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NOVEL ANTIMONY(III) HALIDE COMPLEXES WITH SOME N-ALKYL THIOUREAS: SYNTHESIS, CHARACTERIZATION AND STUDY OF THEIR EFFECT UPON THE CATALYTIC OXIDATION OF LINOLEIC ACID TO HYDROPEROXYLINOLEIC ACID BY LIPOXYGENASE

Year 2017, Volume: 4 Issue: 1, 81 - 98, 09.01.2017
https://doi.org/10.18596/jotcsa.31798

Abstract

Four novel antimony(III) compounds (SbX3; X = Cl or Br) of thiourea derivatives; N-methylthiourea (NMTU)  and N-ethylthiourea (NETU) of formulae [SbCl3(NMTU)3] (1), [SbBr3(NMTU)3] (2), [SbCl3(NETU)3] (3) and [SbBr3(NETU)3] (4) were synthesized. These new antimony(III) halide compounds were characterized by melting point, elemental analysis, molar conductivity, FT-Infrared spectroscopy, FT-Raman spectroscopy, UV-Vis spectroscopy, NMR (1H and 13C) spectroscopy and TG-DTA analysis. The reactions of N-methylthiourea (NMTU) and N-ethylthiourea (NETU) with SbX3 (X = Cl or Br) in a 2:1 ligand/metal rate but unexpectedly products were formed in a 3:1 ligand/metal rate. The compounds are non-electrolytes in solution and spectroscopic data of the compounds are appropriate with six coordinate octahedral geometry by three halide ions and three sulfur atoms from thiourea ligands. N-methythiourea and N-ethylthiourea ligands behave as monodentate in compounds 1-4 with the binding through sulfur.  The influence of these compounds 14, N-methythiourea and N-ethylthiourea upon the catalytic peroxidation of linoleic acid to hyperoxolinoleic acid by lipoxygenase was kinetically studied. 

References

  • Norman NC, Editor. Chemistry of Arsenic, Antimony and Bismuth. Blackie Academic and Professional; 1998. ISBN: 978-0-7514-0389-3.
  • Sun H, Editor. Biological Chemistry of Arsenic, Antimony and Bismuth. Wiley. 2010. ISBN: 978-0-470-71390-7.
  • Parrilha GL, Dias RP, Rocha WR, Mendes IC, Benítez D, Varela J, Cerecetto H, M. González M, Melo CML, Neves JKAL, Pereira VRA, Beraldo H. 2-Acetylpyridine and 2-benzoylpyridine-derived thiosemicarbazones and their antimony(III) complexes exhibit high anti-trypanosomal activity. Polyhedron, 2012; 31; 614-21. DOI:10.1016/j.poly.2011.10.018.
  • Ajaz H, Hussain S, Altaf M, Stoeckli-Evans H, Isab AA, Mahmood R, Altaf S, Ahmad S. Synthesis and Characterization of Antimony(III) Complexes of Thioamides, and Crystal Structure of {[Sb(Imt)2Cl2]2((2-Imt)}Cl2(Imt=Imidazolidine-2-thione). Chinese Journal of Chemistry, 2011; 29; 254-58. DOI: 10.1002/cjoc.201190074.
  • Barnes NA, Godfrey SM, Pritchard RG, Ratcliffe S. The reactions of SbX3 (X = Cl, Br, I) with N-methylbenzothiazole-2-thione (mbtt) and N-methylbenzothiazole-2-selone (mbts). Formation of the mixed mer/fac-complex [mer-SbBr3(mbts)2(μ-mbts)fac-SbBr3(mbts)2]•CH2Cl2. Polyhedron, 2010; 29; 1822-32. DOI:10.1016/j.poly.2010.02.029.
  • Bukvetskii BV, Sedakova TV, Mirochnik AG. Crystal structure and luminescence of antimony(III) bromide with aniline. Journal of Structural Chemistry. 2009; 50; 322-27. DOI:10.1007/s10947-009-0044-9.
  • Barnes NA, Godfrey SM, Pritchard RG, Ratcliffe S. 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. European Journal of Inorganic Chemistry. 2008; 3661–67. DOI: 10.1002/ejic.200800252.
