Hydrophobicity parameters (Log P) of glycoconjugated porphyrins for photodynamic therapy evaluated by reversed phase HPLC

Journal of Porphyrins and Phthalocyanines

Volumn 8, Issue 11, 2004, Pages 1289-1292

  Hirohara, Shiho ^a   Obata, Makoto ^a   Ogura, Shun Ichiro ^b   Okura, Ichiro ^b   Higashida, Suguru ^c   Ohtsuki, Chikara ^d   Ogata, Shin Ichi ^d   Nishikawa, Yoshiko ^d   Takenaka, Makiko ^e   Ono, Hiroshi ^e   Mikata, Yuji ^a   Yano, Shigenobu ^a  

^a NARA WOMEN'S UNIVERSITY   (Japan)

^b Tokyo Institute of Technology ^*  (Japan)

^c Osaka City University   (Japan)

^d NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^e NATIONAL FOOD RESEARCH INSTITUTE   (Japan)

Author keywords

Glycoconjugated porphyrins; Log P; Photodynamic therapy

Indexed keywords

GLYCOCONJUGATE; HYDROCHLORIC ACID; PORPHYRIN; ZINC ION;

ARTICLE; CALIBRATION; CANCER; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROPHOBICITY; PHOTODYNAMIC THERAPY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM YIELD; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 20044362202     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/S1088424604000659     Document Type: Article

References (19)

1. Bonnett R. Chem. Soc. Rev. 1995; 24: 19.
2. Wagnieres G. Photochem. Photobiol. 1998; 68: 32.
3. Moser JG, Montforts FS, Kusch D, Vervoorts A, Kirsch D, Berghahn M, Akgün N, Rueck A, Andrees S and Wagner B. Proc. SPIE. Int. Soc. Opt. Eng. 1998; 22: 2924.
4. Momenteau M, Oulmi D, Maillard Ph and Croisy A. SPIE. Photodynamic Ther. Cancer II. 1994; 2325: 13.
5. Tarak D. J. Porphyrins Phthalocyanines. 2000; 4: 362.
6. Maillard Ph, Guerquin-Kern JL and Momenteau M. Tetrahedron Lett. 1991; 32: 4901.
7. Kohara K, Higashio H, Yamaguchi Y, Koketsu M and Odashima T. Bull. Chem. Soc. Jpn. 1994; 67: 668.
8. Oulmi D, Maillard P, Guerquin-Kern J.-L, Huel C and Momenteau M. J. Org. Chem. 1995; 60: 1554.
9. Mikata Y, Onchi Y, Tabata K, Ogura S, Okura I, Ono H and Yano S. Tetrahedron Lett. 1998; 39: 4505.
10. Hamazawa A, Kinoshita I, Breedlove B, Isobe K, Shibata M, Kakuchi T, Hirohara S, Obata M, Mikata Y and Yano S. Chem. Lett. 2002; 3: 388.
11. Zheng G, Potter WR, Camacho SH, Missert JR, Wang G, Bellnier DA, Henderson BW, Rodgers MAJ and Dougherty TJ, Panddey RK. J. Med. Chem. 2001; 44: 1540.
12. Koenigs W and Knorr E. Ber. 1903; 36: 957.
13. Halazy S, Berges V, Ehrhard A and Dazin C. Bioorg. Chem. 1990; 18: 330.
14. 3 / EtOH to give 2. The synthetic details of all compounds reported will be published elsewhere.
15. In order to remove zinc ion, the crude 2 was washed with 4 M HCl three times. The purification procedure was similar to that of 2.
16. OECD Guidelines for Testing of Chemicals, OECD, Paris 1989; No. 117.
17. -1), and the solution was filtered just before use. Pyridine (Log P = 0.65), benzaldehyde (1.48), quinoline (2.03), chlorobenzene (2.84), benzophenone (3.02), diphenylamine (3.40) and biphenyl (4.00) were used as standards for calibration of Log P and Log k' values.
18. OECD Guidelines for Testing of Chemicals, OECD, Paris 1995; No. 107.
19. Mirrlees MS, Moulton SJ, Murphy CT and Taylor PJ. J. Med. Chem. 1976; 19: 615.