De novo design of chiral organotin cancer drug candidates: Validation of enantiopreferential binding to molecular target DNA and 5′-GMP by UV-visible, fluorescence, 1H and 31P NMR

被引:21
作者
Arjmand, Farukh [1 ]
Sharma, Girish Chandra [1 ]
Sayeed, Fatima [1 ]
Muddassir, Mohd [1 ]
Tabassum, Sartaj [1 ]
机构
[1] Aligarh Muslim Univ, Dept Chem, Aligarh 202002, Uttar Pradesh, India
关键词
Organotin complexes; CT-DNA binding studies; NMR validation with 5 '-GMP; Sn-119; NMR; VITRO ANTITUMOR-ACTIVITY; X-RAY STRUCTURES; SPECTROSCOPIC CHARACTERIZATION; COMPLEXES; DIORGANOTIN(IV); RUTHENIUM(II); TRYPTOPHAN; CHEMISTRY; LIGANDS; PROBE;
D O I
10.1016/j.jphotobiol.2011.08.001
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
N,N-bis[(R-/S-)-1-benzyl-2-ethoxyethane] tin (IV) complexes were synthesized by applying de novo design strategy by the condensation reaction of (R-/S-)2-amino-2-phenylethanol and dibromoethane in presence of dimethyltin dichloride and thoroughly characterized by elemental analysis, conductivity measurements, IR, ESI-MS, H-1, C-13 and Sn-119, multinuclear NMR spectroscopy and XRD study. Enantioselective and specific binding profile of R-enantiomer 1 in comparison to S-enantiomer 2 with ultimate molecular target CT-DNA was validated by UV-visible, fluorescence, circular dichroism, H-1 and P-31 NMR techniques. This was further corroborated well by interaction of 1 and 2 with 5'-GMP. (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码:167 / 174
页数:8
相关论文
共 45 条
  • [41] Wadkins RM, 2000, CURR MED CHEM, V7, P1
  • [42] POLYCYCLIC AROMATIC-HYDROCARBONS PHYSICALLY INTERCALATE INTO DUPLEX REGIONS OF DENATURED DNA
    WOLFE, A
    SHIMER, GH
    MEEHAN, T
    [J]. BIOCHEMISTRY, 1987, 26 (20) : 6392 - 6396
  • [43] Synthesis and DNA binding of μ-[2,9-bis(2-imidazo [4,5-f][1,10]phenanthroline)-1,10-phenanthroline] bis[1,10-phenanthrolinecopper(II)]
    Wu, JZ
    Yuan, L
    Wu, JF
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2005, 99 (11) : 2211 - 2216
  • [44] Effects of the ancillary ligands of polypyridyl ruthenium(II) complexes on the DNA-binding behaviors
    Xu, H
    Zheng, KC
    Deng, H
    Lin, LJ
    Zhang, QL
    Ji, LN
    [J]. NEW JOURNAL OF CHEMISTRY, 2003, 27 (08) : 1255 - 1263
  • [45] Yang Pin, 1998, Metal-Based Drugs, V5, P41, DOI 10.1155/MBD.1998.41