  • Yin HD, Zhai J, Sun YY, Wang DQ. Synthesis, characterizations and crystal structures of new antimony (III) complexes with dithiocarbamate ligands. Polyhedron. 2008; 27; 663-70. DOI:10.1016/j.poly.2007.10.019.
  • Hadjikakou SK, Ozturk II, Banti CN, Kourkoumelis N, Hadjiliadis N. Recent advances on antimony(III/V) compounds with potential activity against tumor cells. Journal of Inorganic Biochemistry. 2015; 153; 293-305. DOI:10.1016/j.jinorgbio.2015.06.006.
  • 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. Inorganica Chimica Acta. 2005; 358; 2861–66. DOI:10.1016/j.ica.2004.06.028.
  • Ozturk II, Hadjikakou SK, Hadjiliadis N, Kourkoumelis N, Kubicki M, Baril M, Butler IS, Balzarini J. Synthesis, structural characterization, and biological studies of new antimony(III) complexes with thiones. The influence of the solvent on the geometry of the complexes. Inorganic Chemistry. 2007; 46; 8652–61. DOI: 10.1021/ic700756e.
  • Ozturk II, Hadjikakou SK, Hadjiliadis N, Kourkoumelis N, Kubicki M, Tasiopoulos AJ, Scleiman H, Barsan MM, Butler IS, Balzarini J. New antimony(III) bromide complexes with thioamides: synthesis, characterization, and cytostatic properties. Inorganic Chemistry. 2009; 48; 2233–45. DOI: 10.1021/ic8019205.
  • Hadjikakou SK, Ozturk II, Xanthopoulou MN, Zachariadis PC, Zartilas S, Karkabounas S and Hadjiliadis N. Synthesis, structural characterization and biological study of new organotin(IV), silver(I) and antimony(III) complexes with thioamides. Journal of Inorganic Biochemistry. 2008; 102; 1007-15. DOI: 10.1016/j.jinorgbio.2007.12.027.
  • Ozturk I, Filimonova S, Hadjikakou SK, Kourkoumelis N, Dokorou V, Manos MJ, Tasiopoulos AJ, Barsan MM, Butler IS, Milaeva ER, Balzarini J, Hadjiliadis N. Structural motifs and biological studies of new antimony(III) iodide complexes with thiones. Inorganic Chemistry. 2010; 49; 488–501. DOI: 10.1021/ic901442e.
  • Ozturk II, Metsios AK, Filimonova-Orlova S, Kourkoumelis N, Hadjikakou SK, Manos E, Tasiopoulos AJ, Karkabounas S, Milaeva ER and Hadjiliadis N. 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. 2012; 21; 3523-31. DOI 10.1007/s00044-011-9905-9.
  • Ozturk II, Kourkoumelis N, Hadjikakou SK, Manos MJ, Tasiopoulos AJ, Butler IS, Balzarini J and Hadjiliadis N. Interaction of antimony(III) chloride with thiourea, 2-mercapto-5-methyl-benzimidazole, 3-methyl-2-mercaptobenzothiazole, 2-mercaptopyrimidine, and 2-mercaptopyridine. Journal of Coordination Chemistry. 2011; 64; 3859-71. DOI: 10.1080/00958972.2011.633603.
  • Ozturk II, Banti CN, Manos MJ, Tasiopoulos AJ, Kourkoumelis N, Charalabopoulos K and Hadjikakou SK. Synthesis, characterization and biological studies of new antimony(III) halide complexes with ω-thiocaprolactam. Journal of Inorganic Biochemistry. 2012; 109; 57-65. DOI: 10.1016/j.jinorgbio.2012.01.014.
  • Ozturk II, Urgut OS, Banti CN, Kourkoumelis N, Owczarzak AM, Kubicki M, Charalabopoulos K and Hadjikakou SK. Synthesis, structural characterization and cytotoxicity of the antimony(III) chloride complex with N,N-dicyclohexyldithiooxamide Polyhedron. 2013; 52; 1403-10. DOI: 10.1016/j.poly.2012.04.038.
