Investigation on the Antitumor Activity of Organotin Compound

Changes in the surface structure of cell membrane and the contents of membrane pro- teins and nuclear DNA of human gastric cancer (BGC-823) cells treated with organotin compound (Et_2SnCl_2phen) were studied with a scanning electron microscope (SEM),a scanning tunneling,micro- scope (STM),and a cytofluorophotometer.It was found that Et_2SnCl_2Phen not only inhibited the cell growth but also remarkably changed the surface structure of the membrane of cancer cells.The surface of Et_2SnCl_2phen treated cancer cells was relatively smooth and showed fewer microvilli under SEM. STM images showed an uneven and loose distribution of the surface of the cell.In comparison with the untreated cancer cells,there was an evident decrease in the content of membrane proteins and nuclear DNA in Et_2SnCl_2phen treated cells.

Synthesis, Crystal Structure and Quantum Chemical Study of the Ladder Organotin Compound {[(C_6H_5CH_2)2Sn]_2(O)(Cl_2)}_2

The title compound {[（C6H5CH2）2Sn]2（O）（Cl2）}2 has been synthesized by the reaction of bisbenzyltin dichloride with NaOH dilute solution, and its structure was determined by X-ray diffraction. The crystal belongs to monoclinic, space group C2/c, with a = 2.5081（17）, b = 1.0089（7）, c = 2.0909（14） nm, β = 94.267（8）°, V= 5.276（6） nm^3, Z = 4, De= 1.734 g/cm^3,μ（MoKa） = 21.55 cm^-1, F（000） = 2704, R = 0.0398 and Rw = 0.1024. According to structural analysis, the tin atom adopts a distorted five-coordinate trigonal bipyramidal geometry, and the ladder-like structure is shaped by one planar four-membered Sn2O2 ring together with two planar four-membered Sn2OCl rings.

Synthesis,Structure and Biological Activities of a Novel Anionic Organotin(Ⅳ)Complex{[(pClC6H4CH2)Sn(H2O)(Cl)2OCOCH(O)CH(O)CO2Sn(H2O)(Cl)2(p-ClC6H4CH2)]·2(HNEt3)}

A novel anionic organotin(Ⅳ) complex {[(pClCHCH)Sn(HO)(Cl)OCOCH(O)CH(O)COSn(HO)(Cl)(p-ClCHCH)]·2(HNEt)}(1) was synthesized by the reaction of di(p-chlorobenzy)tin dichloride with the D-tartaric acid in 2:1 molar in the presence of an organic base triethylamine. The structure was characterized by elemental analysis, IR, TG, XRD and single-crystal X-ray diffraction. It crystallizes in triclinic, P1 space group, with a = 0.7067(1), b = 1.9762(3), c = 2.2383(3) nm, α = 91.544(2)°, β = 90.075(2)°, γ = 90.110(2)°, V = 3.1247(7) nm~3, Z = 3, Dc = 1.621 g/cm~3, m(Mo Kα) = 16.29 cm–1, F(000) = 1530, R = 0.0394, wR = 0.1092,(Δρ)max = 1224 and(Δρ)min = –840 e/nm~3. The stabilities, orbital energies and composition characteristics of some frontier molecular orbitals of 1 have been carefully investigated with quantum chemistry calculation. In addition, the in vitro antitumor activity suggested that 1 had stronger inhibitory activity on H460, MCF7 than on A549.

Synthesis and Crystal Structure of a One-dimensional Infinite Chain Organotin Complex [(n-Bu)_3Sn(OCOC_5H_4NO)]_n

A novel organotin complex [（n-Bu）3Sn（OCOC5H4NO）]n has been synthesized and characterized by elemental analysis, IR and ^1H NMR. The crystal structure has been determined by X-ray single-crystal diffraction. The crystal belongs to monoclinic, space group P2 1/c with a = 8.982（2）, b = 17.908（4）, c = 13.219（3） A, β= 96.981（4）°, Z = 4, V= 2110.6（8） A^3, Dc = 1.347 g/cm^3, μ（MoKa） = 12.23 cm^-1, F（000） = 880, R = 0.0497 and wR = 0.1263. In the molecular structure of the title complex, the tin atoms are five-coordinated in a distorted trigonal bipyramidal geometry. A one-dimensional linear polymer is formed through an interaction between the O atoms of pyridine-3-carboxylic acid N-oxide and tin atoms of an adjacent molecule.

