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Total synthesis and biological evaluation of fluorinated cryptophycins.

ABSTRACT: Cryptophycins are cytotoxic natural products that exhibit considerable activities even against multi-drug-resistant tumor cell lines. As fluorinated pharmaceuticals have become more and more important during the past decades, fluorine-functionalized cryptophycins were synthesized and evaluated in cell-based cytotoxicity assays. The unit A trifluoromethyl-modified cryptophycin proved to be highly active against KB-3-1 cells and exhibited an IC(50) value in the low picomolar range. However, the replacement of the 3-chloro-4-methoxyphenyl-substituent in unit B by a pentafluorophenyl moiety resulted in a significant loss of activity.

SUBMITTER: Weiß C

PROVIDER: S-EPMC3511040 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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Total synthesis and biological evaluation of fluorinated cryptophycins.

Weiß Christine C Bogner Tobias T Sammet Benedikt B Sewald Norbert N

Beilstein journal of organic chemistry 20121123

Cryptophycins are cytotoxic natural products that exhibit considerable activities even against multi-drug-resistant tumor cell lines. As fluorinated pharmaceuticals have become more and more important during the past decades, fluorine-functionalized cryptophycins were synthesized and evaluated in cell-based cytotoxicity assays. The unit A trifluoromethyl-modified cryptophycin proved to be highly active against KB-3-1 cells and exhibited an IC(50) value in the low picomolar range. However, the re ...[more]

PMID: 23209540

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