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Synthesis of dual-action parthenolide prodrugs as potent anticancer agents.

Abstract：

:Cancer stem cells are responsible for the failure of a large number of cancer treatments and the re-emergence of cancer in patients. Parthenolide is a potent anticancer sesquiterpene lactone that is also able to kill cancer stem cells. The main problem with this compound is its poor solubility in water. To solve this problem, medicinal chemists have tried to prepare amino-derivatives of parthenolide, however, most amino-derivatives have less potency than that of parthenolide. In this paper, we proposed a new approach to synthesize parthenolide derivatives with better solubility and higher potency. We prepared novel parthenolide derivatives through the aza-Michael addition of nitrogen-containing anticancer drug molecules (cytarabine and melphalan) to the α-methylene-γ-lactone group of parthenolide. Different types of catalysts were used to catalyze the aza-Michael addition. Among all the used catalysts, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) was found to have the highest catalytic activity. In addition, we examined the effects of parthenolide-anticancer drug hybrids on the growth and proliferation of three cancer cell lines (MCF-7, LNcaP, Hep G2) and CHO. The parthenolide prodrugs showed potent cytotoxic property with IC50 values ranging from 0.2 to 5.2μM, higher than those of parthenolide and anticancer drugs (cytarabine and melphalan).

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Taleghani A,Nasseri MA,Iranshahi M

doi

10.1016/j.bioorg.2017.01.020

subject

Has Abstract

pub_date

2017-04-01 00:00:00

pages

128-134

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(16)30350-9

journal_volume

71

pub_type

杂志文章

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