Synthesis of amphiphilic derivatives of rose bengal and their tumor accumulation

Bioconjugate Chemistry

Volumn 18, Issue 3, 2007, Pages 866-873

  Sugita, Nami ^a   Kawabata, Ken Ichi ^a   Sasaki, Kazuaki ^a   Sakata, Isao ^b   Umemura, Shin Ichiro ^c  

^a HITACHI LTD   (Japan)

^b Minori Co   (Japan)

^c KYOTO UNIVERSITY FACULTY OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTODYNAMIC THERAPY; ULTRASONICS;

AMPHIPHILICS; COMBINATION OF LASERS; LASER LIGHTS; ROSE BENGAL; SENSITISER; SONODYNAMIC THERAPY; SYNTHESISED; TUMOR ACCUMULATION; TUMOR TREATMENT; TUMOUR TISSUE;

TUMORS;

ALKYL GROUP; AMPHOPHILE; CARBOXYL GROUP; OCTANOL; ROSE BENGAL; WATER;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CELL DAMAGE; COLON CARCINOMA; DRUG SYNTHESIS; DRUG TUMOR LEVEL; IN VITRO STUDY; LASER; MALE; MOUSE; NONHUMAN; PARTITION COEFFICIENT; PHOTODYNAMIC THERAPY; STRUCTURE ACTIVITY RELATION; TISSUE DISTRIBUTION; ULTRASOUND;

MUS;

EID: 34347331352     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060189p     Document Type: Article

References (31)

