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 3.06
· DOI :10.1016/0162-0134(96)00039-6
Qingshan Li1
Estimated H-index: 1
(Nanjing University),
Pin Yang9
Estimated H-index: 9
(Shanxi University)
+ 1 AuthorsMaolin Guo3
Estimated H-index: 3
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.
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  • Citations (172)
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References17
Published on Jul 1, 1967in Journal of Molecular Biology 4.89
J.-B. Lepecq1
Estimated H-index: 1
(Institut Gustave Roussy),
Claude Paoletti30
Estimated H-index: 30
(Institut Gustave Roussy)
Abstract At high salt concentrations, ethidium bromide (EB) is shown to form a fluorescent complex with helical polynucleotides which has a strikingly enhanced fluorescence quantum yield. In this paper we present evidence that formation of this complex (complex I) ia specific for base-paired regions either in DNA, RNA or RNA: DNA hybrids, and that the basis of this specificity is intercalation of the dye between base pairs. At low salt concentrations a second mode of binding EB ‡ (as complex II)...
1,895 Citations Source Cite
Published on Aug 15, 1986in Science 41.06
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...
571 Citations Source Cite
Published on Jan 1, 1987in Pure and Applied Chemistry 5.29
Jan Reedijk14
Estimated H-index: 14
220 Citations Source Cite
Published on Sep 21, 1976in Biochemistry 3.00
Mary Howe-Grant2
Estimated H-index: 2
,
Kun C. Wu2
Estimated H-index: 2
+ 1 AuthorsStephen J. Lippard116
Estimated H-index: 116
231 Citations Source Cite
Published on Jan 1, 1991in Journal of Inorganic Biochemistry 3.06
R. Barbieri23
Estimated H-index: 23
(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...
39 Citations Source Cite
Published on Jul 1, 1990in Journal of Inorganic Biochemistry 3.06
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, 1969in Nature 41.58
Barnett Rosenberg35
Estimated H-index: 35
,
Loretta VanCamp3
Estimated H-index: 3
+ 1 AuthorsVirginia H. Mansour2
Estimated H-index: 2
(Michigan State University)
CERTAIN platinum compounds completely but reversibly iiihibit cell division in Gram-negative rods1–4. These compounds have been tested for antitumour activity and we report some of the preliminary results. The platinum compounds inhibit sarcoma 180 and leukaemia L1210 in mice.
2,423 Citations Source Cite
Published on Nov 1, 1991in Journal of the American Chemical Society 14.36
Louis Y. Kuo9
Estimated H-index: 9
(Northwestern University),
Mercouri G. Kanatzidis102
Estimated H-index: 102
(Northwest University (United States))
+ 2 AuthorsTobin J. Marks120
Estimated H-index: 120
(Northwest University (United States))
119 Citations Source Cite
Published on Apr 1, 1989in Journal of the American Chemical Society 14.36
Anna Marie Pyle23
Estimated H-index: 23
,
Jill P. Rehmann3
Estimated H-index: 3
+ 3 AuthorsJacqueline K. Barton85
Estimated H-index: 85
998 Citations Source Cite
Cited By172
Ayaz Mahmood Dar6
Estimated H-index: 6
(Aligarh Muslim University),
Urfi Ishrat2
Estimated H-index: 2
(Aligarh Muslim University)
+ 2 AuthorsManzoor Ahmad Gatoo6
Estimated H-index: 6
(Jawaharlal Nehru Medical College, Aligarh)
Abstract Herein we report synthesis of new steroidal oxadiazinanones from steroidal ketones. After characterization by spectral and analytical data, the interaction studies of compounds ( 4 – 6 ) with DNA were carried out by UV–vis, fluorescence spectroscopy and gel electrophoresis. The compounds bind to DNA preferentially through electrostatic and hydrophobic interactions with K b ; 1.8 × 10 4 M −1 , 2.2 × 10 4 M −1 and 2.6 × 10 4 M −1 , respectively, indicating the higher binding affinity of c...
