Synthesis, characterization, and in vitro antimicrobial activity of organotin(IV) complexes with triazolo-pyrimidine ligands containing exocyclic oxygen atoms

Girasolo, Maria Assunta; Salvo, Clelia Di; Schillaci, Domenico; Barone, Giampaolo; Silvestri, Arturo; Ruisi, Gìuseppe

doi:10.1016/j.jorganchem.2005.07.072

Cited by 40 publications

(22 citation statements)

References 46 publications

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“…Recently, we described complexes of diorganotin(IV) dichlorides with the heterocyclic ligands [1,2,4] [12], 5,7-ditertbutyl-1,2,4-triazolo [1,5-a]pyrimidine (dbtp) and 5,7-diphenyl-1,2,4-triazolo [1,5-a]pyrimidine (dptp) [13] that exhibit antibacterial activity against a group of reference pathogen micro-organisms, thus showing antibacterial activities against a group of reference pathogen micro-organisms, which shows their inhibitory effect. In vitro antimicrobial tests showed that n Bu 2 SnCl 2 (dmtp) [12] has interesting properties as anti Grampositive and antibiofilm agent.…”

Section: Introductionmentioning

confidence: 99%

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Organotin(IV) derivatives with 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine and their cytotoxic activities: The importance of being conformers

Girasolo¹,

Attanzio²,

Sabatino

et al. 2014

Inorganica Chimica Acta

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a b s t r a c tThe organotin(IV) compounds Me 2 SnCl 2 (dbtp)(1), Me 2 SnCl 2 (dbtp) 2 (2), Et 2 SnCl 2 (dbtp) (3), Et 2 SnCl 2 (dbtp) 2 (4), Et 2 SnCl 2 (dptp) (5), n Bu 2 SnCl 2 (dbtp) 2 (6), n Bu 2 SnCl 2 (dptp) (7), Ph 2 SnCl 2 (dbtp) (8), Ph 2 SnCl 2 (EtOH) 2 (dptp) 2 (9), where dbtp = 5,7-di-tert-butyl-1,2,4-triazolo[1,5-a]pyrimidine and dptp = 5,7-diphenyl-1,2,4-triazolo [1,5-a]pyrimidine, have been tested by MTT for their cytotoxic activity on three tumor cell lines, HepG2 (human hepatocellular carcinoma), HeLa (human cervix adenocarcinoma) and MCF-7 (human breast cancer). Except for 1 and 2, which were ineffective, all compounds significantly showed a dosedependent anti-proliferative effect against the three cell lines. By calculated IC 50 values, the cytotoxicity of the complexes followed the order n Bu > Ph > Et > Me for all the selected tumor cells. The cell death of HepG2, induced by organotin(IV) compounds 6-9, was considered to be apoptotic by measuring the exposure of phosphatidylserine to the outer membrane and observing the typical apoptotic morphological change by acridine orange/ethidium bromide staining. Flow cytometric analysis of propidium iodidestained cells also demonstrated that organotin(IV) complexes caused apoptosis of HepG2 cells through cell arrest at G0-G1 phase. The crystal structure of 7, investigated by X-ray diffraction study, exhibited a distorted trigonal bipyramidal geometry with N, Cl as axial atoms and Cl and butyl groups in the equatorial plane. The triazolopyrimidine unit coordinates to the Sn atom through N(3) in a monodentate mode. Two conformational isomers (molecule A and B in the crystallographic independent unit) are co-crystallized in the solid state, a phenomenon that has been observed only occasionally. Conformational mobility of the cytotoxic complex 7 can sum up to the ligands ability to form H-bonds and pÁ Á Áp stacking, facilitating its intracellular uptake.

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Section: Introductionmentioning

confidence: 99%

“…In vitro antimicrobial tests showed that n Bu 2 SnCl 2 (dmtp) [12] has interesting properties as anti Grampositive and antibiofilm agent.…”

Section: Introductionmentioning

confidence: 99%

Organotin(IV) derivatives with 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine and their cytotoxic activities: The importance of being conformers

Girasolo¹,

Attanzio²,

Sabatino

et al. 2014

Inorganica Chimica Acta

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“…The arrangement of the carbon atoms in the Sn(Alk) 3 group can be easily deduced from the tin-carbon stretching modes which occur in the 550-500 cm À1 region of the infrared and Raman spectra [23]. , fully consistent with a trigonal bipyramidal structure with organic groups in the equatorial plane and electronegative ligands in axial positions [24], tin being 5-coordinate.…”

