Browse > Article
http://dx.doi.org/10.5012/bkcs.2010.31.9.2656

Spectroscopic, Redox and Biological Studies of Push-Pull Porphyrins and Their Metal Complexes  

Rajesh, K. (Department of Inorganic Chemistry, University of Madras)
Rahiman, A. Kalilur (PG & Research Department of Chemistry, The New College (Autonomous))
Bharathi, K. Shanmuga (Department of Inorganic Chemistry, University of Madras)
Sreedaran, S. (Department of Chemistry, Arignar Anna Government Arts College)
Gangadevi, V. (School of Biological Sciences, Madurai Kamaraj University)
Narayanan, V. (Department of Inorganic Chemistry, University of Madras)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.9, 2010 , pp. 2656-2664 More about this Journal
Abstract
We have synthesized a series of push-pull porphyrins containing both donor and acceptor substituents at the mesopositions and have examined their spectral and biological properties. The push-pull porphyrins containing both strong donor $NH_2$ and acceptor $NO_2$ at meso-positions, in which donor group condensed with the ligand, (2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formlyphenol (L) to form imine linkages with porphyrin. The Schiff base ligand 5-[4-(2,6-bis(4-methylpiperazine-1-yl-methyl)-4-iminomethylphenol)phenyl]-10,15,20-tris(4-nitrophenyl) porphyrin [$an_3$(TPP)L] can be synthesized from 2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formylphenol (L) and 5-(4-aminophenyl)-10, 15,20-tris(4-nitrophenyl)porphyrin. The push-pull porphyrin [$an_3$(TPP)L] was metallated to get copper, nickel and zinc complexes. The spectral, electrochemical, antibacterial, antifungal and cytotoxicity properties of all the donor- acceptor push-pull porphyrins and their complexes were characterized and studied.
Keywords
Push-Pull porphyrins; N-Methylpiperazine; Antibacterial; Cytotoxicity;
Citations & Related Records

Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 1
연도 인용수 순위
1 Carson, C. F.; Hammer, K. A.; Riley, T. V. Microbios. 1995, 82, 181.
2 Collins, C. H. Microbiological Methods; Butterworths: London, 1964; p 296.
3 Davidson, P. M.; Parish, M. E. Food Technology 1989, 43, 148.
4 Cannon, B. J. Pharm. Sci. 1993, 83, 435.
5 Negri, C.; Bernardi, R.; Braghetti, A.; Ricotti, G. C.; Scovassi, A. I. Carcinogenesis 1993, 142, 559.
6 Lazebnik, Y. A.; Kaufmann, S. H.; Desnoyers, S.; Poirier, G. G.; Earnshaw, W. C. Nature 1994, 371, 346.   DOI
7 Tewari, M.; Quan, L. T.; O’Rourke, K. Cell 1995, 81, 801.   DOI
8 Fang, J.; Sawa, T.; Akaike, T.; Greish, K.; Maeda, H. Int. J. Cancer. 2004, 109, 1.   DOI
9 Kadish, K. M.; Mc Adamas, C. A.; Han, B. C.; Franzen, M. M. J. Am. Chem. Soc. 1990, 112, 8364.   DOI
10 Battioni, F.; Brigaud, O.; Desvaux, H.; Mansuya, D.; Traylor, T. G. Tetrahedron Lett. 1991, 32, 2893.   DOI
11 Guo, C. C.; Tong, R. B.; Li, K. L. Bioorg. Med. Chem. 2004, 12, 2469.   DOI
12 LeCours, S. M.; Guan, H.-W.; DiMagno, S. G.; Wang, C. H.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1504.   DOI
13 Plater, M. J.; Aiken, S.; Bourhill, G. Tetrahedron 2002, 58, 2405.   DOI
14 Liu, W.; Liu, C.; Gong, C.; Lin, W.; Guo, C. Bioorg. Med. Chem. Lett. 2009, 19, 1647.   DOI
15 Dolmans, D. E.; Fukumura, D.; Jain, R. K. Nat. Rev. Cancer 2003, 3, 380.   DOI
16 Suslick, K. S.; Chen, C-T.; Meredith, G. R.; Cheng, L. T. J. Am. Chem. Soc. 1992, 114, 6928.   DOI
17 Chen, C-T.; Hsieh, S. J. J. Chin. Chem. Soc. 1997, 44, 23.
18 Dougherty, T. J. J. Clin. Laser Med. and Surg. 2002, 20, 3.   DOI
19 Peng, C. L.; Lai, P. S.; Chang, C. C.; Lou, P. J.; Shieh, M. J. Dyes and Pigments 2010, 84, 140.   DOI
20 Duff, J. C. J. Chem. Soc. 1941, 547.   DOI
21 Ojadi, E. C. A.; Linschitz, H.; Gouterman, M.; Walter, R. I.; Lindsey, J. S.; Wagner, R. W.; Droupadi, P. R.; Wang, W. J. Phys. Chem. 1993, 97, 13192.   DOI
22 Karolczak, J.; Kowalska, D.; Lukaszewicz, A.; Maciejewski, A.; Steer, R. P. J. Phys. Chem. A 2004, 108, 4570.   DOI
23 Kadish, K. M.; Caemelbecke, E. V. J Solid State Electrochem. 2003, 7, 254.   DOI
24 Stojiljkovic, I.; Kumar, V.; Srinivasan, N. Mol. Microbiol. 1999, 31, 429.   DOI
25 Berenbaum, M. C.; Akande, S. L.; Bonnets, R.; Kaur, H.; Ioannou, S.; White, R. D.; Winfield, U. J. Br. J. Cancer. 1986, 54, 717.   DOI
26 Gouterman, M.; Hall, R. J.; Khalil, G. E.; Martin, P. C.; Shankland, E. G.; Cerny, R. L. J. Am. Chem. Soc. 1989, 111, 3702.   DOI
27 Allison, R. R.; Downie, G. H.; Cuenca, R.; Hu, X. H.; Childs, C. J. H.; Sibata, C. H. Photodiagnosis Photodynamic Ther. 2004, 1, 27.   DOI
28 Venosa, G.; Fukuda, H.; Batlle, A.; MacRobert, A.; Casas, A. J. Photochem. Photobiol. B: Biol. 2006, 83, 129.   DOI
29 Crossley, M. J.; King, L. G. J. Chem. Soc., Perkin Trans. 1 1996, 1251.
30 Fukumura, D.; Kashiwagi, S.; Jain, R. K. Nat. Rev. Cancer 2006, 6, 521.   DOI
31 Durantini, E. N. J. Porphyrins Phthalocyanines 2000, 4, 233.   DOI
32 Stojiljkovic, I.; Stephen, M.; Jennifer, S.; Jadranka, B. J. Polym. Sci. Part A Polym. Chem. 2003, 41, 2297.   DOI
33 Melov, S.; Schneider, J. A.; Day, B. J. Nature Genetics 1998, 18, 159.   DOI   ScienceOn
34 Sen, A.; Krishnan, V. J. Chem. Soc., Faraday Trans. 1997, 93, 4281.   DOI
35 Gust, D.; Moore, T. A.; Luttrull, D. K.; Seely, G. R.; Bittersmann, E.; Bensasson, R. V.; RougeIe, M.; Land, E. J.; De Schryver, F. C.; Auweraer, M. V. Photochem. Photobiol. 1990, 51, 419.   DOI
36 Takahashi, K.; Hase, S.; Komura, T.; Imanaga, H.; Ohno, O. Bull. Chem. Soc. Jpn. 1992, 65, 1475.   DOI
37 Dahal, S.; Krishnan, V. J. Photochem. Photobiol. A: Chem. 1995, 89, 105.   DOI
38 Gong, L. G.; Dolphin, D. Can. J. Chem. 1985, 63, 401.   DOI
39 Gong, L. G.; Dolphin, D. Can. J. Chem. 1985, 63, 406.   DOI
40 Harriman, A.; Hosie, H. J. Chem. Soc., Faraday Trans. 2 1981, 77, 1695.   DOI
41 Harriman, A.; Hosie, H. J. Photochem. 1981, 15, 163.   DOI
42 Collman, J. P.; Gagne, R. R.; Reed, C. A.; Halbert, T. A.; Lang, G.; Robinson, W. T. J. Am. Chem. Soc. 1975, 97, 1427.   DOI
43 Milgrom, L. R. J. Chem. Soc., Perkin. Trans. 1 1984, 12, 1483.
44 Giraudeau, A.; Callot, H. J.; Jordon, J.; Ezhar, I.; Gross, M. J. Am. Chem. Soc. 1979, 101, 3857.   DOI
45 You, Y.; Gibson, S. L.; Detty, M. R. Bioorg. Med. Chem. 2005, 13, 5968.   DOI
46 Baldwin, J. E.; Crossley, M. J.; DeBernardis, J. Tetrahedron 1982, 38, 685.   DOI
47 Shine, A. G.; Padilla, A. G.; Wu, S. M. J. Org. Chem. 1979, 44, 4069.   DOI
48 Catalano, M. M.; Crossley, M. J.; Harding, M. M.; King, L. M. J. Chem. Soc., Chem. Commun. 1984, 1535.
49 Sen, A.; Krishnan, V. Tetrahedron Lett. 1996, 37, 8437.   DOI