Synthesis and Characterization of Platinum (IV) complexes with S-alkyl Derivatives of Thiosalicylic Acid and the Crystal Structure of the S-butyl Derivative of Thiosalicylic Acid

Marina Z. Mijajlovic; Milos V. Nikolic; Dusan Lj. Tomovic; Andriana M. Bukonjic; Aleksandar Kocovic; Verica V. Jevtic; Zoran R. Ratkovic; Olivera Klisuric; Srecko R. Trifunovic; Gordana P. Radic

doi:10.1515/sjecr-2016-0094

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Synthesis and Characterization of Platinum (IV) complexes with S-alkyl Derivatives of Thiosalicylic Acid and the Crystal Structure of the S-butyl Derivative of Thiosalicylic Acid

EABR. Experimental and Applied Biomedical Research

Volume 18 (2017): Issue 3 (October 2017)

By: Marina Z. Mijajlovic, Milos V. Nikolic, Dusan Lj. Tomovic, Andriana M. Bukonjic, Aleksandar Kocovic, Verica V. Jevtic, Zoran R. Ratkovic, Olivera Klisuric, Srecko R. Trifunovic and Gordana P. Radic

Open Access

|Oct 2017

Abstract

New platinum(IV)-complexes with S-alkyl derivatives of thiosalicylic acid (alkyl = benzyl-(L1), methyl-(L2), ethyl-(L3), propyl-(L4), butyl-(L5)) have been synthesized and characterized by microanalysis, infrared spectroscopy, and 1H and 13C NMR spectroscopy. Th e bidentate S,O ligand precursor, the S-butyl derivative of thiosalicylic acid (S-bu-thiosal), was prepared, and its crystal structure was determined. Single crystals suitable for X-ray measurements were obtained by slow crystallization from a DMSO-water system. S-bu-thiosal crystallized in a P21/c space group of a monoclinic crystal system with a = 8.0732 (3) Å, b = 19.6769 (4) Å, c = 8.2291 (3) Å and Z = 4. S-bu-thiosal also has a coplanar geometry.

