synthesis, characterization and biological evaluation of succinate prodrugs of curcuminoids for colon cancer treatment琥珀酸合成、表征和生物评价高活性curcuminoids结肠癌的治疗.pdf

Molecules 2011, 16, 1888-1900; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis, Characterization and Biological Evaluation of Succinate Prodrugs of Curcuminoids for Colon Cancer Treatment Wisut Wichitnithad 1, Ubonthip Nimmannit 1,2, Sumrit Wacharasindhu 3 and Pornchai Rojsitthisak 4,* 1 Pharmaceutical Technology (International) Program, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand; E-Mail: wisutrd@ 2 National Nanotechnology Center (Nanotec), National Science and Technology Development Agency, Pathumthani 12120, Thailand; E-Mail: ubonthip.n@chula.ac.th 3 Natural Products Research Unit, Department of Chemistry, Faculty of Sciences, Chulalongkorn University, Bangkok 10330, Thailand; E-Mail: sumrit.w@chula.ac.th 4 Department of Food and Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand * Author to whom correspondence should be addressed; E-Mail: pornchai.r@chula.ac.th; Tel.: +662-218-8310; Fax: +662-254-5195. Received: 11 January 2011; in revised form: 25 January 2011 / Accepted: 17 February 2011 / Published: 22 February 2011 Abstract: A novel series of succinyl derivatives of three curcuminoids were synthesized as potential prodrugs. Symmetrical (curcumin and bisdesmethoxycurcumin) and unsymmetrical (desmethoxycurcumin) curcuminoids were prepared through aldol condensation of 2,4-pentanedione with different benzaldehydes. Esterificatio