Synthesis of pyrazole substituted methyl pheophorbide-a derivatives and their preliminary in vitro cell viabilities

Photochemical and Photobiological Sciences

Volumn 7, Issue 10, 2008, Pages 1273-1281

  Galindev, Oyunbileg ^a   Badraa, Narangerel ^a   Dalantai, Monkhoobor ^b   Sengee, Gerelt Ireedui ^a   Dorjnamjin, Demberelnyamba ^a   Shim, Young Key ^a  

^a Inje University   (South Korea)

^b NATIONAL UNIVERSITY OF MONGOLIA   (Mongolia)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 ACETYL 3 OXOBUTYL) 3 DEVINYLPHEOPHORBIDE ALPHA METHYL ESTER; 3 [[3,5 DIMETHYL 1 (2 HYDROXYETHYL) PYRAZOL 4 YL]METHYL] 3 DEVINYLPHEOPHORBIDE ALPHA METHYL ESTER; CHLORINE; CHLOROPHYLL A; METHYL PHEOPHORBIDE A DERIVATIVE; PHEOPHORBIDE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; CANCER THERAPY; CELL VIABILITY; CONFERENCE PAPER; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VITRO STUDY; LASER; NONHUMAN; PHOTODYNAMIC THERAPY; PHOTODYNAMICS; PHOTOSENSITIZATION; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY;

EID: 53749089275     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b802433m     Document Type: Conference Paper

References (27)

