Design, synthesis and antimicrobial properties of non-hemolytic cationic α-cyclopeptoids

被引：50

作者：

Comegna, Daniela ^{[1
]}

Benincasa, Monica ^{[2
]}

Gennaro, Renato ^{[2
]}

Izzo, Irene ^{[1
]}

De Riccardis, Francesco ^{[1
]}

机构：

[1] Univ Salerno, Dept Chem, I-84084 Fisciano, SA, Italy

[2] Univ Trieste, Dept Life Sci, I-34127 Trieste, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2010年 / 18卷 / 05期

关键词：

Cyclic peptoids; Antibiotics; Solid-phase synthesis; PEPTOIDS; PEPTIDE; ANTIBACTERIAL; DEFENSINS; BACTERIA; BAC7;

D O I：

10.1016/j.bmc.2010.01.026

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：

The synthesis and screening of neutral and cationic, linear and cyclic peptoids (N-alkylglycine peptidomimetics) is described. Structure-activity relationship studies show that the in vitro activities of the tested peptoids depend on both cyclization and decoration with cationic groups. The most powerful N-lysine cyclopeptoid derivatives showed good antifungal activity against Candida albicans (ATCC90029 and L21) and Candida famata (SA550, Amph B-resistant) and low hemolytic activity. The effects of the cyclic peptoids on membrane permeabilization were evaluated by the propidium iodide exclusion assay. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2010 / 2018

页数：9

共 39 条

[1] Synthesis of some cyclic indolic peptoids as potential antibacterials [J].

Au, Vicki S. ;

Bremner, John B. ;

Coates, Jonathan ;

Keller, Paul A. ;

Pyne, Stephen G. .

TETRAHEDRON, 2006, 62 (40) :9373-9382

[2] Antimicrobial activity of Bac7 fragments against drug-resistant clinical isolates [J].

Benincasa, M ;

Scocchi, M ;

Podda, E ;

Skerlavaj, B ;

Dolzani, L ;

Gennaro, R .

PEPTIDES, 2004, 25 (12) :2055-2061

[3] Fungicidal activity of five cathelicidin peptides against clinically isolated yeasts [J].

Benincasa, Monica ;

Scocchi, Marco ;

Pacor, Sabrina ;

Tossi, Alessandro ;

Nobili, Donatella ;

Basaglia, Giancarlo ;

Busetti, Marina ;

Gennaro, Renato .

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2006, 58 (05) :950-959

[4] Synthesis, antimicrobial activity and binding properties of calix[4]arene based vancomycin mimics [J].

Casnati, A ;

Fabbi, M ;

Pelizzi, N ;

Pochini, A ;

Sansone, F ;

Ungaro, R ;

DiModugno, E ;

Tarzia, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (22) :2699-2704

[5] Conformational preference and potential templates of N-methylated cyclic pentaalanine peptides [J].

Chatterjee, Jayanta ;

Mierke, Dale F. ;

Kessler, Horst .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (05) :1508-1517

[6] Peptoids that mimic the structure, function, and mechanism of helical antimicrobial peptides [J].

Chongsiriwatana, Nathaniel P. ;

Patch, James A. ;

Czyzewski, Ann M. ;

Dohm, Michelle T. ;

Ivankin, Andrey ;

Gidalevitz, David ;

Zuckermann, Ronald N. ;

Barron, Annelise E. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2008, 105 (08) :2794-2799

[7] MODULATION BY SMALL HYDROPHOBIC MOLECULES OF VALINOMYCIN-MEDIATED POTASSIUM-TRANSPORT ACROSS PHOSPHOLIPID VESICLE MEMBRANES [J].

CLEMENT, NR ;

GOULD, JM .

BIOCHEMISTRY, 1981, 20 (06) :1539-1543

[8]

Craik DJ, 2007, CURR OPIN DRUG DISC, V10, P176

[9] The cyclotide family of circular miniproteins: Nature's combinatorial peptide template [J].

Craik, DJ ;

Cemazar, M ;

Wang, CKL ;

Daly, NL .

BIOPOLYMERS, 2006, 84 (03) :250-266

[10] Structures of naturally occurring circular proteins from bacteria [J].

Craik, DJ ;

Daly, NL ;

Saska, I ;

Trabi, M ;

Rosengren, KJ .

JOURNAL OF BACTERIOLOGY, 2003, 185 (14) :4011-4021

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