title: Synthesis and characterization of novel n-9 fatty acid conjugates possessing antineoplastic properties.
abstract: The present study enumerates the synthesis, spectroscopic characterization, and evaluation of anticancer potential of esters of two n-9 fatty acids viz., oleic acid (OLA) and ricinoleic acid (RCA) with 2,4- or 2,6-diisopropylphenol. The synthesis strategy involved esterification of the hydroxyl group of diisopropylphenol (propofol) to the terminal carboxyl group of n-9 fatty acid. The synthesized propofol-n-9 conjugates having greater lipophilic character were tested initially for cytotoxicity in-vitro. The conjugates showed specific growth inhibition of cancer cell lines whereas no effect was observed in normal cells. In general, pronounced growth inhibition was found against the human skin malignant melanoma cell line (SK-MEL-1). The anticancer potential was also determined by testing the effect of these conjugates on cell migration, cell adhesion and induction of apoptosis in SK-MEL-1 cancer cells. Propofol-OLA conjugates significantly induced apoptosis in contrast to propofol-RCA conjugates which showed only weak signals for cytochrome c. Conclusively, the synthesized novel ester conjugates showed considerable moderation of anti-tumor activity. This preliminary study places in-house synthesized conjugates into the new class of anticancer agents that possess selectivity toward cancer cells over normal cells.
authors.affiliation: Interdisciplinary Biotechnology Unit, Aligarh Muslim University, Aligarh 202002, India. azmatbiotech@gmail.com
authors.forename: Azmat A
authors.initials: AA
authors.lastname: Khan
authors.forename: Ahmad
authors.initials: A
authors.lastname: Husain
authors.forename: Mumtaz
authors.initials: M
authors.lastname: Jabeen
authors.forename: Jamal
authors.initials: J
authors.lastname: Mustafa
authors.forename: Mohammad
authors.initials: M
authors.lastname: Owais
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017209:Apoptosis; D002448:Cell Adhesion; D045744:Cell Line, Tumor; D002465:Cell Movement; D002470:Cell Survival; D004305:Dose-Response Relationship, Drug; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D019301:Oleic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D015742:Propofol / Q000737:chemistry / Q000494:pharmacology; D012277:Ricinoleic Acids / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D005231:Fatty Acids, Unsaturated; D012277:Ricinoleic Acids; D019301:Oleic Acid; C030521:ricinoleic acid; D015742:Propofol