Scale-Up Synthesis and In Vivo Anti-Tumor Activity of Curcumin Diethyl Disuccinate, an Ester Prodrug of Curcumin, in HepG2-Xenograft Mice.
HepG2-xenograft mice
anti-tumor activity
curcumin
curcumin diethyl disuccinate
scale-up synthesis
Journal
Pharmaceutics
ISSN: 1999-4923
Titre abrégé: Pharmaceutics
Pays: Switzerland
ID NLM: 101534003
Informations de publication
Date de publication:
01 Aug 2019
01 Aug 2019
Historique:
received:
30
06
2019
revised:
22
07
2019
accepted:
23
07
2019
entrez:
4
8
2019
pubmed:
4
8
2019
medline:
4
8
2019
Statut:
epublish
Résumé
Previously, we synthesized curcumin and a succinate ester prodrug of curcumin namely curcumin diethyl disuccinate (CurDD) in the lab scale, which yielded hundred milligrams to few grams of the compounds. CurDD was found to be more stable in a phosphate buffer pH 7.4 and exhibited better cytotoxicity against Caco-2 cells than curcumin. Here, the one-pot syntheses of curcumin and CurDD were scaled up to afford multigram quantities of both compounds for preclinical studies using a 10-L chemical reactor. The key steps for the synthesis of curcumin were the formation of boron-acetylacetone complex and the decomplexation of boron-curcumin complex. The synthesis of CurDD could be achieved via a one-step esterification between curcumin and succinic acid monoethyl ester chloride using 4-(
Identifiants
pubmed: 31374932
pii: pharmaceutics11080373
doi: 10.3390/pharmaceutics11080373
pmc: PMC6723761
pii:
doi:
Types de publication
Journal Article
Langues
eng
Subventions
Organisme : The 90th Anniversary Chulalongkorn University Fund, Ratchadaphiseksomphot Endowment Fund
ID : Chawanphat Muangnoi; GCUGR1125602002D
Organisme : The Overseas Research Experience Scholarship from the Graduate School and Faculty of Pharmaceutical Sciences, Chulalongkorn University
ID : Chawanphat Muangnoi
Organisme : The Annual Research Fund of The Asia Research Center (ARC), Chulalongkorn University
ID : Pornchai Rojsitthisak; 005/2558
Organisme : Chulalongkorn University, Government Budget
ID : Pornchai Rojsitthisak; GB-A_60_017_33_02
Organisme : Ratchadaphiseksomphot Endowment Fund for the Natural Products for Ageing and Chronic Diseases
ID : GRU 61011633004-1
Organisme : Ratchadaphiseksomphot Endowment Fund of Chulalongkorn University for Article Processing Charge
ID : Pornchai Rojsitthisak
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