Enzymatic preparation of acylated derivatives of silybin in organic and ionic liquid media and evaluation of their antitumor proliferative activity

Theodosiou, E; Katsoura, MM; Loutrari, H; Purchartova, K; Kren, V; Kolisis, FN; Stamatis, H

dc.contributor.author	Theodosiou, E	en
dc.contributor.author	Katsoura, MM	en
dc.contributor.author	Loutrari, H	en
dc.contributor.author	Purchartova, K	en
dc.contributor.author	Kren, V	en
dc.contributor.author	Kolisis, FN	en
dc.contributor.author	Stamatis, H	en
dc.date.accessioned	2014-03-01T01:30:21Z
dc.date.available	2014-03-01T01:30:21Z
dc.date.issued	2009	en
dc.identifier.issn	1024-2422	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/19564
dc.subject	Acylation	en
dc.subject	Antitumor proliferative activity	en
dc.subject	Ionic liquids	en
dc.subject	Lipase	en
dc.subject	Organic solvents	en
dc.subject	Silybin	en
dc.subject.classification	Biochemistry & Molecular Biology	en
dc.subject.classification	Biotechnology & Applied Microbiology	en
dc.subject.other	Acyl donors	en
dc.subject.other	Alkyl chain lengths	en
dc.subject.other	Anti-tumors	en
dc.subject.other	Antiproliferative effect	en
dc.subject.other	Antitumor proliferative activity	en
dc.subject.other	Biocatalytic preparation	en
dc.subject.other	Biocatalytic process	en
dc.subject.other	Candida antarctica lipase B	en
dc.subject.other	Conversion yield	en
dc.subject.other	Enzymatic preparation	en
dc.subject.other	Enzymatic process	en
dc.subject.other	Free fatty acid	en
dc.subject.other	Human leukemia cells	en
dc.subject.other	Imidazolium-based ionic liquid	en
dc.subject.other	Ionic liquid media	en
dc.subject.other	Molar ratio	en
dc.subject.other	Proliferative activity	en
dc.subject.other	Reaction media	en
dc.subject.other	Silybin	en
dc.subject.other	Acetone	en
dc.subject.other	Acylation	en
dc.subject.other	Esterification	en
dc.subject.other	Esters	en
dc.subject.other	Fatty acids	en
dc.subject.other	Ionization of liquids	en
dc.subject.other	Negative ions	en
dc.subject.other	Organic solvents	en
dc.subject.other	Reaction rates	en
dc.subject.other	Ionic liquids	en
dc.subject.other	antineoplastic agent	en
dc.subject.other	flavonolignan	en
dc.subject.other	imidazole derivative	en
dc.subject.other	ionic liquid	en
dc.subject.other	lipase B	en
dc.subject.other	organic solvent	en
dc.subject.other	silibinin	en
dc.subject.other	silybin 23 o butanoate	en
dc.subject.other	silybin 23 o laurate	en
dc.subject.other	silybin 23 o oleate	en
dc.subject.other	unclassified drug	en
dc.subject.other	acylation	en
dc.subject.other	antineoplastic activity	en
dc.subject.other	article	en
dc.subject.other	biocatalyst	en
dc.subject.other	biotransformation	en
dc.subject.other	Candida albicans	en
dc.subject.other	concentration response	en
dc.subject.other	controlled study	en
dc.subject.other	drug structure	en
dc.subject.other	drug synthesis	en
dc.subject.other	growth inhibition	en
dc.subject.other	human	en
dc.subject.other	human cell	en
dc.subject.other	leukemia cell	en
dc.subject.other	Candida antarctica	en
dc.title	Enzymatic preparation of acylated derivatives of silybin in organic and ionic liquid media and evaluation of their antitumor proliferative activity	en
heal.type	journalArticle	en
heal.identifier.primary	10.1080/10242420902937777	en
heal.identifier.secondary	http://dx.doi.org/10.1080/10242420902937777	en
heal.language	English	en
heal.publicationDate	2009	en
heal.abstract	Biocatalytic preparation of acylated derivatives of silybin using several acyl donors (free fatty acids or their esters), catalyzed by immobilized Candida antarctica lipase B, was performed in various organic solvents as well as in imidazolium-based ionic liquids containing either BF4- or PF6- anions. Total conversion of silybin was achieved in acetone using short-chain acyl donors (vinyl butanoate) at a 10: 1 molar ratio of acyl donor to silybin. The enzymatic process in ionic liquids depended strongly on the alkyl chain length of the cation as well the anion used. Higher conversion yields (up to 75.8%) and reaction rates (up to 0.31 mmol h(-1) g(-1) biocatalyst) were obtained in the BF4- as compared with PF6- containing ionic liquids. The amounts of silybin ester formed in a one-step biocatalytic process were high (>40 g L-1) in both reaction media. The antiproliferative effect of acylated silybin derivatives on the growth of K562 human leukemia cells was estimated and compared with that of silybin.	en
heal.publisher	TAYLOR & FRANCIS LTD	en
heal.journalName	Biocatalysis and Biotransformation	en
dc.identifier.doi	10.1080/10242420902937777	en
dc.identifier.isi	ISI:000268032500001	en
dc.identifier.volume	27	en
dc.identifier.issue	3	en
dc.identifier.spage	161	en
dc.identifier.epage	169	en