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In title compound, [Sn(C6H5)3(C9H6BrN2OS2)], the Sn atom is five-coordinated and the 1,3,4-thia­diazole-2-thiol ligand acts as an S,N-bidentate chelating ligand. The five-coordinate SnIV atom forms four primary bonds, three to the phenyl groups and one to the S atom. Thus, the title complex has a distorted cis-trigonal bipyramidal geometry with the S atom and two C atoms occupying the equatorial plane, whereas the N atom and another C atom are in axial positions. In addition, there is a weak intramolecular Sn⋯N interaction. The crystal structure involves weak intra­molecular C—H⋯N and inter­molecular C—H⋯Br hydrogen bonding.

In the polymeric title coordination compound, [Sn(C6H5)3(C7H7O2Se)]n, the SnIV atom has a distorted trigonal–bipyramidal geometry, with two O atoms from two symmetry-related bridging seleninate ligands in axial positions and three phenyl groups in the equatorial plane. In the crystal, the complex exhibits a zigzag chain structure running parallel to the c axis. An intra­chain C—H⋯O hydrogen bond is observed.

The Sn atom in the title compound, [Sn(C6H5)3(C8H16NS2)], is penta­coordinated by two S atoms, derived from an asymmetrically coordinating dithio­carbamate ligand, and three ipso-C atoms. The coordination geometry is inter­mediate between square-pyramidal and trigonal-bipyramidal, with a leaning towards the latter. The presence of close intra­molecular C—H⋯S contacts preclude the S atoms from forming significant inter­molecular inter­actions. Rather, mol­ecules are consolid­ated in the crystal structure by C—H⋯π inter­actions.

In the title complex, [Sn(C6H5)3(C7H3ClNO4)(CH4O)], the five-coordinate SnIV atom exists in a trigonal–bipyramidal environment, formed by a monodentate carboxyl­ate group, three phenyl rings and a methanol mol­ecule. The axial sites are occupied by the O atoms of the methanol mol­ecule and the carboxyl­ate group, while the equatorial plane is formed by the C atoms of three phenyl rings. The benzene ring of the 2-chloro-4-nitro­benzoate ligand makes dihedral angles of 66.18 (7), 74.71 (7) and 77.39 (7)° with respect to the three phenyl rings. In the crystal, the mol­ecules are linked via inter­molecular O—H⋯O and C—H⋯O hydrogen bonds into a column along the b axis.

The synthesis, spectroscopic characterization and in vitro antitumour activity of two triorganotin compounds, triphenyltin ortho-aminophenylthiolate (1) and triphenyltin 2-pyridylthiolate, compound (2) are reported. The structure of 1 is confirmed by X-ray diffraction, with the tin atom in a distorted tetrahedral geometry because of monodentate coordination, as a thiolate (Sn-S 2.431(2) Å), of the ortho-aminophenylthiolate ligand. The in vitro antitumour activities of 1 and 2, against a number of cell lines, are comparable to those exhibited by methotrexate and doxorubicin, and higher than those of carboplatin and cisplatin.

The title compound, [Sn(C6H5)3(C7H5N2O4)]n, forms polymeric chains along [010]. The SnIV ion is five-coordinated in a distorted trigonal–bipyramidal geometry by two monodentate carboxyl­ate groups and three phenyl rings. The axial sites are occupied by the O atoms of two symmetry-related carboxyl­ate groups [O—Sn—O = 170.88 (3)°]. The benzene ring of the 5-amino-2-nitro­benzoate ligand forms dihedral angles of 82.92 (6), 81.10 (6) and 83.54 (6)° with respect to the three phenyl rings. In the crystal, the chains are linked by inter­molecular N—H⋯O and weak C—H⋯O inter­actions into a three-dimensional network. The crystal structure is further stabilized by weak inter­molecular C—H⋯π inter­actions.

The title compound, {(C6H16N)[Sn(C6H5)3(C23H14O6)]}n, has an infinite chain structure, formed through monodentate carboxyl­ate groups of the pamoic acid anion. The anion bridges two symmetry-related Sn(IV) ions and the resulting polymeric chains are parallel to [201] in the crystal. Et3NH+ cations are inserted between the chains. The coordination of the Sn(IV) atom is completed by three phenyl ligands, giving a distorted trigonal–bipyramidal geometry.

