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1.  Preactivated thiomers: Permeation enhancing properties 
International Journal of Pharmaceutics  2012;438(1-2):217-224.
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.
PMCID: PMC3484403  PMID: 22960503
Thiomers; Poly(acrylic acid)-cysteine; Preactivated thiomers; Permeation enhancer
2.  (N-sec-Butyl-N-n-propyl­dithio­carbamato-κ2 S,S′)triphenyl­tin(IV) 
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.
PMCID: PMC3007978  PMID: 21588542
3.  [5-(4-Bromo­phenoxy­meth­yl)-1,3,4-thia­diazole-2-thiol­ato]triphenyl­tin(IV) 
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.
PMCID: PMC2977584  PMID: 21583770
4.  catena-Poly[[triphenyl­tin(IV)]-μ-3-methyl­phenyl­seleninato-κ2 O:O′] 
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.
PMCID: PMC3238714  PMID: 22199591
5.  Triphenyltin Ortho-Aminophenyl- and 2-Pyridyl-Thiolates: Synthesis and In Vitro Antitumour Activity 
Metal-Based Drugs  1996;3(2):75-78.
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.
PMCID: PMC2365004  PMID: 18472799
6.  Structural Properties, Cytotoxicity, and Anti-Inflammatory Activity of Silver(I) Complexes with tris(p-tolyl)Phosphine and 5-Chloro-2-Mercaptobenzothiazole 
The synthesis and characterization of the silver(I) chloride complex of formula {[AgCI(CMBZT)(TPTP)2] · (MeOH)} (1) (CMBZT = 5-chloro-2-mercaptobenzothiazole, TPTP = tris(p-tolyl)phosphine) is described. Also the structure of the hydrate derivative {[AgCI(TPTP)3] · (0.5 · H2O)} (2) of the corresponding known anhydrous silver complex (Zartilas et al., 2009), and the polymorph 3 of the known [AgI(TPTP)3] complex (Zartilas et al., 2009) were determined and compared with the known ones. In addition, the structure of the known one silver(I) cluster {[AgI(TPTP)]4} (4) (Meijboom et al., 2009) was re-determined at 120(2) K and possible Ag-Ag interactions were analyzed. The compounds 1–4 were characterized by X-ray crystallography at r.t (1) and 120 K (2–4). All these complexes and {[(Et3NH)+]2 · [Ag6(μ3-Hmna)4(μ3-mna)2]2− · (DMSO)2 · (H2O)} (5) (Hmna = 2-mercaptonicotinic acid) were evaluated for cytotoxic and anti-inflammatory activity. The in vitro testing of cytotoxic activity of 1–5 against leiomyosarcoma cancer cells (LMS), were evaluated with Trypan Blue and Thiazolyl Blue Tetrazolium Bromide or 3-(4.5-dimethylthiazol-2-yl)-2.5-diphenyltetrazolium bromide (MTT) assays. The flow cytometry assay for complex 1 and showed that at 15 μM of 1, 62.38% of LMS cells undergo apoptosis, while 7% of LMS cells undergo cell necrosis. The antitumor activity of 3 is comparable with that of its reported polymorph (Zartilas et al., 2009). The anti-inflammatory, activity of complexes 1–3 and 5 was also studied. The activity towards cell viability was 2 > 3 > 5 > 1 > 4, while the order of the inhibitory activity in cell growth proliferation follows the order, 2 > 3 > 1 > 4 > 5. The anti-inflammatory activity on the other hand is 1 > 2 > 5 > ⋯ >3.
PMCID: PMC2847381  PMID: 20379345
7.  catena-Poly[triethyl­ammonium [[triphenyl­tin(IV)]-μ-3,3′-dihydroxy-4,4′-methyl­ene­di-2-naphtho­ato]] 
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.