References

1. Kostova I. Platinum complexes as anticancer agents. Recent Pat Anticancer Drug Discov. 2006; 1(1):1-22.10.2174/15748920677524645818221023
Search in Google Scholar Back to article
2. Alderden RA, Hall MD, Hambley TW. The Discovery and Development of Cisplatin. J Chem Educ. 2006; 83(5): 728-33.10.1021/ed083p728
Open DOI Search in Google Scholar Back to article
3. Florea АМ, Busselberg D. Cisplatin as an anti-tumor drug: cellular mechanisms of activity, drug resistance and induced side effects. Cancers. 2011; 3(1): 1351-71.10.3390/cancers3011351375641724212665
Search in Google Scholar Back to article
4. Mishra AK, Mishra SB, Manav N, Saluja D, Chandra R, Kaushik NK. Synthesis, characterization, antibacterial and cytotoxic study of platinum(IV) complexes. Bioorg Med Chem. 2006; 14(18): 6333-40.10.1016/j.bmc.2006.05.04716765599
Open DOI Search in Google Scholar Back to article
5. Mishra AK, Kaushik NK. Synthesis, characterization, cytotoxicity, antibacterial and antifungal evaluation of some new platinum(IV) and palladium(II) complexes of thiodiamines. Eur J Med Chem. 2007; 42(10): 1239-46.10.1016/j.ejmech.2007.03.01717498848
Search in Google Scholar Back to article
6. Wong E, Giandomenico CM. Current status of platinum- based antitumor drugs. Chem Rev. 1999; 99(9): 2451-66.10.1021/cr980420v11749486
Search in Google Scholar Back to article
7. Manav N, Mishra AK, Kaushik NK. In vitro antitumour and antibacterial studies of some Pt(IV) dithiocarbamate complexes. Spectrochim Acta A Mol Biomol Spectrosc. 2006; 65(1): 32-5.10.1016/j.saa.2005.09.02316522376
Search in Google Scholar Back to article
8. Mishra AK, Mishra SB, Manav N, Kumar R, Chandra R, Saluja D, Kaushik NK. Platinum(IV) thiohydrazide, thiodiamine and thiohydrazone complexes: A spectral, antibacterial and cytotoxic study. Spectrochim Acta A Mol Biomol Spectrosc. 2007; 66(4): 1042-7.10.1016/j.saa.2006.04.03816920010
Search in Google Scholar Back to article
9. Hall MD, Mellor HR, Callaghan R, Hambley TW. Basis for design and development of platinum(IV) anticancer complexes. J Med Chem. 2007; 50(15): 3403-11.10.1021/jm070280u17602547
Open DOI Search in Google Scholar Back to article
10. Shader D, Ahluwalia GS, Grosso D. Method of reducing hair growth employing sulfhydryl active compounds. Unated States Patent. 1995.
Search in Google Scholar Back to article
11. Wiener JH, Kloog Y, Wacheck V, Burkhard J. Farnesyl thiosalicylic acid chemosensitizes human melanoma in vivo. J Invest Dermatol. 2003; 120 (1): 1-7.10.1046/j.1523-1747.2003.12009.x12535206
Search in Google Scholar Back to article
12. Smalley KSM, Eisen TG. Farnesyl thiosalicylic acid inhibits the growth of melanoma cells through a combination of cytostatic and pro-apoptotic effects. Int J Cancer. 2002; 98: 514-22.10.1002/ijc.10213
Open DOI Search in Google Scholar Back to article
13. Asadi S, Zhang B, Weng Z, Angelidou A, Kempuraj D, Alysandratos KD, Theoharides TC. Luteolin and thiosalicylate inhibit HgCl2 and thimerosal-induced VEGF release from human mast cells. Int J Immunopathol Pharmacol. 2010; 23(4): 1015-20.10.1177/039463201002300406
Search in Google Scholar Back to article
14. Smith DJ, Yap GP, Kelley JA, Schneider JP. Enhanced stereoselectivity of a Cu(II) complex chiral auxiliary in the synthesis of Fmoc-L-γ-carboxyglutamic acid. J Org Chem. 2011; 76(6):1513-20.10.1021/jo101940k
Search in Google Scholar Back to article
15. Radić GP, Glođović VV, Radojević ID, Stefanović OD, Čomić LjR, Ratković ZR, Valkonen A, Rissanen K, Trifunović SR. Synthesis, characterization and antimicrobial activity of palladium(II) complexes with some alkyl derivates of thiosalicylic acids. Crystal structure of bis(S-benzyl-thiosalicylate)-palladium(II) complex, [Pd(S-bz-thiosal)2]. Polyhedron. 2012; 31: 69-76.10.1016/j.poly.2011.08.042
Search in Google Scholar Back to article
16. Smith DJ, Yap GP, Kelley JA, Schneider JP. Enhanced stereoselectivity of a Cu(II) complex chiral auxiliary in the synthesis of Fmoc-L-γ-carboxyglutamic acid. J Org Chem. 2011; 76(6): 1513-20.10.1021/jo101940k
Search in Google Scholar Back to article
17. Agilent, CrysAlis PRO, Agilent Technologies, Yarnton, Oxfordshire, England (2010)
Search in Google Scholar Back to article
