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, Gìuseppe; Canfora, Loredana; Brunò, Giuseppe; Rotondo, Archimede; Mastropietro, Teresa F.; Debbia, Eugenio A.; Girasolo, Maria Assunta; Megna, Bartolomeo

doi:10.1016/j.jorganchem.2009.11.019

Cited by 30 publications

(10 citation statements)

References 35 publications

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“…Most of the significant investigations with coordination compounds have been directed to the development of anti-tumor compounds of different metals [12] that could show improved therapeutic indexes and wider activity spectra. Such derivatives are interesting for their many biological effects such as antimicrobial [13,14], antitumor [15][16][17][18][19] and antiparasitic [20][21][22] activity.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Activity of Organotin(IV) Derivatives with Triazolopyrimidine Containing Exocyclic Oxygen Atoms

et al. 2020

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In this study cytotoxicity of organotin(IV) compounds with 1,2,4-triazolo[1,5-a]pyrimidines, Me3Sn(5tpO) (1), n-Bu3Sn(5tpO) (2), Me3Sn(mtpO) (3), n-Bu3Sn(mtpO) (4), n-Bu3Sn(HtpO2) (5), Ph3Sn(HtpO2) (6) where 5HtpO = 4,5-dihydro-5-oxo-[1,2,4]triazolo-[1,5-a]pyrimidine, HmtpO = 4,7-dihydro-5-methyl-7-oxo-[1,2,4]triazolo-[1,5-a]pyrimidine, and H2tpO2 = 4,5,6,7-tetrahydro-5,7- dioxo-[1,2,4]triazolo-[1,5-a]-pyrimidine, was assessed on three different human tumor cell lines: HCT-116 (colorectal carcinoma), HepG2 (hepatocarcinoma) and MCF-7 (breast cancer). While 1 and 3 were inactive, compounds 2, 4, 5 and 6 inhibited the growth of the three tumor cell lines with IC50 values in the submicromolar range and showed high selectivity indexes towards the tumor cells (SI > 90). The mechanism of cell death triggered by the organotin(IV) derivatives, investigated on HCT-116 cells, was apoptotic, as evident from the externalization of phosphatidylserine to the cell surface, and occurred via the intrinsic pathway with fall of mitochondrial inner membrane potential and production of reactive oxygen species. While compound 6 arrested the cell progression in the G2/M cell cycle phase and increased p53 and p21 levels, compounds 2, 4 and 5 blocked cell duplication in the G1 phase without affecting the expression of either of the two tumor suppressor proteins. Compounds 1 and 2 were also investigated using single crystal X-ray diffraction and found to be, in both cases, coordination polymers forming 1 D chains based on metal-ligand interactions. Interestingly, for n-Bu3Sn(5tpO)(2) H-bonding interactions between 5tpO− ligands belonging to adjacent chains were also detected that resemble the “base-pairing” assembly and could be responsible for the higher biological activity compared to compound 1. In addition, they are the first example of bidentate N(3), O coordination for the 5HtpO ligand on two adjacent metal atoms.

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Section: Introductionmentioning

confidence: 99%

Cytotoxic Activity of Organotin(IV) Derivatives with Triazolopyrimidine Containing Exocyclic Oxygen Atoms

et al. 2020

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“…Our interest was recently devoted to organotin(IV) complexes of [1,2,4] triazolo-[1,5-a]pyrimidine (tp), its 5,7-dimethyl derivative (dmtp) and a number of oxo-substituted triazolopyrimidines whose antimicrobial activity was excellent [7][8][9]. This promising finding was suggesting a possible use of triazolopyrimidines derivatives as leads for a potential field of novel therapeutic options able to overcome the antibiotic resistant strains which prompted us to undertake the present study by evaluating the change of activity associated with the introduction on the basic heterocycle of different radical groups giving non classical isosteric ligands, expected to be endowed with better hydrophobicity.…”

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confidence: 99%

Synthesis, characterization, crystal structures and in vitro antistaphylococcal activity of organotin(IV) derivatives with 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine

