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Diorganotin(IV) antitumor agent. (C2H5)2SnCl2 (phen)/nucleotides aqueous and solid-state coordination chemistry and its DNA binding studies

Published on Nov 1, 1996in Journal of Inorganic Biochemistry 3.22
· DOI :10.1016/0162-0134(96)00039-6
Qingshan Li1
Estimated H-index: 1
(NU: Nanjing University),
Pin Yang9
Estimated H-index: 9
(Shanxi University)
+ 1 AuthorsMaolin Guo3
Estimated H-index: 3
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Abstract
Abstract This contribution reports a solution and solid-state study of the aqueous nucleotide coordination chemistry of the dieihyltin(IV) antitumor agent, (C 2 H 5 )2SnC1 2 (phen). [trans-en 2 OS(η-H 2 ] (CF 3 SO 3 ) 2 , a versatile 1 H NMR probe for biomolecules, is first used to investigate the interaction of (C 2 H 5 ) 2 SnC1 2 (phen) with DGMP in neutral aqueous solution, and then the synthesis of mixed-ligands complexes formulated as (C 2 Hn5) S nC1(phenXNu) (Nu is nucleotide) by reactions of (C 2 H 5 ) 2 SnC1 2 (phen) with equimolar nucleotides under biologically relevant conditions is described. The new complexes were characterized by 500 MHz 1H, 31 P NMR spectra; these spectroscopic data suggest that one of cis-chloro atoms in (C 2 H 5 ) 2 SnC1 2 (phen) is substituted by nucleotide, and that Sn(IV) is directly coordinated to the phosphate group of the nucleotide. No evidence was found for the coordination via donor atoms of the base. On the basis of the above model studies, absorbance, fluorescence and cyclic voltammetric methods, viscosity determination, as well as agrose gel electrophoresis of superhelical pBR322 plasmid DNA were used to study the interaction of (C 2 H 5 ) 2 SnCl 2 (phen) with DNA. The results indicate that (C 2 H 5 ) 2 SnCl 2 (phen) binds to DNA by double modes. The drug first reacts electrostatically with the sugar-phosphate backbone of DNA; this results in changes of DNA conformation, and then phen ligand can intercalate into double-helix DNA and cause unwinding of the DNA.
  • References (17)
  • Citations (172)
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References17
Newest
Published on Jul 1, 1993in Journal of the American Chemical Society 14.70
Fang Liu5
Estimated H-index: 5
,
Kelley A. Meadows4
Estimated H-index: 4
,
David R. McMillin45
Estimated H-index: 45
We have used a variety of physical methods to investigate the ways by which copper phenanthrolines bind to B-form DNA. To vary the composition of the DNA, we have employed poly(dG-dC)-poly(dG-dC), M. lysodeikticus DNA, salmon testes DNA, and poly(dA-dT)-poly(dA-dT) as hosts. The specific copper complexes we have studied are Cu(dmp) 2 + and Cu(bcp) 2 + where dmp and bcp denote 2,9-dimethyl- 1,10-phenanthroline and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, respectively. The results indicate t...
119 Citations Source Cite
Published on Jan 1, 1991in Journal of Inorganic Biochemistry 3.22
R. Barbieri24
Estimated H-index: 24
(University of Palermo),
Arturo Silvestri21
Estimated H-index: 21
(University of Palermo)
Abstract The reaction of aqueous native DNA (calf thymus) with the solvated organotin (IV) species [CH 3 ) 2 SnCl 2 (C 2 H 5 OH n )], as well as with [CH 3 ) 2 Sn(OH)(H 2 O) n ] + and (CH 3 ) 2 Sn(OH) 2 i.e., the hydrolysis products of aqueous (CH 3 ) 2 SnCl 2 at pH ≈- 5 and pH ≈= 7.4 respectively), was investigated by 119 Sn Mossbauer spectroscopy. The addition of [(CH 3 ) 2 SnCl 2 (C 2 H 5 OH) n ] to DNA yielded a solid product, possibly (CH 3 ) 2 Sn(DNA phosphodiester) 2 , where the environme...
40 Citations Source Cite
Published on Nov 1, 1990in Journal of Inorganic Biochemistry 3.22
Jie Sun1
Estimated H-index: 1
(Duquesne University),
Daniel K.Y. Solaiman1
Estimated H-index: 1
(Duquesne University)
Abstract Cyclic voltammetric studies on iron-tallysomycin complexes have been conducted with and without the presence of calf thymus DNA. Fe(II)-TLM samples exhibit a cyclic voltammogram with only a reduction peak at −230 ± 5 mV vs Ag/AgCl. The addition of DNA substrate causes the shift of this reduction peak to −140 ± 10 mV vs Ag/AgCl. This large shift in the positive direction implies that the regeneration of Fe(II)-TLM through the reduction of Fe(III)-TLM is facilitated with the aid of DNA. I...
