Anna Makal

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.

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Avidin

10.1002/cplu.201600320

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Citations (11)

CCDC 1824996: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Marta Głodek Anna Makal Piotr Paluch Mariola Kądziołka-Gaweł Yasuhiro Kobayashi

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Crystal (programming language)

10.5517/ccdc.csd.cc1z81v4

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CCDC 1543930: Experimental Crystal Structure Determination

The Cambridge Structural Database (2017)

Damian Plażuk Anna Wieczorek Wojciech M. Ciszewski Karolina Kowalczyk Andrzej Błauż

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc1ntl68

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CCDC 938751: Experimental Crystal Structure Determination

The Cambridge Structural Database (2013)

Anna Wieczorek Damian Plażuk Janusz Zakrzewski Anna Makal Krzysztof Woźniak

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Crystal (programming language)

10.5517/cc10hv9n

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CCDC 1057279: Experimental Crystal Structure Determination

The Cambridge Structural Database (2015)

Anna Wrona-Piotrowicz Magdalena Ciechańska Janusz Zakrzewski Rémi Métivier Arnaud Brosseau

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Crystal (programming language)

10.5517/cc14h5sl

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CCDC 759917: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

Anna Makal K. Wozniak

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccthrgh

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CCDC 759914: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

Anna Makal K. Wozniak

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccthrcd

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CCDC 1824998: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Marta Głodek Anna Makal Piotr Paluch Mariola Kądziołka-Gaweł Yasuhiro Kobayashi

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc1z81x6

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CCDC 1544142: Experimental Crystal Structure Determination

The Cambridge Structural Database (2017)

Damian Plażuk Anna Wieczorek Wojciech M. Ciszewski Karolina Kowalczyk Andrzej Błauż

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc1ntt1b

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CCDC 740551: Experimental Crystal Structure Determination

The Cambridge Structural Database (2010)

Anna Szadkowska Anna Makal K. Wozniak Renat Kadyrov Karol Grela

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccsvlry

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i-10 index

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