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  • 1
    Electronic Resource
    Electronic Resource
    The interaction of organotins with native DNA (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 6 (1992), S. 537-542 
    Details
    ISSN: 0268-2605
    Keywords: Organotin ; DNA ; Mössbauer ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The compounds R2SnCl2 and R3SnCl (R=Me, Et, nBu, nOct, Ph, in ethanol solution) as well as the aqueous species [Me2Sn(OH2)n]2+ and [Me3Sn(OH2)2]+, react with aqueous native DNA, yielding solid phases. According to the pointcharge model treatment of the 119Sn Mössbauer parameter nuclear quadrupole splitting, trans-octahedral R2Sn(O2PXY)2, and trigonalbipyramidal R3Sn(O2PXY), (R=Me, Et, nBu), would occur in the pellets, the tin atoms being coordinated by phosphodiester groups of the nucleic acid. The precipitates from Ph2SnIV would consist of the DNA complex as well as of the Ph2SnIV distannoxane obtained by hydrolysis of the reactant, whilst nOct2SnCl2, nOct3SnCl and Ph3SnCl would mainly yield stannoxanes and hydroxides. The water-soluble hydrolyzed species [Me2Sn(OH)(OH2)n]+, Me2Sn(OH)2 and Me3Sn(OH)(OH2) do not show any interaction with native DNA, although they are possibly coordinated by phosphate oxygen atoms in model aqueous systems, in the presence of excess ligand.These trends have been rationalized by QSAR approach (Quantitative Structure-Activity Relationships) in terms of electronic factors related to tin-oxygen (phosphate) Coulomb interactions, as well as the lipophilicity of R in the RnSnIV moieties.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/aoc.590060611
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  • 2
    Electronic Resource
    Electronic Resource
    119Sn Mössbauer studies of bis[cysteinato(1-)-S]- and bis[penicillaminato(1-)-S]-diorganotin(IV) species in the crystalline state and in frozen aqueous solution (1988)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 2 (1988), S. 525-531 
    Details
    ISSN: 0268-2605
    Keywords: organotin ; amino-acid ; cysteine ; penicillamine ; Mössbauer ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The bonding and the configuration of the tin environment in the title compounds {R2Sn[SCH2CH(NH3+)COO-]2 and R2Sn[SC(CH3)2CH(NH3+)COO-]2, indicated in the following as R2Sn(cysH)2 and R2Sn(penH)2 respectively} has been investigated through the determination of the Mössbauer-Zeeman spectra of Ph2Sn(cysH)2 and Ph2Sn(penH)2 in the solid state, and through conventional Mössbauer spectroscopy of Me2Sn(penH)2 in the solid state as well as of Me2Sn(cysH)2 and Me2Sn(penH)2 in aqueous solution (frozen). The treatment of the data by the pointcharge model approach suggested the general occurrence of a tetrahedral C2SnS2 core. In aqueous Hepes buffer, a tertiary amino nitrogen atom has been observed to coordinate tin in Me2Sn(cysH)2 and Me2Sn(penH)2, with formation of trigonal bipyramidal tin environments. The latter solutions undergo slow decomposition reactions at room temperature. From (Me2SnS)3 occurs, as well as formation of soluble complex species in the presence of glycylglycine; Me2Sn(penH)2 appears to undergo a slow desulfuration reaction.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/aoc.590020605
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  • 3
    Electronic Resource
    Electronic Resource
    Organometallic Complexes with Biological Molecules: VIII. Synthesis, Solid State and in vivo Investigation of Triorganotin(IV) Derivatives of L-Homocysteic Acid (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 11 (1997), S. 601-616 
    Details
    ISSN: 0268-2605
    Keywords: triorganotin(IV) ; L-homocysteic acid ; infrared ; Mössbauer ; NMR ; sea urchin ; Paracentrotus lividus (Echinodermata) ; Chemistry ; Industrial Chemistry and Chemical Engineering
