Synthesis, properties and biological activity of a novel phosphines ligand derived from ciprofloxacin

被引:17
作者
Bykowska, Aleksandra [1 ]
Starosta, Radoslaw [1 ]
Brzuszkiewicz, Anna [1 ]
Bazanow, Barbara [2 ]
Florek, Magdalena [2 ]
Jackulak, Natalia [2 ]
Krol, Jaroslaw [2 ]
Grzesiak, Jakub [3 ]
Kalinski, Krzysztof [3 ]
Jezowska-Bojczuk, Malgorzata [1 ]
机构
[1] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland
[2] Wroclaw Univ Environm & Life Sci, Dept Vet Microbiol, PL-50375 Wroclaw, Poland
[3] Wroclaw Univ Environm & Life Sci, Lab Electron Microscopy, PL-50631 Wroclaw, Poland
关键词
Fluoroquinolone; Antibiotic; Ciprofloxacin; Diphenylphosphine; Microbial resistance; Cytotoxicity; ANTIBACTERIAL ACTIVITY; STRUCTURAL CHARACTERIZATION; PLATINUM(II) COMPLEXES; LUMINESCENT PROPERTIES; ANTIBIOTIC-RESISTANCE; IODIDE COMPLEXES; FLUOROQUINOLONES; AGENTS; DNA; APOPTOSIS;
D O I
10.1016/j.poly.2013.04.059
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Novel potential antibacterial agents derived from ciprofloxacin (HCp) were synthesized in the reaction of this antibiotic with hydroxymethyldiphenylphosphine. Detailed analysis by the NMR, IR and MS techniques attested to the identity and structure of the obtained compounds. In addition, the structure of phosphine PPh2CH2-Cp was unambiguously confirmed by X-ray crystal structural analysis. PPh2CH2-Cp exhibited an antibacterial activity comparable to that of the original drug. Cytotoxicity studies revealed that this compound was characterized by lower toxicity against mammalian cells than HCp. Besides, it did not induce a morphological change in cells after its action and was unable to degrade plasmid DNA, as well as parent antibiotic. Our results open up new possibilities in designing novel, less toxic and comparably effective antibiotics drugs. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:23 / 29
页数:7
相关论文
共 57 条
[1]   Resistance to antibiotics: Are we in the post-antibiotic era? [J].
Alanis, AJ .
ARCHIVES OF MEDICAL RESEARCH, 2005, 36 (06) :697-705
[2]   Mode of action of sulfanilyl fluoroquinolones [J].
Alovero, F ;
Nieto, M ;
Mazzieri, MR ;
Then, R ;
Manzo, RH .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1998, 42 (06) :1495-1498
[3]   Comparative study of new benzenesulphonamide fluoroquinolones structurally related to ciprofloxacin against selected ciprofloxacin-susceptible and -resistant Gram-positive cocci [J].
Alovero, F ;
Barnes, A ;
Nieto, M ;
Mazzieri, MR ;
Manzo, RH .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2001, 48 (05) :709-712
[4]   Engineering the specificity of antibacterial fluoroquinolones:: Benzenesulfonamide modifications at C-7 of ciprofloxacin change its primary target in Streptococcus pneumoniae from topoisomerase IV to gyrase [J].
Alovero, FL ;
Pan, XS ;
Morris, JE ;
Manzo, RH ;
Fisher, LM .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2000, 44 (02) :320-325
[5]   The global need for effective antibiotics-A summary of plenary presentations [J].
Alvan, Gunnar ;
Edlund, Charlotta ;
Heddini, Andreas .
DRUG RESISTANCE UPDATES, 2011, 14 (02) :70-76
[6]  
[Anonymous], WHOIERPSP20122
[7]  
[Anonymous], [No title captured]
[8]   Type IIA topoisomerase inhibition by a new class of antibacterial agents [J].
Bax, Benjamin D. ;
Chan, Pan F. ;
Eggleston, Drake S. ;
Fosberry, Andrew ;
Gentry, Daniel R. ;
Gorrec, Fabrice ;
Giordano, Ilaria ;
Hann, Michael M. ;
Hennessy, Alan ;
Hibbs, Martin ;
Huang, Jianzhong ;
Jones, Emma ;
Jones, Jo ;
Brown, Kristin Koretke ;
Lewis, Ceri J. ;
May, Earl W. ;
Saunders, Martin R. ;
Singh, Onkar ;
Spitzfaden, Claus E. ;
Shen, Carol ;
Shillings, Anthony ;
Theobald, Andrew J. ;
Wohlkonig, Alexandre ;
Pearson, Neil D. ;
Gwynn, Michael N. .
NATURE, 2010, 466 (7309) :935-U51
[9]  
Berners-Price S.J., 1988, Bioinorganic Chemistry, P27, DOI DOI 10.1007/3-540-50130-4_2
[10]   NMR and IR characterization of the aluminium complexes of norfloxacin and ciprofloxacin fluoroquinolones [J].
Chattah, Ana K. ;
Linck, Yamila Garro ;
Monti, Gustavo A. ;
Levstein, Patricia R. ;
Breda, Susana A. ;
Manzo, Ruben H. ;
Olivera, Maria E. .
MAGNETIC RESONANCE IN CHEMISTRY, 2007, 45 (10) :850-859