Synthesis, antibacterial activities and molecular docking studies of peptide and Schiff bases as targeted antibiotics

被引：111

作者：

Cheng, Kui ^{[1
]}

Zheng, Qing-Zhong ^{[1
]}

Qian, Yong ^{[1
]}

Shi, Lei ^{[1
]}

Zhao, Jing ^{[1
]}

Zhu, Hai-Liang ^{[1
]}

机构：

[1] Nanjing Univ, State Key Lab Pharmaceut Biotechnol, Nanjing 210093, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2009年 / 17卷 / 23期

基金：

中国国家自然科学基金;

关键词：

Peptide and Schiff base (PSB); Antibacterial activity; Autodock; ecKAS III; FATTY-ACID SYNTHESIS; ANTIMICROBIAL ACTIVITIES; THIOLACTOMYCIN; SYNTHASE; INHIBITOR; ENZYMES; AGENTS; FABH;

D O I：

10.1016/j.bmc.2009.10.037

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

A series of peptide and Schiff bases (PSB) were synthesized by reacting salicylic acid, primary diamines with salicylaldehyde or its derivatives, and 40 of which were newly reported. The inhibitory activities against Escherichia coli beta-ketoacyl-acyl carrier protein synthase III (ecKAS III) were investigated in vitro and molecular docking simulation also surveyed. Top 10 PSB compounds which posses both good inhibitory activity and well binding affinities were picked out, and their antibacterial activities against Gram-negative and Gram-positive bacterial strains were tested, expecting to exploit potent antibacterial agent with broad-spectrum antibiotics activity. The results demonstrate compound N-(3-(5-bromo-2-hydroxybenzylideneamino)propyl)-2-hydroxybenzamide (2d) can be as a potential antibiotics agent, displaying minimal inhibitory concentration values in the range of 0.39-3.13 mu g/mL against various bacteria. Crown Copyright (c) 2009 Published by Elsevier Ltd. All rights reserved.

引用

页码：7861 / 7871

页数：11

共 23 条

[1]

Alkyl-CoA disulfides as inhibitors and mechanistic probes for FabH enzymes [J].

Alhamadsheh, Marnoun M. ;

Musayev, Faik ;

Komissarov, Andrey A. ;

Sachdeva, Sarbjot ;

Wright, H. Tonie ;

Scarsdale, Neel ;

Florova, Galina ;

Reynolds, Kevin A. .

CHEMISTRY & BIOLOGY, 2007, 14 (05) :513-524

[2]

Type II fatty acid synthesis is not a suitable antibiotic target for Gram-positive pathogens [J].

Brinster, Sophie ;

Lamberet, Gilles ;

Staels, Bart ;

Trieu-Cuot, Patrick ;

Gruss, Alexandra ;

Poyart, Claire .

NATURE, 2009, 458 (7234) :83-U5

[3]

Biosynthetic origins of the natural product, thiolactomycin: A unique and selective inhibitor of type II dissociated fatty acid synthases [J].

Brown, MS ;

Akopiants, K ;

Resceck, DM ;

McArthur, HAI ;

McCormick, E ;

Reynolds, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10166-10167

[4]

Structure of the human β-ketoacyl [ACP] synthase from the mitochondrial type II fatty acid synthase [J].

Christensen, Caspar Elo ;

Kragelund, Birthe B. ;

Von Wettstein-Knowles, Penny ;

Henriksen, Anette .

PROTEIN SCIENCE, 2007, 16 (02) :261-272

[5]

Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4]thiadiazol-2-yl)methyl-5-oxo-[1,2,4]triazole and 1-(4-phenyl-5-thioxo-[1,2,4]triazol-3-yl)methyl-5-oxo-{1,2,4]triazole derivatives [J].

Demirbas, N ;

Karaoglu, SA ;

Demirbas, A ;

Sancak, K .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (09) :793-804

[6]

A new class of antituberculosis agents [J].

Jones, PB ;

Parrish, NM ;

Houston, TA ;

Stapon, A ;

Bansal, NP ;

Dick, JD ;

Townsend, CA .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (17) :3304-3314

[7]

Analogues of thiolactomycin as potential antimalarial agents [J].

Jones, SM ;

Urch, JE ;

Kaiser, M ;

Brun, R ;

Harwood, JL ;

Berry, C ;

Gilbert, IH .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (19) :5932-5941

[8]

Nature of copper(II)-lanthanide(III) magnetic interactions and generation of a large magnetic moment with magnetic anisotropy of 3d-4f cyclic cylindrical tetranuclear complexes [CuIILLnIII(hfaC)2]2, (H3L=1-(2-hydroxybenzamido)-2-(2-hydroxy-3-methoxybenzylideneamino)ethane and Hhfac = hexafluoroacetylacetone, LnIII = Eu, Gd, Tb, Dy) [J].

Kido, T ;

Ikuta, Y ;

Sunatsuki, Y ;

Ogawa, Y ;

Matsumoto, N .

INORGANIC CHEMISTRY, 2003, 42 (02) :398-408

[9]

Structure-activity relationships at the 5-position of thiolactomycin:: An intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli [J].

Kim, P ;

Zhang, YM ;

Shenoy, G ;

Nguyen, QA ;

Boshoff, HI ;

Manjunatha, UH ;

Goodwin, MB ;

Lonsdale, J ;

Price, AC ;

Miller, DJ ;

Duncan, K ;

White, SW ;

Rock, CO ;

Barry, CE ;

Dowd, CS .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (01) :159-171

[10]

β-ketoacyl-acyl carrier protein synthase III (FabH) is essential for bacterial fatty acid synthesis [J].

Lai, CY ;

Cronan, JE .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (51) :51494-51503

← 1 2 3 →