18. (a) Altomare A, Burla MC, Cavalli M, Cascarano G, Giacovazzo C, Gagliardi A, Moliterni AG. Polidori G, Spagna R, Sir97: A New Program For Solving and Refining Crystal Structures, Istituto di Ricerca per lo Sviluppo di Metodologie Cristallografiche CNR, Bari (1997); (b) Altomare A, Burla MC, Cavalli M, Cascarano G, Giacovazzo C, Gagliardi A, Moliterni GG, Polidori G, Spagna R, SIR97: a new tool for crystal structure determination and refinement. J Appl Cryst. 1999; 32: 115-119.
Search in Google Scholar Back to article
19. Sheldrick GM. SHELXS-97 and SHELXL-97. Programs for solution and refinement of crystal structures from diffraction data, University of Gottingen, Germany, 1997, Acta Crystallogr. 2008; A64: 112-22.
Search in Google Scholar Back to article
20. Farrugia LJ, WinGX suite for small-molecule singlecrystal crystallography, University of Glasgow, Scotland, 1998; J Appl Cryst. 1999; 32: 837-8.10.1107/S0021889899006020
Search in Google Scholar Back to article
21. Farrugia LJ. ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI), University of Glasgow, Scotland, 1997; J.Appl Cryst 1997; 30: 565.10.1107/S0021889897003117
Search in Google Scholar Back to article
22. Spek AL. Structure validation in chemical crystallography. Acta Crystallogr. 2009; D65: 148-55.10.1107/S090744490804362X
Search in Google Scholar Back to article
23. Schoenberg LN, Cooke DW, Liu CF. Nuclear magnetic resonance determination of the absolute configuration of complexes of cobalt(III) with asymmetric tetradentate ligands. Inorg Chem. 1968; 7: 2386-93.10.1021/ic50069a040
Open DOI Search in Google Scholar Back to article
24. Swaminathan K, Busch DH. The synthesis and infrared absorption spectra of complexes of cobalt with pentadentate propylenediaminetetraacetic acid. J Inorg Nucl Chem. 1961; 20(1): 159-63.10.1016/0022-1902(61)80475-2
Open DOI Search in Google Scholar Back to article
25. Nakamoto К. Infrared spectra of the inorganic and coordination compounds. New York: Willey; 1963.
Search in Google Scholar Back to article
26. Silverstein RM, Bassler CG, Morril TC. Spectrometric identification of organic compounds, 3rd ed. Wiley International Edition, 1974. p.113.
Search in Google Scholar Back to article
27. Nakamoto K. Infrared Spectra of Inorganic and Coordination Compounds, Wiley, New York, 1963. p. 206.
Search in Google Scholar Back to article
28. Sim GA, Monteath Robertson J, Goodwin TH. The crystal and molecule structure of benzoic acid, Acta Cryst. 1955; 8: 157-64.10.1107/S0365110X55000601
Search in Google Scholar Back to article
29. Jones RE, Templeton DH. The crystal structure of acetic acid. Acta Cryst. 1958; 11(7): 484-8.10.1107/S0365110X58001341
Search in Google Scholar Back to article
30. Wright WB, King GSD. The crystal structure of nicotinic acid. Acta Cryst. 1953; 6: 305-17.10.1107/S0365110X53000867
Search in Google Scholar Back to article
31. Van Schalkwyk TGD. The crystal structure of phthalic acid. Acta Cryst. 1954; 7(11): 775.10.1107/S0365110X54002344
Search in Google Scholar Back to article
32. Cohran W. The crystal and molecular structure of salicylic acid. Acta Cryst. 1953; 6: 260-268.10.1107/S0365110X53000752
Search in Google Scholar Back to article

Articles in this issue

DOI: https://doi.org/10.1515/sjecr-2016-0094 | Journal eISSN: 2956-2090 | Journal ISSN: 2956-0454

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Language: English

Page range: 195 - 201

Submitted on: Nov 21, 2016

Accepted on: Nov 30, 2016

Published on: Oct 19, 2017

Published by: University of Kragujevac, Faculty of Medical Sciences

In partnership with: Paradigm Publishing Services

Publication frequency: 4 issues per year

Keywords:

S-alkyl derivative of thiosalicylic acid,

platinum(IV)-complexes,

IR and NMR spectroscopy,

crystal structure

Related subjects:

Medicine,

Clinical medicine,

Clinical medicine, other

© 2017 Marina Z. Mijajlovic, Milos V. Nikolic, Dusan Lj. Tomovic, Andriana M. Bukonjic, Aleksandar Kocovic, Verica V. Jevtic, Zoran R. Ratkovic, Olivera Klisuric, Srecko R. Trifunovic, Gordana P. Radic, published by University of Kragujevac, Faculty of Medical Sciences
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Volume 18 (2017): Issue 3 (October 2017)