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Antimicrobial agents based on new lipophilic alkyl (N-alkyl-N,N-dioctylammoniomethyl)phosphonates

Natal'ya Victorovna Davletshina 1
Natal'ya Victorovna Davletshina
, 
Ekaterina Aleksandrovna Ermakova 1
Ekaterina Aleksandrovna Ermakova
, 
Dilyara Ramilevna Dolgova 1
Dilyara Ramilevna Dolgova
, 
Rustam Rifkhatovich Davletshin 1
Rustam Rifkhatovich Davletshin
, 
Marina Petrovna Shulaeva 2
Marina Petrovna Shulaeva
,  , 
Bulat I Gareev 3
Bulat I Gareev
, 
Rafael Askhatovich Cherkasov 1
Rafael Askhatovich Cherkasov
1 Alexander Butlerov Institute of Chemistry, Kazan Federal University, Kazan, Russian Federation
2 Kazan State Medical Academy, Kazan, Russian Federation
3 Institute of Geology and Petroleum Technologies, Kazan Federal University, Kazan, Russian Federation
10.1016/j.mencom.2023.09.012
Published 2023-09-01
Communication , Volume 33, Issue 5, 627-630
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Davletshina N. V. et al. Antimicrobial agents based on new lipophilic alkyl (N-alkyl-N,N-dioctylammoniomethyl)phosphonates // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 627-630.
GOST all authors (up to 50) Copy
Davletshina N. V., Ermakova E. A., Dolgova D. R., Davletshin R. R., Shulaeva M. P., Stoikov I. I., Gareev B. I., Cherkasov R. A. Antimicrobial agents based on new lipophilic alkyl (N-alkyl-N,N-dioctylammoniomethyl)phosphonates // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 627-630.
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TY - JOUR
DO - 10.1016/j.mencom.2023.09.012
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.012
TI - Antimicrobial agents based on new lipophilic alkyl (N-alkyl-N,N-dioctylammoniomethyl)phosphonates
T2 - Mendeleev Communications
AU - Davletshina, Natal'ya Victorovna
AU - Ermakova, Ekaterina Aleksandrovna
AU - Dolgova, Dilyara Ramilevna
AU - Davletshin, Rustam Rifkhatovich
AU - Shulaeva, Marina Petrovna
AU - Stoikov, Ivan Ivanovich
AU - Gareev, Bulat I
AU - Cherkasov, Rafael Askhatovich
PY - 2023
DA - 2023/09/01
PB - Mendeleev Communications
SP - 627-630
IS - 5
VL - 33
ER -
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@article{2023_Davletshina,
author = {Natal'ya Victorovna Davletshina and Ekaterina Aleksandrovna Ermakova and Dilyara Ramilevna Dolgova and Rustam Rifkhatovich Davletshin and Marina Petrovna Shulaeva and Ivan Ivanovich Stoikov and Bulat I Gareev and Rafael Askhatovich Cherkasov},
title = {Antimicrobial agents based on new lipophilic alkyl (N-alkyl-N,N-dioctylammoniomethyl)phosphonates},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.012},
number = {5},
pages = {627--630},
doi = {10.1016/j.mencom.2023.09.012}
}
MLA
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Davletshina, Natal'ya Victorovna, et al. “Antimicrobial agents based on new lipophilic alkyl (N-alkyl-N,N-dioctylammoniomethyl)phosphonates.” Mendeleev Communications, vol. 33, no. 5, Sep. 2023, pp. 627-630. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.012.

Keywords

antimicrobial properties
betaines
lipophilicity
one-pot syntheses
organophosphorus compounds
phosphonates
quaternary ammonium compounds
zwitterionic compounds.

Abstract

(N-Alkyl-N,N-dioctylammoniomethyl)phosphonates were obtained by alkylation of amino phosphonate potassium salt with alkyl iodides or benzyl chloride. All synthesized compounds demonstrated high antibacterial and antifungal activity against Gram-positive bacterial strains B. cereus and S. aureus and were not active against Gram-negative strains Ps. aeruginosa. Some regularity connecting the structure of the obtained compounds with their antimicrobial action has been established.