  • Ozturk II, Urgut OS, Banti CN, Kourkoumelis N, Owczarzak AM, Kubicki M and Hadjikakou SK. Synthesis, structural characterization and cytostatic properties of N,N-dicyclohexyldithiooxamide complexes of antimony(III) halides (SbX3, X: Br or I). Polyhedron. 2014; 70; 172-79. DOI: 10.1016/j.poly.2013.12.025.
  • Han A, Ozturk II, Banti CN, Kourkoumelis N, Manoli M, Tasiopoulos AJ, Owczarzak AM, Kubicki M and Hadjikakou SK. Antimony(III) halide compounds of thioureas: Structures and biological activity. Polyhedron. 2014; 79; 151-60. DOI: 10.1016/j.poly.2014.05.014.
  • Urgut OS, Ozturk II, Banti CN, Kourkoumelis N, Manoli M, Tasiopoulos AJ and Hadjikakou SK. New antimony(III) halide complexes with dithiocarbamate ligands derived from thiuram degradation: The effect of the molecule's close contacts on in vitro cytotoxic activity. Materials Science and Engineering C. 2016; 58; 396–408. DOI: 10.1016/j.msec.2015.08.030.
  • Urgut OS, Ozturk II, Banti CN, Kourkoumelis N, Manoli M, Tasiopoulos AJ and Hadjikakou SK. Addition of tetraethylthiuram disulfide to antimony(III) iodide; synthesis, characterization and biological activity. Inorganica Chimica Acta. 2016; 443; 141-150. DOI: 10.1016/j.ica.2015.12.028.
  • Samuelsson B, Dahlen SE, Lindgren J, Rouzer CA, Serhan CN. Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science. 1987; 237; 1171-76. DOI: 10.1126/science.2820055
  • Knapp MJ, Klinman JP. Kinetic Studies of Oxygen Reactivity in Soybean Lipoxygenase-1. Biochemistry. 2003; 42; 11466-75. DOI: 10.1021/bi0300884.
  • Ding XZ, Kuszynski CA, El-Metwally TH, Adrian TE. Lipoxygenase Inhibition Induced Apoptosis, Morphological Changes, and Carbonic Anhydrase Expression in Human Pancreatic Cancer Cells. Biochemical and Biophysical Research Communications. 1999; 266; 392-99. DOI: 10.1006/bbrc.1999.1824.
  • Pidgeon GP, Lysaght J, Krishnamoorthy S, Reynolds JV, O’Byrne K, Nie D, Honn KV. Lipoxygenase metabolism: roles in tumor progression and survival. Cancer Metastasis Reviews. 2007; 26; 26 (2007) 503-24. DOI: 10.1007/s10555-007-9098-3.
  • Bourne S, Koch KR. Intramolecular hydrogen-bond controlled unidentate co-ordination of potentially chelating N-acyl-N′-alkylthioureas: crystal structure of cis-bis(N-benzoyl-N′-propylthiourea) dichloroplatinum(II). Journal of the Chemical Society, Dalton Transactions. 1993; 13; 2071–72. DOI: 10.1039/DT9930002071.
  • Kucukguzel I, Kucukguzel SG, Rollas S, Kiras M. Some 3-Thioxo/alkylthio-1,2,4-triazoles with a substituted thiourea moiety as possible antimycobacterials. Bioorganic Medicinal Chemistry Letters. 2001; 11; 1703–07. DOI: 10.1016/S0960-894X(01)00283-9.
  • Venkatachalam TK, Sudbeck EA, Uckun FM. Regiospecific synthesis, X-ray crystal structure and biological activities of 5-bromothiophenethyl thioureas. Tetrahedron Letters. 2001; 42; 6629–32. DOI: 10.1016/S0040-4039(01)01290-4.
  • Campo RD, Criado JJ, Gheorghe R, Gonzalez FJ, Hermosa MR, Sanz F, Manzano JL, Monte E, Rodrıguez-Fernandez E. N-benzoyl-N′-alkylthioureas and their complexes with Ni(II), Co(III) and Pt(II) – crystal structure of 3-benzoyl-1-butyl-1-methyl-thiourea: activity against fungi and yeast. Journal of Inorganic Biochemistry. 2004; 98; 1307–14. DOI: 10.1016/j.jinorgbio.2004.03.019.
