Research Progress in the Prodrugs of Curcumin

doi:10.6023/cjoc1107221

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (05): 852-859.DOI: 10.6023/cjoc1107221 Previous Articles Next Articles

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姜黄素前药的研究进展

涂永元^a,b, 徐先祥^a,b, 邱飞^a,b

a 华侨大学分子药物学研究所泉州 362021;
b 分子药物教育部工程研究中心泉州 362021

收稿日期:2011-07-22 修回日期:2011-11-02 发布日期:2011-12-12
通讯作者: 邱飞 E-mail:qiufei@hqu.edu.cn
基金资助:
国家自然科学基金(No. 30900351)、福建省自然科学基金(No. 2009J05029)、福建省生物医药工程研究生教育创新基地(No. 06070205)和华侨大学科研基金(No. 08BS412)资助项目.

Research Progress in the Prodrugs of Curcumin

Tu Yongyuan^a,b, Xu Xianxiang^a,b, Qiu Fei^a,b

a Institute of Molecular Medicine, Huaqiao University, Quanzhou 362021;
b Engineering Research Center of Molecular Medicine, Ministry of Education, Quanzhou 362021

Received:2011-07-22 Revised:2011-11-02 Published:2011-12-12
Supported by:
Project supported by the National Natural Science Foundation of China (No. 30900351), the Natural Science Foundation of Fujian Province of China (No. 2009J05029), the Fujian Biomedicial Engineering Graduate Student’s Educational Innovation Base (No. 06070205) and the Scientific Research Foundation of Huaqiao University (No. 08BS412).

In recent years, curcumin, a natural product, has been drawing attention from researchers for it has many kinds of significant bioactivities, such as antitumor activity. However, its clinical utility is limited due to a number of undesirable difficulties, such as its low aqueous solubility, instability and low bioavailability. Through conjugated the phenolic hydroxyl group of curcumin with low or high molecular weight carriers, various prodrugs of curcumin have been studied and developed to overcome its disadvantages. The development of prodrugs of curcumin was an effective method to improve the druggability of curcumin. In this paper, the research progresses in the prodrugs of curcumin in recent years are reviewed.

Key words: curcumin, prodrugs, medicinal chemistry, antitumor drug

Cite this article

Tu Yongyuan, Xu Xianxiang, Qiu Fei. Research Progress in the Prodrugs of Curcumin[J]. Chin. J. Org. Chem., 2012, 32(05): 852-859.

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[1] Liang, G.; Tian, J. L.; Shao, L. L.; Yang, S. L.; Li, X. K. Chemistry2008, 71, 110 (in Chinese).(梁广, 田吉来, 邵丽丽, 杨树林, 李校堃, 化学通报, 2008, 71,110.)

[2] Venugopal, P. M.; Adluri, R. S. Adv. Exp. Med. Biol. 2007, 595,105.

[3] Negi, P. S.; Jayaprakasha, G. K.; Jagan, M. R. L.; Sakariah, K. K. J.Agric. Food Chem. 1999, 47, 4297.

[4] Li, K. J.; Hu, X. M. China Trop. Med. 2008, 8, 314 (in Chinese).(李凯杰, 胡锡敏, 中国热带医学, 2008, 8, 314.)

[5] Gururaj, A. E.; Belakavadi, M.; Venkatesh, D. A.; Marmé, D.;Salimath, B. P. Biochem. Biophys. Res. Commun. 2002, 297, 934.

[6] Calabrese, V.; Butterfield, D. A.; Stella, A. M. Ital. J. Biochem. 2003, 52, 177.

[7] Su, J.; Xu, Z. P. Jiangxi J. Trad. Chin. Med. 2010, 41, 78 (in Chinese).(苏菁, 徐宗佩, 江西中医药, 2010, 41, 78.)

[8] Han, T.; Mi, H. M. Pharm. J. Chin. PLA 2001, 17, 95 (in Chinese).(韩婷, 宓鹤鸣, 解放军药学学报, 2001, 17, 95.)

[9] Preetha, A.; Ajaikumar, B.; Kunnumakkara, R. Mol. Pharm. 2007,4, 807.

[10] Kurien, B. T.; Singh, A.; Matsumoto, H.; Scofield, R. H. AssayDrug Dev. Technol. 2007, 5, 567.

[11] Wichitnithad, W.; Nimmannit, U.; Wacharasindhu, S.; Rojsitthisak,P. Molecules 2011, 16, 1888.

[12] Jiang, F. S.; Xu, X. L.; Jin, B.; Chen, N. B.; Gao, C. X.; Ding, Z. S.;Lu, G. Y. Chin. Pharm. J. 2009, 19, 1492 (in Chinese).(蒋福升, 徐秀玲, 金波, 陈铌铍, 高承贤, 丁志山, 吕圭源, 中国药学杂志, 2009, 19, 1492.)

[13] Cao, F.; Ping Q. N.; Chen, J. Acta Pharm. Sin. 2008, 43, 343 (inChinese).(操锋, 平其能, 陈军, 药学学报, 2008, 43, 343.)

[14] Zhang, J.; Guo, W.; Zhai, G. X. Food Drug 2010, 12, 133 (in Chinese).(张军, 郭卫, 翟光喜, 食品与药品, 2010, 12, 133.)

[15] Makoto, T.; Shuntoku, U.; Kensaku, T.; Yonathan, A.; Koji, W. J.Agric. Food Chem. 2009, 57, 9141.

[16] Li, P. Z.; Liu, Z. Q. Eur. J. Med. Chem. 2011, 46, 1821.

[17] Anand, P.; Kunnumakkara, A. B.; Newman, R. A.; Aggarwal, B. B.Mol. Pharm. 2007, 4, 807.

