BibTex RIS Cite

Synthesis and Characterization of CoII, NiII, CuII and ZnII Cation Complexes with Tyrptophan. Investigation of Their Biological Properties ​

Year 2013, Volume: 41 Issue: 2, 167 - 177, 01.06.2013

Abstract

The complexes of CoII, NiII, CuII and ZnII metal cations with tryptophan amino acid were synthesized and characterized by FT-IR, TG/DrTG-DTA, UV-Vis spectroscopy and elemental analysis methods. The complexes were synthesized with high purity. The results of the elemental analysis indicated that the complexes contain two molecules of tryptophan as monoanionic bis-chelated ligands per mole formula unit that are coordinated acidic oxygen κ-O and amine grops κ-N and two moles coordinated aqua ligands in CoII, NiII and ZnII complexes, the CuII has just one mole aqua ligand so its geometry is square pyramidal. The others have octahedral geometry.

References

  • R. Bakhtiar, E.I. Ochiai, Pharmacological applications of inorganic complexes. General Pharmacol., 32 (1999) 525-540.
  • J.R.J. Sorensen, H. Sigel, Metal Ions in Biological Systems, Marcel Dekker, New York, 1982.
  • M. Kato, Y. Muto, Factors affecting the magnetic properties of dimeric copper(II) complexes, Coord. Chem. Rev., 92 (1988) 45.
  • R. Nagar, Syntheses, characterization, and microbial activity of some transition metal complexes involving potentially active O and N donor heterocyclic ligands., J. Inorg. Biochem., 40 (1990) 349.
  • G. Cavigiolio, L. Benedetto, E. Boccaleri, D. Colangelo, I. Viano, D. Osella, Pt(II) complexes with different N-donor aromatic ligands for specific inhibition of telomerase, Inorg. Chim. Acta, 305 (2000) 61.
  • K. Agarwal, A. Sharma, G. Talukder, Effects of copper on mammalian cell components, Chem-Biol. Interact., 691 (1989) 1. S.E. Bryan, D.L. Vizard, D.A. Beary, R.A. LaBiche, K.J. Hardy, Partitioning of zinc and copper within subnuclear nucleoprotein particles, Nucleic Acids Res., 9 (1981) 5811.
  • M. Chikira, DNA-fiber EPR spectroscopy as a tool to study DNA-metal complex interactions: DNA binding of hydrated Cu(II) ions and Cu(II) complexes of amino acids and peptides., J. Inorg. Biochem., 102 (2008) 1016.
  • P.K. Pallaghy, A.P. Melnikova, E.C. Jimenez, B.M. Olivera, R.S. Norton, Solution structure of contryphan-R, a naturally-occurring disulfide-bridged octapeptide containing D-tryptophan: comparison with protein loops, Biochemistry, 38(35) (1999) 11553.
  • L. Patthy, E.L. Smith, Reversible modification of arginine residues. Application to sequence studies by restriction of tryptic hydrolysis to lysine residues, J. Biol. Chem., 250 (1975) 557.
  • G.J. Cox, H. King, “L-Tryptophane, Org. Synth.Coll., 2 (1943) 612.
  • E.R. Radwanski, R.L. Last, Tryptophan biosynthesis and metabolism: biochemical and molecular genetics, Plant Cell, 7 (1995) 921.
  • F. Polyak, W.D. Lubell, Rigid Dipeptide Mimics: Synthesis of Enantiopure 5- and 7-Benzyl and 5,7-Dibenzyl Indolizidinone Amino Acids via Enoliza- tion and Alkylation of delta-Oxo alpha,omega-Di-[N- (9-(9-phenylfluorenyl))amino]azelate Esters, J. Org. Chem., 63 (1998) 5937.
