugates to produce a dysmetallostasis in tumor cells.
Semax is a heptapeptide (Met-Glu-His-Phe-Pro-Gly-Pro) that encompasses the sequence 4-7 of N-terminal domain of the adrenocorticotropic hormone and a C-terminal Pro-Gly-Pro tripeptide. N-terminal amino group acetylation (Ac-Semax) modulates the chemical and biological properties of parental peptide, modifying the ability of Semax to form complex species with Cu(II) ion. At physiological pH, the main complex species formed by Ac-Semax, [CuLH-2]2-, consists in a distorted CuN3O chromophore with a weak apical interaction of the methionine sulphur. Such a complex differs from the Cu(II)-Semax complex system, which exhibits a CuN4 chromophore. The reduced ligand field affects the [CuLH-2]2- formal redox potential, which is more positive than that of Cu(II)-Semax corresponding species. In the amino-free form, the resulting complex species is redox-stable and unreactive against ascorbic acid, unlike the acetylated form. Semax acetylation did not protect from Cu(II) induced toxicity on a SH-SY5Y neuroblastoma cell line, thus demonstrating the crucial role played by the free NH2 terminus in the cell protection. Since several brain diseases are associated either to Cu(II) or Zn(II) dyshomeostasis, here we characterized also the complex species formed by Zn(II) with Semax and Ac-Semax. Both peptides were able to form Zn(II) complex species with comparable strength. Confocal microscopy imaging confirmed that peptide group acetylation does not affect the Zn(II) influx in neuroblastoma cells. Moreover, a punctuate distribution of Zn(II) within the cells suggests a preferred subcellular localization that might explain the zinc toxic effect. A future perspective can be the use of Ac-Semax as ionophore in antibody drug conjugates to produce a dysmetallostasis in tumor cells.
Influence of the N-terminus acetylation of Semax, a synthetic analog of ACTH(4-10), on copper(II) and zinc(II) coordination and biological properties
Influence of the N-terminus acetylation of Semax, a synthetic analog of ACTH(4-10), on copper(II) and zinc(II) coordination and biological properties
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Biochem Pharmacol Biochemical Pharmacology (ISSN: 0006-2952, 1873-2968), 2012 Sep 1; 84(3): 303-311.
Impact Factor: 4.576
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Iiritano S, Chiefari E, Ventura V, Arcidiacono B, Possidente K, Nocera A, Nevolo MT, Fedele M, Greco A, Greco M, Brunetti G, Fusco A, Foti D, Brunetti A
* The HMGA1-IGF-I/IGFBP system: a novel pathway for modulating glucose uptake (860 views)
Molecular Endocrinology (ISSN: 0888-8809, 1944-9917electronic), 2012 Sep; 26(9): 1578-1589.
Impact Factor: 4.746
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Jószai V, Turi I, Kállay C, Pappalardo G, Di Natale G, Rizzarelli E, Sóvágó I
* Mixed metal copper(II)-nickel(II) and copper(II)-zinc(II) complexes of multihistidine peptide fragments of human prion protein (544 views)
J Chem Res (ISSN: 1873-3344, 0162-0134, 0162-0134print), 2012 Jul; 112: 17-24.
Impact Factor: 3.197
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Pilla P, Sandomenico A, Malachovsk V, Borriello A, Giordano M, Cutolo A, Ruvo M, Cusano A
* A protein-based biointerfacing route toward label-free immunoassays with long period gratings in transition mode (633 views)
Biosens Bioelectron (ISSN: 0956-5663, 1873-4235electronic, 0956-5663linking), 2012 Jan 15; 31(1): 486-491.
Impact Factor: 5.437
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Arena G, Pappalardo G, Sovago I, Rizzarelli E
* Copper(ii) Interaction With Amyloid-Beta: Affinity And Speciation (526 views)
Coord Chem Rev (ISSN: 0010-8545), 2012 Jan; 256(1-2): 3-12.
Impact Factor: 11.016
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Diana D, Basile A, De Rosa L, Di Stasi R, Auriemma S, Arra C, Pedone C, Turco MC, Fattorusso R, D'Andrea LD
* Beta-Hairpin Peptide That Targets Vascular Endothelial Growth Factor (vegf) Receptors: Design, Nmr Characterization, And Biological Activity (708 views)
Jbc Papers (ISSN: 1083-351x, 0021-9258, 0021-9258linking), 2011 Dec 2; 286(48): 41680-41691.
Impact Factor: 4.773
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Milite C, Castellano S, Benedetti R, Tosco A, Ciliberti C, Vicidomini C, Boully L, Franci G, Altucci L, Mai A, Sbardella G
* Modulation of the activity of histone acetyltransferases by long chain alkylidenemalonates (LoCAMs) (454 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 1464-3391electronic), 2011 Jun 15; 19(12): 3690-3701.
Impact Factor: 2.921
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Tabbì G, Di Mauro G, Purrello R, Bonomo RP
* Electrochemical characterization of ordered arrays of metallo-porphyrins in aqueous solution (485 views)
Dalton T (ISSN: 1477-9226, 1477-9234, 1477-9234electronic), 2011 Apr 28; 40(16): 4223-4229.
Impact Factor: 3.838
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Correale S, Pirone L, Di Marcotullio L, De Smaele E, Greco A, Mazzà D, Moretti M, Alterio V, Vitagliano L, Di Gaetano S, Gulino A, Pedone E
* Molecular organization of the cullin E3 ligase adaptor KCTD11 (708 views)
Biochimie (ISSN: 0300-9084, 1638-6183, 1638-6183electronic), 2011 Apr; 93(4): 715-724.
