Study on single crystal structure of the antimony(III) bromide complex with 3-methyl-2-mercaptobenzothiazole and biological activity of some antimony(III) bromide complexes with thioamides
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  • 作者:I. I. Ozturk (1) (6)
    A. K. Metsios (1) (4)
    S. Filimonova-Orlova (1) (5)
    N. Kourkoumelis (2)
    S. K. Hadjikakou (1)
    M. Manos (3)
    A. J. Tasiopoulos (3)
    S. Karkabounas (4)
    E. R. Milaeva (5)
    N. Hadjiliadis (1)
  • 关键词:Bioinorganic medicinal chemistry ; Antimony(III) bromide complexes ; 3 ; Methyl ; 2 ; mercaptobenzothiazole ; Lipoxygenase ; Antitumor activity
  • 刊名:Medicinal Chemistry Research
  • 出版年:2012
  • 出版时间:November 2012
  • 年:2012
  • 卷:21
  • 期:11
  • 页码:3523-3531
  • 全文大小:587KB
  • 参考文献:1. Abdellah MA, Hadjikakou SK, Hadjiliadis N, Kubicki M, Bakas T, Kourkoumelis N, Simos YV, Karkabounas S, Barsan MM, Butler IS (2009) Synthesis, characterization, and biological studies of organotin(IV) derivatives with / o- or / p-hydroxybenzoic acids. Bioinorg Chem Appl Artno 542979
    2. Abrantes LT, Comerlato NM, Ferreira GB, Howie RA, Wardell JL (2006) Preparation and characterization of catena-[bromo(tetrahydrofuran-O)(2-thioxo-1,3-dithiole-4,5-dithiolato)antimony(III)], [Br(THF)Sb(dmit)]( / n). Inorg Chem Commun 9:522-25 CrossRef
    3. Alvarado-Rodriguez JG, Andrade-Lopez N, Gonzalez-Montiel S, Merino G, Vela A (2003) Study of the D?->?Sb (D?=?O, S) transannular interaction in Sb-monohalogenated dibenzostibocines—an experimental and theoretical study. Eur J Inorg Chem 3554-562
    4. Balas VI, Hadjikakou SK, Hadjiliadis N, Kourkoumelis N, Light ME, Hursthouse M, Metsios AK, Karkabounas S (2008) Crystal structure and antitumor activity of the novel zwitterionic complex of tri- / n-Butyltin(IV) with 2-thiobarbituric acid. Bioinorg Chem Appl Artno 654137
    5. Bara A, Socaciu C, Silvestru C, Haiduc I (1991) Antitumor organometallics.1. Activity of some diphenyltin(IV) and diphenylantimony(III) derivatives on invitro and invivo ehrlich-ascites tumor. Anticancer Res 11:1651-655
    6. Barnes NA, Godfrey SM, Pritchard RG, Ratcliffe S (2008) The reaction of / N,N -Di-tert-butylthiourea (dtbtu) with antimony(III) halides—formation of the triply bridged [(dtbtu)SbX2(mu-X)(2)(mu-dtbtu)SbX2(dtbtu)] (X?=?Cl, Br) dimers. Eur J Inorg Chem 3661-667
    7. Buchwald SL, Fisher RA, Davis WM (1989) Synthesis and structure of novel antimony thiametallacycles. Organometallics 8:2082-084 CrossRef
    8. CrysAlis CCD (2006) Version 1.171.31.5. Oxford Diffraction Ltd, Abingdon, Oxford
    9. Daga V, Hadjikakou SK, Hadjiliadis N, Kubicki M, dos Santos JHZ, Butler IS (2002) Synthesis, spectroscopic and structural characterization of novel diiodine adducts with the heterocyclic thioamides, thiazolidine-2-thione (tzdtH), benzothiazole-2-thione (bztzdtH) and benzimidazole-2-thione (bzimtH). Eur J Inorg Chem 1718-728
    10. Ding XZ, Kuszynski CA, El-Metwally TH, Adrian TE (1999) Lipoxygenase inhibition induced apoptosis, morphological changes, and carbonic anhydrase expression in human pancreatic cancer cells. Biochem Biophys Res Commun 266:392-99 CrossRef
    11. Dodds CA, Reglinski J, Spicer MD (2006) Lower main-group element complexes with a soft scorpionate ligand: the structural influence of stereochemically active lone pairs. Chemistry 12:931-39 CrossRef
    12. Hadjikakou SK, Xanthopoulou MN, Hadjiliadis N, Kubicki M (2003) Synthesis, structural characterisation and study of mercury(II) complexes with the heterocyclic thioamides pyridine-2-thione (pytH) and thiazolidine-2-thione (tzdtH). Crystal structures of [HgI2(pytH)2] and [HgI2 (tzdtH)2]. Can J Anal Sci Spectrosc 48:38-5