  • Ahmad S, Isab AA, Ahmad S. 1H, 13C, 15N NMR and IR Spectroscopic Studies of a Rh(II) Complex of Thiourea. Journal of Coordination Chemistry. 2003; 56; 1587-95. DOI: 10.1080/00958970310001641688.
  • Rodríguez-Fernández E, Manzano JL, Benito JJ, Hermosa R, Monte E, Criado JJ. Thiourea, triazole and thiadiazine compounds and their metal complexes as antifungal agents. Journal of Inorganic Biochemistry. 2005; 99; 1558-72. DOI: 10.1016/j.jinorgbio.2005.05.004.
  • Plutín AM, Alvarez A, Mocelo R, Ramos R, Castellano EE, da Silva MM, Colina-Vegas L, Pavan FR, Batista AA. Anti-Mycobacterium tuberculosis activity of platinum(II)/N,N-disubstituted-N′-acyl thiourea complexes. Inorganic Chemistry Communications. 2016; 63; 74–80. DOI: 10.1016/j.inoche.2015.11.020.
  • Schwade VD, Kirsten L, Hagenbach A, Lang ES, Abram U. Indium(III), lead(II), gold(I) and copper(II) complexes with isophthaloylbis(thiourea) ligands. Polyhedron. 2013; 55; 155–61. DOI: 10.1016/j.poly.2013.03.008.
  • Bowmaker GA, Pakawatchai C, Saithong S, Skelton BW, White AH, Structural and spectroscopic studies of some adducts of silver(I) halides withthiourea and N-ethyl substituted thioureas. Dalton Transactions. 2010; 39; 4391–4404. DOI: 10.1039/C001398F.
  • Hough E, Nicholson DG. Stereochemical role of lone pairs in main-group elements. Part 2. Structure and bonding in trichloro(tetramethylthiourea)antimony(III) studied by means of X-ray crystallography and antimony-121 Mössbauer spectroscopy. Journal of the Chemical Society, Dalton Transactions. 1981; 10; 2083-87. DOI: 10.1039/DT9810002083.
  • Xanthopoulou MN, Hadjikakou SK, Hadjiliadis N, Milaeva ER, Gracheva YA, Tyurin VY, Kourkoumelis N, Christoforidis KC, Metsios AK, Karkabounas S, and Charalabopoulos K. Biological studies of new organotin(IV) complexes of thioamide ligands. European Journal of Medicinal Chemistry. 2008; 43; 327-35. DOI: 10.1016/j.ejmech.2007.03.028.
  • Xanthopoulou MN, Hadjikakou SK, Hadjiliadis N, Kubicki M, Karkabounas S, Charalabopoulos K, Kourkoumelis N, and Bakas T. 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. Journal of Organometallic Chemistry. 2006; 691; 1780-89. DOI: 10.1016/j.jorganchem.2005.11.073.
  • Glick D, Editor. Methods of Biochemical Analysis, Volume 2. Interscience Publishers. 1955. ISBN: 9780471304593.
  • Lopez-Nicolas JM, Bru R, Sanchez-Ferrer A, Carcia-Carmona A. An Octaethylene Glycol Monododecyl Ether-Based Mixed Micellar Assay for Lipoxygenase Acting at Neutral pH. Analytical Biochemistry. 1994; 221; 410-15. DOI: 10.1006/abio.1994.1435.
  • Axelrod B, Cheesbrough TM, Laakso S. [53] Lipoxygenase from soybeans: EC 1.13.11.12 Linoleate:oxygen oxidoreductase. Methods Enzymology. 1981; 71; 441-451. DOI:10.1016/0076-6879(81)71055-3.
  • Refat MS, Killa HMA, Fetooh H. Spectroscopic and thermal characterization of Cu(II), Co(II), Ni(II) and Mn(II) complexes of fluorescent dye 4-N,N-dimethyl-ethanolamine-N-allyl-1,8-naphthalimide (4DMEAN). Journal of Molecular Structure. 2010; 983; 122–132. DOI:10.1016/j.molstruc.2010.08.041.