PMCID: PMC3050292  PMID: 21522533
8.  Crystal Structure and Antitumor Activity of the Novel Zwitterionic Complex of tri-n-Butyltin(IV) with 2-Thiobarbituric Acid 
A novel tri-n-butyl(IV) derivative of 2-thiobarbituric acid (HTBA) of formula [(n-Bu)3Sn(TBA) H2O] (1) has been synthesized and characterized by elemental analysis and 119Sn-NMR and FT-IR spectroscopic techniques. The crystal structure of complex 1 has been determined by single crystal X-ray diffraction analysis at 120(2) K. The geometry around Sn(IV) is trigonal bipyramidal. Three n-butyl groups and one oxygen atom from a deprotonated 2-thiobarbituric ligand are bonded to the metal center. The geometry is completed with one oxygen from a water molecule. Compound 1 exhibits potent, in vitro, cytotoxicity against sarcoma cancer cells (mesenchymal tissue) from the Wistar rat, polycyclic aromatic hydrocarbons (PAH, benzo[a]pyrene) carcinogenesis. In addition, the inhibition caused by 1, in the rate of lipoxygenase (LOX) catalyzed oxidation reaction of linoleic acid to hyperoxolinoleic acid, has been also kinetically and theoretically studied. The results are compared to that of cisplatin.
PMCID: PMC2288696  PMID: 18401456
9.  (2-Chloro-4-nitro­benzoato)(methanol)triphenyl­tin(IV) 
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.
PMCID: PMC3089065  PMID: 21754275
10.  (Methanol-κO)(2-methyl-3,5-dinitro­benzoato-κO)triphenyl­tin(IV) 
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].
PMCID: PMC3089075  PMID: 21754262
11.  catena-Poly[[triphenyl­tin(IV)]-μ-5-amino-2-nitro­benzoato-κ2 O 1:O 1′] 
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.
PMCID: PMC3200871  PMID: 22064934
12.  [3-(Dimethyl­amino)benzoato]triphenyl­tin(IV) 
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.
PMCID: PMC2959792  PMID: 21581146
13.  (4-Chloro-3-nitro­benzoato)triphenyl­tin(IV) 
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].
PMCID: PMC3200665  PMID: 22065496
14.  Chlorido(dimethyl sulfoxide-κO)triphenyl­tin(IV) 
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.
PMCID: PMC2971969  PMID: 21578630
15.  (Ferrocene­carboxyl­ato-κO)triphenyl­tin(IV) 
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.
PMCID: PMC3006984  PMID: 21587735
16.  (2-Amino-3-nitro­benzoato-κO)triphenyl­tin(IV) 
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.
PMCID: PMC3089114  PMID: 21754293
17.  (O-Methyl di­thio­carbonato-κS)tri­phenyl­tin(IV) 
In the title compound, [Sn(C6H5)3(C2H3OS2)], the SnIV atom adopts a distorted SnC3S tetra­hedral coordination geometry. A short Sn⋯O contact [2.988 (4) Å] is also present. The phenyl rings are each disordered over two sets of sites with an occupancy ratio of 0.550 (8):0.450 (8). The crystal studied was found to be a racemic twin with a twin component ratio of 0.57 (18):0.43 (18).
PMCID: PMC3684880  PMID: 23794982
18.  catena-Poly[[tri­phenyl­tin(IV)]-μ-N-(4-acetyl­phen­yl)maleamato] 
The crystal structure of the polymeric title compound, [Sn(C6H5)3(C12H10NO4)]n, comprises polymeric chains whereby adjacent Sn atoms are bridged by carboxyl­ate and amide carbonyl O atoms [Sn—O = 2.115 (15) and 2.653 (1) Å, respectively]. The SnIV atom is five-coordinated showing a distorted trigonal–bipyramid geometry, with the three phenyl ipso-C atoms defining the trigonal plane and the axial positions occupied by O atoms [O—Sn—O = 171.91 (5)°]. Intra­molecular N—H⋯O hydrogen bonding leads to a seven-membered loop. There is an intra­molecular C—H⋯O inter­action within the polymeric chain. An inter­molecular C—H⋯O inter­action along c links the polymeric chains into sheets which are linked into a three-dimensional network via C—H⋯π inter­actions.
