Synthesis and characterization of novel trimethyltin(IV) and tributylltin(IV) complexes of anticoagulant, WARFARIN: Potential DNA binding and plasmid cleaving agents

被引:14
作者
Kumari, Ranjana [1 ]
Nath, Mala [1 ]
机构
[1] Indian Inst Technol Roorkee, Dept Chem, Roorkee 247667, Uttar Pradesh, India
关键词
Warfarin; Organotin(IV); DNA-binding; Partial intercalation; Gel electrophoresis; NUCLEAR-MAGNETIC-RESONANCE; CELL LUNG-CANCER; LEUKEMIA GROUP-B; ORAL ANTICOAGULATION; ORGANOTIN COMPOUNDS; RANDOMIZED-TRIAL; FLUORESCENCE; ANTITUMOR; SPECTROSCOPY; CHEMOTHERAPY;
D O I
10.1016/j.inoche.2018.07.001
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Novel trimethyltin(IV) (1) and tributyltin(IV) (2) derivatives of an anticoagulant drug warfarin (WR) have been synthesized and characterized through elemental analysis, FTIR studies, multinuclear NMR and ESI mass spectrometry and DFT calculation. Their DNA binding profile (mode and extent of binding with CT DNA) through UV-visible and fluorescence spectrophotometric titrations reveal their partial intercalation inside the base pairs of DNA, and the binding constant (K-b) calculated through UV-visible titration are in the order of 10(4)M(-1) . Their partial intercalation has also been validated through a decrease in the viscosity of CT DNA with increasing the complex concentration. Both the complexes are potential concentration dependent plasmid cleaving agent which has been confirmed though gel electrophoresis of pBR322 plasmid. Both the organotin(IV) complexes have been found to exhibit a greater potential towards DNA binding and fragmentation in comparison to WR.
引用
收藏
页码:40 / 46
页数:7
相关论文
共 44 条
[1]  
Akl EA, 2007, J EXP CLIN CANC RES, V26, P175
[2]   QUENCHING OF DNA-ETHIDIUM FLUORESCENCE BY AMSACRINE AND OTHER ANTITUMOR AGENTS - A POSSIBLE ELECTRON-TRANSFER EFFECT [J].
BAGULEY, BC ;
LEBRET, M .
BIOCHEMISTRY, 1984, 23 (05) :937-943
[3]   ORGANOTIN COMPOUNDS AND DEOXYRIBONUCLEIC-ACID [J].
BARBIERI, R ;
SILVESTRI, A ;
GIULIANI, AM ;
PIRO, V ;
DISIMONE, F ;
MADONIA, G .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (04) :585-590
[4]   Antitumor and antimetastatic effect of warfarin and heparins [J].
Bobek, V ;
Kovarík, J .
BIOMEDICINE & PHARMACOTHERAPY, 2004, 58 (04) :213-219
[5]  
Campbell HA, 1941, J BIOL CHEM, V138, P1
[6]   A RANDOMIZED TRIAL OF ANTICOAGULATION WITH WARFARIN AND OF ALTERNATING CHEMOTHERAPY IN EXTENSIVE SMALL-CELL LUNG-CANCER BY THE CANCER AND LEUKEMIA GROUP-B [J].
CHAHINIAN, AP ;
PROPERT, KJ ;
WARE, JH ;
ZIMMER, B ;
PERRY, MC ;
HIRSH, V ;
SKARIN, A ;
KOPEL, S ;
HOLLAND, JF ;
COMIS, RL ;
GREEN, MR .
JOURNAL OF CLINICAL ONCOLOGY, 1989, 7 (08) :993-1002
[7]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY - STRUCTURE OF ANTICOAGULANT WARFARIN AND RELATED COMPOUNDS IN SOLUTION [J].
GIANNINI, DD ;
CHAN, KK ;
ROBERTS, JD .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1974, 71 (10) :4221-4223
[8]  
GOPALAKRISHNAN S, 2013, ORAL ANTICOAGULANTS, P410
[9]   Thermodynamic and structural study of phenanthroline derivative ruthenium complex/DNA interactions: Probing partial intercalation and binding properties [J].
Grueso, E. ;
Lopez-Perez, G. ;
Castellano, M. ;
Prado-Gotor, R. .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2012, 106 (01) :1-9
[10]   Antiproliferative and anti-tumor activity of organotin compounds [J].
Hadjikakou, Sotiris K. ;
Hadjiliadis, Nick .
COORDINATION CHEMISTRY REVIEWS, 2009, 253 (1-2) :235-249