Graphical abstract

The study was aimed to prepare a series of poly(acrylic acid)-cysteine-2-mercaptonicotinic acid conjugates (preactivated thiomers) and to evaluate the influence of molecular mass or degree of preactivation with 2-mercaptonicotinic acid (2MNA) on their permeation enhancing properties. Preactivated thiomers with different molecular mass and different degree of preactivation were synthesized and categorized on the basis of their molecular mass and degree of preactivation as PAA100-Cys-2MNA (h), PAA250-Cys-2MNA (h), PAA450-Cys-2MNA (h), PAA450-Cys-2MNA (m) and PAA450-Cys-2MNA (l). In vitro permeation studies, the permeation enhancement ability for preactivated thiomers was ranked as PAA450-Cys-2MNA (h) > PAA250-Cys-2MNA (h) > PAA100-Cys-2MNA (h) on both Caco-2 cell monolayers and rat intestinal mucosa. Comparing the influence of degree of preactivation with 2MNA on permeation enhancement, the following order PAA450-Cys-2MNA (h) > PAA450-Cys-2MNA (m) ≈ PAA450-Cys-2MNA (l) on Caco-2 cell monolayers and PAA450-Cys-2MNA (m) > PAA450-Cys-2MNA (h) > PAA450-Cys-2MNA (l) on intestinal mucosa was observed. The Papp of sodium fluorescein was 5.08-fold improved on Caco-2 cell monolayers for PAA450-Cys-2MNA (h) and 2.46-fold improved on intestinal mucosa for PAA450-Cys-2MNA (m), respectively, in comparison to sodium fluorescein in buffer only. These results indicated that preactivated thiomers could be considered as a promising macromolecular permeation enhancing polymer for non-invasive drug administration.

In the title complex, [Sn(C6H5)3(C8H5N2O6)(CH3OH)], the Sn(IV) ion is coordinated in a slightly distorted trigonal–bipyramidal geometry by three phenyl ligands in the equatorial plane and by a 2-methyl-3,5-dinitro­benzene­carboxyl­ato ligand and a methanol ligand at the apical sites. In the crystal, complex mol­ecules are linked via inter­molecular O—H⋯O hydrogen bonds, forming chains along [100].

In the title compound, [Sn(C6H5)3(C9H10NO2)], the Sn atom is coordinated by three phenyl groups and a carboxyl­ate anion in a distorted tetra­hedral geometry. An intra­molecular C—H⋯O inter­action forms an S(7) ring motif. The dihedral angles between the benzoate group and the other three phenyl rings are 76.94 (8), 66.82 (8) and 42.34 (9)°. The crystal structure is further stabilized by inter­molecular C—H⋯π inter­actions.

In the title compound, [Sn(C6H5)3(C7H3ClNO4)], the four-coordinate SnIV atom exists in a distorted tetra­hedral geometry, formed by a monodentate carboxyl­ate group and three phenyl rings. The conformation is stabilized by an intra­molecular C—H⋯O hydrogen bond, which generates an S(5) ring. The aromatic ring of the 4-chloro-3-nitro­benzoate ligand makes dihedral angles of 75.64 (12), 64.37 (12) and 2.97 (12)° with the three phenyl ligands. The O atoms of the nitro group are disordered over two sets of sites in a 0.817 (5):0.183 (5) ratio. In the crystal, mol­ecules are linked via inter­molecular C—H⋯O hydrogen bonds into chains running parallel to [010].

In the title compound, [Sn(C6H5)3Cl(C2H6OS)], the SnIV atom is coordinated by three phenyl groups, a chloride ion and a dimethyl sulfoxide mol­ecule in a distorted trigonal-bipyramidal geometry. In the crystal, adjacent mol­ecules are linked through inter­molecular C—H⋯Cl hydrogen bonds, weak C—H⋯π inter­actions and π–π inter­actions [centroid–centroid distance = 3.934 (3) Å. An intra­molecular C—H⋯π inter­action is also observed.

In the title compound, [FeSn(C5H5)(C6H5)3(C6H4O2)], the SnIV atom displays a distorted tetra­hedral coordination geometry, provided by one O atom of the monodentate ferrocene­carboxyl­ate ligand [Sn—O = 2.079 (2) Å] and by three C atoms of the three phenyl groups [average Sn—C = 2.130 (4) Å]. No classic hydrogen bonds or inter­molecular inter­actions are observed in the crystal.

The synthesis and spectral characterization of six novel triphenyltin compounds are described. The in vitro antitumour activity of three of these compounds against two human tumour cell lines, MCF-7, a mammary tumour, and WiDr, a colon carcinoma, was determined. All three compounds are more active than cis-platin, etoposide and doxorubicin against both tumour cell lines. They are as active as mitomycin C against WiDr, but less active against MCF-7.

A series of di- and triorganotin 3,6-dioxaheptanoates and 3,6,9-trioxadecanoates were synthesized and characterized by 1H, 13 and 117Sn NMR, electrospray mass and 119mSn Mössbauer spectroscopy, as well as elemental analysis. Their in vitro antitumour activity against seven tumoural cell lines of human origin, two breast cancers (MCF-7, EVSA-T), a colon carcinoma (WiDr), an ovarian cancer (IGROV), a melanoma (M 19 MEL), a renal cancer (A 498) and a non small cell lung cancer (H 226), is reported. They are characterized by similar inhibition doses ID50 as the analogous di- and triorganotin derivatives of 4-carboxybenzo-15-crown-5 and -18-crown-6 and in some cases by much lower ID50 values than clinically used reference compounds such as doxorubicine and methotrexate.

In the title compound, [Sn(C6H5)3(C10H13OS)]·0.17C6H6, the SnIV atom exhibits a slightly distorted tetra­hedral coordination geometry built up by four C atoms, which are the three ipso-C atoms of the phenyl rings and the α-C atom of the deprotonated γ-O-functionalized propyl phenyl sulfide. The benzene mol­ecule lies about a threefold rotoinversion axis.

