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Ferrocene-Biotin Conjugates: Synthesis, Structure, Cytotoxic Activity and Interaction with Avidin.
Chempluschem 2016; 81(11):1191-1201C

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.

Authors+Show Affiliations

Cytometry Lab, Department of Molecular Biophysics, Faculty of Biology and Environmental Protection, University of Łódź, 141/143 Pomorska St., 90-236, Łódź, Poland.Cytometry Lab, Department of Molecular Biophysics, Faculty of Biology and Environmental Protection, University of Łódź, 141/143 Pomorska St., 90-236, Łódź, Poland.Department of Chemistry, University of Warsaw, Pasteura, 1, 02-093, Warszawa, Poland.Cytometry Lab, Department of Molecular Biophysics, Faculty of Biology and Environmental Protection, University of Łódź, 141/143 Pomorska St., 90-236, Łódź, Poland.Institute of Technical Biochemistry, Łódź University of Technology, Stefanowskiego 4/10, 90-924, Łódź, Poland.Institute of Technical Biochemistry, Łódź University of Technology, Stefanowskiego 4/10, 90-924, Łódź, Poland.Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 41-403, Łódź, Poland.Department of Chemistry, University of Warsaw, Pasteura, 1, 02-093, Warszawa, Poland.Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 41-403, Łódź, Poland.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31964109

Citation

Błauż, Andrzej, et al. "Ferrocene-Biotin Conjugates: Synthesis, Structure, Cytotoxic Activity and Interaction With Avidin." ChemPlusChem, vol. 81, no. 11, 2016, pp. 1191-1201.
Błauż A, Rychlik B, Makal A, et al. Ferrocene-Biotin Conjugates: Synthesis, Structure, Cytotoxic Activity and Interaction with Avidin. Chempluschem. 2016;81(11):1191-1201.
Błauż, A., Rychlik, B., Makal, A., Szulc, K., Strzelczyk, P., Bujacz, G., ... Plażuk, D. (2016). Ferrocene-Biotin Conjugates: Synthesis, Structure, Cytotoxic Activity and Interaction with Avidin. ChemPlusChem, 81(11), pp. 1191-1201. doi:10.1002/cplu.201600320.
Błauż A, et al. Ferrocene-Biotin Conjugates: Synthesis, Structure, Cytotoxic Activity and Interaction With Avidin. Chempluschem. 2016;81(11):1191-1201. PubMed PMID: 31964109.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ferrocene-Biotin Conjugates: Synthesis, Structure, Cytotoxic Activity and Interaction with Avidin. AU - Błauż,Andrzej, AU - Rychlik,Błażej, AU - Makal,Anna, AU - Szulc,Katarzyna, AU - Strzelczyk,Paweł, AU - Bujacz,Grzegorz, AU - Zakrzewski,Janusz, AU - Woźniak,Krzysztof, AU - Plażuk,Damian, Y1 - 2016/08/19/ PY - 2016/06/15/received PY - 2020/1/23/entrez KW - bioorganometallic chemistry KW - biotin KW - cytotoxicity KW - ferrocene KW - sodium-dependent multivitamin transporter SP - 1191 EP - 1201 JF - ChemPlusChem JO - Chempluschem VL - 81 IS - 11 N2 - 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. SN - 2192-6506 UR - https://www.unboundmedicine.com/medline/citation/31964109/Ferrocene-Biotin_Conjugates:_Synthesis,_Structure,_Cytotoxic_Activity_and_Interaction_with_Avidin L2 - https://doi.org/10.1002/cplu.201600320 DB - PRIME DP - Unbound Medicine ER -