Copyright (c) 2019 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Preparation of New Biologically Active and Water Soluble Dyes: Characterization, Aggregation and Extraction of Metal Ions from Solutions
Corresponding Author(s) : Naceur Hamdi
Asian Journal of Chemistry,
Vol. 31 No. 6 (2019): Vol 31 Issue 6
Abstract
The synthesis of metallo-phthalocyanines complexes (M = Co, Ni, Cu, Zn) containing azo dye were described in this study. The metallophthalocyanines have been supported by elemental analysis, UV-visible, FT-IR and NMR. The aggregation of phthalocyanine compounds was investigated in different solvents and concentrations. The newly synthesized metallophthalocyanines possess modest antibacterial activity against various Gram-positive and Gram-negative bacteria. Moreover, these complexes have been tested as antioxidant and presented remarkable activities by two different in vitro chemical assays. They were able to reduce DPPH % radical with IC50 values ranging from 3.8 to 7.5 μmol L-1 and some of them also reduced ABTS % radical cation.
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- E. Ben-Hur and W.-S. Chan, The Porphyrin Handbook-Applications of Phthalocyanines, Academic Press: New York (2003).
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- F. Dumoulin, M. Durmus, V. Ahsen and T. Nyokong, Coord. Chem. Rev., 254, 2792 (2010); https://doi.org/10.1016/j.ccr.2010.05.002.
- National Committee for Clinical Laboratory Standard, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Conidium – Forming Filamentous Fungi, Proposed Standard M38-P, Wayne: PA, USA (1998).
- O.E. Sielcken, L.A. Van de Kuil, W. Drenth, J. Schoonman and R.J.M. Nolte, J. Am. Chem. Soc., 112, 3086 (1990); https://doi.org/10.1021/ja00164a032.
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- S. Altun, A. Altindal and M. Bulut, Polyhedron, 49, 41 (2013); https://doi.org/10.1016/j.poly.2012.09.055.
- Y. Gok, H. Kantekin, M.B. Kiliçaslan and H. Alp, Dyes Pigments, 74, 692 (2007); https://doi.org/10.1016/j.dyepig.2006.05.001.
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- H. Yanik, D. Aydin, M. Durmus and V. Ahsen, J. Photochem. Photobiol., 206, 18 (2009); https://doi.org/10.1016/j.jphotochem.2009.05.005.
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References
N.B. McKeown, Phthalocyanine Materials: Synthesis, Structure, and Function, Cambridge University Press: Cambridge (1998).
E. Ben-Hur and W.-S. Chan, The Porphyrin Handbook-Applications of Phthalocyanines, Academic Press: New York (2003).
S. Makarov, C. Litwinski, E.A. Ermilov, O. Suvorova, B. Röder and D. Wöhrle, Chem. Eur. J., 12, 1468 (2006); https://doi.org/10.1002/chem.200500617.
N. Kobayashi, T. Furuyama and K. Satoh, J. Am. Chem. Soc., 133, 19642 (2011); https://doi.org/10.1021/ja208481q.
M. Köç, A.G. Gürek, F. Dumoulin and V. Ahsen, Turk. J. Chem., 36, 493 (2012); https://doi.org/10.3906/kim-1202-64.
J. Garcia, A. Gonzalez, A. Gouloumis, E.M. Maya, M.D. Perez, B.D. Rey, P. Vazquez and T. Torres, Turk. J. Chem., 22, 23 (1998).
G. Guillaud, J. Simon and G.P. Germain, Coord. Chem. Rev., 178-180, 1433 (1998); https://doi.org/10.1016/S0010-8545(98)00177-5.
R. Zhou, F. Josse, W. Göpel, Z.Z. Öztürk and Ö. Bekaroglu, Appl. Organomet. Chem., 10, 557 (1996); https://doi.org/10.1002/(SICI)1099-0739(199610)10:8<557::AIDAOC521>3.0.CO;2-3.
M.L. Rodriguez-Méndez, M. Gay and J.A. de Saja, J. Porphyr. Phthalocyan., 13, 1159 (2009); https://doi.org/10.1142/S1088424609001509.