15 Citations Source Cite
Published on Jul 1, 1990in Journal of Inorganic Biochemistry 3.22
Angeles Sánchez González8
Estimated H-index: 8
(University of Santiago de Compostela),
José S. Casas24
Estimated H-index: 24
(University of Santiago de Compostela)
+ 3 AuthorsBenito Regueiro8
Estimated H-index: 8
(University of Santiago de Compostela)
Abstract We report the synthesis of new complexes with the general formula (R 2 SnX 2 ) y ·H 2 BiIm, where y = 1 or 2; R = Me, Et, Bu n ; X = Cl or Br (for R = Et) and H 2 BiIm = 2,2′-Biimidazole. The complexes have been characterized by elemental analysis and Mossbauer, infra-red and 1 H n.m.r. spectroscopy and tested (like the ligand, Me 2 SnCl 2 and Et 2 SnCl 2 ) against P388D 1 leukemic cells.
24 Citations Source Cite
Published on Apr 1, 1989in Journal of the American Chemical Society 14.70
Anna Marie Pyle24
Estimated H-index: 24
,
Jill P. Rehmann3
Estimated H-index: 3
+ 3 AuthorsJacqueline K. Barton85
Estimated H-index: 85
1,010 Citations Source Cite
Published on Jan 1, 1987in Pure and Applied Chemistry 2.35
Jan Reedijk73
Estimated H-index: 73
224 Citations Source Cite
Published on Aug 15, 1986in Science 41.04
Jacqueline K. Barton85
Estimated H-index: 85
Chiral metal complexes provide unique molecular probes for DNA. Chiral reagents that "recognize" different local structures along the DNA strand have been designed by a process in which the asymmetry in shape and size of the complex is matched to that of the DNA helical groove. As a result, the chiral metal complexes provide very sensitive probes for local helical structure, both left- and right-handed. Direct coordination of chiral complexes to the DNA bases adds an element of sequence selectiv...
576 Citations Source Cite
Published on Dec 1, 1984in Inorganica Chimica Acta 2.43
Alan J. Crowe11
Estimated H-index: 11
,
Peter J. Smith41
Estimated H-index: 41
,
Ghanem Atassi33
Estimated H-index: 33
(Institut Jules Bordet)
Abstract The results of screening tests on 115 of the titled compounds against P388 lymphocytic leukaemia are reported and structure/activity relationships discussed.
136 Citations Source Cite
Cited By172
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Published on Jan 7, 2019in Drug Research
Reza Valipour , Mehmet Bertan Yilmaz , Ebrahim Valipour (Zonguldak Karaelmas University)
Escitalopram oxalate (EO) is considered as one of the extensively prescribed antidepressant drug in Turkey and some other countries, therefore this research was aimed to study the interaction of the drug with DNA and study of the substance effect on bacterial growth. The absorption value of the drug solution at 238 nm was increased when DNA was added gradually to it and it showed hyperchromism effect. The value obtained for DNA binding constant (Kb) was 0.035 M −1 . When we added the CuCl2 2H2O ...
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Published on Oct 1, 2018in Biophysical Reviews
Vangelis George Kanellis1
Estimated H-index: 1
(Canberra Hospital),
Cristobal G. dos Remedios46
Estimated H-index: 46
(USYD: University of Sydney)
Various human activities lead to the pollution of ground, drinking, and wastewater with toxic metals. It is well known that metal ions preferentially bind to DNA phosphate backbones or DNA nucleobases, or both. Foreman et al. (Environ Toxicol Chem 30(8):1810–1818, 2011) reported the use of a DNA-dye based assay suitable for use as a toxicity test for potable environmental water. They compared the results of this test with the responses of live-organism bioassays. The DNA-based demonstrated that ...
1 Citations Source Cite
Published on Oct 1, 2018in Talanta 4.92
Yeli Zhang1
Estimated H-index: 1
,
Yan Zhang1
Estimated H-index: 1
+ 1 AuthorsLiujiao Bian1
Estimated H-index: 1
Abstract Based on the fluorescent reversible regulation, a novel sensor platform was designed for the detection of DNA intercalators utilizing the intercalation binding of DNA intercalators to DNA as an inherent exhibition and the fluorescence change of quantum dots (QDs) as an external manifestation. To prove its feasibility, acridine orange (AO) was chosen as an example of DNA intercalator. When different concentrations of herring sperm DNA (hsDNA) were added to cysteamine (CA)-capped ZnSe QDs...
