Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/how-can-the-cross-link-adducts-formed-by-novel-trans-platinum-drug-be-bFrjhN0H6y
References (44)
-
Yu Chen, Zijian Guo, J. Parkinson, P. Sadler (1998)
Kinetic control of reactions of a sterically hindered platinum picoline anticancer complex with guanosine 5′-monophosphate and glutathioneJournal of The Chemical Society-dalton Transactions
-
P. Pavankumar, P. Seetharamulu, S. Yao, J. Saxe, D. Reddy, Frederick Hausheer (1999)
Comprehensive ab initio quantum mechanical and molecular orbital (MO) analysis of cisplatin: Structure, bonding, charge density, and vibrational frequenciesJournal of Computational Chemistry, 20
-
P. Carloni, P. Carloni, W. Andreoni, J. Hutter, A. Curioni, P. Giannozzi, M. Parrinello (1995)
STRUCTURE AND BONDING IN CISPLATIN AND OTHER PT(II) COMPLEXESChemical Physics Letters, 234
-
S. Sherman, D. Gibson, A. Wang, S. Lippard (1988)
Crystal and molecular structure of cis-[Pt(NH3)2{d(pGpG)}], the principal adduct formed by cis-diamminedichloroplatinum(II) with DNAJournal of the American Chemical Society, 110
-
Marijo Beusichem, N. Farrell (1992)
Activation of the trans geometry in platinum antitumor complexes. Synthesis, characterization, and biological activity of complexes with the planar ligands pyridine, N-methylimidazole, thiazole and quinoline. Crystal and molecular structure of trans-dichlorobis (thiazole)platinum(II)Inorganic Chemistry, 31
-
M. Fuertes, C. Alonso, J. Pérez (2003)
Biochemical modulation of Cisplatin mechanisms of action: enhancement of antitumor activity and circumvention of drug resistance.Chemical reviews, 103 3
-
L. Marzilli, Jamil Saad, Zsuzsanna Kuklenyik, Kelly Keating, Yinghai Xu (2001)
Relationship of solution and protein-bound structures of DNA duplexes with the major intrastrand cross-link lesions formed on cisplatin binding to DNA.Journal of the American Chemical Society, 123 12
-
D. Sartori, Bernhard Miller, U. Bierbach, N. Farrell (2000)
Modulation of the chemical and biological properties of trans platinum complexes: monofunctional platinum complexes containing one nucleobase as potential antiviral chemotypesJBIC Journal of Biological Inorganic Chemistry, 5
-
T. Freedman, Xiaolin Cao, D. Young, L. Nafie (2002)
Density functional theory calculations of vibrational circular dichroism in transition metal complexes: Identification of solution conformations and mode of chloride ion association for (+)-tris(ethylenediaminato)cobalt(III)Journal of Physical Chemistry A, 106
-
L. Marzilli, Susan Ano, F. Intini, G. Natile (1999)
New Concepts Relevant to Cisplatin Anticancer Activity from Unique Spectral Features Providing Evidence That Adjacent Guanines in d(GpG), Intrastrand-Cross-Linked at N7 by a cis-Platinum(II) Moiety, Can Adopt a Head-to-Tail ArrangementJournal of the American Chemical Society, 121
-
U. Bierbach, M. Sabat, N. Farrell (2000)
Inversion of the cis geometry requirement for cytotoxicity in structurally novel platinum(II) complexes containing the bidentate N,O-donor pyridin-2-yl-acetate.Inorganic chemistry, 39 9
-
M. Boudvillain, R. Dalbiès, Christophe Aussourd, M. Leng (1995)
Intrastrand cross-links are not formed in the reaction between transplatin and native DNA: relation with the clinical inefficiency of transplatinNucleic acids research, 23 13
-
J. Burda, J. Leszczynski (2003)
How strong can the bend be on a DNA helix from cisplatin? DFT and MP2 quantum chemical calculations of cisplatin-bridged DNA purine bases.Inorganic chemistry, 42 22
-
J. Saad, T. Scarcia, K. Shinozuka, G. Natile, L. Marzilli (2002)
Modification of second-sphere communication, leading to an unusually high abundance of the head-to-head conformer of cisplatin cross-link retro models.Inorganic chemistry, 41 3
