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Ferrocene-Biotin Conjugates: Synthesis, Structure, Cytotoxic Activity and Interaction With Avidin

Ferrocene-Biotin Conjugates: Synthesis, Structure, Cytotoxic Activity and Interaction With Avidin

Andrzej Błauż, Błażej Rychlik, Anna Makal, Katarzyna Szulc, Paweł Strzelczyk, Grzegorz Bujacz, Janusz Zakrzewski, Krzysztof Woźniak, Damian Plażuk

Chempluschem. 2016 Nov;81(11):1191-1201.

PMID: 31964109

Abstract:

Friedel-Crafts acylation of ferrocene with d-biotin, d-homobiotin and d-desthiobiotin gave ferrocenyl ketones. These compounds were diastereoselectively reduced to the corresponding alcohols using (R)- and (S)-Me-CBS-oxazaborolidine-borane complexes as reducing agents. The alcohols were further transformed into azido and finally to amino derivatives with retention of configuration, as confirmed by X-ray crystallography. Ferrocenylbiotin alcohols smoothly underwent dehydration to (E)-alkenes as the major isomers by heating in diluted acetic acid. The synthesized compounds retained high affinity for avidin. They also exhibited high cytotoxicity toward cancer cells expressing various levels of sodium-dependent multivitamin transporter (SMVT) in the absence of biotin in the medium, whereas the presence of free biotin decreased their antiproliferative activity. This revealed that these biotin-ferrocene conjugates might be used as biologically active agents against cancer cells, although there was no clear relationship between their cytotoxicity and cellular SMVT level.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP533482	d-Desthiobiotin		533-48-2	Price

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