Diorganotin Complexes of N-[4-(Diethylamino)salicylidene]-(L)-tryptophane: Syntheses, Structures and Properties

Four chiral diorganotin complexes of N-[4-(diethylamino)salicylidene]-(L)-tryptophane,R2Sn[4-(Et2N)-2-OC6H3CH=NCH(CH2Ind)COO](Ind=3-indolyl;R=Me(1);Et,(2);n-Bu(3);Cy(cyclohexyl)(4)),have been synthesized and characterized by elemental analysis,IR,and 1H and 13C NMR spectra.The crystal structures of 1-CH3OH-CHCl3,2,3-CH3OH and 4-CH3CH2OH have been determined by single-crystal X-ray diffraction.The complexes crystallize in orthorhombic system with P212121 space group,and the tin atoms are in distorted trigonal bipyramidal geometry and form five-and six-membered chelate rings with the chiral ONO tridentate ligand N-[4-(diethylamino)salicylidene]-(L)-tryptophane.In the complexes,the molecules are connected into one-dimensional supramolecular chain by intermolecular N–H…O–H…O=C or N–H…O–C hydrogen bonds.The fluorescence spectrum indicates that the complexes may be explored for potential blue luminescent materials.Bioassay results show that 3 and 4 belong to the efficient cytostatic agents against A549 human tumor cell.

Synthesis and Crystal Structure of the Organotin Complex [(o-Cl-PhCH_2)_3SnOCOC_(10)H_8N]·0.5C_6H_6

A novel organotin complex [(o-Cl-PhCH2)3SnOCOC10H8N]?0.5C6H6 has been syn- thesized, and its crystal structure was determined by X-ray diffraction. The crystal belongs to mo- noclinic, space group C2/c with a = 1.6214(5), b = 1.2033(3), c = 3.2873(10) nm, β = 91.467(5)°, V = 6.411(3) nm3, Mr = 1441.26, Z = 4, Dc = 1.493 g/cm3, μ(MoKα) = 10.79 cm-1, F(000) = 2904, R = 0.0500 and Rw = 0.0884. The bond lengths of Sn–C are 0.2150(5), 0.2157(4) and 0.2164(4) nm, and that of Sn–O is 0.2043(3) nm. The tin atom adopts a distorted tetrahedral geometry.

Synthesis, Structural Investigations and Biological Screening of Diorganotin(IV) Complexes Derived from 5,5-Diethyl Sodium Barbital

Some biologically important tin（Ⅳ） complexes derived from 5,5-diethyl sodium barbital have been synthesized and characterized through various analytical and spectroscopic techniques such as IR, ^1H-, ^13C-NMR and ^119mSn mossbauer. On the basis of these spectroscopic techniques, octahedral geometry has been assigned to all the novel compounds. These complexes, soluble in DMSO and DMF, were screened against a wide range of microorganisms. The results proved that the diphenyltin（Ⅳ） and dibutyltin（Ⅳ） complexes exhibit excellent activity against all types of microorganisms, while the rest of the compounds show significant activity that can be used during the biological study.

Distribution of Different Organotin and Organolead Compounds in Sediment of Suez Gulf

Organotin and organolead compounds were determined in sediments of the Suez Gulf The concentrations of Tributyltin (TBT) ranged from 0.27 to 2.77 with an average value of 1.37 μgg-1;dry wt. However, the concentrations of dibutyltin (DBT) ranged from 0.07 to 2.27 with an average value of 0.58 μgg-1;dry wt. A significant correlation was found between TBT and DBT with r = 0.82, (p = 0.05) indicating that the occurrence of DBT is mainly related to the degradation of TBT. Generally, the high concentration of TBT was attributed to shipping activity in harbours. In addition, Diphenyltin (DPhT) concentrations ranged from not detected to 2.09 with an average of 1.10 μgg-1 dry wt. Antifouling agents, industrial discharge and the influence of sewage discharge are the main sources of pollution by DPhT compounds in Suez Gulf. On the other side, organolead (OLC) concentrations ranged from 10.88 - 440.2 with an average of 168.7 ngg-1;dry wt. A significant setting of OLC recorded in sediments of Suez Gulf was mainly attributed to cars exhaust and/or spelling and direct evaporation of fuels.

