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Synthesis and antimicrobial activity of chiral quaternary N-spiro ammonium bromides with 3',4'-dihydro-1'H-spiro[isoindoline-2,2'-isoquinoline] skeleton

Authors Bielawski K, Leszczyńska K, Kałuża Z, Bielawska A, Michalak O, Daniluk T, Staszewska-Krajewska O, Czajkowska A, Pawłowska N, Gornowicz A

Received 25 January 2017

Accepted for publication 8 May 2017

Published 5 July 2017 Volume 2017:11 Pages 2015—2028

DOI https://doi.org/10.2147/DDDT.S133250

Checked for plagiarism Yes

Review by Single-blind

Peer reviewers approved by Dr Colin Mak

Peer reviewer comments 3

Editor who approved publication: Dr Sukesh Voruganti

Krzysztof Bielawski,1 Katarzyna Leszczyńska,2 Zbigniew Kałuża,3 Anna Bielawska,4 Olga Michalak,3 Tamara Daniluk,2 Olga Staszewska-Krajewska,3 Anna Czajkowska,4 Natalia Pawłowska,1 Agnieszka Gornowicz4

1Department of Synthesis and Technology of Drugs, 2Department of Microbiology, Medical University of Bialystok, Bialystok, 3Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, 4Department of Biotechnology, Medical University of Bialystok, Bialystok, Poland

Abstract: A new class of highly functionalized tetrahydroisoquinolines with a quaternary carbon stereocenter was synthesized starting from an easily accessible l-tartaric acid. Nine strains of bacteria (Staphylococcus aureus, Streptococcus pyogenes, Streptococcus mutans, Streptococcus salivarius, Bacillus subtilis, Enterococcus faecalis, Moraxella catarrhalis, Escherichia coli, Campylobacter jejuni) were used for the determination of minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) of synthesized compounds. The influence of analyzed compounds on viability and induction of apoptosis in human skin fibroblasts was determined. A majority of the synthesized compounds showed the strongest antibacterial properties toward some gram-negative bacteria (M. catarrhalis and C. jejuni) with a high level of selectivity. High antibacterial compounds have bactericidal activity ratio MBC/MIC =4. Our studies also proved that the novel compounds do not possess cytotoxic and proapoptotic potential in normal cells.

Keywords: quaternary ammonium compounds, tetrahydroisoquinolines, antimicrobial activity, antibiotic resistance
 

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