Paweł Strzelczyk

National Cancer Institute

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Grzegorz Bujacz

Lodz University of Technology

Janusz Zakrzewski

University of Łódź

Damian Plażuk

University of Łódź

Alexander Wlodawer

Center for Cancer Research

JŁ

J. Łubkowski

National Institutes of Health

Andrzej Błauż

University of Łódź

Błażej Rychlik

University of Łódź

Katarzyna Szulc

Systems Research Institute

Anna Makal

University of Warsaw

A. Bujacz

Lodz University of Technology

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University of Łódź

National Cancer Institute

National Institutes of Health

Center for Cancer Research

Frederick National Laboratory for Cancer Research

Polish Academy of Sciences

Lodz University of Technology

Centrum Badań Molekularnych i Makromolekularnych Polskiej Akademii Nauk

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Centre National de la Recherche Scientifique

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Ferrocene–Biotin Conjugates: Synthesis, Structure, Cytotoxic Activity and Interaction with Avidin

ChemPlusChem (2016)

Andrzej Błauż Błażej Rychlik Anna Makal Katarzyna Szulc Paweł Strzelczyk

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 1429558: Experimental Crystal Structure Determination

The Cambridge Structural Database (2016)

Andrzej Błauż Błażej Rychlik Anna Makal Katarzyna Szulc Paweł Strzelczyk

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.cc1jzksv

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Ferrocene–Biotin Conjugates Targeting Cancer Cells: Synthesis, Interaction with Avidin, Cytotoxic Properties and the Crystal Structure of the Complex of Avidin with a Biotin–Linker–Ferrocene Conjugate

Organometallics (2013)

Damian Plażuk Janusz Zakrzewski Michèle Salmain Andrzej Błauż Błażej Rychlik

Friedel–Crafts acylation of ferrocene with a biotin-derived carboxylic acid having 6-aminohexanoyl linkers attached to the biotin carboxylic group and with desthiobiotin afforded the corresponding ferrocene–biotin bioconjugates. These compounds as well as biotinyl ferrocenyl ketone exhibit high affinity for avidin. Their cytotoxicity against cancer cell lines having various levels of biotin receptors (SMVT) was measured and revealed that lines displaying high levels of SMVT (SW620) were the most susceptible. This suggests that biotin serves as a biological vector delivering cytotoxic ferrocenyl moieties to cancer cells. The crystal structure of the complex of avidin with a conjugate having two linker units between biotin and ferrocene was determined and revealed stabilization of several different conformations of the ligand within the protein binding pocket.

Avidin

Conjugate

Linker

10.1021/om4003126

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Citations (57)

CCDC 1429556: Experimental Crystal Structure Determination

The Cambridge Structural Database (2016)

Andrzej Błauż Błażej Rychlik Anna Makal Katarzyna Szulc Paweł Strzelczyk

10.5517/ccdc.csd.cc1jzkqs

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Detailed mechanism of catalysis by tetrameric L-glutaminase-asparaginase from Pseudomonas 7A (PGA)

Acta Crystallographica Section A Foundations and Advances (2022)

Paweł Strzelczyk Di Zhang Marzena Dyba Alexander Wlodawer J. Łubkowski

Glutaminase

10.1107/s2053273322097066

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Structural Characterization of the Avidin Interactions with Fluorescent Pyrene-Conjugates: 1-Biotinylpyrene and 1-Desthiobiotinylpyrene

Molecules (2016)

Paweł Strzelczyk Damian Plażuk Janusz Zakrzewski Grzegorz Bujacz

Avidin is a tetrameric protein that belongs to the calycin superfamily. It has been studied mainly because of its extraordinary affinity to biotin, which led to a wide range of applications based on the avidin-biotin system. In the present study, we report the first crystal structures of avidin in a complex with two novel fluorescent pyrene derivatives: 1-biotinylpyrene (B9P) and 1-desthiobiotinylpyrene (D9P). The crystal structures were solved by molecular replacement using the coordinates of avidin molecule as a starting model and the final models of avidin/B9P and avidin/D9P were refined to resolutions of 2.0 Å and 2.1 Å, respectively. Our data reveal changes in loop conformation as well as in overall fold and quaternary arrangement of the avidin upon the binding of these fluorescent probes. Moreover, the crystal structures allowed analysis of the details of the interactions between the protein and the pyrene derivatives. Structural description of the complexes will contribute to the design of conjugates for expanding the capabilities of avidin-biotin technology.

Avidin

Conjugate

10.3390/molecules21101270

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Citations (9)

Crystal structure of Pseudomonas 7A Glutaminase-Asparaginase in complex with L-Asp at pH 5.0

Paweł Strzelczyk D. Zhang Alexander Wlodawer J. Łubkowski

Hydrolase

10.2210/pdb6wyx/pdb

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CCDC 1429553: Experimental Crystal Structure Determination