-
U. Bierbach, N. Farrell (1998)
Structural and reactivity studies on the ternary system guanine/methionine/trans-[PtCl2(NH3)L] (L=NH3, quinoline): implications for the mechanism of action of nonclassical trans-platinum antitumor complexesJBIC Journal of Biological Inorganic Chemistry, 3
-
G. Colonna, Nicola Masi, L. Marzilli, G. Natile (2003)
Ground-state stability and rotational activation parameters for individual rotamers of (R,S,S,R)-(N,N'-dimethyl-2,3-diaminobutane)PtG(2) complexes (G = 9-EtG, 3'-GMP, and 5'-GMP).Inorganic chemistry, 42 4
-
S. Boys, F. Bernardi (1970)
The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errorsMolecular Physics, 100
-
K. Williams, L. Cerasino, †. Natile, L. Marzilli (2000)
cis-Pt(NH3)2(GpG) Properties Interpreted through Comparison with Retro-Model GpG Adducts Having Carrier Ligands Designed to Slow Dynamic Motion and Control Cross-Link HandednessJournal of the American Chemical Society, 122
-
Rozenn DALBItS, D. Payet, M. Leng (1994)
DNA double helix promotes a linkage isomerization reaction in trans-diamminedichloroplatinum(II)-modified DNA.Proceedings of the National Academy of Sciences of the United States of America, 91 17
-
P. Stephens, F. Devlin (2000)
Determination of the structure of chiral molecules using ab initio vibrational circular dichroism spectroscopy.Chirality, 12 4
-
E. Tornaghi, W. Andreoni, P. Carloni, J. Hutter, M. Parrinello (1995)
Carboplatin versus cisplatin: density functional approach to their molecular propertiesChemical Physics Letters, 246
-
J. Caradonna, S. Lippard (1988)
Synthesis and characterization of [d(ApGpGpCpCpT)]2 and its adduct with the anticancer drug cis-diamminedichloroplatinum(II)Inorganic Chemistry, 27
-
E. Wong, C. Giandomenico (1999)
Current status of platinum-based antitumor drugs.Chemical reviews, 99 9
-
I. Dąbkowska, J. Rak, M. Gutowski (2002)
Computational Study of Hydrogen-Bonded Complexes Between the Most Stable Tautomers of Glycine and UracilJournal of Physical Chemistry A, 106
-
T. Kline, L. Marzilli, D. Live, G. Zon (1989)
Investigations of platinum amine induced distortions in single- and double-stranded oligodeoxyribonucleotidesJournal of the American Chemical Society, 111
-
J. Tomasi, M. Persico (1994)
Molecular Interactions in Solution: An Overview of Methods Based on Continuous Distributions of the SolventChemical Reviews, 94
-
M. Shukla, J. Leszczynski (2005)
Effect of hydration on the lowest singlet PiPi* excited-state geometry of guanine: a theoretical study.The journal of physical chemistry. B, 109 36
-
J. Reedijk (1999)
Why does Cisplatin reach Guanine-n7 with competing s-donor ligands available in the cell?Chemical reviews, 99 9
-
M. Baik, R. Friesner, S. Lippard (2003)
Theoretical study of cisplatin binding to purine bases: why does cisplatin prefer guanine over adenine?Journal of the American Chemical Society, 125 46
-
A. Reed, L. Curtiss, F. Weinhold (1988)
Intermolecular interactions from a natural bond orbital, donor-acceptor viewpointChemical Reviews, 88
-
Chengteh Lee, Weitao Yang, R. Parr (1988)
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.Physical review. B, Condensed matter, 37 2
-
D. Gigante, F. Long, Louise Bodack, J. Evans, J. Kallmerten, L. Nafie, T. Freedman (1999)
Hydrogen Stretching Vibrational Circular Dichroism in Methyl Lactate and Related MoleculesJournal of Physical Chemistry A, 103
-
S. Mukundan, Yinghai Xu, G. Zon, L. Marzilli (1991)
Heteronuclear carbon-13-proton NMR investigation of the effects on an oligodeoxyribonucleotide of intrastrand cross-linking by a platinum anticancer drug; a large shift of C3' accompanies an S to N conformational changeJournal of the American Chemical Society, 113
-
