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Effect of C5-Methylation of Cytosine on the UV-Induced Reactivity of Duplex DNA: Conformational and Electronic Factors (83 visite)

Banyasz A, Esposito L, Douki T, Perron M, Lepori C, Improta R, Markovitsi D

J Phys Chem B (ISSN: 1520-5207electronic, 1520-5207linking, 1520-6106), 2016 May 12; 120(18): 4232-4242.

Tipo di articolo: Journal Article,

Impact factor: 3.177

Impact factor a 5 anni: 3.177


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Url: Non disponibile.

C5-methylation of cytosines is strongly correlated with UV-induced mutations detected in skin cancers. Mutational hot-spots appearing at TCG sites are due to the formation of pyrimidine cyclobutane dimers (CPDs). The present study, performed for the model DNA duplex (TCGTA)3.(TACGA)3 and the constitutive single strands, examines the factors underlying the effect of C5-methylation on pyrimidine dimerization at TCG sites. This effect is quantified for the first time by quantum yields varphi. They were determined following irradiation at 255, 267, and 282 nm and subsequent photoproduct analysis using HPLC coupled to mass spectrometry. C5-methylation leads to an increase of the CPD quantum yield up to 80% with concomitant decrease of that of pyrimidine(6-4) pyrimidone adducts (64PPs) by at least a factor of 3. The obtained varphi values cannot be explained only by the change of the cytosine absorption spectrum upon C5-methylation. The conformational and electronic factors that may affect the dimerization reaction are discussed in light of results obtained by fluorescence spectroscopy, molecular dynamics simulations, and quantum mechanical calculations. Thus, it appears that the presence of an extra methyl on cytosine affects the sugar puckering, thereby enhancing conformations of the TC step that are prone to CPD formation but less favorable to 64PPs. In addition, C5-methylation diminishes the amplitude of conformational motions in duplexes; in the resulting stiffer structure, pipi* excitations may be transferred from initially populated exciton states to reactive pyrimidines giving rise to CPDs.
*** IBB - CNR ***