6 Citations Source Cite
Published on Oct 1, 2015in Inorganica Chimica Acta 2.26
Liansheng Cui5
Estimated H-index: 5
(Ocean University of China),
Caifeng Bi13
Estimated H-index: 13
(Ocean University of China)
+ 4 AuthorsZhongyu Zhang3
Estimated H-index: 3
(Ocean University of China)
Abstract We have synthesized three novel organobismuth(V) complexes Ph 3 Bi(OOCC 6 H 3 F 2 ) 2 1 , Ph 3 Bi(OOCC 6 H 4 CF 3 ) 2 2 and Ph 3 Bi(OOCC 4 H 3 S) 2 3 , and their structures were characterized by IR spectroscopy, elemental analysis, 1 H NMR and single crystal X-ray diffraction. X-ray crystallography showed that all of the bismuth atoms adopt distorted trigonal–bipyramidal geometries. The complex molecules lead to one-dimensional chain structure and two-dimensional network structure throu...
2 Citations Source Cite
R. K. Hemakumar Singh8
Estimated H-index: 8
(Manipur University),
N. Shantibala Devi3
Estimated H-index: 3
(Manipur University)
+ 1 AuthorsR.M. Kadam25
Estimated H-index: 25
(Bhabha Atomic Research Centre)
Five New Cu(II) complexes, [bis(1-amidino-O-alkylurea) Cu(II)tartrate], where alkyl= methyl (1), ethyl (2), n-propyl (3), n-butyl (4), or iso-butyl (5) have been synthesized and characterized. The electron paramagnetic resonance spectra of complexes 1 and 2 showed features of mononuclear species whereas complexes 3, 4, and 5 in frozen DMSO solution show the existence of mononuclear and binuclear species in these complexes. Complexes crystallize in a monoclinic structure. The binding of these com...
1 Citations Source Cite
Published on Nov 1, 2015in Inorganica Chimica Acta 2.26
Leila Tabrizi10
Estimated H-index: 10
(Isfahan University of Technology),
Patrick McArdle26
Estimated H-index: 26
(National University of Ireland, Galway)
+ 1 AuthorsHossein Chiniforoshan11
Estimated H-index: 11
(Isfahan University of Technology)
We are grateful for the financial support from the Department of Chemistry, Isfahan University Of Technology (IUT).
11 Citations Source Cite
Published on Jan 1, 2015in Journal of Materials Chemistry B 4.78
Víctor M. Jiménez-Pérez13
Estimated H-index: 13
(Universidad Autónoma de Nuevo León),
María C. García-López3
Estimated H-index: 3
(Universidad Autónoma de Nuevo León)
+ 7 AuthorsArturo Chávez-Reyes4
Estimated H-index: 4
A series of eight new organotin compounds derived from Schiff bases has been prepared by a multicomponent reaction from 2-hydroxy-1-naphthaldehyde or 4-substituted-2-hydroxybenzalhedyde, benzhydrazine, and the corresponding diorganotin oxide (R2SnO, R = nBu or Ph). All of the compounds were fully characterized by NMR (1H, 13C, and 119Sn), IR, UV/vis, elemental analyses and fluorescence spectroscopy. The crystal structures for some organotin compounds were determined by single crystal X-ray diffr...
18 Citations Source Cite
Published on Dec 1, 2015in Steroids 2.52
Ayaz Mahmood Dar6
Estimated H-index: 6
(Aligarh Muslim University),
Shamsuzzaman11
Estimated H-index: 11
(Aligarh Muslim University),
Manzoor Ahmad Gatoo6
Estimated H-index: 6
(Jawaharlal Nehru Medical College, Aligarh)
Abstract A one-pot strategy for the catalytic synthesis of series of new 5α-cholestan-6- spiro -5′-phenylamino-2H-imidazo [1′,2′-a] pyridines ( 4 – 14 ) has been investigated. The synthesized products were obtained in good yields (85–90%) and the protocol uses Multi-component Reaction (MCR) involving steroidal ketones, 2-aminopyridines, isocyanides and propylphosphonic anhydride (®T3P) as a catalyst. After characterization by spectral and analytical data, the interaction studies of compounds ( 4...
