Interaction of 5-amino-1,3,4-thiadiazole-2-thiol and its Violuric Acid Adduct with Pt(II) – Crystals Structures, Spectroscopic Properties and Cytotoxic Activity

M. Kavlakova; A. Bakalova; G. Momekov; D. Ivanov

doi:10.1055/s-0032-1327677

Arzneimittelforschung, Table of Contents

Arzneimittelforschung 2012; 62(12): 599-602
DOI: 10.1055/s-0032-1327677

Original Article

Interaction of 5-amino-1,3,4-thiadiazole-2-thiol and its Violuric Acid Adduct with Pt(II) – Crystals Structures, Spectroscopic Properties and Cytotoxic Activity

M. Kavlakova

¹Department of Chemistry, Faculty of Pharmacy, Medical University, Sofia, Bulgaria

,

A. Bakalova

¹Department of Chemistry, Faculty of Pharmacy, Medical University, Sofia, Bulgaria

,

G. Momekov

²Department of Pharmacology, Pharmacotherapy and Toxicology, Faculty of Pharmacy, Medical University, Sofia, Bulgaria

,

D. Ivanov

¹Department of Chemistry, Faculty of Pharmacy, Medical University, Sofia, Bulgaria

› Author Affiliations

Abstract

The coordination properties of Pt(II) with 5-amino-1,3,4-thiadiazole-2-thiol [CAS 2349-67-9] (L ¹) and its novel violurate adduct (L ²), both in solution and in solid state, are studied by means of conventional IR-spectroscopy, single crystal X-ray diffraction and thermal methods. The complex compounds of L ¹ and L ², with general formulas [Pt(C₂H₂N₃S₂)₂] and [Pt(C₆H₄N₆S₂O₃)(Cl)]Cl respectively, are obtained. Quantum chemical calculations of the ligands are performed with a view to obtain electronic structure and optical properties of the ligands L ¹ and L ², respectively. The cell viability of the ligands and metal complexes on a panel of human tumor cell lines is evaluated.

Key words

5-amino-1,3,4-thiadiazole - violurate adduct - Pt (II) complexes - spectroscopic and structural elucidation - cytotoxic activity

Full Text

References

References
1 Chabner B, Roberts T. Chemotherapy and the war on cancer. Nat Rev Cancer Jan 2005; 5 (01) 65-72
2 Al-sukhun S, Hussain M. Molecular biology of transitional cell carcinoma. Crit Rev Oncol Hematol August 2003; 47 (02) 181-193 61
3 Komarov P, Komarova E, Kondratov R et al. A chemical inhibitor of p53 that protects mice from the side effects of cancer therapy. Science 1999; 285: 1733-1737
4 Koleva B, Kolev T, Lamshöft M et al. Synthesis, spectroscopic analysis and structure deduction of gold(III), palladium(II) and platinum(II) complexes with the tripeptide glycyl-l-phenylalanyl-glycine. Trans Met Chem October 2008; 33 (07) 911-916
5 Kolev T, Koleva B, Zareva S et al. Au(III)-complexes of the alanyl-containing peptides glycylalanine and glycylalanylalanine – Synthesis, spectroscopic and structural characterization. Inorg Chim Acta 2006; 359: 4367-4376
6 Koleva B, Kolev T, Spiteller M et al. Mononuclear Au(III)-complexes with tryptophan-containing dipeptides: Synthesis, spectroscopic and structural elucidation. Inorg Chim Acta 2007; 360: 2224-2230
7 Koleva B, Zareva S, Kolev T et al. New Au(III), Pt(II) and Pd(II) complexes with glycyl-containing homopeptides. J Coord Chem 2008; 61: 3534-3548
8 Asbury R, Blessing J, Moore D. A phase II trial of aminothiadiazole in patients with mixed mesodermal tumors of the uterine corpus: A Gynecologic Oncology Group Study. Am J Clin Oncol 1996; 19: 400-402
9 Engstrom P, Ryan L, Falkson G et al. Phase II study of aminothiadiazole in advanced squamous cell carcinoma of the esophagus. Am J Clin Oncol 1991; 14: 33-35
10 Asbury R, Blessing J, DiSaia P et al. Aminothiadiazole (NSC 4728) in patients with advanced nonsquamous carcinoma of the cervix. A phase II study of the Gynecologic Oncology Group. Am J Clin Oncol 1989; 12 (05) 375-377
11 Matysiak J, Niewiadomy A. Application of sulfinyl bis(2,4-dihydroxythiobenzoyl) in the synthesis of N-substituted 2-amino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles. Synthetic Commun 2006; 36 (11) 1621-1630
12 Matysiak J, Opolski A. Synthesis and antiproliferative activity of N-substituted 2-amino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles. Bioorg Med Chem July 2006; 14 (13) 4483-4489
13 Vergne F, Bernardelli P, Lorthiois E et al. Discovery of thiadiazoles as a novel structural class of potent and selective PDE7 inhibitors. Part 1: Design, synthesis and structure-activity relationship studies. Bioorg Med Chem Lett September 2004; 14 (18) 4607-4613
14 Jung K, Kim S, Gao Z et al. Structure-activity relationships of thiazole and thiadiazole derivatives as potent and selective human adenosine A₃ receptor antagonists. Bioorg Med Chem Fabruary 2004; 12 (03) 613-623
15 Bhattacharya P, Leonard J, Roy K. Exploring QSAR of thiazole and thiadiazole derivatives as potent and selective human adenosine A₃ receptor antagonists using FA and GFA techniques. Bioorg Med Chem February 2005; 13 (04) 1159-1165
16 Clerici F, Pocar D, Guido M et al. Synthesis of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives and evaluation of their antidepressant and anxiolytic activity. J Med Chem March 2001; 44 (06) 931-936
17 Sheldrick G. A short history of SHELX. Acta Crystallogr December 2007; A64 (01) 112-122
18 Blessing H. An empirical correction for absorption anisotropy. Acta Crystallogr January 1995; A51 (01) 33-39
19 Spek A. Single-crystal structure validation with the program PLATON. J Appl Crystallogr February 2003; 36 (01) 7-13
20 Farrugia L. ORTEP-3 for windows – A version of ORTEP-III with a graphical user interface (GUI). J Appl Crystallogr 1997; 30 (05) 565
21 Frisch MJ, Trucks GW, Schlegel HB et al. Gaussian 98. Gaussian, Inc.; Pittsburgh, PA: 1998
22 Dalton 2.0 Program Package http://www.kjemi.uio.no/software/dalton/dalton.html 2005
23 Mosmann T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J Immunol Meths Dec 1983; 65 (1–2) 55-63
24 Konstantinov S, Eibl H, Berger M. BCR-ABL influences the antileukaemic efficacy of alkylphosphocholines Br J Haematol 1999; 107 (02) 365-374
25 Kolev T, Koleva B, Spiteller M et al. 2-Amino-4-nitroaniline, a known compound with unexpected properties. J Phys Chem A October 2007; 111 (40) 10084-10089
26 Koleva B, Kolev T, Seidel R et al. Self-assembly of hydrogensquarates: Crystal structures and properties. J Phys Chem A April 2009; 113 (13) 3088-3095
27 Ivanova BB, Spiteller M. Organic mandelates as promising materials with non-linear optical application. Struct Chem May 2010; 21 (05) 989-993
28 Kolev T, Koleva B, Seidel R et al. Cryst Growth Des August 2009; 9 (08) 3348-3352
29 Ivanova BB, Spiteller M. Possible application of the organic barbiturates as NLO materials. Cryst Growth Des June 2010; 10 (06) 2470-2474