PROBING THE UNDERLYING BASIS FOR THE BINDING-SPECIFICITY OF CALICHEAMICIN GAMMA(1)(I) - A MOLECULAR-DYNAMICS STUDY

被引：13

作者：

LANGLEY, DR ^{[1
]}

DOYLE, TW ^{[1
]}

BEVERIDGE, DL ^{[1
]}

机构：

[1] WESLEYAN UNIV,DEPT CHEM,HALL ATWATER LABS,MIDDLETOWN,CT 06457

来源：

TETRAHEDRON | 1994年 / 50卷 / 05期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4020(01)80625-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Six different models of the DNA-calicheamicin complex were constructed to investigate the mode of binding of the rhamnose, thiobenzoate and thiosugar residues of the carbohydrate-thiabenzoate tail of calicheamicin with DNA. The stability of each model was tested in a 500 psec solvated molecular dynamics simulation. Five of the six models predicted the correct DNA hydrogen abstraction pattern. However, only one model was found to be consistent with air of the available experimental data and provided a clear rationale for the observed 5'-TCCT/3'AGGA sequence specificity.

引用

页码：1379 / 1396

页数：18

共 45 条

[1] INTERACTION OF THE ARYL TETRASACCHARIDE DOMAIN OF CALICHEAMICIN-GAMMA-1(I) WITH DNA - INFLUENCE ON AGLYCON AND METHIDIUMPROPYL-EDTA.IRON(II)-MEDIATED DNA CLEAVAGE [J].

AIYAR, J ;

DANISHEFSKY, SJ ;

CROTHERS, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (19) :7552-7554

[2] CHARMM - A PROGRAM FOR MACROMOLECULAR ENERGY, MINIMIZATION, AND DYNAMICS CALCULATIONS [J].

BROOKS, BR ;

BRUCCOLERI, RE ;

OLAFSON, BD ;

STATES, DJ ;

SWAMINATHAN, S ;

KARPLUS, M .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1983, 4 (02) :187-217

[3] KINETIC NATURE OF THIOL ACTIVATION IN DNA CLEAVAGE BY CALICHEAMICIN [J].

CHATTERJEE, M ;

CRAMER, KD ;

TOWNSEND, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (08) :3374-3375

[4] UNMASKING THE CHEMISTRY OF DNA CLEAVAGE BY THE ESPERAMICINS - MODULATION OF 4'-HYDROGEN ABSTRACTION AND BISTRANDED DAMAGE BY THE FUCOSE ANTHRANILATE MOIETY [J].

CHRISTNER, DF ;

FRANK, BL ;

KOZARICH, JW ;

STUBBE, J ;

GOLIK, J ;

DOYLE, TW ;

ROSENBERG, IE ;

KRISHNAN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :8763-8767

[5] SOLUTION CONFORMATION OF A HEPTADECAPEPTIDE COMPRISING THE DNA-BINDING HELIX-F OF THE CYCLIC-AMP RECEPTOR PROTEIN OF ESCHERICHIA-COLI - COMBINED USE OF H-1 NUCLEAR MAGNETIC-RESONANCE AND RESTRAINED MOLECULAR-DYNAMICS [J].

CLORE, GM ;

GRONENBORN, AM ;

BRUNGER, AT ;

KARPLUS, M .

JOURNAL OF MOLECULAR BIOLOGY, 1985, 186 (02) :435-455

[6] SITE-SPECIFIC ATOM TRANSFER FROM DNA TO A BOUND LIGAND DEFINES THE GEOMETRY OF A DNA CALICHEAMICIN GAMMA-1I COMPLEX [J].

DEVOSS, JJ ;

TOWNSEND, CA ;

DING, WD ;

MORTON, GO ;

ELLESTAD, GA ;

ZEIN, N ;

TABOR, AB ;

SCHREIBER, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9669-9670

[7] THE CARBOHYDRATE DOMAIN OF CALICHEAMICIN GAMMA-1(I) DETERMINES ITS SEQUENCE SPECIFICITY FOR DNA CLEAVAGE [J].

DRAK, J ;

IWASAWA, N ;

DANISHEFSKY, S ;

CROTHERS, DM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (17) :7464-7468

[8] STRUCTURE OF A B-DNA DODECAMER .3. GEOMETRY OF HYDRATION [J].

DREW, HR ;

DICKERSON, RE .

JOURNAL OF MOLECULAR BIOLOGY, 1981, 151 (03) :535-556

[9] MECHANISM OF NEOCARZINOSTATIN ACTION - ROLE OF DNA MICROSTRUCTURE IN DETERMINATION OF CHEMISTRY OF BISTRANDED OXIDATIVE DAMAGE [J].

GOLDBERG, IH .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (07) :191-198

[10] ESPERAMICINS, A NOVEL CLASS OF POTENT ANTITUMOR ANTIBIOTICS .2. STRUCTURE OF ESPERAMICIN-X [J].

GOLIK, J ;

CLARDY, J ;

DUBAY, G ;

GROENEWOLD, G ;

KAWAGUCHI, H ;

KONISHI, M ;

KRISHNAN, B ;

OHKUMA, H ;

SAITOH, K ;

DOYLE, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3461-3462

← 1 2 3 4 5 →