    13. Hadjikakou SK, Antoniadis CD, Hadjiliadis N, Kubicki M, Binolis J, Karkabounas S, Charalabopoulos K (2005) Synthesis and characterization of new water stable antimony(III) complex with pyrimidine-2-thione and in vitro biological study. Inorg Chim Acta 358:2861-866 CrossRef
    14. Kasuga NC, Onodera K, Nakano S, Hayashi K, Nomiya K (2006) Syntheses, crystal structures and antimicrobial activities of 6-coordinate antimony(III) complexes with tridentate 2-acetylpyridine thiosemicarbazone, bis(thiosemicarbazone) and semicarbazone ligands. J Inorg Biochem 100:1176-186 CrossRef
    15. Lazarou K, Bednarz B, Kubicki M, Verginadis II, Charalabopoulos K, Kourkoumelis N, Hadjikakou SK (2010) Structural, photolysis and biological studies of the bis(mu(2)-chloro)-tris(triphenylphosphine)-di-copper(I) and chloro-tris(triphenylphosphine)-copper(I) complexes. Study of copper(I)–copper(I) interactions. Inorg Chim Acta 363:763-72 CrossRef
    16. Oxford Diffraction (2006) CRYSALIS CCD and CRYSALIS RED, version p171.29.2. Oxford Diffraction Ltd., Abingdon, Oxford
    17. Ozturk II, Hadjikakou SK, Hadjiliadis N, Kourkoumelis N, Kubicki M, Baril M, Butler IS, Balzarini J (2007) Synthesis, structural characterization, and biological studies of new antimony(III) complexes with thiones. The influence of the solvent on the geometry of the complexes. Inorg Chem 46:8652-661 CrossRef
    18. Ozturk II, Hadjikakou SK, Hadjiliadis N, Kourkoumelis N, Kubicki M, Tasiopoulos AJ, Scleiman H, Barsan MM, Butler IS, Balzarini J (2009) New antimony(III) bromide complexes with thioamides: synthesis, characterization, and cytostatic properties. Inorg Chem 48:2233-245 CrossRef
    19. Ozturk I, Filimonova S, Hadjikakou SK, Kourkoumelis N, Dokorou V, Manos MJ, Tasiopoulos AJ, Barsan MM, Butler IS, Milaeva ER, Balzarini J, Hadjiliadis N (2010) Structural motifs and biological studies of new antimony(III) iodide complexes with thiones. Inorg Chem 49:488-01 CrossRef
    20. Popov A, Davidovich R, Li I, Skulbeda A, Hu S-Z (2005) Cytotoxic and antitumor activity of antimony(III) nitrilotriacetate complexes M2SB(Nta)(HNta)·nH2O (M?=?NH4, Na; n?=?1, 2). Pharm Chem J 39:119 CrossRef
    21. Sheldrick GM (1990) Phase annealing in Shelx-90—direct methods for larger structures. Acta Cryst A 46:467-73 CrossRef
    22. Sheldrick GM (1997) SHELXL-97, program for the refinement of crystal structures. University of Gottingen, Gottingen
    23. Silvestru C, Socaciu C, Bara A, Haiduc I (1990) The 1st organoantimony(III) compounds possessing antitumor properties—diphenylantimony(III) derivatives of dithiophosphorus ligands. Anticancer Res 10:803-04
    24. Silvestru C, Haiduc L, Tiekink ERT, Devos D, Biesemans M, Willem R, Gielen M (1995) Synthesis, structural characterization and in vitro antitumor properties of triorganoantimony(V) disalicylates—crystal and molecular-structures of [5-Y-2-(Ho)C(6)H3coo](2)Sbme(3) (Y?=?H, Me, Meo). Appl Organomet Chem 9:597-07 CrossRef
    25. Thomsen R, Christensen MH (2006) MolDock: a new technique for high-accuracy molecular docking. J Med Chem 49:3315-321 CrossRef
    26. Tiekink ERT (2002) Antimony and bismuth compounds in oncology. Crit Rev Oncol Hematol 42:217-24 CrossRef
    27. Xanthopoulou MN, Hadjikakou SK, Hadjiliadis N, Kubicki M, Karkabounas S, Charalabopoulos K, Kourkoumelis N, Bakas T (2006) Synthesis and characterization of a new chloro-di-phenyltin(IV) complex with 2-mercapto-nicotinic acid: study of its influence upon the catalytic oxidation of linoleic acid to hydroperoxylinoleic acid by the enzyme lipoxygenase. J Organomet Chem 691:1780-789 CrossRef