2 Citations Source Cite
Published on Sep 1, 2018in Inorganic Chemistry Communications 1.79
Ranjana Kumari2
Estimated H-index: 2
(IITR: Indian Institute of Technology Roorkee),
Mala Nath22
Estimated H-index: 22
(IITR: Indian Institute of Technology Roorkee)
Abstract 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 ) calculat...
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Saqib Ali29
Estimated H-index: 29
(QAU: Quaid-i-Azam University),
Saira Shahzadi16
Estimated H-index: 16
(QAU: Quaid-i-Azam University),
Imtiaz-ud-Din10
Estimated H-index: 10
(QAU: Quaid-i-Azam University)
The excellent anticarcinogenicity and toxicity of organotin(IV) complexes of certain acrylates, methylenedioxyphenylpropenoic acid, piperonylic acid, phenylethanoates, carboxylic acid, acetic acid, benzohydroxamato, peptides, dipeptides, benzoates, schiff bases, xylene, nicotinic acid, pyrimidine, and aminoalcohols have been reviewed here. The high cytotoxic activity of complexes is affected by (1) the availability of coordination positions at Sn and (2) the occurrence of relatively stable ligan...
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Published on Mar 12, 2018in Journal of Biomolecular Structure & Dynamics 3.31
Fatemeh Safa Shams Abyaneh1
Estimated H-index: 1
(IAU: Islamic Azad University),
Mahboube Eslami Moghadam6
Estimated H-index: 6
+ 1 AuthorsAdeleh Divsalar21
Estimated H-index: 21
(Kharazmi University)
Investigation of side effects and solubility of anticancer drugs is a major challenge in chemotherapy science. Thus, design and synthesis of cisplatin analogs with higher lipophilicity as novel water-soluble anticancer drugs is valuable. In this work, two new Pt(II) complexes were synthesized with formula cis-[Pt(NH3)2(amylgly)]NO3 and cis-[Pt(amylamine)2(amylgly)]NO3, where gly is penthyl glycine as an amino acid. The new compounds were synthesized and extensively characterized using analytical...
4 Citations Source Cite
Published on Feb 1, 2018in Applied Organometallic Chemistry 3.26
Roghayeh Fekri1
Estimated H-index: 1
(Semnan University),
Mehdi Salehi18
Estimated H-index: 18
(Semnan University)
+ 1 AuthorsMaciej Kubicki30
Estimated H-index: 30
(Adam Mickiewicz University in Poznań)
Co(III) complexes of tridentate Schiff base ligands derived from N-(2-hydroxybenzylideneamino)benzamide (H2L1) and 2-(2-hydroxybenzylidene)hydrazine-1-carboxamide (H2L2) were synthesized and characterized using IR, Raman, 1H–NMR and UV–Vis spectroscopies. X-ray single crystal structures of complexes 1 and 2 have also been determined, and it was indicated that these Co(III) complexes are in a distorted octahedral geometry. The cyclic voltammetry (CV) of the complexes indicates an irreversible red...
1 Citations Source Cite
Published on Feb 1, 2018in Applied Organometallic Chemistry 3.26
Jeyaraman Porkodi1
Estimated H-index: 1
,
N. Raman26
Estimated H-index: 26
Flavonoids are a group of plant phenolics that provide various health benefits through cell signalling pathways and antioxidant effects. In the present study, a new series of mixed ligand complexes of Co(II), Ni(II), Cu(II) and Zn(II) were synthesized by incorporating curcumin and quercetin flavonoid precursors. The structural features of the synthesized complexes were explored using elemental analysis, thermogravimetric analysis, UV–visible, infrared, NMR, mass and electron paramagnetic resonan...
2 Citations Source Cite
Published on Dec 1, 2017in DARU 2.70
Durdana Waseem3
Estimated H-index: 3
(QAU: Quaid-i-Azam University),
Arshad Farooq Butt1
Estimated H-index: 1
(Allama Iqbal Open University)
+ 2 AuthorsGul Majid Khan14
Estimated H-index: 14
(QAU: Quaid-i-Azam University)
Background Tributyltin (IV) compounds are promising candidates for drug development. In the current study, we evaluated in-vitro and in-silico profile of carboxylate derivatives of tributyltin (IV) complexes.
4 Citations Source Cite