  • Nadeem S, Rauf MK, Ahmad S, Ebihara M, Tirmizi SA, Bashir SA, Badshah A. Synthesis and characterization of palladium(II) complexes of thioureas. X-ray structures of [Pd(N,N'-dimethylthiourea)4]Cl2.2H2O and [Pd(tetramethylthiourea)4]Cl2. Transition Metal Chemistry. 2009; 34; 197–202. DOI: 10.1007/s11243-008-9177-5.
Year 2017, Volume: 4 Issue: 1, 81 - 98, 09.01.2017
https://doi.org/10.18596/jotcsa.31798

Abstract

References

  • Norman NC, Editor. Chemistry of Arsenic, Antimony and Bismuth. Blackie Academic and Professional; 1998. ISBN: 978-0-7514-0389-3.
  • Sun H, Editor. Biological Chemistry of Arsenic, Antimony and Bismuth. Wiley. 2010. ISBN: 978-0-470-71390-7.
  • Parrilha GL, Dias RP, Rocha WR, Mendes IC, Benítez D, Varela J, Cerecetto H, M. González M, Melo CML, Neves JKAL, Pereira VRA, Beraldo H. 2-Acetylpyridine and 2-benzoylpyridine-derived thiosemicarbazones and their antimony(III) complexes exhibit high anti-trypanosomal activity. Polyhedron, 2012; 31; 614-21. DOI:10.1016/j.poly.2011.10.018.
  • Ajaz H, Hussain S, Altaf M, Stoeckli-Evans H, Isab AA, Mahmood R, Altaf S, Ahmad S. Synthesis and Characterization of Antimony(III) Complexes of Thioamides, and Crystal Structure of {[Sb(Imt)2Cl2]2((2-Imt)}Cl2(Imt=Imidazolidine-2-thione). Chinese Journal of Chemistry, 2011; 29; 254-58. DOI: 10.1002/cjoc.201190074.
  • Barnes NA, Godfrey SM, Pritchard RG, Ratcliffe S. The reactions of SbX3 (X = Cl, Br, I) with N-methylbenzothiazole-2-thione (mbtt) and N-methylbenzothiazole-2-selone (mbts). Formation of the mixed mer/fac-complex [mer-SbBr3(mbts)2(μ-mbts)fac-SbBr3(mbts)2]•CH2Cl2. Polyhedron, 2010; 29; 1822-32. DOI:10.1016/j.poly.2010.02.029.
  • Bukvetskii BV, Sedakova TV, Mirochnik AG. Crystal structure and luminescence of antimony(III) bromide with aniline. Journal of Structural Chemistry. 2009; 50; 322-27. DOI:10.1007/s10947-009-0044-9.
  • Barnes NA, Godfrey SM, Pritchard RG, Ratcliffe S. 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. European Journal of Inorganic Chemistry. 2008; 3661–67. DOI: 10.1002/ejic.200800252.
  • Yin HD, Zhai J, Sun YY, Wang DQ. Synthesis, characterizations and crystal structures of new antimony (III) complexes with dithiocarbamate ligands. Polyhedron. 2008; 27; 663-70. DOI:10.1016/j.poly.2007.10.019.
  • Hadjikakou SK, Ozturk II, Banti CN, Kourkoumelis N, Hadjiliadis N. Recent advances on antimony(III/V) compounds with potential activity against tumor cells. Journal of Inorganic Biochemistry. 2015; 153; 293-305. DOI:10.1016/j.jinorgbio.2015.06.006.
  • 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. Inorganica Chimica Acta. 2005; 358; 2861–66. DOI:10.1016/j.ica.2004.06.028.
  • Ozturk II, Hadjikakou SK, Hadjiliadis N, Kourkoumelis N, Kubicki M, Baril M, Butler IS, Balzarini J. Synthesis, structural characterization, and biological studies of new antimony(III) complexes with thiones. The influence of the solvent on the geometry of the complexes. Inorganic Chemistry. 2007; 46; 8652–61. DOI: 10.1021/ic700756e.
