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

共 50 条

[31] Drug screening for influenza neuraminidase inhibitors
Liu, AL
Cao, HP
Du, GH
SCIENCE IN CHINA SERIES C-LIFE SCIENCES, 2005, 48 (01): : 1 - 5
[32] Influenza viruses resistant to neuraminidase inhibitors
Nitsch-Osuch, Aneta
Brydak, Lidia Bernadeta
ACTA BIOCHIMICA POLONICA, 2014, 61 (03) : 505 - 508
[33] Design and synthesis of benzoic acid derivatives as influenza neuraminidase inhibitors using structure-based drug design
Chand, P
Babu, YS
Bantia, S
Chu, NM
Cole, LB
Kotian, PL
Laver, WG
Montgomery, JA
Pathak, VP
Petty, SL
Shrout, DP
Walsh, DA
Walsh, GW
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (25) : 4030 - 4052
[34] Pyrrolidinobenzoic acid inhibitors of influenza virus neuraminidase: The hydrophobic side chain influences type A subtype selectivity
Li, Yanwu
Silamkoti, Arundutt
Kolavi, Gundurao
Mou, Liyuan
Gulati, Shelly
Air, Gillian M.
Brouillette, Wayne J.
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (14) : 4582 - 4589
[35] Impact of influenza A virus neuraminidase mutations on the stability, activity, and sensibility of the neuraminidase to neuraminidase inhibitors
Richard, Mathilde
Deleage, Claire
Barthelemy, Mendy
Lin, Yi Pu
Hay, Alan
Lina, Bruno
Ferraris, Olivier
JOURNAL OF CLINICAL VIROLOGY, 2008, 41 (01) : 20 - 24
[36] Synthesis and Activity Evaluation of Benzoic Acid Derivatives as Neuraminidase Inhibitors
Wang, Jing
Yuan, Jian-Yong
Liu, Pan-He
Hu, Ye-Min
Li, Yan-Wu
Jingxi Huagong/Fine Chemicals, 2018, 35 (06): : 1029 - 1036
[37] Use of neuraminidase inhibitors to combat pandemic influenza
Democratis, Jane
Pareek, Manish
Stephenson, Iain
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2006, 58 (05) : 911 - 915
[38] Guanidinobenzoic acid inhibitors of influenza virus neuraminidase
Sudbeck, EA
Jedrzejas, MJ
Singh, S
Brouillette, WJ
Air, GM
Laver, WG
Babu, YS
Bantia, S
Chand, P
Chu, N
Montgomery, JA
Walsh, DA
Luo, M
JOURNAL OF MOLECULAR BIOLOGY, 1997, 267 (03) : 584 - 594
[39] Neuraminidase inhibitors take bite out of influenza
Vicki Glaser
Nature Biotechnology, 1998, 16 : 1002 - 1002
[40] Mechanisms of resistance of influenza virus to neuraminidase inhibitors
McKimm-Breschkin, J
Sahasrabudhe, A
Blick, T
McDonald, M
OPTIONS FOR THE CONTROL OF INFLUENZA IV, 2001, 1219 : 855 - 861

← 1 2 3 4 5 →