LIDYL, CEA, CNRS, Universite Paris Saclay, F-91191 Gif-sur-Yvette, France., Istituto Biostrutture e Bioimmagini - CNR , 80134 Napoli, Italy., Universite Grenoble Alpes, INAC, LCIB, LAN & CEA, INAC, SCIB, LANF-38000 Grenoble, France.,
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Santoro F, Barone V, Improta R
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Ronga L, Palladino P, Costantini S, Facchiano A, Ruvo M, Benedetti E, Ragone R, Rossi F
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Pappalardo G, Milardi D, Magna A, Attanasio F, Impellizzeri G, La Rosa C, Grasso D, Rizzarelli E
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Langella E, Improta R, Crescenzi O, Barone V
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Tizzano B, Palladino P, De Capua A, Marasco D, Rossi F, Benedetti E, Pedone C, Ragone R, Ruvo M
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Di Natale G, Impellizzeri G, Pappalardo G
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De Pinto V, Messina A, Aiello R, Tomasello F, La Mendola D, Magri A, Milardi D, Pappalardo G
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* Conformational conversion of prion proteins: Role synthetic PRP 173-195 fibrillogenic peptide (108 visite)
Peptide Revolution, 2004; N/D: N/D-N/D.
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Barone V, Formaggio F, Improta R, Polo F, Maran F
* Electron transfer to and conformational preferences of Aib oligo-peptides (111 visite)
Proc Electrochem Soc, 2004; 10: 29-32.
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La Mendola D, Magrì A, Pappalardo G, Rizzarelli E, Impellizzeri G
* PEG-AMYLIN FRAGMENTS AS MODELS FOR CONFORMATIONAL STUDIES (114 visite)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2004; 10: N/D-N/D.
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Zaccaro L, Bucci E, Vitale RM, Perretta G, Fattorusso R, Benedetti E, Saviano M, Pedone C
* Synthetic peptides mimicking the interleukin-6/gp130 interaction: a two-helix bundle system. Design and conformational studies (129 visite)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2003 Feb; 9(2): 105-105.
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D'Amore M, Improta R, Barone V
* Conformational behavior and magnetic properties of a nitroxide amino acid derivative in vacuo and in aqueous solution (91 visite)
J Phys Chem A (ISSN: 1089-5639, 1520-5215electronic), 2003; 107(32): 6264-6269.
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Langella E, Improta R, Barone V
* Conformational and spectroscopic analysis of the tyrosyl radical dipeptide analogue in the gas phase and in aqueous solution by a density functional/continuum solvent model (85 visite)
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2002 Sep 25; 124(38): 11531-11540.
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Langella E, Rega N, Improta R, Crescenzi O, Barone V
* Conformational analysis of the tyrosine dipeptide analogue in the gas phase and in aqueous solution by a density functional/continuum solvent model (92 visite)
J Comput Chem (ISSN: 0192-8651, 1096-987xelectronic), 2002 Apr 30; 23(6): 650-661.
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Benzi C, Improta R, Scalmani G, Barone V
* Quantum mechanical study of the conformational behavior of proline and 4R-hydroxyproline dipeptide analogues in vacuum and in aqueous solution (84 visite)
J Comput Chem (ISSN: 0192-8651, 1096-987xelectronic), 2002 Feb; 23(3): 341-350.
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Pavone V, Lombardi A, Saviano M, De Simone G, Nastri F, Maglio O, Omote Y, Yamanaka Y, Yamada T
Conformational behavior of C(α, α)-diphenyl glycine: Extended conformation in tripeptides containing consecutive Dφg residues (114 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2000 Feb; 53(2): 161-168.
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Pavone V, Lombardi A, Saviano M, Nastri F, Zaccaro L, Maglio O, Pedone C, Omote Y, Yamanaka Y, Yamada T
Conformational Behaviour Of C (alpha, Alpha)-Diphenylglycine: Folded Vs. Extended Structures In Dphig-Containing Tripeptides (128 visite)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 1998 Feb; 4(1): 21-32.
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Pavone V, Lombardi A, Saviano M, Nastri F, Zaccaro L, Maglio O, Pedone C, Omote Y, Yamanaka Y, Yamada T
Conformational Behaviour Of C-Alpha-Alpha-Diphenylglicine. Folded Versus Extended Structures In Dfg-Containing Tripeptides (109 visite)
Journal Of Peptide Science, 1998; 4: 21-32.
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Gatos M, Formaggio F, Crisma M, Valle G, Toniolo C, Bonora GM, Saviano M, Iacovino R, Menchise V, Galdiero S, Pedone C, Benedetti E
Conformational Characterization Of Peptides Rich In The Cycloaliphatic C Alpha, Alpha-Disubstituted Glycine 1-Aminocyclononane-1-Carboxylic Acid (128 visite)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 1997 Sep; 3(5): 367-382.
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Benedetti E, Iacovino R, Pedone C, Rossi F, Saviano M, Isernia C, Montesarchio D, DeNapoli L, Piccialli G
β-Amino acid residues: Conformational characterization of an N- and C-protected homo-β-(S)-leucine (81 visite)
International Journal Of Peptide Research And Therapeutics (ISSN: 0929-5666, 1573-3149), 1997 Jun; 4(3): 129-134.
