9-Hydroxystearic acid (9-HSA) is an endogenous cellular lipid that possesses antiproliferative and selective effects against cancer cells. A series of derivatives were synthesized in order to investigate the effect of the substituent in position 9 and on the methyl ester functionality on the biological activity. The two separate enantiomers of methyl 9-hydroxystearate and of methyl 9-aminostearate showed antiproliferative activity against the HT29 cell line. This indicates the importance of position 9 groups being able to make hydrogen bonding with the molecular target. Further, this effect must be preserved when the carboxy group of 9-HSA is esterified. The biological tests showed that the amines, contrarily to methyl esters, resulted in cytotoxicity. A deep investigation on the effect of methyl (R)-9-hydroxystearate on HT29 cells showed an antiproliferative effect acting through the CDKN1A and MYCBP gene expression.
Synthesis of 9-hydroxystearic acid derivatives and their antiproliferative activity on HT 29 cancer cells / Calonghi N.; Boga C.; Telese D.; Bordoni S.; Sartor G.; Torsello C.; Micheletti G.. - In: MOLECULES. - ISSN 1420-3049. - ELETTRONICO. - 24:20(2019), pp. 3714.1-3714.16. [10.3390/molecules24203714]
Synthesis of 9-hydroxystearic acid derivatives and their antiproliferative activity on HT 29 cancer cells
Calonghi N.
Investigation
;Boga C.
Conceptualization
;Telese D.Investigation
;Bordoni S.Investigation
;Sartor G.Resources
;Torsello C.Investigation
;Micheletti G.Investigation
2019
Abstract
9-Hydroxystearic acid (9-HSA) is an endogenous cellular lipid that possesses antiproliferative and selective effects against cancer cells. A series of derivatives were synthesized in order to investigate the effect of the substituent in position 9 and on the methyl ester functionality on the biological activity. The two separate enantiomers of methyl 9-hydroxystearate and of methyl 9-aminostearate showed antiproliferative activity against the HT29 cell line. This indicates the importance of position 9 groups being able to make hydrogen bonding with the molecular target. Further, this effect must be preserved when the carboxy group of 9-HSA is esterified. The biological tests showed that the amines, contrarily to methyl esters, resulted in cytotoxicity. A deep investigation on the effect of methyl (R)-9-hydroxystearate on HT29 cells showed an antiproliferative effect acting through the CDKN1A and MYCBP gene expression.File | Dimensione | Formato | |
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