Correlation relationships of molar refraction and ten topological indices for 47 organotin compounds

Correlation relationships of 10 topological indices and molar refraction for 47 struc- turally-complicated organotins which included 16 ionic compounds R_mSnX_(4-m) and 31 covalent ones R_4Sn that is 41 aliphatic compounds(15 unsaturated and 26 saturated)and 6 aromatic ones were studied.Suitability of these ten topological parameters for describing the structure of elemental or- ganic compounds was then evaluated according to the correlation results.Two lately improved molecular connectivity indices(MCIs)-radius-corrected MCI ~1X^r and bond-length-corrected MCI ~1X^b were applied and proved to be most suitable for the structure expression in QSA(P)R studies of organotins or other elemental organic compounds.

Synthesis and Anion Recognition of a Novel Heterocyclic Organotin Complex

A novel heterocyclic hexacoordinate organotin(Ⅳ) complex, bis(O-vanillin)-semi ethylenediamino dibenzyltin (VEDBT) was synthesized by the reaction of dibenzyltin dichloride with bis(O-vanillin)-semiethyenediamine, its structure has been characterized by spectral methods. The electrodes using VEDBT as a neutral carrier show high selectivity for salicylate anions.

Preparation and Tribological Performance of Novel Organotin Compound as Lubricant Additive

Oil-soluble stannous naphthenate (SN) is synthesized by using naphthenatic acid and SnO. And its molecular structure is confirmed by IR and multielement oil analyzer (MOA). The tribological performances of the organotin as lubricant additive are evaluated with a four-ball friction and wear tester. These experiments indicate that the wear scar diameter (WSD) and friction coefficient are diminished while the load-carrying capability increased by comparison with that of base oil. The elemental composition of the boundary lubricating film is examined by means of Auger electron spectroscopy (AES). Synergistic effect is found in the load-carrying capability of the complex of SN and sulfured olefin. The analytical results of AES indicate that the good performance of stannous naphthenate is attributed to the formation of a boundary lubricating film containing Sn on the rubbed surface.

Formation,Structure and In Vitro Antitumour Activity of a Novel Binuclear Organotin Complex

A 1：1 reaction of triphenyltin chloride with potassium N-[（3,5-dibromo-2-hydroxylphenyl）methylene]valinate in benzene led to the formation of a novel mixed organotin dinuclear complex, （HL）SnPh3oPh2SnL [L=2-O-3,5-Br2C6H3CH=NCH（i-Pr）COO], by means of a facile phenyl-tin bond cleavage process. In the complex, there are two distinct types of carboxylate moieties and a trans-O2SnC2N and a trans-O2SnC3 in distorted trigonal bipyramidal geometries were bridged by a carboxylate group. In vitro antitumor activity of the complex against three human tumour cell lines （HeLa, CoLo205 and MCF-7） was found to be much higher than cis-platin used in clinic.

Synthesis and structure of a new 1D infinite neutral chain based on organotin and selenious acid monoethyl ester

A new 1D infinite neutral chain （Ph3SnO2SeOCH2CH3）n （1） based on organotin and selenious acid monoethyl ester has been synthesized successfully and characterized by IR, elemental analysis, and X-ray single-crystal diffraction. In the compound 1, the Sn atom exists in slightly distorted trigonal bipyramidal geometry and the Se center is tri-coordinated with a distorted pyramidal arrangement. It is noted that the synthesis is facile and selenium oxide is directly introduced into synthesis route replacing organoseleninic acid under room temperature.