6 Citations Source Cite
Published on Nov 1, 2014in Inorganica Chimica Acta 2.26
Santiago Gómez-Ruiz24
Estimated H-index: 24
(King Juan Carlos University),
Željko Žižak15
Estimated H-index: 15
,
Goran N. Kaluđerović7
Estimated H-index: 7
(Leibniz Association)
Abstract The reaction of α,α′-dimercapto- o -xylene (H 2 dmox) with SnPh 2 Cl 2 (1:1) and SnPh 3 Cl (1:2) in the presence of two equivalents of NEt 3 led to the formation of the complexes [SnPh 2 (dmox)] ( 1 ) and [SnPh 3 ( μ -dmox)] 2 ( 2 ), respectively. Both complexes have been characterized by multinuclear NMR and IR spectroscopy, mass spectrometry and elemental analysis. In addition, the molecular structure of complex 2 has been determined by single crystal X-ray diffraction studies. The cy...
4 Citations Source Cite
Published on Mar 1, 2013in Medicinal Chemistry Research 1.61
Imran Ali54
Estimated H-index: 54
(Jamia Millia Islamia),
Kishwar Saleem18
Estimated H-index: 18
(Jamia Millia Islamia)
+ 1 AuthorsAshanul Haque11
Estimated H-index: 11
(Jamia Millia Islamia)
Knoevenagel condensates of curcumin I were synthesized with p-hydroxybenzaldehyde and 4-hydroxy-3,5-dimethoxy benzaldehyde and allowed to react with semicarbazide to form the corresponding curcumin I-based ligands. The ligands were complexed with ruthenium(III) metal ions. These complexes (C1 and C2) were purified by chromatography and characterized as octahedral geometries by analytical techniques. The binding affinities of these compounds for calf thymus DNA were determined. DNA binding consta...
33 Citations Source Cite
Published on Feb 1, 2010in Polyhedron 2.07
Unchulee Chaveerach4
Estimated H-index: 4
(Khon Kaen University),
Atittaya Meenongwa3
Estimated H-index: 3
(Khon Kaen University)
+ 2 AuthorsPrapansak Chaveerach5
Estimated H-index: 5
(Khon Kaen University)
Abstract The two designed copper(II) complexes, [Cu(L 1m ) 2 ]Cl 2 ( 1 ) (L 1m = amidino- O -methylurea) and [Cu(L 2m ) 2 ]Cl 2 ( 2 ) (L 2m = N -methylphenyl-amidino- O -methylurea), have been investigated for their interaction with calf thymus DNA by utilizing the absorption titration method, viscometric studies and thermal denaturation. The cleavage reaction on pBR322 DNA has been monitored by agarose gel electrophoresis. The results suggest that the two complexes can bind to DNA by non-interc...
87 Citations Source Cite
Published on Jun 1, 2005in Journal of Inorganic Biochemistry 3.06
Claudia Pellerito14
Estimated H-index: 14
(University of Palermo),
Paolo D’Agati4
Estimated H-index: 4
(University of Palermo)
+ 5 AuthorsL. Pellerito21
Estimated H-index: 21
(University of Palermo)
Abstract Four new organotin(IV) chlorin derivatives, [chlorin = chlorin-e 6 = 21H,23H-porphine-2-propanoic acid, 18-carboxy-20-(carboxymethyl)-8-ethenyl-13-ethyl-2,3-di-hydro-3,7,12,17-tetramethyl-(2 S - trans )–], with formula (R 2 Sn) 3 (chlorin) 2 · 2H 2 O (R = Me, n -Bu) and (R 3 Sn) 3 chlorin · 2H 2 O (R = Me, Ph) have been synthesized. The solid state and solution phase structures have been investigated by FT-IR, 119 Sn Mossbauer, 1 H and 13 C NMR spectroscopy. In the solid state, (R 2 Sn)...
51 Citations Source Cite