Synthesis, antimicrobial evaluation and molecular modeling of 5-hydroxyisoquinolinium salt series; the effect of the hydroxyl moiety

Bioorganic & Medicinal Chemistry
Ondrej SoukupKamil Kuca

Abstract

In the present paper, we describe the synthesis of a new group of 5-hydroxyisoquinolinium salts with different lengths of alkyl side-chain (C10-C18), and their chromatographic analysis and biological assay for in vitro activity against bacterial and fungal strains. We compare the lipophilicity and efficacy of hydroxylated isoquinolinium salts with the previously published (non-hydroxylated) isoquinolinium salts from the point of view of antibacterial and antifungal versatility and cytotoxic safety. Compound 11 (C18) had to be excluded from the testing due to its low solubility. Compounds 9 and 10 (C14, C16) showed only moderate efficacy against G+ bacteria, notably with excellent potency against Staphyloccocus aureus, but no effect against G- bacteria. In contrast, non-hydroxylated isoquinolinium salts showed excellent antimicrobial efficacy within the whole series, particularly 14 (C14) against G+ strains and 15 (C16) against fungi. The electronic properties and desolvation energies of 5-hydroxyisoquinolinium and isoquinolinium salts were studied by quantum-chemistry calculations employing B3LYP/6-311++G(d,p) method and an implicit water-solvent simulation model (SCRF). Despite the positive mesomeric effect of the hydroxyl moi...Continue Reading

References

Mar 1, 1979·Antimicrobial Agents and Chemotherapy·J M TanzerE R Scheer
Feb 4, 2006·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Halide Akbaş, Ciğdem Kartal
Nov 6, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kamil KucaDaniel Jun
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Sep 10, 2013·BMJ : British Medical Journal·Suzy Frisch
Feb 27, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jan MarekKamil Kuca

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Citations

May 10, 2017·Materials Science & Engineering. C, Materials for Biological Applications·Wenqiang TanZhanyong Guo
May 15, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sarka SalajkovaOndrej Soukup
Nov 18, 2017·Archives of Virology·Camyla Alves LeonelJaqueline Maria Siqueira Ferreira
Apr 30, 2017·Food Science and Biotechnology·Eunsuk KimHyunjin Yoon

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