Does usnic acid affect microtubules in human cancer cells?;Oácido úsnico pode afetar microtúbulos em células cancerosas humanas?

Brazilian Journal of Biology

Volumn 70, Issue 3, 2010, Pages 659-664

  O'Neill, M A ^a   Mayer, M M ^b,c,d   Murray, K E ^a   Rolim Santos, H M L ^c,d,e   Santos Magalhaes N S ^c,d   Thompson, A M ^a   Appleyard, V C L ^a  

^a UNIVERSITY OF DUNDEE   (United Kingdom)

^b UNIVERSIDADE FEDERAL RURAL DE PERNAMBUCO   (Brazil)

^c FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

^d Centro de Ciências Biológicas   (Brazil)

^e FEDERAL UNIVERSITY OF PIAUÍ   (Brazil)

Author keywords

Breast cancer; Lung cancer; Microtubules; Usnic acid

Indexed keywords

EID: 77956757577     PISSN: 15196984     EISSN: 16784375     Source Type: Journal    
DOI: 10.1590/S1519-69842010005000013     Document Type: Article

References (39)

1. ABO-KHATWA, AN., AL-ROBAI, AA. and AL-JAWHARI, DA., 1996. Lichen acids as uncouplers of oxidative phosphorylation of mouse-liver mitochondria. Natural Toxins, vol. 4, no. 2, p. 96-102.
2. AL-BEKAIRI, AM., QURESHI, S., CHAUDHRY, MA., KRISHNA, DR. and SHAH, AH., 1991. Mitodepressive, clastogenic and biochemicaleffects of (+)-usnic acid in mice. Journal of Ethnopharmacology, vol. 33, no. 3, p. 217-220.
3. BAZIN, MA., LE-LAMER, AC., DELCROS, JG., ROUAUD, I., URIAC, P., BOUSTIE, J., CORBEL, JC. and TOMASI, S., 2008. Synthesis and cytotoxic activities of usnic acid derivatives. Bioorganic & Medicinal Chemistry Letters, vol. 16, no. 14, p. 6860-6866.
4. BUCAR, F., SCHNEIDER, I., ÖGMUNDSDÓTTIR, H. and INGÓLFSDÓTTIR, K., 2004. Anti-proliferative lichen compounds with inhibitory activity on 12(S)-HETE production in human platelets. Phytomedicine, vol. 11, no. 7-8, p. 602-606.
5. BUDAVARI, S., 1989. The Merck index: an encyclopedia of chemicals, drugs, and biologicals. 11 ed. Rahway: Merck and Co. p. 1557.
6. CAMPANELLA, L., DELFINI, M., ERCOLE, P., IACOANGELI, A. and RISULEO, G., 2002. Molecular characterization and action of usnic acid: a drug that inhibits proliferation of mouse polyomavirus in vitro and whose main target is RNA transcription. Biochimie, vol. 84, no. 4, p. 329-334.
7. CARDARELLI, M., SERINO, G., CAMPANELLA, L., ERCOLE, P., CICCO-NARDOLE, F., ALESIANO, O. and ROSSIELLO, F., 1997. Antimitotic effects of usnic acid on different biological systems. Cellular and Molecular Life Sciences, vol. 53, no. 8, p. 667-672.
8. CARVALHO, EAB., ANDRADE, PP., SILVA, NH., PEREIRA, EC. and FIGUEIREDO, RCBQ., 2005. Effect of usnic acid from the lichen Cladonia substellata on Trypanosoma cruzi in vitro: an ultrastructural study. Micron, vol. 36, no. 2, p. 155-161.
9. CHECCI, PM., NETTLES, JH., ZHOU, J., SNYDER, JP. and JOSHI, HC., 2003. Microtubule-interacting drugs for cancer treatment. Trends in Pharmacological Sciences, vol. 24, no. 7, p. 361-365.
10. COCCHIETTO, M., SKERT, N., NIMIS, PL. and SAVA, GA., 2002. Review on usnic acid, an interesting natural compound. Naturwissenschaften, vol. 89, no. 4, p.137-146.