1. Dougherty, T. J., Kaufman, J. E., Goldfarb, A., Weishaupt, K. R., Boyle, D., and Mittleman, A. (1978) Photoradiation therapy for the treatment of malignant tumors. Cancer Res. 38, 2628-2635.
2. Hayata, Y., Kato, H., Konaka, C., Ono, J., and Takizawa, N. (1982) Hematoporphyrin derivative and laser photoradiation in the treatment of lung cancer. Chest 81, 269-277.
3. Kremkau, F. W., Kaufmann, J. S., Walker, M. M., Burch, P. G., and Spurr, C. L. (1976) Ultrasonic enhancement of nitrogen mustard cytotoxicity in mouse leukemia. Cancer 37, 1643-1647.
4. Akimoto, R. (1985) An experimental study on enhancement of the effect of anti-cancer drug by ultrasound. J. Jpn. Soc. Cancer Ther. 20, 562-570.
5. Yumita, N., Okumura, A., Nishigaki, R., Umemura, K., and Umemura, S. (1987) The combination treatment of ultrasound and antitumor drugs on Yoshida sarcoma. Jpn. J. Hypertherm. Oncol. 3, 175-182.
6. Lynn, J. G., Zwemer, R. L., Chick, A. J., and Miller, A. F. (1942) A new method for the generation and use of focused ultrasound in experimental biology. J. Gen. Physiol. 26, 179-193.
7. Fry, W. J., Barnard, J. W., Fry, F. J., and Brennan, J. F. (1955) Ultrasonically produced localized selective lesions in the central nervous system. Am. J. Phys. Med. 34, 413-423.
8. Sanghvi, N. T., and Hawes, R. H. (1994) High-intensity focused ultrasound. Gastrointest. Endosc. Clin. N. Am. 4, 383-395.
9. Yumita, N., Nishigaki, R., Umemura, K., and Umemura, S. (1989) Hematoporphyrin as a sensitizer of cell-damaging effect of ultrasound. Jpn. J. Cancer Res. 80, 219-222.
10. Umemura, S., Yumita, N., Nishigaki, R., and Umemura, K. (1990) Mechanism of cell damage by ultrasound in combination with Hematoporphyrin. Jpn. J. Cancer Res. 81, 962-966.
11. Umemura, S., Yumita, N., and Nishigaki, R. (1993) Enhancement of ultrasonically induced cell damage by a gallium-porphyrin complex, ATX-70. Jpn. J. Cancer Res. 84, 582-588.
12. Umemura, S., Kawabata, K., Sasaki, K., Yumita, N., Umemura, K., and Nishigaki, R. (1996) Recent advances in sonodynamic approach to cancer therapy. Ultrason. Sonochem. 3, S187-S191.
13. Yumita, N., Nishigaki, R., Sakata, I., Nakajima, S., and Umemura, S. (2000) Sonodynamically induced antitumor effect of 4-formyloximethylidene-3- hydroxy-2-vinyl-deuterio-porphynyl(IX)-6,7-di aspatric acid (ATX-S10). Jpn. J. Cancer Res. 91, 255-260.
14. Yumita, N., Sasaki, K., Umemura, S., and Nishigaki, R. (1996) Sonodynamically induced antitumor effect of a gallium-porphyrin complex, ATX-70. Jpn. J. Cancer Res. 87, 310-316.
15. Sasaki, K., Yumita, N., Nishigaki, R., and Umemura, S. (1998) Antitumor effect sonodynamically induced by focused ultrasound in combination with Ga-porphyrin complex. Jpn. J. Cancer Res. 89, 452-456.
16. Umemura, S., Kawabata, K., and Sasaki, K. (1996) Enhancement of sonodynamic tissue damage production by second-harmonic superimposition: Theoretical analysis of its mechanism. IEEE Trans. Ultrason. Ferroelect. Freq. Contr. 43, 1054-1062.
17. Umemura, S., Kawabata, K., and Sasaki, K. (1997) In vitro and in vivo enhancement of sonodynamically active cavitation by second-harmonic superimposition. J. Acoust. Soc. Am. 101, 569-577.
18. Kawabata, K., and Umemura, S. (1997) Xanthene dyes for reducing acoustic cavitation threshold in aqueous solution. Ultrasonics 35, 469-474.
19. Gandin, E., Lion, Y., and Van de Vorst, A. (1983) Quantum yield of singlet oxygen production by xanthene derivatives. Photochem. Photobiol. 37, 271-278.
20. Umemura, S., Yumita, N., Umemura, K., and Nishigaki, R. (1999) Sonodynamically induced effect of rose bengal on isolated sarcoma 180 cells. Cancer Chemother. Pharmacol. 43, 389-393.
21. Kochevar, I. E., Bouvier, J., Lynch, M., and Lin, C. (1994) Influence of dye and protein location on photosensitization of the plasma membrane. Biochim. Biophys. Acta 1196, 172-180.
22. Fischer, E., and Varga, F. (1979) Hepatic storage and biliary excretion of rose bengal in the rat. Acta Physiol. Acad. Sci. Hung. 54, 89-94.
23. Dougherty, T. J. (1987) Photosensitizers: Therapy and detection of malignant tumors. Photocem. Photobiol. 45, 879-889.
24. Nakajima, S., Hayashi, H., Omote, Y., Yamazaki, Y., Hirata, S., Maeda, T., Kubo, Y., Takemura, T., Kakiuchi, Y., Shindo, Y., Koshimizu, K., and Sakata, I. (1990) The tumor-localizing properties of porphyrin derivatives. J. Photochem. Photobiol. B: Biol. 7, 189-198.
25. Lamberts, J. J. M., and Neckers, D. C. (1984) Rose bengal and non-polar derivatives: The birth of dye sensitizers for photooxidation. Z. Naturforsch. 39b, 474-484.
26. Lamberts, J. J. M., and Neckers, D. C. (1985) Rose bengal derivatives as singlet oxygen sensitizers. Tetrahedron 41, 2183-2190.
27. Neckers, D. C., and Valdes-Aguilera, O. M. (1993) Photochemistry of the xanthene dyes. Advances in Photochemistry (Volman D., Hammond G. S., and Neckers, D. C., Eds.) pp 316-394, Volume 18, John Wiley & Sons, Inc., Hoboken, NJ.
28. Wang, H. K., Miyachi, S., Yamazaki, M., Sawada, Y., Chung, Y. B., Iga, T., Hanano, M., and Sugiyama, Y. (1992) Nonlinear pharmacokinetics of hepatobiliary transport of rose bengal in rats after iv bolus administration with varying doses. Biopharm. Drug Dispos. 13, 647-662.
29. Zheng, G., Potter, W. R., Camacho, S. H., Missert, J. R., Wang, G., Bellnier, D. A., Henderson, B. W., Rodgers, M. A., Dougherty, T. J., and Pandey, R. K. (2001) 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. 44, 1540-1559.
30. Kim, Y., Song, R., Kim, D. H., Jun, M. J., and Sohn, Y. S. (2003) Synthesis, biodistribution and antitumor activity of hematoporphyrin-platinum (II) conjugates. Bioorg. Med. Chem. 11, 1753-1760.
31. Zhang, X., Su, Z., Ballinger, J. R., Rauth, A. M., Pollak, A., and Thornback, J. R. (2000) Targeting hypoxia in tumors using 2-nitroimidazoles with peptidic chelators for technetium-99m: Effect of lipophilicity. Bioconjugate Chem. 11, 401-407.