  • F.A. Cotton, V.W. Day, E.E. Hazen Jr., S. Larsen, S.T.K. Wong, Structure of bis(methylguanidinium) monohydrogen orthophosphate. Model for the arginine-phosphate interactions at the active site of staphylococcal nuclease and other phosphohydrolytic enzyimes, J. Am. Chem. Soc., 96 (1974) 4471.
  • M.B. Strom, O. Rekdal, J.S. Svendsen., Antimicrobial activity of short arginine- and tryptophan-rich peptides, J. Pept. Sci., 8 (2002) 431.
  • A. Stanila, A. Marcu, D. Rusu, M. Rusu, L. David, Spectroscopic studies of some copper(II) complexes with amino acids, J. Mol. Struc. 834–836 (2007) 364.
  • M.Z. Iqbal, S. Khurshid, M.S. Iqbal, Antibacterial activity of copper-amino acid complexes, J. Pak. Med. Assoc., 40 (1990) 221.
  • T. Venelinov, S. Arpadjan, I. Karadjova, J. Beattie, Properties of the copper(II)-histidine complex obtained after dialysis of human plasma with histidine, Acta Pharm., 56 (2006) 105.
  • D.L. Stone, D.K. Smith, A.C. Whitwood, Copper amino- acid complexes - towards encapsulated metal centres, Polyhedron, 23 (2004) 1709.
  • Z.H. Chohan, M. Arif, M.A. Akhtar, C.T. Supuran, Metal-based antibacterial and antifungal agents: synthesis, characterization, and in vitro biological evaluation of Co(II), Cu(II), Ni(II), and Zn(II) complexes with amino acid-derived compounds, Bioinorg. Chem. App., (2006) 1.
  • (a) D.A. Köse, H. Necefoğlu, Synthesis and Characterization of Bis(Nicotinamide) M-Hydroxyben- zoate Complexes of Co(II), Ni(II), Cu(II) and Zn(II), J. Therm. Anal. Cal., 93(2), (2008) 509. (b) D.A. Köse, H. Necefoğlu, H. İcbudak, Synthesis and characterization of N,N-diethylnicotinamide- acetylsalicylato complexes of Co(II), Ni(II), Cu(II), and Zn(II)J. Coord. Chem., 61(21), (2008) 3508. (c) D.A. Köse, G. Gökçe, S. Gökçe, İ. Uzun, bis(N,N- diethylnicotinamide) p-chlorobenzoate complexes of Ni(II), Zn(II) and Cd(II), J. Therm. Anal. Cal., 95(1), (2009) 247.
  • K. Nakamoto, Infrared and raman spectra of inorganic and coordination compounds, 5th edn. Interscience- Wiley, NewYork, (1997)59.
  • (a) B. Kaitner, N. Paulic, N. Raos, Stereochemistry of Complexes with N-Alkylated Amino Acids. III. Crystal Structure and Conformational Analysis of bis-(L-N,N- Dimethylisoleucinato)Copper(II), J. Coord. Chem., 22, (1991) 269. B. Kaitner, N. Paulic, G. Pavlovic, J. Sabolovic, Bis(l- N,N-dipropylalaninato)copper(II) - X-ray crystal structure, the crystal structure prediction and conformational analysis with a new force field, Polyhedron, 18, (1999) 2301.
  • M.A. Hitchman, L. Kwan, L.M. Engelhardt, A.H. White, Electron spin resonance and electronic spectra and crystal and molecular structures of copper(II) amino acid complexes, Chem. Soc. Dalton Trans., (1987) 457.
  • P.R. Levstein, R. Calvo, E.E. Castellano, O.E. Piro, B.E. Rivero, Molecular Structure and Exchange Interactions in trans-Bis(L-2-aminobutyrato) copper (II) and trans-Bis(D,L-2-aminobutyrato) copper (II), Inorg. Chem., 29, (1990) 3918.
  • S.M. Moussa, R.R. Fenton, B.J. Kennedy, R.O. Piltz, Hydrogen bonding in cis-bis(l-alaninato)copper(II): a single crystal neutron diffraction study, Inorg. Chim. Acta, 288(1), (1999) 29.
  • R.J. Butcher, G.M. Mockler, O. McKern, catena- Poly[[(pyridine-kN)copper(II)]-µ-N-salicylidene- glycinato-k4O,N,O’:O’], Acta. Cryst. E59, (2003) 1104.

