Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties.
The monoesters of curcumin, a symmetric diphenol with valine and glycine have been prepared by a novel solid phase synthesis and its diesters with valine, glutamic acid and demethylenated piperic acid have been prepared by solution phase method. The assessment of their antimicrobial and anticancer (antiproliferative) activities suggested that diesters of curcumin are relatively more active than curcumin itself due to their increased solubility, slow metabolism and better cellular uptake. Furthermore, significant observation was that monoesters of curcumin have even better antimicrobial activity than their corresponding diesters, emphasizing the role of free phenolic group. The conjugate of curcumin with demethylenated piperic acid in which methylenedioxy ring was open also shows enhanced activity than the corresponding piperic acid conjugate, emphasizing the role of free phenolics in the transport or in the binding processes.
Dubey
Shiv K
SK
Centre for Biotechnology, University of Allahabad, and Kamla Nehru Hospital, Allahabad 211002, India.
Sharma
Anuj K
AK
Narain
Upma
U
Misra
Krishna
K
Pati
Uttam
U
D000596:Amino Acids / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D003474:Curcumin / Q000737:chemistry* / Q000494:pharmacology*; D015195:Drug Design; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D018698:Glutamic Acid / Q000737:chemistry; D005998:Glycine / Q000737:chemistry; D006801:Humans; D014633:Valine / Q000737:chemistry
D000596:Amino Acids; D000890:Anti-Infective Agents; D005231:Fatty Acids, Unsaturated; D018698:Glutamic Acid; C017637:piperic acid; D014633:Valine; D003474:Curcumin; D005998:Glycine