    28. Xanthopoulou MN, Hadjikakou SK, Hadjiliadis N, Milaeva ER, Gracheva JA, Tyurin VY, Kourkoumelis N, Christoforidis KC, Metsios AK, Karkabounas S, Charalabopoulos K (2008) Biological studies of new organotin(IV) complexes of thioamide ligands. Eur J Med Chem 43:327-35 CrossRef
    29. Zartilas S, Kourkoumelis N, Hadjikakou SK, Hadjiliadis N, Zachariadis P, Kubicki M, Denisov AY, Butler IS (2007) A new silver(I) aggregate having an octagonal Ag4S4 core where mu(3)–S bonding interactions lead to a nanotube assembly that exhibits quasiaromaticity. Eur J Inorg Chem 1219-224
  • 作者单位:I. I. Ozturk (1) (6)
    A. K. Metsios (1) (4)
    S. Filimonova-Orlova (1) (5)
    N. Kourkoumelis (2)
    S. K. Hadjikakou (1)
    M. Manos (3)
    A. J. Tasiopoulos (3)
    S. Karkabounas (4)
    E. R. Milaeva (5)
    N. Hadjiliadis (1)

    1. Section of Inorganic and Analytical Chemistry, Department of Chemistry, University of Ioannina, 45110, Ioannina, Greece
    6. Section of Inorganic Chemistry Department of Chemistry, Nam?k Kemal University, Tekirdag, Turkey
    4. Department of Experimental Physiology, Medical School, University of Ioannina, Ioannina, Greece
    5. Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119992, Moscow, Russian Federation
    2. Medical Physics Laboratory, Medical School, University of Ioannina, Ioannina, Greece
    3. Department of Chemistry, University of Cyprus, 1678, Nicosia, Cyprus
文摘
Crystals of the [SbBr3(MMBZT)2] (1) complex (MMBZT?=?N-methyl-2-mercaptobenzothiazole) were grown from acetonitrile/methanol of the filtrate derived from the reaction between 3-methyl-2-mercaptobenzothiazole (MMBZT) in methanol, with antimony(III) bromide in acetonitrile. The crystal structure of 1 (C16H14Br3N2S4Sb) was determined by X-ray diffraction at 100(2)?K, in space group P-1, with a?=?10.738(2)??, b?=?11.387(3)??, c?=?11.439(3)??, α?=?62.764°, β?=?63.36(2)°, γ?=?85.074(2)°, and Z?=?2. The geometry around the metal center of complex 1 is square pyramidal, with two sulfur atoms from thione ligands and three bromide anions around Sb(III). Complex is monomer. The equatorial plane is formed by two sulfur and two bromide atoms in complex, in a cis-S, cis-Br arrangement. The in vitro cytotoxicity against leiomyosarcoma cells (LMS) of antimony(III) bromide complexes with thioamide ligands with formulae: [SbBr3(MMBZT)2] (1), [SbBr3(TU)2] (2), [SbBr3(MMI)2] (3), {[SbBr2(MBZIM)4]+·[Br]?/sup>·H2O} (4), {[SbBr2(μ 2-Br)(MMBZIM)2]2} (5), {[SbBr2(μ 2-Br)(EtMBZIM)2]2·MeOH} (6), {[SbBr3(μ 2-S-tHPMT)(tHPMT)] n } (7), {[SbBr2(μ 2-Br)(PYT)2) n } (8), {[SbBr2(μ 2-Br)(MTZD)2] n } (9), and {[SbBr5]2?/sup>[(PMTH2 +)2]} (10) (where TU?=?thiourea, MMI?=?methylimidazole, MBZIM?=?2-mercaptobenzimidazole, MMBZIM?=?2-mercapto-5-methyl-benzimidazole, EtMBZIM?=?5-ethoxy-2-mercaptobenzimidazole, tHPMT?=?2-mercapto-3,4,5,6-tetrahydro-pyrimidine, PYT?=?2-mercaptopyridine, MTZD?=?2-mercapto-thiazolidine, and PMTH?=?2-mercaptopyrimidine) were evaluated. Complex 8 shows the strongest activity against LMS cells with IC50 value 1.7?±?0.1?μΜ. The results are compared with their activity against human cervix carcinoma cell lines. Complexes 1, 6-strong class="a-plus-plus">9 were also tested for their inhibitory activity upon the catalytic peroxidation of linoleic acid to hydroperoxylinoleic acid by the enzyme lipoxygenase. Computational studies using multivariate linear regression and considering biological results (50% inhibitory concentration, IC50) as dependent variables derived a theoretical equation for IC50 values of the complexes studied. The calculated IC50 values are compared adequately with the experimental inhibitory activity of the complexes measured.

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