  • Ozturk II, Hadjikakou SK, Hadjiliadis N, Kourkoumelis N, Kubicki M, Tasiopoulos AJ, Scleiman H, Barsan MM, Butler IS, Balzarini J. New antimony(III) bromide complexes with thioamides: synthesis, characterization, and cytostatic properties. Inorganic Chemistry. 2009; 48; 2233–45. DOI: 10.1021/ic8019205.
  • Hadjikakou SK, Ozturk II, Xanthopoulou MN, Zachariadis PC, Zartilas S, Karkabounas S and Hadjiliadis N. Synthesis, structural characterization and biological study of new organotin(IV), silver(I) and antimony(III) complexes with thioamides. Journal of Inorganic Biochemistry. 2008; 102; 1007-15. DOI: 10.1016/j.jinorgbio.2007.12.027.
  • Ozturk I, Filimonova S, Hadjikakou SK, Kourkoumelis N, Dokorou V, Manos MJ, Tasiopoulos AJ, Barsan MM, Butler IS, Milaeva ER, Balzarini J, Hadjiliadis N. Structural motifs and biological studies of new antimony(III) iodide complexes with thiones. Inorganic Chemistry. 2010; 49; 488–501. DOI: 10.1021/ic901442e.
  • Ozturk II, Metsios AK, Filimonova-Orlova S, Kourkoumelis N, Hadjikakou SK, Manos E, Tasiopoulos AJ, Karkabounas S, Milaeva ER and Hadjiliadis N. 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. 2012; 21; 3523-31. DOI 10.1007/s00044-011-9905-9.
  • Ozturk II, Kourkoumelis N, Hadjikakou SK, Manos MJ, Tasiopoulos AJ, Butler IS, Balzarini J and Hadjiliadis N. Interaction of antimony(III) chloride with thiourea, 2-mercapto-5-methyl-benzimidazole, 3-methyl-2-mercaptobenzothiazole, 2-mercaptopyrimidine, and 2-mercaptopyridine. Journal of Coordination Chemistry. 2011; 64; 3859-71. DOI: 10.1080/00958972.2011.633603.
  • Ozturk II, Banti CN, Manos MJ, Tasiopoulos AJ, Kourkoumelis N, Charalabopoulos K and Hadjikakou SK. Synthesis, characterization and biological studies of new antimony(III) halide complexes with ω-thiocaprolactam. Journal of Inorganic Biochemistry. 2012; 109; 57-65. DOI: 10.1016/j.jinorgbio.2012.01.014.
  • Ozturk II, Urgut OS, Banti CN, Kourkoumelis N, Owczarzak AM, Kubicki M, Charalabopoulos K and Hadjikakou SK. Synthesis, structural characterization and cytotoxicity of the antimony(III) chloride complex with N,N-dicyclohexyldithiooxamide Polyhedron. 2013; 52; 1403-10. DOI: 10.1016/j.poly.2012.04.038.
  • Ozturk II, Urgut OS, Banti CN, Kourkoumelis N, Owczarzak AM, Kubicki M and Hadjikakou SK. Synthesis, structural characterization and cytostatic properties of N,N-dicyclohexyldithiooxamide complexes of antimony(III) halides (SbX3, X: Br or I). Polyhedron. 2014; 70; 172-79. DOI: 10.1016/j.poly.2013.12.025.
  • Han A, Ozturk II, Banti CN, Kourkoumelis N, Manoli M, Tasiopoulos AJ, Owczarzak AM, Kubicki M and Hadjikakou SK. Antimony(III) halide compounds of thioureas: Structures and biological activity. Polyhedron. 2014; 79; 151-60. DOI: 10.1016/j.poly.2014.05.014.
  • Urgut OS, Ozturk II, Banti CN, Kourkoumelis N, Manoli M, Tasiopoulos AJ and Hadjikakou SK. New antimony(III) halide complexes with dithiocarbamate ligands derived from thiuram degradation: The effect of the molecule's close contacts on in vitro cytotoxic activity. Materials Science and Engineering C. 2016; 58; 396–408. DOI: 10.1016/j.msec.2015.08.030.
