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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)
  • Received : 2010.04.08
  • Accepted : 2010.07.20
  • Published : 2010.09.20

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

References

  1. Suslick, K. S.; Chen, C-T.; Meredith, G. R.; Cheng, L. T. J. Am. Chem. Soc. 1992, 114, 6928. https://doi.org/10.1021/ja00043a055
  2. Sen, A.; Krishnan, V. J. Chem. Soc., Faraday Trans. 1997, 93, 4281. https://doi.org/10.1039/a704663d
  3. 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. https://doi.org/10.1111/j.1751-1097.1990.tb01733.x
  4. Takahashi, K.; Hase, S.; Komura, T.; Imanaga, H.; Ohno, O. Bull. Chem. Soc. Jpn. 1992, 65, 1475. https://doi.org/10.1246/bcsj.65.1475
  5. Dahal, S.; Krishnan, V. J. Photochem. Photobiol. A: Chem. 1995, 89, 105. https://doi.org/10.1016/1010-6030(94)04017-V
  6. Gong, L. G.; Dolphin, D. Can. J. Chem. 1985, 63, 401. https://doi.org/10.1139/v85-066
  7. Gong, L. G.; Dolphin, D. Can. J. Chem. 1985, 63, 406. https://doi.org/10.1139/v85-067
  8. Harriman, A.; Hosie, H. J. Chem. Soc., Faraday Trans. 2 1981, 77, 1695. https://doi.org/10.1039/f29817701695
  9. Harriman, A.; Hosie, H. J. Photochem. 1981, 15, 163. https://doi.org/10.1016/0047-2670(81)85008-3
  10. Collman, J. P.; Gagne, R. R.; Reed, C. A.; Halbert, T. A.; Lang, G.; Robinson, W. T. J. Am. Chem. Soc. 1975, 97, 1427. https://doi.org/10.1021/ja00839a026
  11. Milgrom, L. R. J. Chem. Soc., Perkin. Trans. 1 1984, 12, 1483.
  12. Giraudeau, A.; Callot, H. J.; Jordon, J.; Ezhar, I.; Gross, M. J. Am. Chem. Soc. 1979, 101, 3857. https://doi.org/10.1021/ja00508a024
  13. You, Y.; Gibson, S. L.; Detty, M. R. Bioorg. Med. Chem. 2005, 13, 5968. https://doi.org/10.1016/j.bmc.2005.07.006
  14. Baldwin, J. E.; Crossley, M. J.; DeBernardis, J. Tetrahedron 1982, 38, 685. https://doi.org/10.1016/0040-4020(82)80211-1
  15. Shine, A. G.; Padilla, A. G.; Wu, S. M. J. Org. Chem. 1979, 44, 4069. https://doi.org/10.1021/jo01337a010
  16. Catalano, M. M.; Crossley, M. J.; Harding, M. M.; King, L. M. J. Chem. Soc., Chem. Commun. 1984, 1535.
  17. Sen, A.; Krishnan, V. Tetrahedron Lett. 1996, 37, 8437. https://doi.org/10.1016/0040-4039(96)01912-0
  18. Crossley, M. J.; King, L. G. J. Chem. Soc., Perkin Trans. 1 1996, 1251.
  19. Gouterman, M.; Hall, R. J.; Khalil, G. E.; Martin, P. C.; Shankland, E. G.; Cerny, R. L. J. Am. Chem. Soc. 1989, 111, 3702. https://doi.org/10.1021/ja00192a030
  20. Kadish, K. M.; Mc Adamas, C. A.; Han, B. C.; Franzen, M. M. J. Am. Chem. Soc. 1990, 112, 8364. https://doi.org/10.1021/ja00179a021
  21. Battioni, F.; Brigaud, O.; Desvaux, H.; Mansuya, D.; Traylor, T. G. Tetrahedron Lett. 1991, 32, 2893. https://doi.org/10.1016/0040-4039(91)80641-I
  22. Guo, C. C.; Tong, R. B.; Li, K. L. Bioorg. Med. Chem. 2004, 12, 2469. https://doi.org/10.1016/j.bmc.2004.01.045
  23. LeCours, S. M.; Guan, H.-W.; DiMagno, S. G.; Wang, C. H.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1504. https://doi.org/10.1021/ja952690q