Triptofan-CoII, NiII, CuII ve ZnII Katyon Komplekslerinin Sentezi ve Karakterizasyonu. Bu Komlekslerin Biyolojik Özelliklerinin İncelenmesi

Year 2013, Volume: 41 Issue: 2, 167 - 177, 01.06.2013

Abstract

T riptofan amino asidi-CoII, NiII, CuII ve ZnII metal katyon kompleksleri sentezlenmiş ve FT-IR, TG / DrTG- DTA, UV-Vis spektroskopisi ve elementel analiz yöntemleriyle karakterize edilmiştir. Kompleksler yüksek saflıkta sentezlendi. Elementel analiz sonuçları, komplekslerin, koordine asidik oksijen k-O ve amin grupları k-N olan bir mol formül birimi için mono anyonik bis-şelatlayıcı ligand olarak 2 triptofan molekülü ve CoII, NiII ve ZnIIkomplekslerinde iki mol koordine su ligandı içerdiğini göstermektedir. CuII bir mol su ligandına sahiptir ve dolayısıyla geometrisi kare piramittir. Diğerleri oktahedral geometriye sahiptir.Son olarak, komplekslerinin biyolojik aktiviteleri, anti-bakteriyel, anti-mikrobiyal ve anti-mantar olarak incelenmiştir. Sentezlenen metal kompleksleri disk difüzyon yöntemi ile anti-mikrobiyal aktivite için test edilmiştir. Bu çalışmaların sonuçları, metal komplekslerinin, bir veya daha fazla türe karşı daha fazla antimikrobiyal olduğunu göstermektedir. Ayrıca, metal komplekslerinin toplam antioksidan kapasitesinin Zn II -trp ve Ni II -trp kompleksleri için diğer komplekslerden daha fazla olduğu belirlenmiştir