D. Akyüz, B. Keskin, U. Sahintürk and A. Koca, Appl. Catal. B, 188, 217 (2016); https://doi.org/10.1016/j.apcatb.2016.02.003.
G. Simonneaux and P. Tagliatesta, J. Porphyr. Phthalocyan., 8, 1166 (2004); https://doi.org/10.1142/S1088424604000507.
J.H. Zagal, S. Griveau, J.F. Silva, T. Nyokong and F. Bedioui, Coord. Chem. Rev., 254, 2755 (2010); https://doi.org/10.1016/j.ccr.2010.05.001.
M. Bressan, N. d’Alessandro, L. Liberatore and A. Morvillo, Coord. Chem. Rev., 185-186, 385 (1999); https://doi.org/10.1016/S0010-8545(99)00024-7.
M.M. Ayhan, A. Singh, C. Hirel, A.G. Gürek, V. Ahsen, E. Jeanneau II, I. Ledoux-Rak, J. Zyss, C. Andraud and Y. Bretonnière, J. Am. Chem. Soc., 134, 3655 (2012). https://doi.org/10.1021/ja211064a.
D. Dini, M. Barthel and M. Hanack. Eur. J. Org. Chem., 3759 (2001). https://doi.org/10.1002/1099-0690(200110)2001:20<3759::AIDEJOC3759>3.0.CO;2-U.
G. de la Torre, P. Vazquez, F. Agullo-Lopez and T. Torre, Chem. Rev., 104, 3723 (2004). https://doi.org/10.1021/cr030206t.
F. Dumoulin and M. Durmus, eds.: T. Nyokong ad V. Ahsen, Photosensitizers in Medicine, Environment and Security, eds.; Springer: New York (2012).
V.N. Nemykin and E.A. Lukyanets, ARKIVOC, 136 (2010); https://doi.org/10.3998/ark.5550190.0011.104.
M.J. Cook, J. Mater. Chem., 6, 677 (1996); https://doi.org/10.1039/jm9960600677.
M. Kandaz, S.L.J. Michel and B.M. Hoffman, J. Porphyr. Phthalocyan., 7, 700 (2003); https://doi.org/10.1142/S1088424603000872.
M. Allen, W.M. Sharman and J.E. Van Lier, J. Porphyr. Phthalocyan., 5, 161 (2001); https://doi.org/10.1002/jpp.324.
M. Kandaz and O. Bekaro.Lu, Chem. Ber., 130, 1833 (1997); https://doi.org/10.1002/cber.19971301220.
N. Kobayashi, N. Sasaki, Y. Higashi and T. Osa, Inorg. Chem., 34, 1636 (1995); https://doi.org/10.1021/ic00111a004.
M.N. Yarasir, M. Kandaz, A. Koca and B. Salih, Polyhedron, 26, 1139 (2007); https://doi.org/10.1016/j.poly.2006.10.002.
A. Kalkan, S. Guner and Z.A. Bayir, Dyes Pigments, 74, 636 (2007); https://doi.org/10.1016/j.dyepig.2006.04.003.
K. Kameyama, A. Satake and Y. Kobuke, Tetrahedron Lett., 45, 7617 (2004); https://doi.org/10.1016/j.tetlet.2004.08.101.
A.C.H. Ng, X. Li and D.K.P. Ng, Macromolecules, 32, 5292 (1999); https://doi.org/10.1021/ma990367s.
A. Ogunsipe, T. Nyokong and M. Durmus, J. Porphyr. Phthalocyan., 11, 635 (2007); https://doi.org/10.1142/S1088424607000746.