Heteropolytungstates Containing Organotin and Cobalt or Zinc Atom

Organotin substituted heteropolytungstates with cobalt or zinc atom as the central atom, \{K 6H[XW 11 O 39 (RSn)]\}· n H 2O(X=Zn, Co; R=CH 3OOCCH 2CH 2, CH 2OOCCH(CH 3)CH 2, NCCH 2CH 2) were prepared and characterized by elemental analysis, IR, UV Vis spectroscopy, ESR, NMR spectroscopy and electrochemical study. The results show that these anions possess Keggin like structures.

Synthesis and Characterization of Tri(organotin)Substituted Heteropolytungstates

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Diagnosis and treatment of organotin poisoned patients

BACKGROUND： With the development of industry and agriculture, organotin compounds have been widely used in China. Organotin compounds cause a common occupational poisoning. The toxicity of organotin was reported in animal studies; however the reports about human organotin intoxication are very rare. In this study we retrospectively analyzed the clinical manifestations of 15 organotin-poisoned patients who had been treated at our hospital from 2002 through 2007.METHODS： Fifteen patients with organotin poisoning were admitted to Sir Run Run Shaw Hospital Affiliated to Zhejiang University School of Medicine from 2002 to 2007. They were 9 males and 6 females, aged from 25 to 52 years. Clinical manifestations and Glasgow Coma Scales showed that the poisoning was mild in 4 patients, moderate in 6 and severe in 5. The severe patients were given glucocorticoid after hospitalization by intravenous guttae of 500 mg methylprednisolone for the first day, followed by 160 mg methylprednisolone per day for three days, and then 80 mg methylprednisolone per day for another three days. Potassium glutamate and sodium glutamate were intravenously dripped to reduce blood ammonia; intravenous guttae plus oral administration of potassium 9 g/day was used to correct intractable hypokalemia; sodium bicarbonate was used to correct metabolic acidosis, and sedatives were used to control spasm and twitch; mechanical ventilators were used in 4 patients with dyspnea.RESULTS： Most of the patients showed elevated level of blood ammonia, decreased level of blood potassium and metabolic acidosis, but some had demyelination changes shown by CT and MRI. Treatments included correction of metabolic acids, blood potassium and ammonia, and mechanical ventilation when necessary. For patients with injuries of the nervous system, glucocorticoids were given immediately after hospitalization. These patients showed intractable hypokalemia and metabolic acidosis during the treatment. Forteen patients recovered completely without long-term side-effect. One patient in the aphasiac stage restored the linguistic capacity during a 6-month follow-up.CONCLUSION： Elevated level of blood ammonia, decresed level of blood potassium, and metabolic acidosis are common in patients with organotin poisoning. Demyelination can be observed in patients with severe poisoning. The abnormalities of the patients are reversible alter suitable treatments.

Synthesis, spectral characterization and biological activities of Organotin(IV) complexes with <i>ortho</i>-vanillin-2-hydrazinopyridine (VHP)

Five new organotin(IV) complexes of ortho-vanillin-2-hydrazinopyridine hydrazone with formula [RnSnCl4–n(VHP)] [R = Me2, n = 2 (2);R = Ph2, n = 2 (3);R= nBu2, n = 2 (4);R = nBu, n = 2 (5) and R = 1, n = 0 (6)] have been synthesized by direct reaction of ortho-vanillin-2-hydrazinopyridine hydrazone [(VHP), (1)], base and organotin(IV) chloride(s) in absolute methanol. The hydrazone ligand [(VHP), (1)] and its organotin(IV) complexes (2-6) have been characterized by UV-Visible, FT-IR and 1H NMR spectral studies. Spectroscopic data suggested that in the complexes (2-4), the ligand (1) acted as a neutral bidentate ligand and is coordinated to the tin(IV) atom via the azomethine nitrogen and pyridyl nitrogen atoms, whereas the ligand (1) acted as a uninegative tridentate ligand and coordinated to the tin(IV) atom through phenolic-O, azomethine-N and pyridyl-N atoms in complexes (5-6). The toxicity of the ligand (1) and its organotin (IV) complexes (2-6) were determined against Artemia salina. Organotin(IV) complexes showed moderate activity against Artemia salina. The ligand (1) and its organotin(IV) complexes (2-6) were also tested against four types of bacteria namely Bacillus cereus, Staphylococcus aureus, Escherichia coli and Enterobacter aerogenes. All organotin(IV) complexes and the free ligand (1) showed better antibacterial activities against bacteria. Among the organotin(IV) complexes (2-6), diphenyltin(IV) complex (3) showed higher activity against the four types of bacteria.