Triphenyltin coumarin-3-carboxylate and its coordination complexes with ethanol, triphenylphosphine oxide, triphenylarsine oxide, diphenylcyclopropenone and quinoline N-oxide exhibited high in vitro cytotoxicity (LC50 values in the range 0.25-3.4 μg/mL) when tested against EBV-DNA positive Raji cells and P-388 leukaemia cells, compared to the standard drug 5-Fluorouracil, which showed LC50 values of 11 and >50 μg/mL, respectively, against these cells. Additional tests performed on the Raji cells incubated with the quinoline N-oxide complex in the presence of the tumour promoters, TPA and sodium butyrate, revealed that the diffused and restricted protein components of the early antigen complex were suppressed relative to the control containing only the promoters, indicating impaired function of the genes involved as transactivators in the early lytic cycle of the EBV. The failure of the restriction enzymes Eco R1 and Hind III to cleave the extracted DNA from such treated cells in contrast to the control, coupled with the amplification of the BMLF-1 gene by the PCR technique which was realised only with the DNA of the control and not of the treated sample, point to a punitive interaction of the organotin with the nuclear DNA of the Raji cells.

The title compound, [Sn2(C6H5)6(C7H4O4S)], contains two molecules with similar conformations in the asymmetric unit. In each mol­ecule, the Sn atoms adopt a distorted tetra­hedral geometry arising from three C atoms of three phenyl rings and one O atom from the bridging 3-thienylmalonato ligand. The mol­ecules lie about inversion centers with the ligands facing each other, with C⋯O distances of 3.417 (10) and 3.475 (10) Å.

In the title polymeric coordination compound, [Sn(C6H5)3(C9H8N3O3)]n, the SnIV atom is in a distorted trigonal-bipyramidal geometry, being coordinated by two O atoms from two 2-(2-picolinoylhydrazono)propanoate ligands and three phenyl groups. Adjacent Sn atoms are bridged by the 2-(2-picolinoylhydrazono)propanoate ligand through one carbonyl O atom and one carboxyl­ate O atom, forming a chain structure propagating parallel to [100]. An intra­molecular N—H⋯O hydrogen bond is observed.

The title compound, [Sn2(C6H5)6(C8H5NO4)], contains two triphenyl­tin groups bridged by a 2-amino­terephthalate ligand. The two SnIV centers have similar distorted tetra­hedral coordination geometries. Each SnIV atom is bonded to three phenyl C atoms and one O atom from a carboxyl­ate group. The other O atom of the carboxyl­ate group has a weak inter­action with the Sn atom. The amino group is disordered over two sites, with site-occupancy factors of 0.779 (11) and 0.221 (11). Intra­molecular N—H⋯O hydrogen bonds are observed.

In the title compound, [Sn(C6H5)3(C14H9N2O4)], the Sn atom has a distorted tetra­hedral geometry with one of the carboxyl­ate O atoms and the C atoms from three phenyl groups. The other carboxyl­ate O atom of the benzoate ligand inter­acts weakly with the Sn atom, with an Sn⋯O distance of 2.790 (2) Å, which causes a distortion of the tetra­hedral coordination geometry.

The asymmetric unit of the title compound, [Sn(C6H5)3(C7H5N2O4)], consists of two independent mol­ecules. In each mol­ecule, the four-coordinated SnIV atom exists in a distorted tetra­hedral geometry and two intra­molecular N—H⋯O hydrogen bonds with S(6) ring motifs are present. In one mol­ecule, the benzene ring of the 2-amino-3-nitro­benzoate ligand makes dihedral angles of 42.74 (11), 89.66 (13) and 53.04 (10)° with the three phenyl rings. The corresponding dihedral angles for the other mol­ecule are 6.29 (11), 66.55 (11) and 62.33 (10)°. In the crystal, a weak inter­molecular C—H⋯π inter­action and a π–π stacking inter­action with a centroid–centroid distance of 3.5877 (12) Å are observed.

The SnIV atom in the monomeric title compound, [Sn(C6H5)3(C9H9O3)] exists in a distorted SnC3O tetra­hedral geometry. In the crystal structure, inversion dimers arise from pairs of O—H⋯O hydrogen bonds.

The five-coordinate Sn atom in the title compound, [Sn(C6H5)3(C8H6NO4)(CH3OH)], exists in a trans-C3SnO2 trigonal-bipyramidal coordination polyhedron of which the O atoms of the methanol mol­ecule and carboxyl­ate group occupy the apical sites. In the crystal, adjacent mol­ecules are linked by inter­molecular O—H⋯O inter­actions, generating a helical hydrogen-bonded chain running along the b axis.

The title compound, [Sn(C6H5)3(C11H14NS2)], features a tetra­hedrally coordinated Sn atom, as the dithio­carbamate ligand coordinates in a monodentate fashion. Due to the proximity of the non-coordinating thione S atom, distortions from ideal tetra­hedral geometry about the metal atom are evident with the widest C—Sn—S angle being 117.26 (5)°. In the crystal, mol­ecules are linked by C—H⋯S inter­actions, which generate helical supra­molecular chains along the b axis.