Synthesis of neamine-carboline conjugates for RNA binding and their antibacterial activities

被引：19

作者：

Wu, Shan

Fu, Yunsha

Yan, Ribai

Wu, Yanfen ^{[1
]}

Lei, Xiaoping

Ye, Xin-Shan

机构：

[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

来源：

TETRAHEDRON | 2010年 / 66卷 / 19期

基金：

中国国家自然科学基金;

关键词：

Aminoglycoside; beta-Carboline; RNA binding; Antibacterial activity; Synthesis; RIBOSOMAL-RNA; AMINOGLYCOSIDE MIMETICS; NEOMYCIN-B; ANTIBIOTICS; DESIGN; RECOGNITION; DERIVATIVES; SITE; HIV; INHIBITORS;

D O I：

10.1016/j.tet.2010.03.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three types of neamine-beta-carboline conjugates were synthesized in good yields by the coupling of neamine and beta-carboline-3-carboxylic acids using aliphatic diamine as a linker, The binding properties of these conjugates to 16S rRNA and 18S rRNA were evaluated by surface plasmon resonance (SPR), showing that some conjugates had stronger binding affinities than neamine. In vitro antimicrobial activities were also evaluated and the results showed that some synthetic compounds exhibited better antibacterial activities than neamine. The preliminary structure-activity relationship was discussed. The present experimental data demonstrated that synthetic neamine-carboline conjugates might hold the potential as new antibiotics. (C) 2010 Elsevier Ltd. All rights reserved.

引用

收藏

页码：3433 / 3440

页数：8

相关论文

共 33 条

[1] A simple structural-based approach to prevent aminoglycoside inactivation by bacterial defense proteins.: Conformational restriction provides effective protection against neomycin-B nucleotidylation by ANT4 [J].

Asensio, JL ;

Hidalgo, A ;

Bastida, A ;

Torrado, M ;

Corzana, F ;

Chiara, JL ;

García-Junceda, E ;

Cañada, J ;

Jiménez-Barbero, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) :8278-8279

[2] Exploring the use of conformationally locked aminoglycosides as a new strategy to overcome bacterial resistance [J].

Bastida, A ;

Hidalgo, A ;

Chiara, JL ;

Torrado, M ;

Corzana, F ;

Pérez-Cañadillas, JM ;

Groves, P ;

Garcia-Junceda, E ;

Gonzalez, C ;

Jimenez-Barbero, J ;

Asensio, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :100-116

[3] Conformational constraint as a means for understanding RNA-aminoglycoside specificity [J].

Blount, KF ;

Zhao, F ;

Hermann, T ;

Tor, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (27) :9818-9829

[4] Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics [J].

Carter, AP ;

Clemons, WM ;

Brodersen, DE ;

Morgan-Warren, RJ ;

Wimberly, BT ;

Ramakrishnan, V .

NATURE, 2000, 407 (6802) :340-348

[5] Pyranmycins, a novel class of aminoglycosides with improved acid stability: The SAR of D-pyranoses on ring III of pyranmycin [J].

Chang, CWT ;

Hui, Y ;

Elchert, B ;

Wang, JH ;

Li, J ;

Rai, R .

ORGANIC LETTERS, 2002, 4 (26) :4603-4606

[6]

Davis TM, 2001, METHOD ENZYMOL, V340, P22

[7] Design and synthesis of paromomycin-related heterocycle-substituted aminoglycoside mimetics based on a mass spectrometry RNA-binding assay [J].

Ding, YL ;

Hofstadler, SA ;

Swayze, EE ;

Risen, L ;

Griffey, RH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (29) :3409-3412

[8] Structure of the A site of Escherichia coli 16S ribosomal RNA complexed with an aminoglycoside antibiotic [J].

Fourmy, D ;

Recht, MI ;

Blanchard, SC ;

Puglisi, JD .

SCIENCE, 1996, 274 (5291) :1367-1371

[9] A new class of branched aminoglycosides: Pseudo- pentasaccharide derivatives of neomycin B [J].

Fridman, M ;

Belakhov, V ;

Yaron, S ;

Baasov, T .

ORGANIC LETTERS, 2003, 5 (20) :3575-3578

[10] Molecular basis of HIV-1 TAR RNA specific recognition by an acridine tat-antagonist [J].

Gelus, N ;

Hamy, F ;

Bailly, C .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (06) :1075-1079

← 1 2 3 4 →