11. DUMONTET, C. and SIKIC, BI., 1999. Mechanisms of action of and resistance to antitubulin agents: microtubule dynamics, drug transport, and cell death. Journal of Clinical Oncology, vol. 17, no. 3, p. 1061-70.
12. GOLIAS, CH., CHARALABOPOULOS, A. and CHARALABOPOULOS, K., 2004. Cell proliferation and cell cycle control: a mini review. International Journal of Clinical Practice, vol. 58, no. 12, p. 1134-1141.
13. HAIT, WN., RUBIN, E. and GOODIN, S., 2003. Tubulin-targeting agents. Cancer Chemotherapy Biological Response Modifiers, vol. 21, p. 41-67.
14. HALAMA, P. and Van HALUWIN, C., 2004. Antifungal activity of lichen extracts and lichenic acids. Biocontrol, vol. 49, no. 1, p. 95-107.
15. HAN, D., MATSUMARU, K., RETTORI, D. and KAPLOWITZ, N., 2004. Usnic acid-induced necrosis of cultured mouse hepatocytes: inhibition of mitochondrial function and oxidative stress. Biochemical Pharmacology, vol. 67, no. 3, p. 439-451.
16. HONDA, NK. and VILEGAS, W., 1998. The chemistry of lichens. Química Nova, vol. 21, no. 1, p. 110-125.
17. INGÓLFSDÓTTIR, K., 2002. Usnic acid. Phytochemistry, vol. 61, no. 7, p. 729-736.
18. JORDAN, MA., 2002. Mechanism of action of antitumor drugs that interact with microtubules and tubulin. Current Medicinal Chemistry: Anti-Cancer Agents, vol. 2, no. 1, p. 1-17.
19. JORDAN, MA., WENDELL, K., GARDINER, S., DERRY, WB., COPP, H. and WILSON, L., 1996. Mitotic block induced in HeLa cells by low concentrations of paclitaxel (Taxol) results in abnormal mitotic exit and apoptotic cell death. Cancer Research, vol. 56, p. 816-825.
20. JORDAN, MA. and WILSON, L., 2004. Microtubules as a target for anticancer drugs. Nature Reviews Cancer, vol. 4, p. 253-265.
21. KARP, G., 2005. Cell and molecular biology: concepts and experiments. 4th ed. Hoboken: John Wiley and Sons. 864 p.
22. KUMAR, S. and MÜLLER K., 1999. Lichen metabolites 2: antiproliferative and cytotoxic activity of gyrophoric, usnic and diffractaic acid on human keratinocyte growth. Journal of Natural Products, vol. 62, no. 6, p. 821-823.
23. KUPCHAN, M. and KOPPERMAN, HL., 1975. Usnic acid: tumor inhibitor isolated from lichens. Experientia, vol. 31, no. 6, p. 625.
24. MAYER, M., O'NEILL, MA., MURRAY, KE., SANTOS-MAGALHÃES, NS., CARNEIRO-LEÃO, AMA., THOMPSON, AM. and APPLEYARD, VCL., 2005. Usnic acid: a non-genotoxic compound with anti-cancer properties. Anticancer Drugs, vol. 16, no. 8, p. 805-809.
25. MÜLLER, K., 2001. Pharmaceutically relevant metabolites from lichens. Applied Microbiology and Biotechnology, vol. 56, no. 1-2, p. 9-16.
26. ÖGMUNDSDÓTTIR, HM., ZOËGA, GM., GISSURARSON, SR. and INGÓLFSDÓTTIR, K., 1998. Anti-proliferative effects of lichens-derived inhibitors of 5-lipoxygenase on malignant cell-lines and mitogen-stimulated lymphocytes. Journal of Pharmacy and Pharmacology, vol. 50, p. 107-115.
27. OKUYAMA, E., UMEYAMA, K., YAMAZAKI, M., KINOSHIATA, Y. and YAMAMOTO, Y., 1995. Usnic acid and diffractaic acid as analgesic and antipyretic components of Usnea diffract. Planta Medica, vol. 61, no. 2, p. 113-115.