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Several new triorganotin(IV) derivatives of L-homocysteic acid (L-HCAH) with formula R3Sn(L-HCA) (R=Me, nBu, Ph) have been synthesized. Their solid-state configurations were determined by IR and Mössbauer spectroscopy. The tin(IV) atom is five-coordinated in all the complexes, with the L-homocysteic acid behaving as a monoanionic bidentate ligand coordinating the tin(IV) atom through a chelating or bridging carboxylate group. The sulfonate (SO3-) and NH3+ groups of L-homocysteic acid maintain their free acid configuration and hence do not participate to the coordination of the tin(IV) atom. Coordination hypotheses have been checked through the correlation between the Mössbauer parameter isomer shift, δ, and partial atomic charge on the tin atoms, QSn, performed, for all the new organotin(IV) compounds, on the basis of an equalization procedure applied to idealized trigonal-bipyramidal structures for R3Sn(L-HCA).1H and 13C NMR spectra of the complexes show that pentacoordination of the tin atom, with R groups in the equatorial plane of a trigonal bipyramid, is retained in DMSO solution. The NMR data confirm also that the uncoordinated NH3+ group of the ligand is still present in solution.Results gathered after exposure of two- to four-cell embryos of the sea urchin Paracentrotus lividus (Echinodermata) to the triorganotin(IV) L-homocysteate derivatives as well as to the parent triorganotin(IV) chlorides document cytotoxicity of the complexes, while free L-homocysteic acid exerts no significant toxic activity. The trimethyltin(IV) L-homocysteate derivative seems to exert a lower cytotoxicity than the tributyl- and triphenyl-tin(IV) ones. Different structural lesions have been identified by comparative analysis of mitotic chromosomes from untreated embryos (negative controls) and embryos treated with triorganotin(IV) L-homocysteate derivatives, such as (1) suppression of the stretch among sister chromatids at the beginning of anaphase stage; (2) deeply stained zones mainly located at the telomeric regions of chromosomes; (3) arm breakages; and (4) chromosome bridges among daughter chromosomes at anaphase stage. A colchicine-like effect of triorganotin(IV) L-homocysteate derivatives was observed. © 1997 John Wiley & Sons, Ltd.
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  • 4
    Electronic Resource
    Electronic Resource
    Diorganotin(IV)-2-mercaptopyrimidine complexes (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 12 (1998), S. 861-871 
    Details
    ISSN: 0268-2605
    Keywords: diorganotin ; Pyrimidine ; complex ; Mössbauer ; IR ; NMR ; Chemistry ; Industrial Chemistry and Chemical Engineering
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The complexes formed between the diorganotin(IV) moieties, R2Sn(IV), and the ligand 2-mercaptopyrimidine, (H)SPym, were investigated. Complexes R2SnHal(SPym) and R2Sn(SPym)2 [R = Me, iPr, nBu, iBu, tBu, cyclohexyl(Cy), Ph] were synthesized, and characterized by elemental analysis. In the solid state, chelation of SPym through S and N donors was established by IR spectroscopy, and the nature of the environment of tin centers was investigated by 119Sn Mössbauer spectroscopy. From the dynamics of 119Sn nuclei determined by variable-temperature measurements on representative compounds [Me2SnCl(SPym) and Cy2SnBr(SPym)], as well as by point-charge model treatment of nuclear quadrupole splitting parameters, it was inferred that Me2SnCl-­(SPym) may assume a trans-Me2 octahedral coordination geometry around tin in a monodimensional polymer, or a monomeric trigonal-bipyramidal structure (distorted). The latter type of structure was assigned to the other R2SnHal(SPym) species, while R2Sn(SPym)2 complexes assume a trans-octahedral, or skew trapezoidal, tin environment. In CHCl3-CDCl3 solutions, monomeric species occur (according to vapor-pressure osmometry), where 1H and 13C NMR spectroscopic parameters of SPym indicate the persistence of Sn chelation by S and N donor atoms. The Me2SnCl(SPym) species assume trigonal-bipyramidal structures with a chelating SPym ligand, in CDCl3 and C2H5OH solutions, according to the coupling constants 1J(119Sn,13C), as well as IR and 119Sn Mössbauer spectroscopic data. 119Sn NMR parameters fully correspond with data for the homologous complexes with 2-mercaptopyridine. Copyright © 1998 John Wiley & Sons, Ltd.