1. T. J. Dougherty An update on photodynamic therapy applications J. Clin. Laser Med. Surg. 2002 20 3 7
2. T. J. Dougherty C. J. Gomer B. W. Henderson G. Jori D. Kessel M. Korbelik J. Moan Q. Peng Photodynamic therapy J. Natl. Cancer Inst. 1998 90 889 905
3. G. Zheng W. R. Potter S. H. Camacho J. R. Missert G. Wang D. A. Bellnier B. W. Henderson M. A. J. Rodgers T. J. Dougherty R. K. Pandey Synthesis, photophysical properties, tumor uptake, and preliminary in vivo photosensitizing efficacy of a homologous series of 3-(1′-alkyloxy)ethyl-3- devinylpurpurin-18-N-alkylimides with variable lipophilicity J. Med. Chem. 2001 44 1540 1559
4. R. Bonnet Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy Chem. Soc. Rev. 1995 19
5. D. A. Firey M. A. J. Rodgers Photoproperties of silicon phthalocyanines, a potential photosensitizer for photodynamic therapy Photochem. Photobiol. 1987 45 535 538
6. A. Rungta G. Zheng J. R. Missert W. R. Potter T. J. Dougherty R. K. Pandey Purpurinimides as photosensitizers: Effect of the presence and position of the substituents in the in vivo photodynamic efficacy Bioorg. Med. Chem. Lett. 2000 10 1463 1466
7. A. R. Morgan A. Rampersaud R. W. Keck S. H. Selman Verdins: new photosensitizers for photodynamic therapy Photochem. Photobiol. 1987 46 441 444
8. M. Kobayashi, H. Kise, C. Tanielian, C. Wolff, M. Toriya, M. Nakazato, M. Sasaki, M. Matsuda and M. Hisatome, Photocleavage of DNA by Chlorophylls and Porphyrins-Electron Transfer from Nucleic Acid Base to Dyes in the Singlet Excited States, in Food Factors for Cancer Prevention, ed., H. Ohigashi,,, T. Osawa,,, J. Terao,,, S. Watanabe, and, T. Yoshikawa,, Springer-Verlag, Tokyo, 1997, pp. 572-576
9. A. G. Grichine A. Feofanov T. Karmakova N. Kazachkina E. Pecherskin R. Yakubovskaya A. Mironov M. Egret-Charlier P. Vigny Influence of substitution of 3-vinyl by 3-formyl group on the photodynamic properties of chlorin p6: molecular, cellular and in vivo studies Photochem. Photobiol. 2001 73 267 277
10. A. S. Brandis, Y. Salomon and A. Scherz, Chlorophyll sensitizers in photodynamic therapy, Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications, ed. by, B. Grimm,,, R. J. Porra,,, W. Rudiger, and, H. Scheer,, Springer, Dortrecht, 2006, pp. 461-483
11. R. K. Pandey A. B. Sumlin W. R. Potter D. A. Bellnier B. W. Henderson S. Constantine M. Aoudia M. R. J. Rodgers K. M. Smith T. J. Dougherty Structure and photodynamic efficacy among the alkyl ether analogous of chlorophyll-a derivatives Photochem. Photobiol. 1996 63 194 205
12. R. K. Pandey N. Jagerovic J. M. Ryan T. J. Dougherty K. M. Smith Syntheses and preliminary in vivo photodynamic efficacy of benzoporphyrin derivatives from phylloerythrin and rhodoporphyrin XV methyl esters and aspartyl amides Tetrahedron 1996 52 5349 5362
13. 2-hydroxybacteriochlorophyllide a methyl ester studies by fluorescence spectroscopy on Lewis lung carcinoma bearing mice Proc. SPIE 1994 2078 427 437
14. A. S. Brandis, Y. Salomon and A. Scherz, Bacteriochlorophyll sensitizers in photodynamic therapy, Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications, ed., B. Grimm,,, R. J. Porra,,, W. Rudiger, and, H. Scheer,, Springer, Dortrecht, 2006, pp. 485-494
15. G. Li A. Graham Y. Chen M. P. Dobhal J. Morgan G. Zheng A. Kozyrev A. Oseroff T. J. Dougherty R. K. Pandey Synthesis, comparative photosensitizing efficacy, human serum albumin (Site II) ability and intracellular localization characteristics of novel benzobacteriochlorins derived from vicdihydroxybacteriochlorins J. Med. Chem. 2003 46 349 5359
16. R. K. Pandey L. N. Goswami Y. Chen A. Gryshuk J. R. Missert A. Oseroff T. J. Dougherty Nature: A rich source for developing multifunctional agents. Tumor-imaging and photodynamic therapy Laser Surg. Med. 2006 38 445 467
17. I. M. Karnaukh A. S. Moskovkin G. V. Ponomarev Mass spectra of porphyrins containing β-diketone residues Chem. Heterocycl. Compd. 1993 29 1271 1276
18. A. V. Reshetnickov T. A. Babushkina G. V. Kirillova G. V. Ponomarev Synthesis and chemical transformations of porphyrins and chlorins with 2-acetyl-1-methyl-3-oxybutyl substituents Chem. Heterocycl. Compd. 2001 37 191 200
19. G. V. Ponomarev V. Y. Pavlov I. O. Konstantinov V. P. Timofeev B. G. Kimel Synthesis of pyrazoleporphyrins and pyrazolechlorins by cyclization of peripheral β-diketone groups of porphyrins and chlorins with phenylhydrazines. Russ. J. Org. Chem. 2003 39 1683 1684
20. S. A. Gamage J. A. Spicer G. W. Rewcastle J. Milton S. Sohal W. Dangerfield P. Mistry N. Vicker P. A. Charlton W. A. Denny Structure-activity relationships for pyrido-, imidazo-, pyrazolo-, pyrazino-, and pyrrolophenazinecarboxamides as topoisomerase-targeted anticancer agents J. Med. Chem. 2002 45 740 743
21. K. M. Smith D. A. Goff D. J. Simpson Meso substitution of chlorophyll derivatives: Direct route for transformation of bacteriopheophorbides-d into bacteriopheophorbides-c J. Am. Chem. Soc. 1985 107 4946 4954
22. A. F. Mironov A. N. Kozyrev P. Y. Perepyolkin New sensitizers for diagnosis and photodynamic therapy of malignant tissues Proc. SPIE 1994 2078 186 192
23. A. F. Mironov Synthesis and properties of new chlorin and bacteriochlorin photosensitizers Proc. SPIE 1996 2625 23 32
24. A. F. Mironov R. D. Ruziev V. S. Lebedeva Synthesis and chemical transformation of N-hydroxy- and N-hydroxyalkylcycloimides of chlorin p6, Russian J. Bioorg. Chem. 2004 30 466 476
25. 2-methoxycarbonyl moiety? An in vitro model study Photosynth. Res. 1999 61 23 31
26. 6 amide derivatives Mendeleev Commun. 2002 2 1 2
27. W. S. Ahn S. M. Bae S. W. Huh J. M. Lee S. E. Namkoong S.-J. Han C. K. Kim J.-K. Kim Y.-W. Kim Necrosis-like death with plasma membrane damage against cervical cancer cells by photodynamic therapy Int. J. Gynecol. Cancer 2004 14 475 482