Copyright (c) 2016 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Antimicrobial Activity of L-Tryptophan Coordinated Copper(II) N,N-Donor Amino Acid Complexes
Corresponding Author(s) : D. Jesudurai
Asian Journal of Chemistry,
Vol. 28 No. 12 (2016): Vol 28 Issue 12
Abstract
Three L-tryptophan coordinated mixed amino acid copper(II) complexes of the type [Cu(L-Trp)(AA)] (where AA = L-proline, L-isoleucine and L-methionine) are synthesized. Two N,N-donor base-coordinated L-tryptophan complexes of the type [Cu(L-Trp)(B)] (where B = ethylene diamine and o-phenylene diamine) are also prepared in good yield. The stoichiometric reaction between metal and ligand is in the ratio of 1:1. The resulting complexes are characterized by UV-visible, FT-IR, EPR spectroscopic techniques and also by mass spectrometry. Infrared spectra show that amino acids act as bidentate ligands in all the complexes. Infrared spectroscopy confirms the ligand coordination to the metal ions through carboxyl and amino groups. The electrochemical behaviour of the complexes 1-5 was investigated using in the presence of 0.1 M PBS as supporting electrolyte. The antibacterial activity of complexes 1-5 was tested against Gram-negative and Gram-positive micro-organisms. There is an enhanced antibacterial activity was observed with complex 2 compared to the other complexes 1, 3, 4 and 5.
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- T.A. Churchward-Venne, C.H. Murphy, T.M. Longland and S.M. Phillips, Amino Acids, 45, 231 (2013); doi:10.1007/s00726-013-1506-0.
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- G. Wu, Amino Acids, 45, 407 (2013); doi:10.1007/s00726-013-1500-6.
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- D. Frankenberger and A. Khalid, Pak. J. Bot., 42, 1771 (2010).
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- R. Buchtík, Z. Trávnícek and J. Vanco, J. Inorg. Biochem., 116, 163 (2012); doi:10.1016/j.jinorgbio.2012.07.009.
- M. Grzeszczuk, A. Grańska and R. Szostak, Int. J. Electrochem. Sci., 8, 8951 (2013).
- Y.C. Zhu, G.J. Cheng and S.J. Dong, Biophys. Chem., 97, 129 (2002); doi:10.1016/S0301-4622(02)00045-5.
- B.R. James and R.J.P. Williams, J. Am. Chem. Soc., 61, 2007 (1961); doi:10.1039/JR9610002007.
- S. Belaid, A. Landreau, S. Djebbar, O. Benali-Baitich, G. Bouet and J.-P. Bouchara, J. Inorg. Biochem., 102, 63 (2008); doi:10.1016/j.jinorgbio.2007.07.001.
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References
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G. Wu, Z. Wu, Z. Dai, Y. Yang, W. Wang, C. Liu, B. Wang, J. Wang and Y. Yin, Amino Acids, 44, 1107 (2013); doi:10.1007/s00726-012-1444-2.
R. Azeredo, P.D. Rosales, A. Afonsa, H. Peres, A. Oliva and T. Benjamin, Fish Shellfish Immun., 42, 353 (2015); doi:10.1016/j.fsi.2014.11.024.
G. Wu, Amino Acids, 45, 407 (2013); doi:10.1007/s00726-013-1500-6.
A. Evangeliou and D. Vlassopoulos, Curr. Pharm. Biotechnol., 4, 211 (2003); doi:10.2174/1389201033489829#sthash.yZIzKCOZ.dpuf.
D.C. Bassett, I. Madzovska, K.S. Beckwith, T.B. Melø, B. Obradovic and P. Sikorski, Biomed. Mater., 10, 015006 (2015); doi:10.1088/1748-6041/10/1/015006.
D.K.C. Fung, W.Y. Lau, W.T. Chan and A. Yan, J. Bacteriol., 195, 4556 (2013); doi:10.1128/JB.00543-13.
L. Crépin, I. Sanchez, T. Nidelet, S. Dequin and C. Camarasa, Microb. Cell Fact., 13, 109 (2014); doi:10.1186/s12934-014-0109-0.
W. Meier-Augenstein and I. Fraser, Sci. Justice, 48, 153 (2008); doi:10.1016/j.scijus.2007.10.010.
D. Frankenberger and A. Khalid, Pak. J. Bot., 42, 1771 (2010).
M.S. Bukharov, V.G. Shtyrlin, A.S. Mukhtarov, G.V. Mamin, S. Stapf, C. Mattea, A.A. Krutikov, A.N. Il’in and N.Y. Serov, Phys. Chem. Chem. Phys., 16, 9411 (2014); doi:10.1039/c4cp00255e.
P.R. Reddy and A.M. Reddy, Proc. Indian Acad. Sci. (Chem. Sci.), 112, 593 (2000); doi:10.1007/BF02704366..
G. Indira Devi and P. Smitha, Int. Res. J. Biol. Sci., 2, 16 (2013).
A. Stanila, C. Braicu, S. Stanila and R.M. Pop, Not. Bot. Horti. Agrobo. Cluj-Napoca, 39, 124 (2011); doi:10.15835/nbha3926847.
