Coumarin derivatives with tumor-specific cytotoxicity and multidrug resistance reversal activity

In Vivo

Volumn 19, Issue 4, 2005, Pages 705-712

  Kawase, Masami ^a   Sakagami, Hiroshi ^b   Motohashi, Noboru ^c   Hauer, Hermann ^d   Chatterjee, Shyam S ^d   Spengler, Gabriella ^e   Vigyikanne, Aniko Varadi ^e   Molnár, Annamaria ^e   Molnár, Joseph ^e  

^a JOSAI UNIVERSITY   (Japan)

^b MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

^c MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

^d DR WILLMAR SCHWABE GMBH AND CO KG   (Germany)

^e UNIVERSITY OF SZEGED   (Hungary)

Author keywords

Coumarin; Cytotoxic activity; Multidrug resistance; Oral tumor cells; Structure activity relationship

Indexed keywords

3 (2 HYDROXYETHYL) 4 METHYL 7 METHOXYCOUMARIN; 3 ETHYL 6 HYDROXY 7 METHOXY 4 METHYLCOUMARIN; 4 HYDROXY 3 NITROCOUMARIN; 4 TRIFLUOROMETHYL 7 DIMETHYLAMINOCOUMARIN; 6 HYDROXY 7 METHOXY 4 METHYL 3 ISOPROPYLCOUMARIN; 6 NITRO 3,4 BENZOCOUMARIN; ANTINEOPLASTIC AGENT; COUMARIN DERIVATIVE; CYTOTOXIC AGENT; ETHYLCOUMARIN 3 CARBOXYLIC ACID; GALLIC ACID; HERNIARIN ACETATE; MULTIDRUG RESISTANCE PROTEIN 1; UNCLASSIFIED DRUG; VERAPAMIL;

ANIMAL CELL; ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL COUNT; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG SPECIFICITY; DRUG STRUCTURE; FLUORESCENCE ANALYSIS; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; MOUSE; MOUTH CARCINOMA; MULTIDRUG RESISTANCE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; TUMOR CELL;

EID: 21344470405     PISSN: 0258851X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Tsuruo T, Naito M, Tomida A, Fujita N, Mashima T, Sakamoto H and Haga N: Molecular targeting therapy of cancer: drug resistance, apoptosis and survival signal. Cancer Sci 94: 15-21, 2003.
2. Robert J and Jarry C: Multidrug resistance reversal agents. J Med Chem 46: 4805-4817, 2003.
3. Kawase M and Motohashi N: New multidrug resistance reversal agents. Current Drug Targets 4: 31-43, 2003.
4. Thomas H and Coley H: Overcoming multidrug resistance in cancer: an update on the clinical strategy of inhibiting P-glycoprotein. Cancer Control 10: 159-165, 2003.
5. Murray RDH, Mendez J and Brown SA: The Natural Coumarins: Occurrence, Chemisty and Biochemistry. John Wiley, New York, pp. 282-289, 1982.
6. Finn GJ, Creaven BS and Egan DA: Daphnetin induced differentiation of human renal carcinoma cells and its mediation by p38 mitogen-activated protein kinase. Biochem Pharmacol 67: 1779-1788, 2004.
7. Derferme S and Augustijins P: The effect of food components on the absorption of P-gp substances: a review. J Pharm Pharmacol 55: 153-162, 2003.
8. Shah A, Naliapara Y, Sureja D, Motohashi N, Kawase M, Miskolci C, Szabo D and Molnar J: 6,12-Dihydro-1-benzopyrano[3,4-b][1,4]benzothiazin-6-ones: synthesis and mdr reversal in tumor cells. Anticancer Res 18: 3001-3004, 1998.
9. Egan D, James P, Cooke D and O'Kennedy R: Studies on the cytostatic and cytotoxic effects and mode of action of 8-nitro-7-hydroxycoumarin. Cancer Lett 118: 201-211, 1997.
10. Finn GJ, Creaven BS and Egan DA: Investigation of intracellular signaling events mediating the mechanism of action of 7-hydroxycoumarin and 6-nitro-7-hydroxycoumarin in human renal cells. Cancer Lett 205: 69-79, 2004.
11. Wu JY, Fong W, Zhang J, Leung C, Kwong H, Yang M, Li D and Cheung H: Reversal of multidrug resistance in cancer cells by pyranocoumarins isolated from Radix peucedani. Eur J Pharmacol 473: 9-17, 2003.
12. Kawase M, Sakagami H, Hashimoto K, Tani S, Hauer H and Chatterjee SS: Structure-cytotoxic activity relationships of simple hydroxylated coumarins. Anticancer Res 23: 3243-3246, 2003.
13. Kawase M, Tanaka T, Sohara Y, Tani S, Sakagami H, Hauer H and Chatterjee SS: Structural requirements of hydroxylated coumarins for in vitro anti-Helicobacter pylori activity. Anticancer Res 23: 3243-3246, 2003.
14. von Pechmann H and Duisberg C: Uber die Verbindungen der Phenole mit Acetessigather. Ber 16: 2119-2128, 1883.
15. Chatterjee SS, Noeldner M and Hauer H: Preparation of piperidinylalkoxy- and piperazinylalkoxybenzopyranones as neuroprotectants and anticonvulsants. Ger. Offen. (1992) DE 4,111,861 (Chem Abstr 118:124397j).
16. Chatterjee A, Ganguly D and Sen R: New synthesis of 4-phenyl coumarins: dalbergin and nordalbergin. Tetrahedron 32: 2407-2408, 1976.
17. Hauer H, Chatterjee SS and Noeldner M: Preparation of 3-(piperazinylethyl)benzopyran-2-ones and related compounds as NMDA antagonists. Ger. Offen. (1994) DE 4233963 (Chem Abstr 121: 57533).
18. Kuwayama Y: Pechmann reaction of acetobutyrolactone. Yakugaku Zasshi 80: 913-916, 1960.
19. Sakagami H, Jiang Y, Kusama K, Atsumi T, Ueha T, Toguchi M, Iwakura I, Satoh V, Ito H, Hatano and Yoshida T: Cytotoxic activity of hydrolyzable tannins against human oral tumor cell lines - a possible mechanism. Phytomedicine 7: 39-47, 2000.
20. Sakagami H, Satoh K, Ohata H, Takahashi H, Yoshida H, Iida M, Kuribayashi N, Sakagami T, Momose K and Takeda M: Relationship between ascorbyl radical intensity and apoptosis-inducing activity. Anticancer Res 16: 2635-2644, 1996.
21. Kessel D: Exploring multidrug resistance using rhodamine 123. Cancer Commun 1: 145-149, 1989.
22. Weaver JL, Szabo G, Pine PS, Gottesman MM, Goldenberg S and Aszalos A: The effect of ion channel blockers, immunosuppressive agents, and other drugs on the activity of the multi-drug transporter. Int J Cancer 54: 456-461, 1993.
23. Pomona College Medicinal Chemistry Project, Claremont, CA, USA.
24. Szabo D, Keyzer H, Kaiser HE and Molnar J: Reversal of multidrug resistance of tumor cells. Anticancer Res 20: 4261-4274, 2000.
25. Lee JS, Paull K, Alvarez M, Hose C, Monks A, Grever M, Fojo AT and Bates SE: Rhodamine efflux patters predict P-glycoprotein substrates in the National Cancer Institute Drug Screen. Mol Pharmacol 46: 627-638, 1994.
26. Klopman G, Shi LM and Ramu A: Quantitative structure-activity relationship of multidrug resistance reversal agents. Mol Pharmacol 52: 323-334, 1997.