R. Kendall, J. Simons, M. Gutowski, G. Chałasiński (1989)
The Ab initio energy and structure of hydride-hydrogen (H-(H2)2)The Journal of Physical Chemistry, 93
-
P. Siegbahn, M. Blomberg (2000)
Transition-metal systems in biochemistry studied by high-accuracy quantum chemical methods.Chemical reviews, 100 2
-
T. Hambley (1988)
Molecular mechanics analysis of the influence of interligand interactions on isomer stabilities and barriers to isomer interconversion in diammine- and bis(amine)bis(purine)platinum(II) complexesInorganic Chemistry, 27
-
M. Coluccia, Anna Nassi, F. Loseto, A. Boccarelli, Maria Mariggiò, Domenico Giordano, F. Intini, Paola Caputo, G. Natile (1993)
A trans-platinum complex showing higher antitumor activity than the cis congeners.Journal of medicinal chemistry, 36 4
-
E. Jamieson, S. Lippard (1999)
Structure, Recognition, and Processing of Cisplatin-DNA Adducts.Chemical reviews, 99 9
-
L. Nafie, T. Freedman (1998)
Vibrational circular dichroism: an incisive tool for stereochemical applications.Enantiomer, 3 4-5
-
Susan Ano, F. Intini, G. Natile, L. Marzilli (1999)
Retro Models of Pt Anticancer Drug DNA Adducts: Chirality-Controlling Chelate Ligand Restriction of Guanine Dynamic Motion in (2,2'-Bipiperidine)PtG(2) Complexes (G = Guanine Derivative).Inorganic chemistry, 38 12
-
J. Kašpárková, Victoria Marini, Y. Najajreh, D. Gibson, V. Brabec (2003)
DNA binding mode of the cis and trans geometries of new antitumor nonclassical platinum complexes containing piperidine, piperazine, or 4-picoline ligand in cell-free media. Relations to their activity in cancer cell lines.Biochemistry, 42 20
-
F. Devlin, P. Stephens, J. Cheeseman, M. Frisch (1997)
Ab Initio Prediction of Vibrational Absorption and Circular Dichroism Spectra of Chiral Natural Products Using Density Functional Theory: Camphor and FenchoneJournal of Physical Chemistry A, 101
-
T. Hambley (1997)
The influence of structure on the activity and toxicity of Pt anti-cancer drugsCoordination Chemistry Reviews, 166
-
A. Becke (1993)
Density-functional thermochemistry. III. The role of exact exchangeJournal of Chemical Physics, 98
- Publisher
- Wiley
- Copyright
- Copyright © 2006 Wiley Subscription Services, Inc., A Wiley Company
- ISSN
- 1001-604X
- eISSN
- 1614-7065
- DOI
- 10.1002/cjoc.200690286
- Publisher site
- See Article on Publisher Site
Abstract
A systematic quantum chemical characterization of intrinsic structure, energies and spectral properties of all the studied cross‐link adducts formed by the novel trans platinum with thiazole ligand has been carried out at B3LYP/6‐31G* level of theory with the Lanl2dz pseudo potential basis set for the Pt atom. Special attention has been paid to the relative stability of these complexes and the factors that probably alter the order of the relative stability. The important influence of hydrogen bond on the structures, the energies and the spectral property was revealed. Other factors that contribute to relative stability including solvation effect, entropy and electronic delocalization energy were taken into account. The stability energy of the whole complex, and the interaction energy between two purine bases and the [Pt‐(NH3)thiazole]2+ group were adopted to study the interplay among subsystems and their contribution to relative stability of all the studied cross‐link model. Finally, basic spectral properties of these complexes including H(8) chemical shifts of all the studied complexes and the VCD (vibrational circular dichroism) spectra of two pairs of GG chelate enantiomers, were provided in order to define the structure of the most possible duplex bearing novel trans platinum drug lesions.
Journal
Chinese Journal of Chemistry – Wiley
Published: Nov 1, 2006
Keywords: ; ; ; ;