Structure-activity of novel rhodacyanine dyes as antitumor agents

Journal of Medicinal Chemistry

Volumn 41, Issue 1, 1998, Pages 130-142

  Kawakami, Masayuki ^a   Koya, Keizo ^a   Tatsuta, Toshinao ^b   Noriaki, Ukai T ^a   Ikegawa, Akihiko ^a   Ogawa, Keizo ^a   Shishido, Tadao ^a   Chen, Lan Bo ^a  

^a FUJIFILM CORPORATION   (Japan)

^b HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATIONIC RHODACYANINE; CYANINE DYE; RHODACYANINE DYE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; COLON CARCINOMA; DRUG DESIGN; DRUG SOLUBILITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; SOLID TUMOR; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL SURVIVAL; COLONIC NEOPLASMS; CRYSTALLOGRAPHY, X-RAY; HUMANS; KB CELLS; MICE; MICE, INBRED STRAINS; MICE, NUDE; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES; TRANSPLANTATION, HETEROLOGOUS; TUMOR CELLS, CULTURED;

EID: 0031937255     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970590k     Document Type: Article

References (16)

1. Chen, L. B. Mitochondria Membrane Potential in Living Cells. Annu. Rev. Cell Biol. 1988, 4, 155-181.
2. Lampids, T. J.; Bemal, S. D.; Summerhayes, I. C.; Chen, L. B. Selective Toxicity of Rhodamine-123 in Carcinoma Cells in Vitro. Cancer Res. 1983, 43, 716-720.
3. Nadakavukaren, K. K.; Nadakavukaren, J. J.; Chen, L. B. Increased Rhodamine-123 Uptake by Carcinoma Cells. Cancer Res. 1985, 45, 6093-6099.
4. Anderson, W. M.; Delinck, D. L.; Benniner, L.; Wood, J. M.; Smiley, S. T.; Chen L. B. Cytotoxic Effect of Thiacarbocyanine Dyes on Human Colon Carcinoma Cell and Inhibiton of Bovine Heart Mitchondorial NADH-Ubiquinone Reductase Activity via a Rotenone-type Mechanism by Two of the Dyes. Biochem. Pharmacol. 1993, 45, 691-696.
5. Sun, X; Wong J. R.; Song, K.; Hu J.; Garlid, K. D.; Chen L. B. AA-1, a Newly Synthesized Monovalent Lipophilic Cation, Expresses Potent In Vivo Antitumor Activity. Cancer Res. 1994, 54, 1465-1471.
6. Modica-Napolitano, J. S.; Aprille, J. R. Basis for the Selective Cytotoxicity of Rhodamine 123. Cancer Res. 1987, 47, 43614365.
7. Dairkee, S. H.; Deng, G.; Stampfer, M. R.; Waldman, F. M.; Smith, H. S. Selective Cell Culture of Primary Breast Carcinoma. Cancer Res. 1995, 55, 2516-2519.
8. Kawakami, M.; Koya, K.; Ukai, T.; Tatsuta, N.; Ikegawa, A.; Ogawa, K.; Shishido, T.; Chen, L. B. Synthesis and Evaluation of Novel Rhodacyanine Dyes that Exhibit Antitumor Activity. J. Med. Chem., in press.
9. Jeffreys, R. A.; Knott, E. B. The Color of Organic Compounds. Part VI. A Comparison of Isomeric Dyes from 3-Alkyl-2-thiothiazolid-4- and -5-ones. J. Chem. Soc. 1952, 4632-4637.
10. Knott, E. B.; Jeffreys, R. A. The Color of Organic Compounds. Part VII. Complex Cyanines and meroCyanines. J. Chem. Soc. 1952, 4762-4775.
11. Modica-Napolitano, J. S.; Koya, K.; Weisberg, E.; Brunelli, B. T.; Li, Y.; Chen, L. B. Selective Damage to Carcinoma Mitochondria by the Rhodacyanine MKT-077. Cancer Res. 1996,56, 544-550.
12. Weisberg, E.; Koya, K.; Modica-Napolitano, J.; Li, Y.; Chen, L. B. In Vivo Administration of MKT-077 Causes Partial yet Reversible Impairment of Mitochondria Function. Cancer Res. 1996, 56, 551-555.
13. Koya, K.; Wang, Y. L. H.; Ukai, T.; Tatsuta, N.; Kawakami, M.; Shishido, T.; Chen, L. B. MKT-077, a Novel Rhodacyanine Dyes in Clinical Trials, Exhits Anticarcinoma Activity in Preclinical Studies Based on Selective Mitochondria Accumulation. Cancer Res. 1996, 56, 538-543.
14. Dunnett, C. W. A Multiple Comparison Procedure for Comparing Several Treatments with a Control. J. Am. Stat. Assoc. 1955, 50, 1096-1121.
15. In Simultaneous Statistical Inference, 2nd ed.; Miller, R. G., Jr., Ed.; Springer-Verlag: New York, 1982; pp 165-172.
16. Hollander, M.; Wolfe, D. A. Nonparametric Statistical Methods; John Wiley & Sons: New York, 1973; pp 129-132.