Browse > Article
http://dx.doi.org/10.5012/bkcs.2011.32.1.169

Synthesis and Photodynamic Activities of Pyrazolyl and Cyclopropyl Derivatives of Purpurin-18 Methyl Ester and Purpurin-18-N-butylimide  

Yoon, Il (PDT Research Institute, School of Nano System Engineering, Inje University)
Park, Ho-Sung (PDT Research Institute, School of Nano System Engineering, Inje University)
Cui, Bing Cun (PDT Research Institute, School of Nano System Engineering, Inje University)
Kim, Jung-Hwa (PDT Research Institute, School of Nano System Engineering, Inje University)
Shim, Young-Key (PDT Research Institute, School of Nano System Engineering, Inje University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.1, 2011 , pp. 169-174 More about this Journal
Abstract
The synthesis of new pyrazolyl and cyclopropyl derivatives of purpurin-18 methyl ester and purpurin-18-N-butylimide 1a, 1b, 2a, 2b and 8 is described. The new compounds were characterized by NMR, UV-vis spectroscopy and mass spectrometry. UV-vis spectra of the new compounds showed long wavelength absorption of ranges 692 - 708 nm ($\lambda_{max}$). Photodynamic effects of the chlorin derivatives 1a, 1b, 2a and 2b were investigated by WST-1 assay in A549 cells, and showed good photodynamic activities with high photocytotoxicity and low cytotoxicity in the dark. In comparison between pyrazolyl and cyclopropyl derivatives, purpurin-18 methyl ester compounds 1a and 1b showed comparable photocytotoxicity result of the cell viabilities, otherwise, pyrazolyl derivative of purpurin-18-N-butylimide 2a showed better cell viabilities than those of cyclopropyl derivative 2b. And cyclopropyl derivative of purpurin-18-N-butylimide 2b showed higher dark cytotoxicity than that of others.
Keywords
Cyclopropyl and pyrazolyl units; In vitro study; Photodynamic therapy; Purpurin-18 methyl ester; Purpurin-18-N-butylimide;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
1 Smith, K. M. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975.
2 Kozyrev, A. N.; Alderfer, J. L.; Robinson, B. C. Tetrahedron 2003, 59, 499.   DOI   ScienceOn
3 Wang, J.-J.; Li, J.-Z.; Gryko, D.; Shim, Y. K. Bull. Korean Chem. Soc. 2006, 27, 1083.   DOI   ScienceOn
4 Galindev, O.; Badraa, N.; Shim, Y. K. J. Porphyrins Phthalocyanines 2007, 11, 829.   DOI
5 Rungta, A.; Zheng, G.; Missert, J. R.; Potter, W. R.; Dougherty, T. J.; Pandey, R. K. Bioorg. Med. Chem. Lett. 2000, 10, 1463.   DOI   ScienceOn
6 Nishizaki, M.; Meyn, R. E.; Levy, L. B.; Atkinson, E. N.; White, R. A.; Roth, J. A.; Ji, L. Clinical Cancer Research 2001, 7, 2887.
7 Zheng, G.; Potter, W. R.; Camacho, S. H.; Missert, J. R.; Wang, G.; Bellnier, D. A.; Henderson, B. W.; Rodgers, M. A. J.; Dougherty, T. J.; Pandey, R. K. J. Med. Chem. 2001, 44, 1540.   DOI   ScienceOn
8 Ngamwongsatit, P.; Banada, P. P.; Panbangred, W.; Bhunia, A. K. J. Microbiol. Methods 2008, 73, 211.   DOI   ScienceOn
9 Smith, K. M.; Goff, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.   DOI
10 Bonnet, R. In Chemical Aspects of Photodynamic Therapy; Gordon and Breach Science Publishers: Netherlands, 2000.
11 Pandey, R. K.; Zheng, G. In Porphyrins as Photosensitizers in Photodynamic Therapy, In The Porphyrin Handbook; Kadish, Smith, Guilard, Eds.; Academic Press: New York, 2000; Vol. 6, p 157.
12 Sharman, W. M.; van Lier, J. E.; Allen, C. M. Adv. Drug Delivery Rev. 2004, 56, 53.   DOI   ScienceOn
13 Kim, N. R.; Kim, S.; Kim, J. D.; Huh, D. S.; Shim, Y. K.; Choe, S. J. Bull. Korean Chem. Soc. 2009, 30, 205.   DOI   ScienceOn
14 Luguya, R.; Jensen, T. J.; Smith, K. M.; Vicente, M. G. H. Bioorg. Med. Chem. 2006, 14, 5890.   DOI   ScienceOn
15 Kessel, D. Photochem. Photobiol. 2008, 84, 809.   DOI   ScienceOn
16 Bayarmaa, B.; Bayarmaa, B.; Lee, W.-K.; Shim, Y. K. Bull. Korean Chem. Soc. 2008, 29, 237.   DOI   ScienceOn
17 Pandey, R. K. J. Porphyrins Phthalocyanines 2000, 4, 368.   DOI   ScienceOn
18 Faust, R. Eur. J. Org. Chem. 2001, 2797.
19 Manna, F.; Chimenti, F.; Fioravanti, R.; Bolasco, A.; Secci, D.; Chimenti, P.; Ferlini, C.; Scambia, G. Bioorg. Med. Chem. Lett. 2005, 15, 4632.   DOI   ScienceOn
20 Salaun, J.; Bair, M. S. Curr. Med. Chem. 1995, 2, 511.