Section: Spectroscopic Datamentioning

confidence: 81%

“…Introduction [1,2,4]Triazolo [1,5-a]pyrimidine derivatives have been extensively used in the synthesis of metal-ion complexes obtaining a variety of new compounds with interesting structural features and relevant biological properties [1,2]. Organotin(IV) complexes were also recently investigated [3,4]. The coordination studies were essentially devoted to alkyl-or oxo-substituted triazolopyrimidines, other substituents being ignored.…”

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confidence: 99%

Triorganotin(IV) derivatives of 7-amino-2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylic acid. Synthesis, spectroscopic characterization, in vitro antimicrobial activity and X-ray crystallography

Ruisi

Canfora

Brunò

et al. 2010

Journal of Organometallic Chemistry

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“…The aim of this work is to synthesize complexes of Arginine, effector of recognition, with organotin(IV) ions (R 2 Sn 2+ and R 3 Sn antimicrobial [5], anti-inflammatory activities [6]. L-Arginine is an essential aminoacid with a side-chain guanidino group, which is strongly basic and protonated in a wide range of pH values and serves as a biological recognition site through hydrogen bonding [7].…”

Section: Introductionmentioning

confidence: 99%

New organotin(IV) complexes with l-Arginine, Nα-t-Boc-l-Arginine and l-Alanyl-l-Arginine: Synthesis, structural investigations and cytotoxic activity

Girasolo

Rubino

Portanova

et al. 2010

Journal of Organometallic Chemistry

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Organotin(IV) NMR Cytotoxic activity a b s t r a c tNovel diorganotin(IV) derivatives of L-Arginine (HArg), N a -(tert-Butoxycarbonyl)-L-Arginine (Boc-Arg-OH) and L-Ala-L-Arg (H 2 Ala-Arg), H 2 NC(@NH)NH(CH 2 ) 3 CH(NHR 0 )CO 2 H, where H COSY NMR spectroscopy, in solution. The spectroscopic characterization leading to the proposed molecular structures was accomplished on the basis of these experiments. L-Arginine appears to behave as a chelating ligand through carboxylate and -NH 2 groups in Me 2 Sn(Arg) 2 , while in N a -t-Boc-L-Arginine complex, the N a -protected amino group being exempted from coordination, only the carboxylate groups are effectors of bonding to the organometallic moieties. FT-IR spectra give a clear indication that guanidino groups in all the complexes are not involved in coordination, since m(C@N-H) frequency of the terminal guanidino group is fairly constant and unshifted relative to the free ligand. The biological activity of organotin(IV)-complexes was also investigated by use of human HT29 colorectal carcinoma cells. The cytotoxic activity of the compounds was determined by the MTT quantitative colorimetric assay, capable of detecting viable cells in comparison with that exerted by cisplatin. A marked cytotoxic activity for nearly all complexes, is evident being higher than that exerted by cisplatin, while no significant improvement of activity was observed for Me 2 Sn(Arg) 2 and Me 2 Sn(Ala-Arg), which was confirmed by IC 50 values. Then, we assessed whether the cytotoxicity induced by organotin(IV) complexes was associated with the induction of apoptosis. Light microscopy analysis, performed to study the morphological changes induced in HT29 cells, confirmed the results obtained with MTT test. No significant morphological alterations were observed in HT29 cells after treatment with Me 2 Sn(Ala-Arg) and Me 2 Sn(L-Arg) 2 . Cells treated with n Bu 2 Sn(Boc-Arg) 2 , n Bu 2 Sn(Ala-Arg), n Bu 3 Sn(Boc-Arg) and Me 3 Sn(Boc-Arg), appeared rounded, isolated and detached from culture substrate, indicating the commitment to apoptotic cell death.

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Synthesis, characterization, and in vitro antimicrobial activity of organotin(IV) complexes with triazolo-pyrimidine ligands containing exocyclic oxygen atoms

Cited by 40 publications

References 46 publications

Organotin(IV) derivatives with 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine and their cytotoxic activities: The importance of being conformers

Organotin(IV) derivatives with 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine and their cytotoxic activities: The importance of being conformers

Triorganotin(IV) derivatives of 7-amino-2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylic acid. Synthesis, spectroscopic characterization, in vitro antimicrobial activity and X-ray crystallography

New organotin(IV) complexes with l-Arginine, Nα-t-Boc-l-Arginine and l-Alanyl-l-Arginine: Synthesis, structural investigations and cytotoxic activity

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