M. Idowu and T. Nyokong, J. Lumin., 129, 356 (2009); https://doi.org/10.1016/j.jlumin.2008.11.005.
S. Moeno and T. Nyokong, J. Photochem. Photobiol., 203, 204 (2009); https://doi.org/10.1016/j.jphotochem.2009.01.021.
N. Masilela and T. Nyokong, Dyes Pigments, 84, 242 (2010); https://doi.org/10.1016/j.dyepig.2009.09.011.
Z. Biyiklioglu and H. Kantekin, Dyes Pigments, 80, 17 (2009); https://doi.org/10.1016/j.dyepig.2008.04.006.
H. Cakici, A.A. Esenpinar and M. Bulut, Polyhedron, 27, 3625 (2008); https://doi.org/10.1016/j.poly.2008.09.016.
H.A. Dincer, A. Koca, A. Gul and M.B. Kocak, Dyes Pigments, 76, 825 (2008); https://doi.org/10.1016/j.dyepig.2006.07.035.
M.S. Agirtas, Dyes Pigments, 79, 247 (2008); https://doi.org/10.1016/j.dyepig.2008.03.004.
Z. Biyiklioglu, S.Z. Yildiz and H. Kantekin, J. Organomet. Chem., 695, 1729 (2010); https://doi.org/10.1016/j.jorganchem.2010.04.014.
I. Acar, Z. Biyiklioglu, A. Koca and H. Kantekin, Polyhedron, 29, 1475 (2010); https://doi.org/10.1016/j.poly.2010.01.032.
Z. Biyiklioglu, I. Acar and H. Kantekin, Inorg. Chem. Commun., 11, 630 (2008); https://doi.org/10.1016/j.inoche.2008.02.030.
F. Dumoulin, M. Durmus, V. Ahsen and T. Nyokong, Coord. Chem. Rev., 254, 2792 (2010); https://doi.org/10.1016/j.ccr.2010.05.002.
National Committee for Clinical Laboratory Standard, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Conidium – Forming Filamentous Fungi, Proposed Standard M38-P, Wayne: PA, USA (1998).
O.E. Sielcken, L.A. Van de Kuil, W. Drenth, J. Schoonman and R.J.M. Nolte, J. Am. Chem. Soc., 112, 3086 (1990); https://doi.org/10.1021/ja00164a032.
M. Kandaz, A.T. Bilgiçli and A. Altindal, Synth. Met., 160, 52 (2010); https://doi.org/10.1016/j.synthmet.2009.09.039.
S. Altun, A. Altindal and M. Bulut, Polyhedron, 49, 41 (2013); https://doi.org/10.1016/j.poly.2012.09.055.
Y. Gok, H. Kantekin, M.B. Kiliçaslan and H. Alp, Dyes Pigments, 74, 692 (2007); https://doi.org/10.1016/j.dyepig.2006.05.001.
H.A. Dincer, A. Gul and M.B. Kocak, J. Porphyr. Phthalocyan., 8, 1204 (2004); https://doi.org/10.1142/S1088424604000544.
Y. Arslanoglu and E. Hamuryudan, Dyes Pigments, 75, 150 (2007); https://doi.org/10.1016/j.dyepig.2006.05.019.
H. Yanik, D. Aydin, M. Durmus and V. Ahsen, J. Photochem. Photobiol., 206, 18 (2009); https://doi.org/10.1016/j.jphotochem.2009.05.005.
M. Durmus, M.M. Ayhan, A.G. Gurek and V. Ahsen, Dyes Pigments, 77, 570 (2008); https://doi.org/10.1016/j.dyepig.2007.08.010.
H. Engelkamp and R.J.M. Nolte, J. Porphyr. Phthalocyan., 4, 454 (2000); https://doi.org/10.1002/1099-1409(200008)4:5<454::AIDJPP261>3.0.CO;2-D.
S.-C. Qiu, Q. Li, J. Zhang, Z.-Z. Gao, Y.-Q. Zhang, S.-F. Xue, Q.-J. Zhu, X. Xiao and Z. Tao, J. Incl. Phenom. Macrocycl. Chem., 86, 1 (2016); https://doi.org/10.1007/s10847-016-0634-z.
I. Kostova, S. Raleva, P. Genova and R. Argirova, Bioinorg. Chem. Appl., 2006, Article ID 68274 (2006); https://doi.org/10.1155/BCA/2006/68274.
S. Kirkiachiarian, R. Bakhchinian, H. Chidiak, M. Mazmanian and C. Planche, Ann. Pharm. Fr., 57, 251 (1999).