    Additional Material: 5 Ill.
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  • 5
    Electronic Resource
    Electronic Resource
    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)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 11 (1997), S. 869-888 
    Details
    ISSN: 0268-2605
    Keywords: organotin ; pyridine-2-thiolate complexes ; pyrimidine-2-thiolate complexes ; crystal structure ; Mössbauer ; IR ; NMR ; Chemistry ; Industrial Chemistry and Chemical Engineering
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Mono-organotin(IV) and tin(IV) derivatives of 2-mercaptopyridine (HSPy) and 2-mercaptopyrimidine (HSPym), RSnL3 (R=Me, n-Bu, Ph; L=SPy, SPym; R=Bz=benzyl, o-ClBz, o-ClC6H4, p-ClC6H4, o-tolyl, p-tolyl; L=SPy), RSnClL2 (R=Me, n-Bu, Ph; L=SPy, SPym), RSnCl2L (R=Me, n-Bu; L=SPy, SPym) and SnCl4-nLn (L=SPy, SPym; n=2, 4) were obtained from RSnCl3 or SnCl4 and NaL or by neutralization (R=Ph, p-tolyl; L=SPy, SPym). RSnClL2 and RSnCl2L were better prepared by comproportionation of RSnCl3 and RSnL3.MeSn(SPy)3 and PhSn(SPy)3·1.5CHCl3 crystals, as determined by single-crystal X-ray diffraction, are monoclinic. In the discrete monomeric RSn(SPy)3 units, three bidentate SPy ligands together with R form a distorted pentagonal bipyramid around tin. One S and the C(R) atom are in the axial positions. Two S atoms and three N atoms form the pentagonal plane.From 119Sn Mössbauer and IR data, analogous structures are inferred for the other solid RSnL3 compounds, except for R=Bz, o-ClBz, o-ClC6H4 and o-tolyl, in which tin would be hexacoordinated. In the compounds RSnClL2 and RSnCl2L, tin is at the center of an octahedron or a trigonal bipyramid, respectively. For Sn(SPym)4 and SnCl2(SPym)2, the same type of octahedral structure as was previously found for Sn(SPy)4·HSPy and SnCl2(SPy)2 is proposed.According to IR and 1H, 13C and 119Sn NMR data, the solid-state molecular structures are retained in chloroform and dimethyl sulfoxide solution. © 1997 John Wiley & Sons, Ltd.
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  • 6
    Electronic Resource
    Electronic Resource
    Synthesis and spectroscopic characterization of diethyltin (IV) derivatives of dipeptides: Crystal and molecular structure of diethyltin glycyltrosinateThis paper is dedicated to Prof. Dr. Peter Sartori with appreciation.Further X-ray structure determination data is available from the authors. (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 6 (1992), S. 75-82 
    Details
    ISSN: 0268-2605
    Keywords: Diorganotin dipeptides ; X-ray structure determination ; 13C ; 119Sn NMR ; IR ; Mössbauer ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Dipeptide complexes of the diethyltin(IV) moiety, Et2SnL, have been synthesized, H2L being glycylglycine (H2GlyGly), glycylalanine (H2GlyAla), alanylalanine (H2AlaAla), glycylvaline (H2GlyVal), valylvaline (H2ValVal), glycylmethionine (H2GlyMet), glycyltyrosine (H2GlyTyr). The crystal and molecular structure of the complex Et2SnGlyTyr has been determined by singlecrystal X-ray diffraction. It consists of monomeric units, with the tin atom having a considerably distorted trigonal bipyramidal environment. The dipeptide acts as a tridentate ligand bonding the tin of the C2Sn fragment (equatorial carbon atoms) with the peptide nitrogen atom (equatorial) and axial (monodentate) carboxyl oxygen and amino nitrogen atoms, into a monomeric unit. Bond lengths and angles are reported. Infrared spectroscopic data show the occurrence of monodentate carboxyl in all solid compounds, as well as in methanol solutions of some representative complexes. 119Sn Mössbauer spectroscopic data, and their rationalization through point-charge model (literal version) calculations of the parameter nuclear quadrupole splitting (ΔE) confirm the general occurrence of trigonal bipyramidal structures of the Et2SnGlyTyr type, in the solid state, and give evidence of variations of the C—Sn—C angle in the individual Et2SnL species. Monomers occur in CH3OH solution as suggested by osmometric measurements. 13C and 119Sn NMR spectroscopic data in CD3OD show the persistence of the solid-state structures also in the solution phase, where the order of magnitude of the C—Sn—C angles, as estimated from the coupling constants |1J(119Sn,13C)|, corresponds to that shown by Et2SnGlyTyr in the solid state. 119Sn Mössbauer parameters of Et2SnGlyGly in frozen CH3OH solution are consistent with the assumptions from the NMR studies.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/aoc.590060110
