Hydrophobic benzoic acids as inhibitors of influenza neuraminidase

被引：38

作者：

Atigadda, VR

Brouillette, WJ ^{[1
]}

Duarte, F

Babu, YS

Bantia, S

Chand, P

Chu, NM

Montgomery, JA

Walsh, DA

Sudbeck, E

Finley, J

Air, GM

Luo, M

Laver, GW

机构：

[1] Univ Alabama, Dept Chem, Birmingham, AL 35294 USA

[2] Univ Alabama, Ctr Macromol Crystallog, Birmingham, AL 35294 USA

[3] BioCryst Pharmaceut Inc, Birmingham, AL 35244 USA

[4] Univ Oklahoma, Dept Biochem & Mol Biol, Oklahoma City, OK 73190 USA

[5] Australian Natl Univ, John Curtin Sch Med Res, Canberra, ACT 2601, Australia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 1999年 / 7卷 / 11期

关键词：

neuraminidase; influenza virus; sialidase; structure-based drug design;

D O I：

10.1016/S0968-0896(99)00197-2

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Neuraminidase (NA) plays a critical role in the life cycle of influenza virus and is a target for new therapeutic agents. A new benzoic acid inhibitor (11) containing a lipophilic side chain at C-3 and a guanidine at C-5 was synthesized. The X-ray structure of 4-(N-acetylamino)-5-guanidino-3-(3-pentyloxy)benzoic acid in complex with NA revealed that the lipophilic side chain binds in a newly created hydrophobic pocket formed by the movement of Glu 278 to interact with Arg 226, whereas the guanidine of 11 interacts In a negatively charged pocket created by Asp 152, Glu 120 and Glu 229. Compound 11 was highly selective for type A (H2N2) influenza NA (IC50 1 mu M) over type B (B/Lee/40) influenza NA (IC50 500 mu M). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2487 / 2497

页数：11

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