Inhibitors of HIV-1 protease by using in situ click chemistry

被引:494
作者
Whiting, M
Muldoon, J
Lin, YC
Silverman, SM
Lindstrom, W
Olson, AJ
Kolb, HC
Finn, MG
Sharpless, KB
Elder, JH
Fokin, VV
机构
[1] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
关键词
click chemistry; drug design; HIV-1; protease; inhibitors; triazoles;
D O I
10.1002/anie.200502161
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Twice poor equals potent: HIV-1 Protease assembles its own potent inhibitor through formation of the triazole linkage from azide- and alkyne-containing fragments that are themselves poor binders. © 2006 Wiley-VCH Verlag GmbH S. Co. KGaA.
引用
收藏
页码:1435 / 1439
页数:5
相关论文
共 35 条
[1]   PRODUCTION OF ACQUIRED IMMUNODEFICIENCY SYNDROME-ASSOCIATED RETROVIRUS IN HUMAN AND NONHUMAN CELLS TRANSFECTED WITH AN INFECTIOUS MOLECULAR CLONE [J].
ADACHI, A ;
GENDELMAN, HE ;
KOENIG, S ;
FOLKS, T ;
WILLEY, R ;
RABSON, A ;
MARTIN, MA .
JOURNAL OF VIROLOGY, 1986, 59 (02) :284-291
[2]   Overview of the effectiveness of triple combination therapy in antiretroviral-naive HIV-1 infected adults [J].
Bartlett, JA ;
DeMasi, R ;
Quinn, J ;
Moxham, C ;
Rousseau, F .
AIDS, 2001, 15 (11) :1369-1377
[3]   1,2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors [J].
Brik, A ;
Alexandratos, J ;
Lin, YC ;
Elder, JH ;
Olson, AJ ;
Wlodawer, A ;
Goodsell, DS ;
Wong, CH .
CHEMBIOCHEM, 2005, 6 (07) :1167-+
[4]   Rapid diversity-oriented synthesis in microtiter plates for in situ screening of HIV protease inhibitors [J].
Brik, A ;
Muldoon, J ;
Lin, YC ;
Elder, JH ;
Goodsell, DS ;
Olson, AJ ;
Fokin, VV ;
Sharpless, KB ;
Wong, CH .
CHEMBIOCHEM, 2003, 4 (11) :1246-1248
[5]   IN-VIVO EMERGENCE OF HIV-1 VARIANTS RESISTANT TO MULTIPLE PROTEASE INHIBITORS [J].
CONDRA, JH ;
SCHLEIF, WA ;
BLAHY, OM ;
GABRYELSKI, LJ ;
GRAHAM, DJ ;
QUINTERO, JC ;
RHODES, A ;
ROBBINS, HL ;
ROTH, E ;
SHIVAPRAKASH, M ;
TITUS, D ;
YANG, T ;
TEPPLER, H ;
SQUIRES, KE ;
DEUTSCH, PJ ;
EMINI, EA .
NATURE, 1995, 374 (6522) :569-571
[6]   Making drugs on proteins: site-directed ligand discovery for fragment-based lead assembly [J].
Erlanson, DA ;
Hansen, SK .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2004, 8 (04) :399-406
[7]   Unexpected formation of an epoxide-derived multisubstrate adduct inhibitor on the active site of GAR transformylase [J].
Greasley, SE ;
Marsilje, TH ;
Cai, H ;
Baker, S ;
Benkovic, SJ ;
Boger, DL ;
Wilson, IA .
BIOCHEMISTRY, 2001, 40 (45) :13538-13547
[8]   ACTIVE HUMAN IMMUNODEFICIENCY VIRUS PROTEASE IS REQUIRED FOR VIRAL INFECTIVITY [J].
KOHL, NE ;
EMINI, EA ;
SCHLEIF, WA ;
DAVIS, LJ ;
HEIMBACH, JC ;
DIXON, RAF ;
SCOLNICK, EM ;
SIGAL, IS .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (13) :4686-4690
[9]   In situ selection of lead compounds by click chemistry: Target-guided optimization of acetylcholinesterase inhibitors [J].
Krasinski, A ;
Radic, Z ;
Manetsch, R ;
Raushel, J ;
Taylor, P ;
Sharpless, KB ;
Kolb, HC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (18) :6686-6692
[10]   Analysis of the S3 and S3′ subsite specificities of feline immunodeficiency virus (FIV) protease:: Development of a broad-based protease inhibitor efficacious against FIV, SIV and HIV in vitro and ex vivo [J].
Lee, T ;
Laco, GS ;
Torbett, BE ;
Fox, HS ;
Lerner, DL ;
Elder, JH ;
Wong, CH .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (03) :939-944