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis and spectroscopic characterization of dimethyl-, di-n-butyl-, di-t-butyl-and diphenyl-tin(iv) derivatives of dipeptides: Crystal and molecular structure of di-n-butyltin(iv) glycylvalinateDedicated to Prof. Dr. Mult. Dr. h.c. Alois Haas (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 6 (1992), S. 83-94 
    Details
    ISSN: 0268-2605
    Keywords: Organotin ; dipeptides ; structures ; X-ray diffraction ; NMR ; Mössbauer ; infrared ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The dipeptide complexes R2SnL listed below have been synthesized: (a) Me2SnL; H2L = glycylalanine (H2GlyAla), glycylvaline (H2GlyVal), glycylmethionine (H2GlyMet), glycyltryptophan (H2GlyTrp), glycyltyrosine (H2GlyTyr); (b) nBu2SnL; H2L = H2GlyAla, H2GlyVal; (c) nBu2SnL.H2O; H2L = glycylglycine (H2GlyGly), H2GlyAla; (d) tBu2SnL; H2L = H2GlyAla, H2GlyVal; (e) tBu2SnGlyGly. H2O; (f) Ph2SnL; H2L = H2GlyAla, H2GlyVal, H2GlyTyr, H2GlyTrp; (g) Ph2Sn(HGlyVal)2. The crystal and molecular structures of nBu2SnGl Val have been determined by single-crystal X-ray diffraction. The polyhedron around tin is a distorted trigonal bipyramid, analogous to that of Et2SnGlyTyr (see Vornefeld et al., Appl. Organomet. Chem., 1992, 6: 75). According to infrared and 119Sn (ΔE parameters) Mössbauer spectroscopic data the R2SnL derivatives can be classified by their solid-state structure into two types which are distinguished by the nature of the axial carboxylate [(i) monodentate, as in nBu2SnGlyVal; (ii) bidentate]. Bonding in R2SnL.H2O and Ph2Sn(HGlyVal)2 has been discussed on the basis of vibrational data. Rationalization of the 119Sn Mössbauer parameters has been attempted by ‘literal’ point-charge model, calculations of ΔE in the structural context described above. According to 13C NMR spectra, compounds Me2SnL are undissociated in methanol solutions, whilst dissociation is inferred for aqueous solutions, probably concerning the carboxyl and amino groups only. Five-coordination in methanol and aqueous solutions has been assumed for Me2Snl from 119Sn NMR chemical shifts. Values of coupling constants |2J(119Sn, 1H)|, determined from 1H NMR spectra, gave estimates of C—Sn—C angles in Me2SnL in the range 128-136° in methanol and aqueous solutions, which correspond to values from 119Sn Mössbauer ΔE parameters (129.6-133.8°). The structural relationship of R2SnL molecules in the solid state and in solution phase has been discussed.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/aoc.590060111
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  • 8
    Electronic Resource
    Electronic Resource
    Interactions of organotins with biological systems (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 6 (1992), S. 127-138 
    Details
    ISSN: 0268-2605
    Keywords: Organotin ; biological molecules ; Mössbauer ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The bonding and structure in the environments of tin atoms in organotin-biological molecules has been investigated by 119Sn Mössbauer spectroscopy, mainly through the rationalization of the nuclear quadrupole splitting parameter by pointcharge model approaches.Organotin moieties R2SnIV and R3SnIV (R = Me, nBu, Ph) generally assume trigonal-bipyramidal type configurations in membranes of human erythrocytes, when incubated with whole erythrocytes and erythrocyte ghosts at the level of micromolar (μmol dm-3) organotin