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Synthesis, Characterization and Antimicrobial Activity of Triazamacrocyclic Based Polymeric Ligand and its Polymer-Metal Complexes
Corresponding Author(s) : Saad M. Alshehri
Asian Journal of Chemistry,
Vol. 27 No. 6 (2015): Vol 27 Issue 6
Abstract
A triazamacrocyclic-based polymeric ligand (poly-H3L) was synthesized via polycondensation of 1,4,7-triazacyclonone-1,4,7-tripropionic acid (NOTPA) and ethylenediamine and polymer-metal complexes were prepared with Cu(II), Zn(II), In(III) and Ga(III) ions. All of the synthesized polymers were characterized by elemental, spectral and thermal analyses. The elemental and spectral data revealed that the poly-HLM(II) are five-coordinate complexes in which the metals are coordinated to three nitrogen atoms in the macrocycle and are coordinate covalently bound to two amide groups. However, the poly-LM(III) are six-coordinate complexes. The thermal kinetics, such as the activation energy and the thermodynamic parameters of the synthesized polymers were evaluated during pyrolysis using the Coats-Redfern equation. In addition, the antimicrobial activity of the synthesized polymers was evaluated against several microorganisms using agar-well diffusion methods. Among all of the polymer-metal complexes, the antimicrobial activity of the Cu(II)-chelated polymer exhibited the largest zone of inhibition.
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- A.B. Abibe, S.T. Amancio-Filho, J.F. dos Santos and E. Hage Jr., Mater. Des., 46, 338 (2013); doi:10.1016/j.matdes.2012.10.043.
- T. Ahamad and S.M. Alshehri, Polym. Int., 61, 1640 (2012); doi:10.1002/pi.4254.
- T. Ahamad and S.M.Alshehri, Spectrochim. Acta A, 96, 179 (2012); doi:10.1016/j.saa.2012.05.032.
- T. Ahamad and S.M. Alshehri, J. Coat. Technol. Res., 9, 515 (2012); doi:10.1007/s11998-011-9393-3.
- T. Ahamad and S.M. Alshehri, Spectrochim. Acta A, 108, 26 (2013); doi:10.1016/j.saa.2013.01.053.
- T. Ahamad, V. Kumar and N. Nishat, J. Biomed. Mater. Res. A, 88, 288 (2009); doi:10.1002/jbm.a.31872.
- T. Ahamad, V. Kumar, S. Parveen and N. Nishat, Appl. Organomet. Chem., 21, 1013 (2007); doi:10.1002/aoc.1331.
- T. Ahamad and N. Nishat, J. Appl. Polym. Sci., 107, 2280 (2008); doi:10.1002/app.27234.
- N. Nishat, T. Ahamad, M. Zulfequar and S. Hasnain, J. Appl. Polym. Sci., 110, 3305 (2008); doi:10.1002/app.28752.
- C.L. Ferreira, D.T.T. Yapp, D. Mandel, R.K. Gill, E. Boros, M.Q. Wong, P. Jurek and G.E. Kiefer, Bioconjug. Chem., 23, 2239 (2012); doi:10.1021/bc300348d.
- C. Förster, M. Schubert, H.J. Pietzsch and J. Steinbach, Molecules, 16, 5228 (2011); doi:10.3390/molecules16065228.
- J. Gao, N. Wang, X. Xiong, C. Chen, W. Xie, X. Ran, Y. Long, S. Yue and Y. Liu, CrystEngComm, 15, 3261 (2013); doi:10.1039/c3ce00049d.
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- A. Kiviniemi, J. Mäkelä, J. Mäkilä, T. Saanijoki, H. Liljenbäck, P. Poijärvi-Virta, H. Lönnberg, T. Laitala-Leinonen, A. Roivainen and P. Virta, Bioconjug. Chem., 23, 1981 (2012); doi:10.1021/bc300253t.
- J. Notni, K. Pohle and H.J. Wester, EJNMMI Res., 2, 28 (2012); doi:10.1186/2191-219X-2-28.
- J. Šimeček, P. Hermann, H.J. Wester and J. Notni, ChemMedChem, 8, 95 (2013); doi:10.1002/cmdc.201200471.
- J. Šimeček, M. Schulz, J. Notni, J. Plutnar, V. Kubíček, J. Havlíčková and P. Hermann, Inorg. Chem., 51, 577 (2012); doi:10.1021/ic202103v.
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- J.F. Desreux, Inorg. Chem., 19, 1319 (1980); doi:10.1021/ic50207a042.
- N. Nishat, T. Ahamad, S. Ahmad and S. Parveen, J. Coord. Chem., 64, 2639 (2011); doi:10.1080/00958972.2011.570754.
- N. Nishat, T. Ahamad, S.M. Alshehri and S. Parveen, Eur. J. Med. Chem., 45, 1287 (2010); doi:10.1016/j.ejmech.2009.11.047.
- P.F. Kelly, A.M.Z. Slawin and A. Soriano-Rama, J. Chem. Soc., Dalton Trans., 1, 53 (1996); doi:10.1039/dt9960000053.
- I.H. Hall, S.Y. Chen, B.J. Barnes and D.X. West, Met. Based Drugs, 6, 143 (1999); doi:10.1155/MBD.1999.143.
- A.B.P. Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, The Netherlands, p. 420 (1968).
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- D. Kivelson and R. Neiman, J. Chem. Phys., 35, 149 (1961); doi:10.1063/1.1731880.