References

  • R. Bakhtiar, E.I. Ochiai, Pharmacological applications of inorganic complexes. General Pharmacol., 32 (1999) 525-540.
  • J.R.J. Sorensen, H. Sigel, Metal Ions in Biological Systems, Marcel Dekker, New York, 1982.
  • M. Kato, Y. Muto, Factors affecting the magnetic properties of dimeric copper(II) complexes, Coord. Chem. Rev., 92 (1988) 45.
  • R. Nagar, Syntheses, characterization, and microbial activity of some transition metal complexes involving potentially active O and N donor heterocyclic ligands., J. Inorg. Biochem., 40 (1990) 349.
  • G. Cavigiolio, L. Benedetto, E. Boccaleri, D. Colangelo, I. Viano, D. Osella, Pt(II) complexes with different N-donor aromatic ligands for specific inhibition of telomerase, Inorg. Chim. Acta, 305 (2000) 61.
  • K. Agarwal, A. Sharma, G. Talukder, Effects of copper on mammalian cell components, Chem-Biol. Interact., 691 (1989) 1. S.E. Bryan, D.L. Vizard, D.A. Beary, R.A. LaBiche, K.J. Hardy, Partitioning of zinc and copper within subnuclear nucleoprotein particles, Nucleic Acids Res., 9 (1981) 5811.
  • M. Chikira, DNA-fiber EPR spectroscopy as a tool to study DNA-metal complex interactions: DNA binding of hydrated Cu(II) ions and Cu(II) complexes of amino acids and peptides., J. Inorg. Biochem., 102 (2008) 1016.
  • P.K. Pallaghy, A.P. Melnikova, E.C. Jimenez, B.M. Olivera, R.S. Norton, Solution structure of contryphan-R, a naturally-occurring disulfide-bridged octapeptide containing D-tryptophan: comparison with protein loops, Biochemistry, 38(35) (1999) 11553.
  • L. Patthy, E.L. Smith, Reversible modification of arginine residues. Application to sequence studies by restriction of tryptic hydrolysis to lysine residues, J. Biol. Chem., 250 (1975) 557.
  • G.J. Cox, H. King, “L-Tryptophane, Org. Synth.Coll., 2 (1943) 612.
  • E.R. Radwanski, R.L. Last, Tryptophan biosynthesis and metabolism: biochemical and molecular genetics, Plant Cell, 7 (1995) 921.
  • F. Polyak, W.D. Lubell, Rigid Dipeptide Mimics: Synthesis of Enantiopure 5- and 7-Benzyl and 5,7-Dibenzyl Indolizidinone Amino Acids via Enoliza- tion and Alkylation of delta-Oxo alpha,omega-Di-[N- (9-(9-phenylfluorenyl))amino]azelate Esters, J. Org. Chem., 63 (1998) 5937.
  • F.A. Cotton, V.W. Day, E.E. Hazen Jr., S. Larsen, S.T.K. Wong, Structure of bis(methylguanidinium) monohydrogen orthophosphate. Model for the arginine-phosphate interactions at the active site of staphylococcal nuclease and other phosphohydrolytic enzyimes, J. Am. Chem. Soc., 96 (1974) 4471.
  • M.B. Strom, O. Rekdal, J.S. Svendsen., Antimicrobial activity of short arginine- and tryptophan-rich peptides, J. Pept. Sci., 8 (2002) 431.
  • A. Stanila, A. Marcu, D. Rusu, M. Rusu, L. David, Spectroscopic studies of some copper(II) complexes with amino acids, J. Mol. Struc. 834–836 (2007) 364.
  • M.Z. Iqbal, S. Khurshid, M.S. Iqbal, Antibacterial activity of copper-amino acid complexes, J. Pak. Med. Assoc., 40 (1990) 221.
  • T. Venelinov, S. Arpadjan, I. Karadjova, J. Beattie, Properties of the copper(II)-histidine complex obtained after dialysis of human plasma with histidine, Acta Pharm., 56 (2006) 105.
  • D.L. Stone, D.K. Smith, A.C. Whitwood, Copper amino- acid complexes - towards encapsulated metal centres, Polyhedron, 23 (2004) 1709.
  • Z.H. Chohan, M. Arif, M.A. Akhtar, C.T. Supuran, Metal-based antibacterial and antifungal agents: synthesis, characterization, and in vitro biological evaluation of Co(II), Cu(II), Ni(II), and Zn(II) complexes with amino acid-derived compounds, Bioinorg. Chem. App., (2006) 1.
  • (a) D.A. Köse, H. Necefoğlu, Synthesis and Characterization of Bis(Nicotinamide) M-Hydroxyben- zoate Complexes of Co(II), Ni(II), Cu(II) and Zn(II), J. Therm. Anal. Cal., 93(2), (2008) 509. (b) D.A. Köse, H. Necefoğlu, H. İcbudak, Synthesis and characterization of N,N-diethylnicotinamide- acetylsalicylato complexes of Co(II), Ni(II), Cu(II), and Zn(II)J. Coord. Chem., 61(21), (2008) 3508. (c) D.A. Köse, G. Gökçe, S. Gökçe, İ. Uzun, bis(N,N- diethylnicotinamide) p-chlorobenzoate complexes of Ni(II), Zn(II) and Cd(II), J. Therm. Anal. Cal., 95(1), (2009) 247.
  • K. Nakamoto, Infrared and raman spectra of inorganic and coordination compounds, 5th edn. Interscience- Wiley, NewYork, (1997)59.
  • (a) B. Kaitner, N. Paulic, N. Raos, Stereochemistry of Complexes with N-Alkylated Amino Acids. III. Crystal Structure and Conformational Analysis of bis-(L-N,N- Dimethylisoleucinato)Copper(II), J. Coord. Chem., 22, (1991) 269. B. Kaitner, N. Paulic, G. Pavlovic, J. Sabolovic, Bis(l- N,N-dipropylalaninato)copper(II) - X-ray crystal structure, the crystal structure prediction and conformational analysis with a new force field, Polyhedron, 18, (1999) 2301.
  • M.A. Hitchman, L. Kwan, L.M. Engelhardt, A.H. White, Electron spin resonance and electronic spectra and crystal and molecular structures of copper(II) amino acid complexes, Chem. Soc. Dalton Trans., (1987) 457.
  • P.R. Levstein, R. Calvo, E.E. Castellano, O.E. Piro, B.E. Rivero, Molecular Structure and Exchange Interactions in trans-Bis(L-2-aminobutyrato) copper (II) and trans-Bis(D,L-2-aminobutyrato) copper (II), Inorg. Chem., 29, (1990) 3918.
  • S.M. Moussa, R.R. Fenton, B.J. Kennedy, R.O. Piltz, Hydrogen bonding in cis-bis(l-alaninato)copper(II): a single crystal neutron diffraction study, Inorg. Chim. Acta, 288(1), (1999) 29.
  • R.J. Butcher, G.M. Mockler, O. McKern, catena- Poly[[(pyridine-kN)copper(II)]-µ-N-salicylidene- glycinato-k4O,N,O’:O’], Acta. Cryst. E59, (2003) 1104.
There are 26 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Aliye Kaşarcı This is me

