Triphenylphosphonium Analogs of Short Peptide Related to Bactenecin 7 and Oncocin 112 as Antimicrobial Agents

Tereshchenkov, A.G.; Khairullina, Z.Z.; Volynkina, I.A.; Lukianov, D.A.; Nazarov, P.A.; Pavlova, J.A.; Tashlitsky, V.N.; Razumova, E.A.; Ipatova, D.A.; Timchenko, Y.V.; Senko, D.A.; Efremenkova, O.V.; Paleskava, A.; Konevega, A.L.; Osterman, I.A.; Rodin, I.A.; Sergiev, P.V.; Dontsova, O.A.; Bogdanov, A.A.; Sumbatyan, N.V. Triphenylphosphonium Analogs of Short Peptide Related to Bactenecin 7 and Oncocin 112 as Antimicrobial Agents. Pharmaceutics 2024, 16, 148. Tereshchenkov, A.G.; Khairullina, Z.Z.; Volynkina, I.A.; Lukianov, D.A.; Nazarov, P.A.; Pavlova, J.A.; Tashlitsky, V.N.; Razumova, E.A.; Ipatova, D.A.; Timchenko, Y.V.; Senko, D.A.; Efremenkova, O.V.; Paleskava, A.; Konevega, A.L.; Osterman, I.A.; Rodin, I.A.; Sergiev, P.V.; Dontsova, O.A.; Bogdanov, A.A.; Sumbatyan, N.V. Triphenylphosphonium Analogs of Short Peptide Related to Bactenecin 7 and Oncocin 112 as Antimicrobial Agents. Pharmaceutics 2024, 16, 148.

Abstract

Triphenylphosphonium (TPP) derivatives of a decapeptide related to sequences of bactenecin 7 (Bac7) and oncocin (Onc112) were synthesized and studied as potential antimicrobial compounds using various biochemical and microbiological assays. It was shown that while the reduction of the Bac7 length to 10 a.a. residues dramatically decreases the affinity to bacterial ribosomes, the modification of peptide with alkyl-TPP moieties leads to an increase in the affinity. New analogs which structure combines a decapeptide related to Bac7 and Onc112 — Bac(1-10, R/Y) — and TPP, attached to the C-terminal amino acid residue through alkylamide linkers, inhibit translation in vitro and are found to be more selective inhibitors of bacterial translation as compared with eukaryotic translation, than Onc112 and Bac7. Triphenylphosphonium analogs of a decapeptide related to Bac7 and Onc112 suppress the growth of both gram-negative bacteria, similar to Onc112 and Bac7, and gram-positive ones as alkyl-TPP derivatives, and also act against some resistant laboratory strains. Bac(1-10, R/Y)-C2-TPP, containing a short alkylamide linker between the decapeptide and TPP, is transferred into the E. coli cells via the SbmA transporter protein. TPP derivatives of the decapeptide Bac(1-10, R/Y) containing either decylamide or ethylamide linker cause B. subtilis membrane depolarization, similar to alkyl-TPP. The Bac(1-10, R/Y)-C2-TPP analog is proved to be non-toxic for mammalian cells by MTT-test.

Keywords

alkyl(triphenyl)phosphonium; proline arginine rich antimicrobial peptides; bactenecin 7; oncocin 112; bacterial ribosome; bacterial membrane potential; antimicrobial activity

Subject

Biology and Life Sciences, Biochemistry and Molecular Biology

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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