PMCID: PMC3793673  PMID: 24109260
19.  Synthesis, Characterization and High In Vitro Antitumour Activity of Novel Triphenyltin Carboxylates 
Metal-Based Drugs  1994;1(4):305-309.
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.
PMCID: PMC2364906  PMID: 18476244
20.  Synthesis, Characterization and In Vitro Antitumour Activity of Di-n-Butyl, Tri-n-Butyl and Triphenyltin 3,6-Dioxaheptanoates and 3,6,9-Trioxadecanoates 
Metal-Based Drugs  1998;5(4):189-196.
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.
PMCID: PMC2365126  PMID: 18475843
21.  Preactivated thiomers as mucoadhesive polymers for drug delivery 
Biomaterials  2012;33(5):1528-1535.
This study was aimed to synthesize polymeric excipients with improved mucoadhesive, cohesive and in situ-gelling properties to assure a prolonged retention time of dosage forms at a given target site, thereby achieving an increased uptake and improved oral bioavailability of certain challenging therapeutic agents such as peptides and proteins. Accordingly, poly(acrylic acid)-cysteine-2-mercaptonicotinic acid (PAA-cys-2MNA) conjugates were synthesized by the oxidative S–S coupling of PAA-cys (100-, 250- and 450 kDa) with 2-mercaptonicotinic acid (2MNA). Unmodified PAAs, PAAs-cys (thiomers) and PAA-cys-2MNA (100-, 250- and 450 kDa) conjugates were compressed into tablets to perform disintegration tests, mucoadhesion studies and rheological measurements. Moreover, cytotoxicty of the polymers was determined using Caco-2 cells. The resulting PAA-cys-2MNA (100-, 250- and 450 kDa) conjugates displayed 113.5 ± 12.7, 122.7 ± 12.2 and 117.3 ± 4.6 μmol/g of 2-mercaptonicotinic acid, respectively. Due to the immobilization of 2MNA, the PAA-cys-2MNA (pre-activated thiomers) conjugates exhibit comparatively higher swelling properties and disintegration time to the corresponding unmodified and thiolated polymers. On the rotating cylinder, tablets based on PAA-cys-2MNA (100-, 250- and 450 kDa) conjugates displayed 5.0-, 5.4- and 960-fold improved mucoadhesion time in comparison to the corresponding unmodified PAAs. Results achieved from tensile studies were found in good agreement with the results obtained by rotating cylinder method. The apparent viscosity of PAA-cys-2MNA (100-, 250- and 450 kDa) conjugates was improved 1.6-, 2.5- and 206.2-fold, respectively, in comparison to the corresponding unmodified PAAs. Moreover, pre-activated thiomers/mucin mixtures showed a time dependent increase in viscosity up to 24 h, leading to 7.0-, 18.9- and 2678-fold increased viscosity in comparison to unmodified PAAs (100-, 250- and 450 kDa), respectively. All polymers were found non-toxic over Caco-2 cells. Thus, on the basis of achieved results the pre-activated thiomers seem to represent a promising generation of mucoadhesive polymers which are safe to use for prolonged residence time of drug delivery systems to target various mucosa.
PMCID: PMC3260419  PMID: 22118819
Thiomers; Poly(acrylic acid)-cysteine; 2-Mercaptonictic acid; Pre-activated thiomers; Mucoadhesion; Oral drug delivery
22.  [3-Meth­oxy-1-(phenyl­sulfan­yl)prop­yl]triphenyl­tin(IV) benzene 0.17-solvate 
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.
PMCID: PMC3274883  PMID: 22346830
23.  μ-3-Thienylmalonato-κ2 O 1:O 3-bis­[triphenyl­tin(IV)] 
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.
PMCID: PMC2959414  PMID: 21201052
24.  catena-Poly[[triphenyl­tin(IV)]-μ-2-(2-picolinoylhydrazono)propanoato-κ2 O 1:O 2] 
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.
PMCID: PMC2971240  PMID: 21578076
25.  μ-2-Amino­terephthalato-κ2 O 1:O 4-bis­[triphenyl­tin(IV)] 
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.
PMCID: PMC2971378  PMID: 21578180

Results 1-25 (547627)