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- R.S. Bottei and J.T. Fangman, J. Inorg. Nucl. Chem., 28, 1259 (1966); doi:10.1016/0022-1902(66)80452-9.
References
A.B. Abibe, S.T. Amancio-Filho, J.F. dos Santos and E. Hage Jr., Mater. Des., 46, 338 (2013); doi:10.1016/j.matdes.2012.10.043.
T. Ahamad and S.M. Alshehri, Polym. Int., 61, 1640 (2012); doi:10.1002/pi.4254.
T. Ahamad and S.M.Alshehri, Spectrochim. Acta A, 96, 179 (2012); doi:10.1016/j.saa.2012.05.032.
T. Ahamad and S.M. Alshehri, J. Coat. Technol. Res., 9, 515 (2012); doi:10.1007/s11998-011-9393-3.
T. Ahamad and S.M. Alshehri, Spectrochim. Acta A, 108, 26 (2013); doi:10.1016/j.saa.2013.01.053.
T. Ahamad, V. Kumar and N. Nishat, J. Biomed. Mater. Res. A, 88, 288 (2009); doi:10.1002/jbm.a.31872.
T. Ahamad, V. Kumar, S. Parveen and N. Nishat, Appl. Organomet. Chem., 21, 1013 (2007); doi:10.1002/aoc.1331.
T. Ahamad and N. Nishat, J. Appl. Polym. Sci., 107, 2280 (2008); doi:10.1002/app.27234.
N. Nishat, T. Ahamad, M. Zulfequar and S. Hasnain, J. Appl. Polym. Sci., 110, 3305 (2008); doi:10.1002/app.28752.
C.L. Ferreira, D.T.T. Yapp, D. Mandel, R.K. Gill, E. Boros, M.Q. Wong, P. Jurek and G.E. Kiefer, Bioconjug. Chem., 23, 2239 (2012); doi:10.1021/bc300348d.
C. Förster, M. Schubert, H.J. Pietzsch and J. Steinbach, Molecules, 16, 5228 (2011); doi:10.3390/molecules16065228.
J. Gao, N. Wang, X. Xiong, C. Chen, W. Xie, X. Ran, Y. Long, S. Yue and Y. Liu, CrystEngComm, 15, 3261 (2013); doi:10.1039/c3ce00049d.
H. Hong, Y. Zhang, H. Orbay, H.F. Valdovinos, T.R. Nayak, J. Bean, C.P. Theuer, T.E. Barnhart and W. Cai, Mol. Pharm., 10, 709 (2013); doi:10.1021/mp300507r.
A. Kiviniemi, J. Mäkelä, J. Mäkilä, T. Saanijoki, H. Liljenbäck, P. Poijärvi-Virta, H. Lönnberg, T. Laitala-Leinonen, A. Roivainen and P. Virta, Bioconjug. Chem., 23, 1981 (2012); doi:10.1021/bc300253t.
J. Notni, K. Pohle and H.J. Wester, EJNMMI Res., 2, 28 (2012); doi:10.1186/2191-219X-2-28.
J. Šimeček, P. Hermann, H.J. Wester and J. Notni, ChemMedChem, 8, 95 (2013); doi:10.1002/cmdc.201200471.
J. Šimeček, M. Schulz, J. Notni, J. Plutnar, V. Kubíček, J. Havlíčková and P. Hermann, Inorg. Chem., 51, 577 (2012); doi:10.1021/ic202103v.
K. Suzuki, M. Satake, J. Suwada, S. Oshikiri, H. Ashino, H. Dozono, A. Hino, H. Kasahara and T. Minamizawa, Nucl. Med. Biol., 38, 1011 (2011); doi:10.1016/j.nucmedbio.2011.02.015.
J.F. Desreux, Inorg. Chem., 19, 1319 (1980); doi:10.1021/ic50207a042.
N. Nishat, T. Ahamad, S. Ahmad and S. Parveen, J. Coord. Chem., 64, 2639 (2011); doi:10.1080/00958972.2011.570754.
N. Nishat, T. Ahamad, S.M. Alshehri and S. Parveen, Eur. J. Med. Chem., 45, 1287 (2010); doi:10.1016/j.ejmech.2009.11.047.
P.F. Kelly, A.M.Z. Slawin and A. Soriano-Rama, J. Chem. Soc., Dalton Trans., 1, 53 (1996); doi:10.1039/dt9960000053.
I.H. Hall, S.Y. Chen, B.J. Barnes and D.X. West, Met. Based Drugs, 6, 143 (1999); doi:10.1155/MBD.1999.143.
A.B.P. Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, The Netherlands, p. 420 (1968).
E. Cole, R.C.B. Copley, J.A.K. Howard, D. Parker, G. Ferguson, J.F. Gallagher, B. Kaitner, A. Harrison and L. Royle, J. Chem. Soc., Dalton Trans., 1619 (1994); doi:10.1039/dt9940001619.
D. Kivelson and R. Neiman, J. Chem. Phys., 35, 149 (1961); doi:10.1063/1.1731880.
K. Narang and V. Singh, Transition Met. Chem., 21, 5079 (1996); doi:10.1007/BF00229701.
H. Pan, T.F. Shupe and C.Y. Hse, J. Appl. Polym. Sci., 108, 1837 (2008); doi:10.1002/app.27756.
R.S. Bottei and J.T. Fangman, J. Inorg. Nucl. Chem., 28, 1259 (1966); doi:10.1016/0022-1902(66)80452-9.