28. PERRY, NB., BENN, MH., BRENNAN, NJ., BURGESS, EJ., ELISS, G., GALLOWAY, DJ., LORIMER, SD. and TANGNEY, RS., 1999. Antimicrobial, antiviral and cytotoxic activity of New Zealand lichens. Lichenologist, vol. 31, p. 627-636.
29. PLICHET, A., 1955. Usnic acid from lichens in therapy of tuberculosis. Presse Med, vol. 63, no. 17, p. 350.
30. ROSOLEN, A., PILLON, M., GARAVENTA, A., BURNELLI, R., D'AMORE, ES., GIULIANO, M., COMIS, M., CESARO, S., TETTONI, K., MOLETI, ML., TAMARO, P., VISITIN, G. and ZANESCO, L., 2005. Anaplastic large cell lymphoma treated with a leukaemia-like therapy: report of the Italian Association of Pediatric Hematology and Oncology (AIEOP) LNH-92 protocol. Cancer, vol. 104, no. 10, p. 2133-2140.
31. RUSAN, NM., FAGERSTROM, CJ., YVON, AM. and WADSWORTH, P., 2001. Cell cycle-dependent changes in microtubule dynamics in living cells expressing green fluorescent protein-alpha tubulin. Molecular Biology of the Cell, vol. 12, no. 4, p. 971-980.
32. SANTOS, LC., HONDA, NK., CARLOS, IZ. and VILEGAS, W., 2004. Intermediate reactive oxygen and nitrogen from macrophages induced by Brazilian lichens. Fitoterapia, vol. 75, no. 5, p. 473-479.
33. SANTOS, NP., NASCIMENTO, SC., SILVA, JF., PEREIRA, ECG., SILVA, NH., HONDA, NK. and SANTOS-MAGALHÃES, NS., 2005. Usnic acid-loaded nanocapsules: an evaluation of cytotoxicity. Journal Drug Deliver Science Technology, vol. 15, no. 5, p. 355-361.
34. SANTOS, NP., NASCIMENTO, SC., PEREIRA, EC., SILVA, NH. and SANTOS-MAGALHÃES, NS., 2006. Nanoencapsulation of usnic acid: improvement on the antitumour activity and reduction of hepatotoxicity. European Journal of Pharmaceuticals and Biopharmaceutics, vol. 64, no. 2, p. 154-160.
35. SCIRPA, P., SCAMBIA, G., MASCIULLO, V., BATTAGLIA, F., FOTI, E., LOPEZ, R., VILLA, P., MALECORE, M. and MANCUSO, S., 1999. A zinc sulphate and usnic acid preparation used as post-surgical adjuvant therapy in genitallesions by human Papillomavirus. Minerva Ginecologica, vol. 51, no. 6, p. 255-260.
36. SON, YO., KIM, J., LIM, JC., CHUNG, Y., CHUNG, GH. and LEE, JC., 2003. Ripe fruits of Solanum nigrum L. inhibit cell growth and induces apoptosis in MCF7 cells. Food and Chemical Toxicology, vol. 41, no. 10, p. 1421-1428.
37. TAKAI, M., UEHARA, Y. and BEISLER, JA., 1979. Usnic acid derivatives as potential antineoplastic agents. Journal of Medicinal Chemistry, vol. 22, no. 11, p. 1380-1384.
38. VIJAYAKUMAR, CS., VISWANATHAN, S., REDDY, MK., PARVATHAVARTHINI, AB., KUNDU, AB. and SUKUMAR, E., 2000. Anti-inflammatory activity of (+)-usnic acid. Fitoterapia, vol. 71, no. 5, p. 564-566.
39. YASUDA, S., NOGUCHI, T., GOHD, AM., ARAI, T., TSUTSUI, N., NAKAUAMA, Y., MATSUDA, T. and NONOGI, H., 2002. Local delivery of low-dose docetaxel, a novel microtubule polymerizing agent, reduces neointimal hyperplasia in a ballon-injured rabbit iliac artery model. Cardiovascular Research, vol. 53, p. 481-486.