PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity

Izabella Jastrzebska; Stefano Mellea; Valerio Salerno; Pawel Adam Grzes; Leszek Siergiejczyk; Katarzyna Niemirowicz-Laskowska; Robert Bucki; Bonifacio Monti; Claudio Santi

doi:10.3390/ijms20092121

PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity

Int J Mol Sci. 2019 Apr 29;20(9):2121. doi: 10.3390/ijms20092121.

Authors

Izabella Jastrzebska¹, Stefano Mellea², Valerio Salerno³, Pawel Adam Grzes⁴, Leszek Siergiejczyk⁵, Katarzyna Niemirowicz-Laskowska⁶, Robert Bucki⁷, Bonifacio Monti⁸, Claudio Santi⁹

Affiliations

¹ Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland. i.jastrzebska@uwb.edu.pl.
² Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland. stefano.mellea@gmail.com.
³ Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland. vale_1192@hotmail.it.
⁴ Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland. felolix@gmail.com.
⁵ Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland. nmrbial@uwb.edu.pl.
⁶ Department of Microbiological and Nanobiomedical Engineering, Medical University of Białystok, ul. Mickiewicza 2C, 15-222 Bialystok, Poland. katia146@wp.pl.
⁷ Department of Microbiological and Nanobiomedical Engineering, Medical University of Białystok, ul. Mickiewicza 2C, 15-222 Bialystok, Poland. buckirobert@gmail.com.
⁸ Group of Catalysis and Organic Green Chemistry⁻Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06132 Perugia, Italy. bonifaciomonti@gmail.com.
⁹ Group of Catalysis and Organic Green Chemistry⁻Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06132 Perugia, Italy. claudio.santi@unipg.it.

Abstract

We report here the reaction of in situ prepared PhSeZnCl with steroid derivatives having an epoxide as an electrophilic functionalization. The corresponding ring-opening reaction resulted to be regio- and stereoselective affording to novel phenylselenium-substituted steroids. Assessment of their antibacterial properties against multidrug-resistant bacteria, such as Pseudomonas aeruginosa Xen 5 strain, indicates an interesting bactericidal activity and their ability to prevent bacterial biofilm formation.

Keywords: antibacterial; antibiofilm; selenium; steroids.

MeSH terms

Anti-Bacterial Agents / chemical synthesis
Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / pharmacology*
Biofilms / drug effects
Chlorides / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Organoselenium Compounds / chemical synthesis
Organoselenium Compounds / chemistry*
Organoselenium Compounds / pharmacology*
Pseudomonas aeruginosa / drug effects
Steroids / chemistry*
Zinc Compounds / chemistry*

Substances

Anti-Bacterial Agents
Chlorides
Organoselenium Compounds
Steroids
Zinc Compounds
zinc chloride