per mg of membrane protein. Corresponding structures are assumed by Me2SnIV and Me3SnIV in the cytoplasm. Ethanolic Me2SnCl2 yielded distorted trans-octahedral species when reacted with ghost cells. These configurations may in principle originate through coordination of the metal by donor nitrogen or oxygen atoms from the cell constituents, such as protein side chains and related component molecules, carbohydrate fragments, and phospholipids, according to data from various model systems. Hydrolyzed species, such as bis(chlorodiorganotin) oxides and triorganotin hydroxides, could also occur for the n-butyltin and phenyltin species.The moieties Me2SnIV and Alk3SnIV (Alk = Me, Et, nBu), present as the hydrolysis products Me2Sn(OH)2 and Alk3SnOH at physiological pH in the aqueous phase (eventually coordinated by donor atoms from buffers), react with thiol groups of model molecules, as well as of feline and rat hemoglobin, forming tetrahedral or trigonalbipyramidal tin sites characterized by covalent Sn—S bonds (C2SnS, C2SnS2 and C3SnS skeletons); tin atoms are eventually further coordinated by nitrogen donors from amino acid fragments or from buffers, as well as by hydroxyl oxygen.
    Additional Material: 10 Ill.
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    URL: http://dx.doi.org/10.1002/aoc.590060205
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  • 9
    Electronic Resource
    Electronic Resource
    Synthesis and spectroscopic characterization of R3SnIV derivatives of N-acetyldipeptides (1993)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 7 (1993), S. 243-252 
    Details
    ISSN: 0268-2605
    Keywords: Organotin ; biocidal ; biological ; Mössbauer ; NMR ; IR ; peptide ; protein ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Triorganotin(IV) derivatives of N-acetyldipeptides R3SnAcDip; R=Me, Et, n-Bu, n-Oct, Cy or Ph (HAcDip=N-acetylglycylglycine and N-acetylglycylvaline; R=Me, n-Bu, Cy, HAcDip=N-acetylglycylalanine) were obtained by neutralization of R3SnOH and HAcDip. The complexes were studied by means of 119Sn Mössbauer, IR and 1H, 13C and 119Sn NMR spectroscopy. The C—Sn—C bond angles have been inferred by rationalization of Mössbauer nuclear quadrupole splittings as well as from NMR coupling constants. Correlations of Mössbauer isomer shifts with partial atomic charges on tin atoms have been determined: Polymeric trigonal bipyramidal structures, with near-planar R3Sn units and axial carboxylate (unidentate) and C=O amide donor groups are inferred for all the compounds in the solid state, except for Cy3SnAcGlyVal for which a tetrahedral structure is proposed. In solution the complexes are monomeric; in methanol a solvent molecule is coordinated to tin which then is still in a trigonal bipyramidal environment.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/aoc.590070404
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  • 10
    Electronic Resource
    Electronic Resource
    Stannacycloalkyl and stannepinyl derivatives of dipeptides (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 8 (1994), S. 113-117 
    Details
    ISSN: 0268-2605
    Keywords: Organotin ; stannacycloalkyl compounds ; dipeptides ; Mössbauer ; NMR ; IR ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Stannacyclohexyl and stannacycloheptyl derivatives of dipeptides (CH2)nSnAA · xH2O (H2AA = H2GlyGly, with n = 5, x = 2 or n = 6, x = 1; H2AA = H2GlyAla, H2GlyVal, H2GlyMet, with n = 5, 6, x = 1) and stannepinyl glycylglycinate monohydrate have been obtained by the reaction of (CH2)nSnCl2 or stannepinyl dichloride with Na2AA. According to infrared and 119Sn Mössbauer data of the solid compounds, AA acts as a tridentate ONN ligand and tin has a trigonalbipyramidal environment. An analogous structure has been inferred from 1H, 13C, and 119Sn NMR data for the undissociated molecules in methanol solution.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/aoc.590080206
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