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D'Andrea LD, Mazzeo M, Isernia C, Rossi F, Saviano M, Gallo P, Paolillo L, Pedone C
Solution conformational preferences of a peptidic analogue of a natural macrolide (93 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1997; 42(3): 349-361.
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Lombardi A, Saviano M, Nastri F, Maglio O, Mazzeo M, Pedone C, Isernia C, Pavone V
Unusual conformational preferences of β-alanine containing cyclic peptides. VII (128 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1996 Jun; 38(6): 683-691.
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Saviano M, Rossi F, Filizola M, Isernia C, Di Blasio B, Benedetti E, Pedone C, Siemion IZ, Pedyczak A
Bioactive peptides: conformational studies of [Tyr4] cyclolinopeptide (116 visite)
Biopolymers (ISSN: 0006-3525print, 0006-3525linking, 1097-0282electronic), 1995 Oct; 26(12): 453-460.
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Di Blasio B, Saviano M, Del Duca V, De Simone G, Rossi F, Pedone C, Benedetti E, Lorenzi GP
CONFORMATIONAL STUDIES OF HETEROCHIRAL PEPTIDES WITH DIASTEREOISOMERIC RESIDUES - CRYSTAL AND MOLECULAR-STRUCTURES OF LINEAR DIPEPTIDES DERIVED FROM LEUCINE, ISOLEUCINE, AND ALLO-ISOLEUCINE (136 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1995 Oct; 36(4): 401-408.
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Mazzeo M, Isernia C, Rossi F, Saviano M, Pedone C, Paolillo L, Benedetti E, Pavone V
Conformational Behaviour of a Cyclolinopeptide A Analogue: Two-dimensional NMR study of cyclo(Pro(1)-Pro-Phe-Phe-Ac(6)c-Ile-ala-Val(8)) (100 visite)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 1995 Sep; 1(5): 330-340.
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Caraglia M, Tagliaferri P, Correale P, Genua G, Pinto A, Del Vecchio S, Esposito G, Bianco AR
CYTOSINE-ARABINOSIDE INCREASES THE BINDING OF I-125 LABELED EPIDERMAL GROWTH-FACTOR AND I-125 TRANSFERRIN AND ENHANCES THE IN-VITRO TARGETING OF HUMAN TUMOR-CELLS WITH ANTI-(GROWTH FACTOR-RECEPTOR) MAB (112 visite)
Cancer Immunology Immunotherapy (ISSN: 0340-7004), 1993 Sep; 37(3): 150-156.
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Zanotti G, Maione A, Rossi F, Saviano M, Pedone C, Tancredi T
BIOACTIVE PEPTIDES - CONFORMATIONAL STUDY OF A CYSTINYL CYCLOHEPTAPEPTIDE IN ITS FREE AND CALCIUM COMPLEXED FORMS (127 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1993 Jul; 33(7): 1083-1091.
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De Simone C, Mancini M, Vaccaro O, Riccardi G, Gallotta LA, Ferrara G, Cicerano U, Postiglione A
Cerebrovascular Reactivity By Transcranial Doppler Ultrasonography In Insulin-Dependent Diabetic Patients (71 visite)
Cerebrovasc Dis, 1993; 3(2): 111-115.
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Caraglia M, Correale P, Genua G, Pepe S, Del Vecchio S, Esposito G, Bianco AR, Tagliaferri P
EPIDERMAL GROWTH-FACTOR (EGFR) AND TRANSFERRIN (TRFR) RECEPTOR UP-REGULATION IS INDUCED BY ARABINOSIDE CYTOSINE (ARA-C) ON HUMAN TUMOR-CELLS (92 visite)
(ISSN: 0361-090x), 1993; 17(2): 337-338.
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DIBLASIO B, ROSSI F, BENEDETTI E, PAVONE V, SAVIANO M, PEDONE C, ZANOTTI G, TANCREDI T
BIOACTIVE PEPTIDES - X-RAY AND NMR CONFORMATIONAL STUDY OF [AIB(5, 6)-D-ALA(8)]CYCLOLINOPEPTIDE-A (122 visite)
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 1992 Oct 7; 114(21): 8277-8283.
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Saviano M, Rossi F, Pavone V, Di Blasio B, Pedone C
Molecular dynamics simulation in vacuo and in solution of [Aib5, 6-D- Ala8] Cyclolinopeptide A: A conformational and comparative study (102 visite)
J Biomol Struct Dyn (ISSN: 0739-1102, 1538-0254electronic, 0739-1102linking), 1992 Jun; 9(6): 1045-1060.
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Tancredi T, Benedetti E, Grimaldi M, Pedone C, Rossi F, Saviano M, Temussi PA, Zanotti G
Ion binding of cyclolinopeptide A: An NMR and CD conformational study (79 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1991 May; 31(6): 761-767.
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Ferrara LA, Soro S, Marotta T, Mancini M
Chronobiological Evaluation Of Cardiovascular Reactivity (83 visite)
Atherosclerosis And Cardiovascular Disease Descovich G C Gaddi A Magri Gl Lenzi S, 1989; 4(a): 10-10.
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Marotta T, Soro S, Mancini M, Ferrara LA
The Adrenergic Nervous System Reactivity: A Chronobiological Study (89 visite)
7th International Meeting On Atherosclerosis And Cardiovascular Disease Bologna, 1989; N/D: 27-27.
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Mancini M, De Chiara S, Ferrara LA, Gallotta G, Postiglione A
TRANSCRANIAL DOPPLER EVALUATION OF CEREBROVASCULAR REACTIVITY TO ACETAZOLAMIDE IN NORMAL SUBJECTS (92 visite)
15th World Congress Angiology Rome, 1989; 20(4): 284-284.
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Ferrara LA, Pisanti N, Fasano ML, Mancini M
Effects of sodium intake on blood pressure and adrenergic vascular reactivity (71 visite)
J Clin Hypertens (ISSN: 0748-450x), 1986; 2(4): 315-321.
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87 Records (73 escludendo Abstract e Conferenze).
Impact factor totale: 249.618 (226.176 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 269.786 (244.555 escludendo Abstract e Conferenze).







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