Girasolo

Canfora

Sabatino

et al. 2012

Journal of Inorganic Biochemistry

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New organotin(IV) complexes of 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) with 1:1 and/or 1:2 stoichiometry were synthesized and investigated by X-ray diffraction, Sn Mössbauer in the solid state and by 1 H and 13 C NMR spectroscopy, in solution. Moreover, the crystal and molecular structures of Et 2 SnCl 2 (dbtp) 2 and Ph 2 SnCl 2 (EtOH) 2 (dptp) 2 are reported. The complexes contain hexacoordinated tin atoms: in Et 2 SnCl 2 (dbtp) 2 two 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine molecules coordinate classically the tin atom through N(3) atom and the coordination around the tin atom shows a skew trapezoidal structure with axial ethyl groups. In Ph 2 SnCl 2 (EtOH) 2 (dptp) 2 two ethanol molecules coordinate tin through the oxygen atom and the 5,7-diphenyl-1,2,4-triazolo [1,5-a]pyrimidine molecules are not directly bound to the metal center but strictly H-bonded, through N (3), to the \OH group of the ethanol moieties; Ph 2 SnCl 2 (EtOH) 2 (dptp) 2 has an all-trans structure and the C-Sn-C fragment is linear. On the basis of Mössbauer data, the 1:2 diorganotin(IV) complexes are advanced to have the same structure of Et 2 SnCl 2 (dbtp) 2 , while Me 2 SnCl 2 (dptp) 2 to have a regular all-trans octahedral structure. A distorted cis-R 2 trigonal bipyramidal structure is assigned to 1:1 diorganotin(IV) complexes. The in vitro antibacterial activities of the synthesized complexes have been tested against a group of reference pathogen micro-organisms and some of them resulted active with MIC values of 5 μg/mL, most of all against staphylococcal strains, which shows their inhibitory effect.

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“…In addition, the complexes with triazolopyrimidine derivatives were investigated for their antimicrobial [ 13 , 14 , 15 ], antitumor [ 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 ] and antiparasitic [ 26 , 27 ] features. Among these, organotin(IV) complexes with disubstituted [1,2,4]triazolo[1,5- a ]pyrimidines showed in vitro efficiency against Gram-positive bacteria [ 13 ], such as staphylococcal strains [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Physico-chemical Characterization, Crystal Structure and Influence on Microbial and Tumor Cells of Some Co(II) Complexes with 5,7-Dimethyl-1,2,4-triazolo[1,5-a]pyrimidine

et al. 2017

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Three complexes, namely [Co(dmtp)2(OH2)4][CoCl4] (1), [Co(dmtp)2Cl2] (2) and [Co(dmtp)2(OH2)4]Cl2∙2H2O (3) (dmtp: 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine), were synthesized and characterized by spectral (IR, UV-Vis-NIR), and magnetic measurements at room temperature, as well as single crystal X-ray diffraction. Complex (1) crystallizes in monoclinic system (space group C2/c), complex (2) adopts an orthorhombic system (space group Pbca), and complex (3) crystallizes in triclinic system (space group P1¯). Various types of extended hydrogen bonds and π–π interactions provide a supramolecular architecture for all complexes. All species were evaluated for antimicrobial activity towards planktonic and biofilm-embedded microbial cells and influence on HEp-2 cell viability, cellular cycle and gene expression.

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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

Cited by 30 publications

References 35 publications

Cytotoxic Activity of Organotin(IV) Derivatives with Triazolopyrimidine Containing Exocyclic Oxygen Atoms

Cytotoxic Activity of Organotin(IV) Derivatives with Triazolopyrimidine Containing Exocyclic Oxygen Atoms

Synthesis, characterization, crystal structures and in vitro antistaphylococcal activity of organotin(IV) derivatives with 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine

Synthesis, Physico-chemical Characterization, Crystal Structure and Influence on Microbial and Tumor Cells of Some Co(II) Complexes with 5,7-Dimethyl-1,2,4-triazolo[1,5-a]pyrimidine

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