  • Urgut OS, Ozturk II, Banti CN, Kourkoumelis N, Manoli M, Tasiopoulos AJ and Hadjikakou SK. Addition of tetraethylthiuram disulfide to antimony(III) iodide; synthesis, characterization and biological activity. Inorganica Chimica Acta. 2016; 443; 141-150. DOI: 10.1016/j.ica.2015.12.028.
  • Samuelsson B, Dahlen SE, Lindgren J, Rouzer CA, Serhan CN. Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science. 1987; 237; 1171-76. DOI: 10.1126/science.2820055
  • Knapp MJ, Klinman JP. Kinetic Studies of Oxygen Reactivity in Soybean Lipoxygenase-1. Biochemistry. 2003; 42; 11466-75. DOI: 10.1021/bi0300884.
  • Ding XZ, Kuszynski CA, El-Metwally TH, Adrian TE. Lipoxygenase Inhibition Induced Apoptosis, Morphological Changes, and Carbonic Anhydrase Expression in Human Pancreatic Cancer Cells. Biochemical and Biophysical Research Communications. 1999; 266; 392-99. DOI: 10.1006/bbrc.1999.1824.
  • Pidgeon GP, Lysaght J, Krishnamoorthy S, Reynolds JV, O’Byrne K, Nie D, Honn KV. Lipoxygenase metabolism: roles in tumor progression and survival. Cancer Metastasis Reviews. 2007; 26; 26 (2007) 503-24. DOI: 10.1007/s10555-007-9098-3.
  • Bourne S, Koch KR. Intramolecular hydrogen-bond controlled unidentate co-ordination of potentially chelating N-acyl-N′-alkylthioureas: crystal structure of cis-bis(N-benzoyl-N′-propylthiourea) dichloroplatinum(II). Journal of the Chemical Society, Dalton Transactions. 1993; 13; 2071–72. DOI: 10.1039/DT9930002071.
  • Kucukguzel I, Kucukguzel SG, Rollas S, Kiras M. Some 3-Thioxo/alkylthio-1,2,4-triazoles with a substituted thiourea moiety as possible antimycobacterials. Bioorganic Medicinal Chemistry Letters. 2001; 11; 1703–07. DOI: 10.1016/S0960-894X(01)00283-9.
  • Venkatachalam TK, Sudbeck EA, Uckun FM. Regiospecific synthesis, X-ray crystal structure and biological activities of 5-bromothiophenethyl thioureas. Tetrahedron Letters. 2001; 42; 6629–32. DOI: 10.1016/S0040-4039(01)01290-4.
  • Campo RD, Criado JJ, Gheorghe R, Gonzalez FJ, Hermosa MR, Sanz F, Manzano JL, Monte E, Rodrıguez-Fernandez E. N-benzoyl-N′-alkylthioureas and their complexes with Ni(II), Co(III) and Pt(II) – crystal structure of 3-benzoyl-1-butyl-1-methyl-thiourea: activity against fungi and yeast. Journal of Inorganic Biochemistry. 2004; 98; 1307–14. DOI: 10.1016/j.jinorgbio.2004.03.019.
  • Ahmad S, Isab AA, Ahmad S. 1H, 13C, 15N NMR and IR Spectroscopic Studies of a Rh(II) Complex of Thiourea. Journal of Coordination Chemistry. 2003; 56; 1587-95. DOI: 10.1080/00958970310001641688.
  • Rodríguez-Fernández E, Manzano JL, Benito JJ, Hermosa R, Monte E, Criado JJ. Thiourea, triazole and thiadiazine compounds and their metal complexes as antifungal agents. Journal of Inorganic Biochemistry. 2005; 99; 1558-72. DOI: 10.1016/j.jinorgbio.2005.05.004.
  • Plutín AM, Alvarez A, Mocelo R, Ramos R, Castellano EE, da Silva MM, Colina-Vegas L, Pavan FR, Batista AA. Anti-Mycobacterium tuberculosis activity of platinum(II)/N,N-disubstituted-N′-acyl thiourea complexes. Inorganic Chemistry Communications. 2016; 63; 74–80. DOI: 10.1016/j.inoche.2015.11.020.
