Synthesis, characterization and in vitro anti-cancer activity of N-(ferrocenyl)benzoyl tri- and tetrapeptide esters

被引：23
作者：
Corry, Alan J. [1 ]
Mooney, Aine [1 ]
O'Sullivan, Dermot [2 ]
Kenny, Peter T. M. [1 ,2 ]
机构：
[1] Dublin City Univ, Sch Chem Sci, Dublin 9, Ireland
[2] Natl Inst Cellular Biotechnol, Dublin 9, Ireland
来源：
INORGANICA CHIMICA ACTA | 2009年 / 362卷 / 09期
关键词：
Ferrocene; Anti-cancer; Bioorganometallic chemistry; Peptides; RAY CRYSTAL-STRUCTURE; ELECTROCHEMICAL ANION RECOGNITION; BENZOYL DIPEPTIDE ESTERS; AMINO-ACID ESTERS; STRUCTURAL-CHARACTERIZATION; SPECIAL-ISSUE; METHYL-ESTER; FERROCENE; REDOX; DERIVATIVES;
D O I：
10.1016/j.ica.2009.01.021
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
N-ortho, N-meta and N-para-(ferrocenyl)benzoyl tri- and tetrapeptide esters (2-7) were prepared by coupling ortho, meta and para-ferrocenyl benzoic acids to the tri- and tetrapeptide ethyl esters of GlyGlyGly(OEt) and GlyGlyGlyGly(OEt) in the presence of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride and 1-hydroxybenzotriazole. The compounds were characterized by a range of NMR spectroscopic techniques, mass spectrometry and cyclic voltammetry. The anti-proliferative effects of the ortho derivatives 2 and 5 were measured in vitro against H1299 lung cancer cells and both gave IC50 values greater than 50 mu M. Therefore, extending the length of the peptide chain had a negative effect on activity, relative to N-(ferrocenyl)benzoyl amino acid and dipeptide derivatives. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码：2957 / 2961
页数：5
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