  24. Plater, M. J.; Aiken, S.; Bourhill, G. Tetrahedron 2002, 58, 2405. https://doi.org/10.1016/S0040-4020(02)00109-6
  25. Liu, W.; Liu, C.; Gong, C.; Lin, W.; Guo, C. Bioorg. Med. Chem. Lett. 2009, 19, 1647. https://doi.org/10.1016/j.bmcl.2009.02.005
  26. Dolmans, D. E.; Fukumura, D.; Jain, R. K. Nat. Rev. Cancer 2003, 3, 380. https://doi.org/10.1038/nrc1071
  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. https://doi.org/10.1016/S1572-1000(04)00007-9
  28. Venosa, G.; Fukuda, H.; Batlle, A.; MacRobert, A.; Casas, A. J. Photochem. Photobiol. B: Biol. 2006, 83, 129. https://doi.org/10.1016/j.jphotobiol.2006.01.002
  29. Fukumura, D.; Kashiwagi, S.; Jain, R. K. Nat. Rev. Cancer 2006, 6, 521. https://doi.org/10.1038/nrc1910
  30. Durantini, E. N. J. Porphyrins Phthalocyanines 2000, 4, 233. https://doi.org/10.1002/(SICI)1099-1409(200004/05)4:3<233::AID-JPP200>3.0.CO;2-H
  31. Stojiljkovic, I.; Stephen, M.; Jennifer, S.; Jadranka, B. J. Polym. Sci. Part A Polym. Chem. 2003, 41, 2297. https://doi.org/10.1002/pola.10773
  32. Melov, S.; Schneider, J. A.; Day, B. J. Nature Genetics 1998, 18, 159. https://doi.org/10.1038/ng0298-159
  33. Dougherty, T. J. J. Clin. Laser Med. and Surg. 2002, 20, 3. https://doi.org/10.1089/104454702753474931
  34. Peng, C. L.; Lai, P. S.; Chang, C. C.; Lou, P. J.; Shieh, M. J. Dyes and Pigments 2010, 84, 140. https://doi.org/10.1016/j.dyepig.2009.07.008
  35. Duff, J. C. J. Chem. Soc. 1941, 547. https://doi.org/10.1039/jr9410000547
  36. Chen, C-T.; Hsieh, S. J. J. Chin. Chem. Soc. 1997, 44, 23.
  37. 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. https://doi.org/10.1021/j100152a025
  38. Karolczak, J.; Kowalska, D.; Lukaszewicz, A.; Maciejewski, A.; Steer, R. P. J. Phys. Chem. A 2004, 108, 4570. https://doi.org/10.1021/jp049898v
  39. Kadish, K. M.; Caemelbecke, E. V. J Solid State Electrochem. 2003, 7, 254. https://doi.org/10.1007/s10008-002-0306-3
  40. Stojiljkovic, I.; Kumar, V.; Srinivasan, N. Mol. Microbiol. 1999, 31, 429. https://doi.org/10.1046/j.1365-2958.1999.01175.x
  41. Berenbaum, M. C.; Akande, S. L.; Bonnets, R.; Kaur, H.; Ioannou, S.; White, R. D.; Winfield, U. J. Br. J. Cancer. 1986, 54, 717. https://doi.org/10.1038/bjc.1986.232
  42. Carson, C. F.; Hammer, K. A.; Riley, T. V. Microbios. 1995, 82, 181.
  43. Collins, C. H. Microbiological Methods; Butterworths: London, 1964; p 296.
  44. Davidson, P. M.; Parish, M. E. Food Technology 1989, 43, 148.
  45. Cannon, B. J. Pharm. Sci. 1993, 83, 435.
  46. Negri, C.; Bernardi, R.; Braghetti, A.; Ricotti, G. C.; Scovassi, A. I. Carcinogenesis 1993, 142, 559.
  47. Lazebnik, Y. A.; Kaufmann, S. H.; Desnoyers, S.; Poirier, G. G.; Earnshaw, W. C. Nature 1994, 371, 346. https://doi.org/10.1038/371346a0
  48. Tewari, M.; Quan, L. T.; O’Rourke, K. Cell 1995, 81, 801. https://doi.org/10.1016/0092-8674(95)90541-3
  49. Fang, J.; Sawa, T.; Akaike, T.; Greish, K.; Maeda, H. Int. J. Cancer. 2004, 109, 1. https://doi.org/10.1002/ijc.11644

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