Dursun Ali Kose This is me

Gülçin Alp Avcı This is me

Emre Avci This is me

Publication Date June 1, 2013
Published in Issue Year 2013 Volume: 41 Issue: 2

Cite

APA Kaşarcı, A., Kose, D. A., Avcı, G. A., Avci, E. (2013). Synthesis and Characterization of CoII, NiII, CuII and ZnII Cation Complexes with Tyrptophan. Investigation of Their Biological Properties ​. Hacettepe Journal of Biology and Chemistry, 41(2), 167-177.
AMA Kaşarcı A, Kose DA, Avcı GA, Avci E. Synthesis and Characterization of CoII, NiII, CuII and ZnII Cation Complexes with Tyrptophan. Investigation of Their Biological Properties ​. HJBC. June 2013;41(2):167-177.
Chicago Kaşarcı, Aliye, Dursun Ali Kose, Gülçin Alp Avcı, and Emre Avci. “Synthesis and Characterization of CoII, NiII, CuII and ZnII Cation Complexes With Tyrptophan. Investigation of Their Biological Properties ​”. Hacettepe Journal of Biology and Chemistry 41, no. 2 (June 2013): 167-77.
EndNote Kaşarcı A, Kose DA, Avcı GA, Avci E (June 1, 2013) Synthesis and Characterization of CoII, NiII, CuII and ZnII Cation Complexes with Tyrptophan. Investigation of Their Biological Properties ​. Hacettepe Journal of Biology and Chemistry 41 2 167–177.
IEEE A. Kaşarcı, D. A. Kose, G. A. Avcı, and E. Avci, “Synthesis and Characterization of CoII, NiII, CuII and ZnII Cation Complexes with Tyrptophan. Investigation of Their Biological Properties ​”, HJBC, vol. 41, no. 2, pp. 167–177, 2013.
ISNAD Kaşarcı, Aliye et al. “Synthesis and Characterization of CoII, NiII, CuII and ZnII Cation Complexes With Tyrptophan. Investigation of Their Biological Properties ​”. Hacettepe Journal of Biology and Chemistry 41/2 (June 2013), 167-177.
JAMA Kaşarcı A, Kose DA, Avcı GA, Avci E. Synthesis and Characterization of CoII, NiII, CuII and ZnII Cation Complexes with Tyrptophan. Investigation of Their Biological Properties ​. HJBC. 2013;41:167–177.
MLA Kaşarcı, Aliye et al. “Synthesis and Characterization of CoII, NiII, CuII and ZnII Cation Complexes With Tyrptophan. Investigation of Their Biological Properties ​”. Hacettepe Journal of Biology and Chemistry, vol. 41, no. 2, 2013, pp. 167-7.
Vancouver Kaşarcı A, Kose DA, Avcı GA, Avci E. Synthesis and Characterization of CoII, NiII, CuII and ZnII Cation Complexes with Tyrptophan. Investigation of Their Biological Properties ​. HJBC. 2013;41(2):167-7.

HACETTEPE JOURNAL OF BIOLOGY AND CHEMİSTRY

Copyright © Hacettepe University Faculty of Science

http://www.hjbc.hacettepe.edu.tr/

https://dergipark.org.tr/tr/pub/hjbc