Organotin Compounds in Sediments of Northern Lakes, Egypt

This pioneered study is aimed to determine the levels and distributions of organotin compounds (OTCs) in sediment samples collected from five Egyptian lakes located in the southern-eastern Mediterranean Sea. The paper has given an account of and the reasons for the widespread distribution of Tributyltin (TBT) in northern lakes. The percentage of TBT ranged from 4% - 100% OTC revealing recent inputs of TBT. The highest average of TBT (2.84 μg/g Sn dry wt) was measured in lake Edku. Dibutyltin (DBT) was observed at most sampled sites. Relatively higher abundance of DBT was observed in sediments of EL-Burullus (0.69 μg/g Sn dry wt). One of most significant findings to emerge from this study is the absence of any strong and significant correlation between TBT and DBT in sediments from five northern lakes. The absence of such correlation might give a clear evidence that both compounds did not come from the same source. The observed OTC levels indicate some highly localized areas of contamination which are severe enough to cause harmful effects on marine flora and fauna. Except for El-Burllus, Triphenyltin (TPhT) was not measured in sediments of most stations. TPhT was the predominant species in El-Burullus, which indicate a source of pollution mostly originated from industrial and agricultural waste water discharge, organic wastes, commercial fertilizers, chemical wastes and pesticides. The percentages of OTC to total tin ranged from 1% to 35%. El-Brullus, Edku and El-Bardaweel exhibited the highest percentages. As a result of lack of enforcement on the control of OTC, the study has thrown up many questions need further detailed environmental assessment of OTC.

Synthesis and Crystal Structure of a Novel Mercapto-organotin Complex: [Et_3NH] [Ph_2SnCl(μ~2-SCH_2COO^-)]

A novel complex [Et3NH] [Ph2SnCl(μ2- SCH2COO-)] has been unexpectedly obtained by the reaction of Ph3SnCl and HSCH2COOH in 2:1 molar ratio in the presence of organic base Et3N. Possible dephenylation mechanism was illustrated. The X-ray diffraction study has shown that the title complex consists of cation moiety [Et3NH] and anion moiety [Ph2SnCl(μ2 - SCH2COO)] with tin(IV) in a trigonal bipyramidal coordination geometry.

Synthesis, Characterization and Biological Activity of Diorganotin（IV） Complexes of N-（3,5-Dibromosalicylidene）-α-amino Acid

The diorganotin（Ⅳ） complexes of N-（3,5-dibromosalicylidene）-α-amino acid, R2Sn（2-O-3,5-Br2C6H2CH= NCHRCOO）（where R=H, Me, i-Pr, Bz; R＇=n-Bu, Cy）, were synthesized by the reactions of diorganotin dichlorides with in situ formed potassium salt of N-（3,5-dibromosalicylidene）-α-amino acid and characterized by elemental analysis, IR and NMR （^1H, ^13C and ^119Sn） spectra. The crystal structures of n-Bu2Sn（2-O-3,5-Br2C6H2CH= NCHRCOO）（R=i-Pr, Bz） and Cy2Sn（2-O-3,5-Br2C6H2CH=NCHRCOO）（R=Me, Bz） were determined by X-ray single crystal diffraction and showed that the tin atoms are in a distorted trigonal bipyramidal geometry to form five- and six-membered chelate rings with the tridentate ligand. Bioassay results indicated that the compounds possess better in vitro antitumour activity against three human tumour cell lines, HeLa, CoLo205 and MCF-7, than cis-platin and moderate anti-bacterial activity against two bacteria, E. coli and S. aureus.