  • Schwade VD, Kirsten L, Hagenbach A, Lang ES, Abram U. Indium(III), lead(II), gold(I) and copper(II) complexes with isophthaloylbis(thiourea) ligands. Polyhedron. 2013; 55; 155–61. DOI: 10.1016/j.poly.2013.03.008.
  • Bowmaker GA, Pakawatchai C, Saithong S, Skelton BW, White AH, Structural and spectroscopic studies of some adducts of silver(I) halides withthiourea and N-ethyl substituted thioureas. Dalton Transactions. 2010; 39; 4391–4404. DOI: 10.1039/C001398F.
  • Hough E, Nicholson DG. Stereochemical role of lone pairs in main-group elements. Part 2. Structure and bonding in trichloro(tetramethylthiourea)antimony(III) studied by means of X-ray crystallography and antimony-121 Mössbauer spectroscopy. Journal of the Chemical Society, Dalton Transactions. 1981; 10; 2083-87. DOI: 10.1039/DT9810002083.
  • Xanthopoulou MN, Hadjikakou SK, Hadjiliadis N, Milaeva ER, Gracheva YA, Tyurin VY, Kourkoumelis N, Christoforidis KC, Metsios AK, Karkabounas S, and Charalabopoulos K. Biological studies of new organotin(IV) complexes of thioamide ligands. European Journal of Medicinal Chemistry. 2008; 43; 327-35. DOI: 10.1016/j.ejmech.2007.03.028.
  • Xanthopoulou MN, Hadjikakou SK, Hadjiliadis N, Kubicki M, Karkabounas S, Charalabopoulos K, Kourkoumelis N, and Bakas T. 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. Journal of Organometallic Chemistry. 2006; 691; 1780-89. DOI: 10.1016/j.jorganchem.2005.11.073.
  • Glick D, Editor. Methods of Biochemical Analysis, Volume 2. Interscience Publishers. 1955. ISBN: 9780471304593.
  • Lopez-Nicolas JM, Bru R, Sanchez-Ferrer A, Carcia-Carmona A. An Octaethylene Glycol Monododecyl Ether-Based Mixed Micellar Assay for Lipoxygenase Acting at Neutral pH. Analytical Biochemistry. 1994; 221; 410-15. DOI: 10.1006/abio.1994.1435.
  • Axelrod B, Cheesbrough TM, Laakso S. [53] Lipoxygenase from soybeans: EC 1.13.11.12 Linoleate:oxygen oxidoreductase. Methods Enzymology. 1981; 71; 441-451. DOI:10.1016/0076-6879(81)71055-3.
  • Refat MS, Killa HMA, Fetooh H. Spectroscopic and thermal characterization of Cu(II), Co(II), Ni(II) and Mn(II) complexes of fluorescent dye 4-N,N-dimethyl-ethanolamine-N-allyl-1,8-naphthalimide (4DMEAN). Journal of Molecular Structure. 2010; 983; 122–132. DOI:10.1016/j.molstruc.2010.08.041.
  • Nadeem S, Rauf MK, Ahmad S, Ebihara M, Tirmizi SA, Bashir SA, Badshah A. Synthesis and characterization of palladium(II) complexes of thioureas. X-ray structures of [Pd(N,N'-dimethylthiourea)4]Cl2.2H2O and [Pd(tetramethylthiourea)4]Cl2. Transition Metal Chemistry. 2009; 34; 197–202. DOI: 10.1007/s11243-008-9177-5.
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Details

Journal Section Articles
Authors

İbrahim İsmet Öztürk

Publication Date January 9, 2017
Submission Date July 23, 2016
Published in Issue Year 2017 Volume: 4 Issue: 1

Cite

Vancouver Öztürk İİ. NOVEL ANTIMONY(III) HALIDE COMPLEXES WITH SOME N-ALKYL THIOUREAS: SYNTHESIS, CHARACTERIZATION AND STUDY OF THEIR EFFECT UPON THE CATALYTIC OXIDATION OF LINOLEIC ACID TO HYDROPEROXYLINOLEIC ACID BY LIPOXYGENASE. JOTCSA. 2017;4(1):81-98.