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Precursor-Directed Synthesis of Apoptosis-Initiating N-Hydroxyalkyl Phenylbenzoisoquinolindione Alkaloids.

ABSTRACT: A precursor-directed approach to access N-hydroxyalkyl phenylbenzoisoquinolindiones (PBIQs) has been developed. Incubation of plant material of Xiphidium caeruleum with hydroxylamines of various chain lengths (C₂ , C₄ , C₆ , C₈ , C₁₀ and C₁₂ ) resulted in 11 new 5-hydroxy- and 5-methoxy PBIQs with different N-hydroxyalkyl side chain lengths. The antiproliferative effect and the cytotoxicity against HUVEC, K-562, and HeLa cell lines of 26 previously reported PBIQs and the 11 newly synthesized N-hydroxyalkyl PBIQs was determined for the first time. The results revealed that introducing long-chain N-aliphatic amine moieties improved the antiproliferative effect and cytotoxicity of PBIQs when compared to derivatives with N-amino acids as side chains.

SUBMITTER: Chen Y

PROVIDER: S-EPMC9728486 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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Precursor-Directed Synthesis of Apoptosis-Initiating N-Hydroxyalkyl Phenylbenzoisoquinolindione Alkaloids.

Chen Yu Y Dahse Hans-Martin HM Paetz Christian C Schneider Bernd B

ChemistryOpen 20221201 12

A precursor-directed approach to access N-hydroxyalkyl phenylbenzoisoquinolindiones (PBIQs) has been developed. Incubation of plant material of Xiphidium caeruleum with hydroxylamines of various chain lengths (C2 , C4 , C6 , C8 , C10 and C12 ) resulted in 11 new 5-hydroxy- and 5-methoxy PBIQs with different N-hydroxyalkyl side chain lengths. The antiproliferative effect and the cytotoxicity against HUVEC, K-562, and HeLa cell line ...[more]

PMID: 36478420

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