Y.S. Rao, B. Prathima, S.A. Reddy, K. Madhavi and A.V. Reddy, J. Chin. Chem. Soc., 57(4A), 677 (2010); doi:10.1002/jccs.201000094.
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S.A.L. Rodriguez, T.Y. Wang, K.F. Bruggeman, C.C. Horgan, R. Li, R.J. Williams, C.L. Parish and D.R. Nisbet, J. Mater. Chem. B, 2, 7771 (2014); doi:10.1039/C4TB01391C.
J. Sabolovic, C.S. Tautermann, T. Loerting and K.R. Liedl, Inorg. Chem., 42, 2268 (2003); doi:10.1021/ic025967d.
Y.S. Rao, B. Prathima, S.A. Reddy, K. Madhavi and A.V. Reddy, J. Chil. Chem. Soc., 57, 677 (2010); doi:10.1002/jccs.201000094.
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K. Ashis Patra, T. Gupta, S. Roy and A.R. Chakravarthy, Indian J. Chem., 47A, 643 (2008).
T. Kavitha, A. Kulandaisamy and P. Thillaiarasu, Int. J. Chem. Technol. Res., 4, 1571 (2012).
T. Rosu, M. Negoiu and V. Carcu, Rev. Roum. Chim., 51, 391 (2006).
P.R. Reddy and N. Raju, Indian J. Chem., 48A, 1638 (2009).
Aiyelabola, I.A. Ojo, A.C. Adebajo, G.O. Ogunlusi, O. Oyetunji, E.O. Akinkunmi and A.O. Adeoye, Adv. Biol. Chem., 2, 268 (2012); doi:10.4236/abc.2012.23034.
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I. Martí, A. Ferrer, J. Escorihuela, M.I. Burguete and S.V. Luis, Dalton Trans., 41, 6764 (2012); doi:10.1039/c2dt12459a.
W. Barnum, J. Inorg. Nucl. Chem., 21, 221 (1961); doi:10.1016/0022-1902(61)80297-2.
R.H. Holm and F.A. Cotton, J. Am. Chem. Soc., 80, 5658 (1958); doi:10.1021/ja01554a020.
F.A. Cotton and C.W. Wilkinson, Advanced Inorganic Chemistry, Interscience Publisher, New York, edn 3 (1972).
B. Gray and C.J. Ballhausen, J. Am. Chem. Soc., 85, 260 (1963); doi:10.1021/ja00886a002.
S.A. Komaei, G.A. Albada and J. Reedijk, Transition Met. Chem., 24, 104 (1999); doi:10.1023/A:1006993017555.
L. Rodríguez, E. Labisbal, A. Sousa-Pedrares, J.A. García-Vázquez, J. Romero, M.L. Durán, J.A. Real and A. Sousa, Inorg. Chem., 45, 7903 (2000); doi:10.1021/ic0602594.
C.C. Wagner and E.J. Baran, Acta Farm. Bonaerense, 23, 339 (2004).
T.H. Bennur, D. Srinivas and P. Ratnasamy, Micropor. Mesopor. Mater., 48, 111 (2001); doi:10.1016/S1387-1811(01)00345-6.
A. Garcia-Raso, J.J. Fiol, B. Adrover, V. Moreno, I. Mata, E. Espinosa and E. Molins, J. Inorg. Biochem., 95, 77 (2003); doi:10.1016/S0162-0134(03)00121-1.
K. Nakomoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley, New York, p. 14 (1977).
A. Trivella, T. Gaillard, R.H. Stote and P. Hellwig, J. Chem. Phys., 132, 115105 (2010); doi:10.1063/1.3356027.
C.C. Wagner and E.J. Baran, Acta Farm. Bonaerense, 21, 287 (2002).
G. Aruldhas, Molecular Structure and Spectroscopy, McGraw-Hill Publishing Company, New Delhi, p. 191 (2005).
R. Buchtík, Z. Trávnícek and J. Vanco, J. Inorg. Biochem., 116, 163 (2012); doi:10.1016/j.jinorgbio.2012.07.009.
M. Grzeszczuk, A. Grańska and R. Szostak, Int. J. Electrochem. Sci., 8, 8951 (2013).
Y.C. Zhu, G.J. Cheng and S.J. Dong, Biophys. Chem., 97, 129 (2002); doi:10.1016/S0301-4622(02)00045-5.
B.R. James and R.J.P. Williams, J. Am. Chem. Soc., 61, 2007 (1961); doi:10.1039/JR9610002007.
S. Belaid, A. Landreau, S. Djebbar, O. Benali-Baitich, G. Bouet and J.-P. Bouchara, J. Inorg. Biochem., 102, 63 (2008); doi:10.1016/j.jinorgbio.2007.07.001.
N. Dharmaraj, P. Viswanathamurthi and K. Natarajan, Transition Met. Chem., 26, 105 (2001); doi:10.1023/A:1007132408648.