Synthesis of novel ciprofloxacin analogues and evaluation of their anti-proliferative effect on human cancer cell lines

被引:48
作者
Suresh, Narva [1 ]
Nagesh, Hunsur Nagendra [1 ]
Sekhar, Kondapalli Venkata Gowri Chandra [1 ]
Kumar, Anil [2 ]
Shirazi, Amir N. [3 ]
Parang, Keykavous [3 ]
机构
[1] Birla Inst Technol & Sci Pilani, Dept Chem, Hyderabad 500078, Andhra Pradesh, India
[2] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India
[3] Univ Rhode Isl, Coll Pharm, Dept Biomed & Pharmaceut Sci, Kingston, RI 02881 USA
关键词
Ciprofloxacin; Fluoroquinolones Anti-cancer; Anti-proliferative; Substituted piperazines; PROSTATE-CANCER; BIOLOGICAL EVALUATION; CYCLE ARREST; TOPOISOMERASE; GROWTH; INHIBITORS; FLUOROQUINOLONES; DERIVATIVES; CARCINOMA; APOPTOSIS;
D O I
10.1016/j.bmcl.2013.09.077
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of twenty two novel 1-cyclopropyl-6-fluoro-4-oxo-7-(4-substituted piperazin-1-yl)-1,4-dihydroquinoline- 3-carboxylic acid analogues have been synthesized, characterized (1H NMR, 13C NMR and LCMS) and evaluated for their inhibitory activity on the proliferation of human caucasian acute lymphoblastic leukemia cells (CCRF-CEM), breast adenocarcinoma cells (MDA-MB-468) and human colon carcinoma cells (HCT-116). Among all the synthesized ciprofloxacin analogues 3t at 50 lM showed comparable potency to doxorubicin (10 lM) in all three cell lines and 3j inhibited proliferation of MDA-MB-468 up to 35% selectively over other two cell lines. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6292 / 6295
页数:4
相关论文
共 23 条
[1]   Synthesis and biological evaluation of tetracyclic fluoroquinolones as antibacterial and anticancer agents [J].
Al-Trawneh, Salah A. ;
Zahra, Jalal A. ;
Kamal, Marwan R. ;
El-Abadelah, Mustafa M. ;
Zani, Franca ;
Incerti, Matteo ;
Cavazzoni, Andrea ;
Alfieri, Roberta R. ;
Petronini, Pier G. ;
Vicini, Paola .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (16) :5873-5884
[2]  
[Anonymous], 2012, CANC FACTS FIG
[3]  
Aranha O, 2000, CLIN CANCER RES, V6, P891
[4]  
Aranha O, 2003, INT J ONCOL, V22, P787
[5]   7-((4-Substituted)piperazin-1-yl) derivatives of ciprofloxacin: Synthesis and in vitro biological evaluation as potential antitumor agents [J].
Azema, Joelle ;
Guidetti, Brigitte ;
Dewelle, Janique ;
Le Calve, Benjamin ;
Mijatovic, Tatjana ;
Korolyov, Alexander ;
Vaysse, Julie ;
Malet-Martino, Myriam ;
Martino, Robert ;
Kiss, Robert .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (15) :5396-5407
[6]   Ciprofloxacin decreases survival in HT-29 cells via the induction of TGF-β1 secretion and enhances the anti-proliferative effect of 5-fluorouracil [J].
Bourikas, Leonidas A. ;
Kolios, George ;
Valatas, Vassilis ;
Notas, George ;
Drygiannakis, Ioannis ;
Pelagiadis, Iordanis ;
Manousou, Pinelopi ;
Klironomos, Stefanos ;
Mouzas, Ioannis A. ;
Kouroumalis, Elias .
BRITISH JOURNAL OF PHARMACOLOGY, 2009, 157 (03) :362-370
[7]  
CLEMENT JJ, 1995, CANCER RES, V55, P830
[8]  
Ebisuno S., 1997, CANCER, V15, P2263
[9]  
El-Rayes BF, 2002, INT J ONCOL, V21, P207
[10]   Influence of ciprofloxacin on glioma cell line GL26: A new application for an old antibiotic [J].
Esmaeilzadeh, Abdolreza ;
Ebtekar, Massoumeh ;
Biglari, Alireza ;
Hassan, Zuhair Mohammad .
AFRICAN JOURNAL OF MICROBIOLOGY RESEARCH, 2012, 6 (23) :4891-4896