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

Medicinal Chemistry Research

Volumn 21, Issue 11, 2012, Pages 3523-3531

  Ozturk, I I ^a,e   Metsios, A K ^a,b   Filimonova Orlova, S ^a,b   Kourkoumelis, N ^b   Hadjikakou, S K ^a   Manos, M ^c   Tasiopoulos, A J ^d   Karkabounas, S ^c   Milaeva, E R ^d   Hadjiliadis, N ^a  

^a UNIVERSITY OF IOANNINA   (Greece)

^b UNIVERSITY OF IOANNINA   (Greece)

^c UNIVERSITY OF CYPRUS   (Cyprus)

^d MOSCOW STATE UNIVERSITY   (Russian Federation)

^e NAMIK KEMAL UNIVERSITY   (Turkey)

Author keywords

3 Methyl 2 mercaptobenzothiazole; Antimony(III) bromide complexes; Antitumor activity; Bioinorganic medicinal chemistry; Lipoxygenase

Indexed keywords

ANION; ANTIMONY DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; BROMINE DERIVATIVE; LINOLEIC ACID; LIPOXYGENASE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ATOM; BIOLOGICAL ACTIVITY; CANCER CELL; CONCENTRATION RESPONSE; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYTOTOXICITY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LEIOMYOSARCOMA; LIPID PEROXIDATION; STRUCTURE ACTIVITY RELATION; UTERINE CERVIX CARCINOMA; X RAY DIFFRACTION;

EID: 84871408032     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9905-9     Document Type: Article

References (29)

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 9:522-525
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 3554-3562
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 ehrlichascites tumor. Anticancer Res 11:1651-1655
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 3661-3667
7. Buchwald SL, Fisher RA, DavisWM(1989) Synthesis and structure of novel antimony thiametallacycles. Organometallics 8:2082-2084
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 1718-1728
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 266:392-399
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 12:931-939
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 48:38-45
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 358:2861-2866
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 100:1176-1186
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 363:763-772
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 46:8652-8661
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 48:2233-2245
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 49:488-501
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
21. Sheldrick GM (1990) Phase annealing in Shelx-90 -direct methods for larger structures. Acta Cryst A 46:467-473
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 10:803-804
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 9:597-607
25. Thomsen R, Christensen MH (2006) MolDock: A new technique for high-Accuracy molecular docking. J Med Chem 49:3315-3321
26. Tiekink ERT (2002) Antimony and bismuth compounds in oncology. Crit Rev Oncol Hematol 42:217-224
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-diphenyltin (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 691:1780-1789
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 43:327-335
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 1219-1224