Flavone acetic acid

Flavone-8-acetic acid (117) Flavone derivative ASA404 (DMXAA, ASA1404) (118) Oncology Vascular targeting and angiogenesis inhibition Phase III Antisoma (University of Auckland)/ Novartis 709-713... 

Pharmacodynamics and causes of dose-dependent pharmacokinetics of flavone-8-acetic acid (LM-975 NSC-347512) in mice. Cancer Chemother. Pharmacol. 24, 15-22. 

Baguley, B. C., Cole, G., Thomsen, L. L and Zhuang, L. (1993) Serotonin involvement in the antitumour and host effects of flavone-8-acetic acid and 5,6-dimethylxanthenone-4-acetic acid. Cancer Chemother. Pharmacol. 33,77-81. 

Thomsen, L. L., Ching, L. M., Zhuang, L Gavin, J. B., and Baguley, B. C. (1991) Tumor-dependent increased plasma nitrate concentrations as an indication of the antitumor effect of flavone-8-acetic acid and analogues in mice. Cancer Res. 51, 77-81. 

Elavones were found to possess a wide spectrum of pharmacological activities for instance, polyhydroxyflavones possess anti-inflammatory and flavone-8-acetic acid (25) antitumor properties [68]. 

Eentanyl 434 Flavane 340 Flavanol 340 Flavazin 248 Flavin see isalloxazin Flavone 337,340 Flavone-8-acetic acid 340 Flavonol 340 Flavylium ion 327 Flunarizine 487 Fluoresceine 340 5-Fluorouracil 473 Folic acid 490 Furan 61,77... 

Ornithine decarboxylase catalyzes the transformation of ornithine to the polycationic bases, putresine, spermine, and spermidine. These compounds exert regulatory effects on cell growth. It has been shown that quercetin (10 to 30 pmol/mouse) markedly suppressed the stimulatory effect of the transporters associated with antigen processing (TPA) on ornithine decarboxylase (ODC) activity and on skin tumor formation in mice initiated with dimethylbenzanthracene. Such inhibition may be related to the activation of the catalytic site, which is under nonconventional regulation by small molecules. Also, the synthetic flavonoid flavone acetic acid was shown to inhibit the activity of ODC in stimulated human peripheral blood lymphocytes and human colonic lamina propria lymphocytes. 

Flavone acetic acid (FAA, structure shown in Fig. 1), developed originally for its anti-inflammatory properties (41), has been shown to be a very effective agent against murine tumors (42). It appears to mediate its antitumor action in... 

Plowman, J., Narayanan, V. L., Dykes, D., Szarvasi, E., Briet, P., Yoder, O. C., and Pauli, K. D. (1986) Flavone acetic acid a novel agent with preclinical antitumor activity against colon adenocarcinoma 38 in mice. Cancer. Treat. Rep. 70,631-638. 

Finlay, G. J., Smith, G. P., Fray, L. M., and Baguley, B. C. (1988) Effect of flavone acetic acid (NSC 347512) on Lewis lung carcinoma evidence for an indirect effect. J. Natl. Cancer Inst. 80, 241-245. 

Evelhoch, J. L., Bissery, M.-C., Chabot, G. G., Simpson, N. E., McCoy, C. L., Heilbrun, L. K., and Corbett, T. H. (1988) Flavone acetic acid (NSC 347512)-induced modulation of murine tumor physiology monitored by in vivo nuclear magnetic resonance spectroscopy. Cancer Res. 48, 4749-4755. 

Hill, S., Williams, K. B., and Denekamp, J. (1989) Vascular collapse after flavone acetic acid. A possible machanism of its antitumour action. Eur. J. Cancer Clin. Oncol. 25, 1419-1423. 

Bibby, M. C., Double, J. A., Loadman, P. M., and Duke, C. V. (1989) Reduction of tumor blood flow by flavone acetic acid a possible component of therapy. J. Natl. Cancer Inst. 81, 216-220. 

Zwi, L. J., Baguley, B. C., Gavin, J. B and Wilson, W. R. (1994) The morphological effects of the anti-tumour agents flavone acetic acid and 5,6-dimethylxanthenone acetic acid on the colon 38 mouse tumour. Pathology 26,161-169. 

Honess, D. J. and Bleehen, N. M. (1991) Effects of two tumour blood flow modifiers, hydralazine and flavone acetic acid, on KHT tumours and normal tissues in mice. Inti. J. Radiat. Biol. 60,249-253. 

Mace, K. F., Homung, R. L., Wiltrout, R. H and Young, H. A. (1990) Correlation between in vivo induction of cytokine gene expression by flavone acetic acid and strict dose dependency and therapeutic efficacy against murine renal cancer. Cancer Res. 50,1742-1747. 

Mahadevan, V., Malik, S. T. A., Meager, A., Fiers, W., Lewis, G. P., and Hart, I. R. (1990) Role of tumor necrosis factor in flavone acetic acid-induced tumor vasculature shutdown. Cancer Res. 50, 5537-5542. 

Sakaguchi, Y., Maehara, Y., Baba, H Kusumoto, T Sugimachi, K., and Newman, R. A. (1992) Flavone acetic acid increases the antitumor effect of hyperthermia in mice. Cancer Res. 52, 3306-3309. 

O Reilly, S. M., Rustin, G. J. S., Farmer, K., Burke, M Hill, S., and Denekamp, J. (1993) Flavone acetic acid (FAA) with recombinant interleukin-2 (rIL-2) in advanced malignant melanoma. 1. Clinical and vascular studies. Br. J. Cancer 67,1342-1345. 

Futami, H., Eader, L. A., Komschlies, K. L., Bull, R., Grays, M. E., Ortaldo, J. R., Young, H. A., and Wiltrout, R. H. (1991) Flavone acetic acid directly induces expression of cytokine genes in mouse splenic leukocytes but not in human peripheral blood leukocytes. Cancer Res. 51, 6596-6602. 

Ching, L. M., Joseph, W. R., Crosier, K. E., and Baguley, B. C. (1994) Induction of tumor necrosis factor-alpha messenger RNA in human and murine cells by the flavone acetic acid analogue 5,6-dimethylxanthenone-4-acetic acid (NSC 640488). Cancer Res. 54, 870-872. 

Hill, S. A., Sampson, L. E., and Chaplin, D. J. (1995) Anti-vascular approaches to solid tumour therapy evaluation of vinblastine and flavone acetic acid. Inti. J. Cancer 63, 119-123. 

Zwi, L. J. (1992) The mechanism of the anti-tumour action of flavone acetic acid and its xanthenone acetic acid analogs. Thesis, The University of Auckland, New Zealand. 

Zaharko DS, Grieshaber CK, Plowman J, Cradock JC. Therapeutic and pharmacokinetic relationships of flavone acetic acid an agent with activity against solid tumors. Cancer Treat Rep 1986 70 1415-1421. 

Harris SR, Panaro NJ, Tborgeirsson UP. Oxidative stress contributes to tbe anti-prohferative effects of flavone acetic acid on endothelial cells. Anticancer Res 2000 20 2249-2254. 

Under these conditions, the O-benzoyl derivative immediately enolizes and is O-acylated again to yield a dibenzoate. Without isolation, this product is cyclized by treatment with aqueous potassium hydroxide to yield 2-hydroxy-2,3-dihydroflavone. Dehydration to flavone is then effected by the action of glacial acetic acid containing sulfuric acid. 

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