Impact Factor: 3.022
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Pizzo E, Merlino A, Turano M, Russo Krauss I, Coscia F, Zanfardino A, Varcamonti M, Furia A, Giancola C, Mazzarella L, Sica F, D'Alessio G
* A new RNase sheds light on the RNase/angiogenin subfamily from zebrafish (961 views)
Biochem J (ISSN: 1470-8728electronic, 0264-6021linking, 0264-6021print), 2011 Jan 15; 433(2): 345-355.
Impact Factor: 4.897
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Pensato S, Saviano M, Bianchi N, Borgatti M, Fabbri E, Gambari R, Romanelli A
* Gamma-Hydroxymethyl Pnas: Synthesis, Interaction With Dna And Inhibition Of Protein/Dna Interactions (413 views)
Bioorg Chem, 2010 Sep; 38(5): 196-201.
Impact Factor: 2.141
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Turi I, Kállay C, Szikszai D, Pappalardo G, Di Natale G, De Bona P, Rizzarelli E, Sóvágó I
* Nickel(II) complexes of the multihistidine peptide fragments of human prion protein (555 views)
J Chem Res (ISSN: 1873-3344, 0162-0134, 0162-0134print), 2010 Sep; 104(8): 885-891.
Impact Factor: 3.317
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La Mendola D, Magrì A, Campagna T, Campitiello MA, Raiola L, Isernia C, Hansson O, Bonomo RP, Rizzarelli E
* A doppel alpha-helix peptide fragment mimics the copper(II) interactions with the whole protein (1284 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2010 Jun 1; 16(21): 6212-6223.
Impact Factor: 5.476
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Roviello GN, Di Gaetano S, Capasso D, Cesarani A, Bucci EM, Pedone C
* Synthesis, spectroscopic studies and biological activity of a novel nucleopeptide with Moloney murine leukemia virus reverse transcriptase inhibitory activity (545 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 May; 38(5): 1489-1496.
Impact Factor: 4.106
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Roviello GN, Musumeci D, De Cristofaro A, Capasso D, Di Gaetano S, Bucci EM, Pedone C
* Alternate dab-aegPNAs: synthesis, nucleic acid binding studies and biological activity (603 views)
Mol Biosyst (ISSN: 1742-2051, 1742-206x, 1742-2051electronic), 2010 Jan; 6(1): 199-205.
Impact Factor: 3.825
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Osz K, Nagy Z, Pappalardo G, Di Natale G, Sanna D, Micera G, Rizzarelli E, Sóvágó I
* Copper(II) interaction with prion peptide fragments encompassing histidine residues within and outside the octarepeat domain: speciation, stability constants and binding details (749 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2007; 13(25): 7129-7143.
Impact Factor: 5.33
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Dalla Bona A, Formaggio F, Peggion C, Kaptein B, Broxterman Quirinus B, Galdiero S, Galdiero M, Vitiello M, Benedetti E, Toniolo C
* Synthesis, conformation, and bioactivity of novel analogues of the antiviral lipopeptide halovir (682 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2006 Dec; 12(12): 748-757.
Impact Factor: 1.801
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Saviano M, Romanelli A, Bucci E, Pedone C, Mischiati C, Bianchi N, Feriotto G, Borgatti M, Gambari R
Computational procedures to explain the different biological activity of DNA/DNA, DNA/PNA and PNA/PNA hybrid molecules mimicking NF-κB binding sites (704 views)
J Biomol Struct Dyn (ISSN: 0739-1102, 1538-0254electronic, 0739-1102linking), 2000 Dec; 18(3): 353-362.
Impact Factor: 1.826
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Bonomo RP, Imperllizzeri G, Pappalardo G, Rizzarelli E, Tabbì G
Copper(II) binding modes in the prion octapeptide PHGGGWGQ: A spectroscopic and voltammetric study (572 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2000 Nov 17; 6(22): 4195-4202.
Impact Factor: 4.698
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Caliendo G, Fiorino F, Grieco P, Perissutti E, De Luca S, Giuliano A, Santelli G, Califano D, Severino B, Santagada V
Synthesis and biological activity of pseudopeptides inhibitors of Ras farnesyl transferase containing unconventional amino acids (720 views)
Farmaco (ISSN: 0014-827x), 1999 Nov; 54(11-12): 785-790.
Impact Factor: 0.406
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Bonomo RP, Cucinotta V, D'Alessandro F, Impellizzeri G, Maccarrone G, Rizzarelli E, Vecchio G, Carima L, Corradini R, Sartor G, Marchelli R
Chiral recognition by the copper(ii) complex of 6-deoxy-6-n-(2 - methylaminopyridine)-β-cyclodextrin (588 views)
Chirality (ISSN: 0899-0042), 1997; 9(4): 341-349.
Impact Factor: 1.915
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35 Records (35 excluding Abstracts).
Total impact factor: 149.18 (149.18 excluding Abstracts).
Total 5 year impact factor: 152.09 (152.09 excluding Abstracts).
Total impact factor: 149.18 (149.18 excluding Abstracts).
Total 5 year impact factor: 152.09 (152.09 excluding Abstracts).
291 views. Last view on Monday 07 October 2024, 17:27:55
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