The interaction of S,N‐coordinated dimethyltin(IV) derivatives with deoxyribonucleic acid: structure and dynamics by 119Sn Mössbauer spectroscopy

Complexes Me2SnCl(SPy) and Me2SnCl(SPym) (HSPy = 2-mercaptopyridine; HSPym = 2-mercaptopyrimidine), from ethanol solutions, interact with aqueous calf-thymus DNA yielding condensed phases with probable Me2Sn(SPy,SPym) (DNA monomer) stoichiometries of 1:1; the condensation of DNA is inferred originated from electrostatic bonding between complex cations Me2Sn(SPy,SPym)+ and the phosphate oxygen of the phosphodiester groups. Octahedral-or trigonal-bipyramidal tin environments are inferred from the point-charge model treatment of the 119Sn Mossbauer parameter nuclear quadrupole splitting, considering the bonding by S and N, or only S donor atoms from the ligand, as well as possible coordination by H2O molecules. The dynamics of tin atoms in the condensed systems Me2Sn(SPym) (DNA monomer), in both gel and lyophilized phases, have been investigated by variable-temperature 119Sn Mossbauer spectroscopy, obtaining evidence of a general correspondence as reported in the literature for the lyophilized condensates Alk2Sn(DNA monomer)2; possible analogies for Me2Sn(SPym) (DNA monomer) and Alk2Sn(DNA monomer)2 in DNA bonding, and structures of tin environments, are discussed. ‘Neutral’ complexes, such as Me2Sn(SPy)2, neither induce DNA condensation, nor bind to DNA in solution phases. Copyright © 1999 John Wiley & Sons, Ltd.

[1]  A. Silvestri,et al.  Diorganotin(IV)2-mercaptopyrimidine complexes , 1998 .

[2]  L. Pellerito,et al.  119mSn Mössbauer studies on tin compounds , 1998 .

[3]  A. Silvestri,et al.  Mono-organotin(IV) and tin(IV) derivatives of 2-mercaptopyridine and 2-mercaptopyrimidine: X-ray structures of methyl-tris(2-pyridinethiolato)tin(IV) and phenyl-tris(2-pyridinethiolato)tin(IV)·1.5CHCl3 , 1997 .

[4]  D. Lyster,et al.  Synthesis and radioiodination of a stannyl oligodeoxyribonucleotide. , 1997, Nucleic acids research.

[5]  C. Alonso,et al.  Palladium(II) 4,5-diphenylimidazole cyclometalated complexes : DNA interaction , 1997 .

[6]  N. Farrell,et al.  EFFECTS OF QUINOLINE AS LIGAND IN BINDING OF MONONUCLEAR AND DINUCLEAR PLATINUM COMPLEXES TO DNA , 1997 .

[7]  M. Palaniandavar,et al.  Spectroscopic and voltammetric studies of copper(II) complexes of bis(pyrid-2-yl)-di/trithia ligands bound to calf thymus DNA , 1997 .

[8]  V. Bloomfield DNA condensation by multivalent cations. , 1997, Biopolymers.

[9]  H. Shindo,et al.  How amino acids control the binding of Cu(II) ions to DNA: I—The role of the hydroxyl group of serine and threonine in fixing the orientation of the complexes , 1996 .

[10]  P. Yang,et al.  Diorganotin(IV) antitumor agent. (C2H5)2SnCl2 (phen)/nucleotides aqueous and solid-state coordination chemistry and its DNA binding studies. , 1996, Journal of inorganic biochemistry.

[11]  K. Singh,et al.  Effect of thiobase incorporation into duplex DNA during the polymerization reaction. , 1996, Research communications in molecular pathology and pharmacology.

[12]  A. Giannetto,et al.  Relationship between binding affinity for calf-thymus DNA of [Pt(2,2′-bpy)(n-Rpy)2]2+(n= 2,4) and basicity of coordinated pyridine , 1996 .

[13]  E. Nordmeier Advances in polyelectrolyte research: counterion binding phenomena, dynamic processes, and the helix‐coil transition of DNA , 1995 .

[14]  F. D. Giallo,et al.  Dynamics of tin nuclei in alkyltin(IV)–deoxyribonucleic acid condensates by variable-temperature tin-119 Mössbauer spectroscopy , 1995 .

[15]  G. Ruisi,et al.  Synthesis and characterization of diorganotin(IV) derivatives of 2-mercaptopyridine and crystal structure of diphenyl pyridine-2-thiolatochlorotin(IV) , 1994 .

[16]  K. Nambiar,et al.  Synthesis of oligodeoxynucleotides containing 2-thiopyrimidine residues--a new protection scheme. , 1994, Nucleic acids research.

[17]  H. Preut,et al.  Diphenylbis(2-pyridinethiolato)tin(IV) , 1993 .

[18]  A. Silvestri,et al.  Organotin compounds and deoxyribonucleic acid , 1992 .

[19]  A. Silvestri,et al.  The interaction of native DNA with dimethyltin(IV) species. , 1991, Journal of inorganic biochemistry.

[20]  R. Ghirlando,et al.  Extensive interference of DNA packaging processes affected by chemotherapeutic drugs. , 1990, The Journal of biological chemistry.

[21]  J. Vittal,et al.  Synthesis and multinuclear magnetic resonance study of some tin(IV) complexes of pyridine-2-thiolate and related ligands, and the X-ray structural analysis of Sn(C5H4NS)4•C5H5NS , 1990 .

[22]  A. Silvestri,et al.  Tin-119 ‘Mössbauer titration’ of dimethyl- and trimethyl-tin(IV) hydroxides with model ligands mimicking nucleic acid phosphate sites, and with deoxyribonucleic acid , 1990 .

[23]  M. Hynes,et al.  Interactions of the trimethyltin(IV) cation with carboxylic acids, amino acids, and related ligands , 1987 .

[24]  S. Kennedy,et al.  Manganese-deoxyribonucleic acid binding modes. Nuclear magnetic relaxation dispersion results. , 1986, Biophysical journal.

[25]  A. Silvestri,et al.  The antitumor activity of di-n-butyltin(IV) glycylglycinate, and the correlation with the structure of dialkyltin(IV) glycylglycinates in solution studied by conductivity measurements and by infrared, nuclear magnetic resonance, and Mössbauer spectroscopic methods. , 1985, Journal of inorganic biochemistry.

[26]  J. Kister,et al.  Ultraviolet Spectrometry Study of Diazoles and Diazines-1, 3: Pyrimidinethione-2 and Alkyl (Allyl, Benzyl) Thio-2 Pyrimidines , 1980 .

[27]  M. Masaki,et al.  The Crystal and Molecular Structure of Dichlorobis(2-pyridinethiolato)tin(IV) , 1978 .

[28]  R. H. Platt,et al.  Simple molecular-orbital model for the correlation of Mössbauer quadrupole splitting with stereochemistry in organotin(IV) compounds , 1972 .

[29]  J. Carbon,et al.  Thiobases in Escherchia coli Transfer RNA: 2-Thiocytosine and 5-Methylaminomethyl-2-thiouracil , 1968, Science.

[30]  A. Albert,et al.  479. Ionization constants of heterocyclic substances. Part III. Mercapto-derivatives of pyridine, quinoline, and isoquinoline , 1959 .

[31]  A. Katritzky,et al.  721. Tautomeric pyridines. Part I. Pyrid-2- and -4-thione , 1958 .

[32]  J. Mcomie,et al.  712. Pyrimidines. Part II. The ultra-violet absorption spectra of some monosubstituted pyrimidines , 1952 .