[18] Ohtsu, H.; Xiao, Z.; Ishida, J.; Nagai, M.; Wang, H. K.; Itokawa,H.; Su, C. Y.; Shih, C.; Chiang, T.; Chang, E.; Lee, Y.; Tsai, M. Y.;Chang, C.; Lee, K. H. J. Med. Chem. 2002, 45, 5037.

[19] Parvathy, K. S.; Negi, P. S.; Srinivas, P. Food Chem. 2010, 120,523.

[20] Kapoor, N.; Narain, U.; Misra, K. J. Sci. Ind. Res. 2007, 66, 647.

[21] Mishra, S.; Kapoor, N.; Mubarak, A. A.; Pardhasaradhi, B. V.;Kumari, A. L.; Khar, A.; Misra, K. Free Radical Biol. Med. 2005,38, 1353.

[22] Lu, P.; Tong, Q. S.; Jiang F. C. Chin. Pharmacol. Bull. 2006, 22,321 (in Chinese).(陆鹏, 童强松, 姜凤超, 陈方敏, 郑丽端, 张胜民, 曾甫清, 董继华, 中国药理学通报, 2006, 22, 321.)

[23] Dubey, S. K.; Sharma, A. K.; Narain, U.; Misra, K.; Pati, U. Eur. J.Med. Chem. 2008, 43, 1837.

[24] Mishra, S.; Narain, U.; Mishra, R.; Misra, K. Bioorg. Med. Chem.2005, 13, 1477.

[25] Shoba, G.; Joy, D.; Joseph, T.; Majeed, M.; Rajendran, R.; Srinivas,P. S. Planta Med. 1998, 64, 353.

[26] Qiu, J. B.; He, L. Prog. Pharm. Sci. 2009, 33, 385 (in Chinese).(邱嘉斌, 何玲, 药学进展, 2009, 33, 385.)

[27] Qiao, J.; Chen X. H. Prog. Pharm. Sci. 2008, 32, 145 (in Chinese).(乔静, 陈秀华, 药学进展, 2008, 32, 145.)

[28] Arafa, H. M. Invest. New Drugs 2010, 28, 306.

[29] Shi, W.; Dolai, S.; Rizk, S.; Hussain, A.; Tariq, H.; Averick, S.;L'Amoreaux, W.; El ldrissi, A.; Banerjee, P.; Raja, K. Org. Lett.2007, 9, 5461.

[30] Li, J. L.; Feng X.; Yuan Y. J. Chin. J. Org. Chem. 2001, 21, 428 (inChinese).(李金亮, 冯霞, 元英进, 有机化学, 2001, 21, 428.)

[31] Wu, C. Y.; Quan, J.; Li, S. B. Chem. World 2009, 50, 561 (in Chinese).(吴承尧, 权静, 李树白, 化学世界, 2009, 50, 561.)

[32] Tang, H.; Murphy, C. J.; Zhang, B. Nanomedicine (London, U. K.)2010, 5, 855.

[33] Meister, A.; Anderson, M. Ann. Rev. Biochem. 1983, 52, 711.

[34] He, L. World Clin. Drugs 2006, 27, 55 (in Chinese).(何亮, 世界临床药物, 2006, 27, 55.)

[35] White, L. K.; Wright, W. E.; Shay, J. W. Trends Biotechnol. 2001,19, 114.

[36] Kapoor, N.; Sharma, A. K.; Dwivedi, V. Cancer Lett. 2007, 248,245.

[37] Lu, J.; Luo, G.; Wang, Y. M.; Liu, Q. F. Chin. J. Org. Chem. 2009,29, 1167 (in Chinese).(路娟, 刘清飞, 罗国安, 王义明, 有机化学, 2009, 29, 1167.)

[38] Sun, Z. L.; Wang, K.; Lin, X. H. Strait Pharm. J. 2008, 20, 7 (inChinese).(孙洲亮, 王昆, 林新华, 海峡药学, 2008 , 20, 7.)

[39] Safavy, A.; Raisch, K. P.; Mantena, S.; Sanford, L. L. J. Med.Chem. 2007, 50, 6284.

[40] Kim, C. Y.; Bordenave, N.; Ferruzzi, M. G. J. Agric. Food Chem.2011, 59, 1012.

[41] Li, J.; Wang, Y.; Yang, C. Mol. Pharmacol. 2009, 76, 81.

[42] Yu, Y.; Lu, T. L.; Sun, G. W.; Chen, T. Chin. Pharm. J. 2009, 22,1681 (in Chinese).(于洋, 卢婷利, 孙伟光, 陈涛, 中国药学杂志, 2009, 22, 1681.)

[43] Tang, H.; Murphy, C. J.; Zhang, B.; Shen, Y.; Van, K. E. A.;Murdoch, W. J,; Radosz, M. Biomaterials 2010, 31, 7139.

[44] Shu, J.; Peng, M.; Chen, Q. Chem. J. Chin. Univ. 2007, 28, 1398 (inChinese).(舒婕, 彭敏, 余家会, 高等学校化学学报, 2007 , 28, 1398.)

[45] Kim, J. K.; Garripelli, V. K.; Jeong, U. H.; Park, J. S.; Repka, M.A.; Jo, S. Int. J. Pharm. 2010, 401, 79.

[46] Zheng, J. M. Polymers in Pharmaceutics, Chinese Medical Scienceand Technology Press, Beijing, 2007, p. 156 (in Chinese).(郑俊民, 药用高分子材料学, 中国医药科技出版社, 北京,2007, p. 156.)

[47] Manju, S.; Sreenivasan, K. J. Pharm. Sci. 2011, 100, 504.

姜黄素前药的研究进展

Research Progress in the Prodrugs of Curcumin

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