References

.
Reactions of Triphenylphospine with ω-Bromoalkanecarboxylic Acids
Romanov S.R., Khafizova A.I., Gerasimov A.V., Islamov D.R., Shulaeva M.P., Pozdeev O.K., Galkina I.V., Galkin V.I., Bakhtiyarova Y.V.
Russian Journal of General Chemistry, 2022
.
Synthesis and antimicrobial activity of phosphorylated betaines
Gayneev A., Davletshin R., Galkina I., Davletshina N., Sedov A., Mirkhuzina M., Kuchaev E., Islamov D.
Phosphorus, Sulfur and Silicon and the Related Elements, 2022
.
Davletshin R.R., Gayneev A.M., Ermakova E.A., Davletshina N.V., Galkina I.V., Ivshin K.A., Shulaeva M.P., Pozdeev O.K.
Mendeleev Communications, 2022
.
The Phosphorus Analogues of Aminocarboxylic Acids
Kukhar' V.P., Solodenko V.A.
Russian Chemical Reviews, 1987
.
Ion conduction in zwitterionic-type molten salts and their polymers
Yoshizawa M., Hirao M., Ito-Akita K., Ohno H.
Journal of Materials Chemistry A, 2001
.
Synthesis, structure and bioactivity of novel carboxylate phosphabetaine derivatives with long alkyl chains
Minnullin R.R., Bakhtiyarova Y.V., Morozov M.V., Bakhtiyarov D.I., Shulaeva M.P., Oskar K.P., Gerasimov A.V., Galkina I.V., Galkin V.I.
Phosphorus, Sulfur and Silicon and the Related Elements, 2019
.
Polymeric lipid assemblies as novel theranostic tools.
Puri A., Blumenthal R.
Accounts of Chemical Research, 2011
.
Biomimetic Design and Performance of Polymerizable Lipids
Cashion M.P., Long T.E.
Accounts of Chemical Research, 2009
.
Specific Ion Effects on Adsorbed Zwitterionic Copolymers
Jumai’an E., Garcia E., Herrera-Alonso M., Bevan M.A.
Macromolecules, 2020
.
Effects of additional salts on the interfacial tension of crude oil/zwitterionic gemini surfactant solutions
Lv K., Jia K., Yang Y., Huang W., Wu H., Pan W., Jia H.
Journal of Dispersion Science and Technology, 2018
.
Structure and Complexing Properties of Butyl [(N-Benzyl-N,N-dibutylammonio)methyl] Phosphonate
Davletshina N.V., Dolgova D.R., Ermakova E.A., Davletshin R.R., Ivshin K.A., Cherkasov R.A.
Russian Journal of General Chemistry, 2022
.
Synthesis and Biological Activity of New Aminophosphabetaines
Gaineev A.M., Galkina I.V., Davletshin R.R., Davletshina N.V., Kuznetsov N.O., Grishaev D.Y., Shulayeva M.P., Pozdeev O.K.
Russian Journal of General Chemistry, 2022
.
Extraction and Membrane Transport Properties of 8-(1-O,O-Diamylphosphoryl-3,5-dioxapentane)quinoline
Davletshina N.V., Khabibullina A.R., Gaynullin A.Z., Davletshin R.R., Osipova E.V., Cherkasov R.A.
Russian Journal of General Chemistry, 2021
.
Synthesis and Biological Activity of Aminophosphabetaines with Long-chain Substitutes at the Nitrogen Atom
Davletshin R.R., Gayneev A.M., Davletshina N.V., Galkina I.V., Ivshin K.A., Shulaeva M.P.
Russian Journal of Organic Chemistry, 2022
.
Quaternary Ammonium Salts as Germicides. III. Quaternary Ammonium Salts Derived from Cyclic Amines
Shelton R.S., Campen M.G., Tilford C.H., Lang H.C., Nisonger L., Bandelin F.J., Rubenkoenig H.L.
Journal of the American Chemical Society, 1946
.
Quaternary Ammonium Salts as Germicides. I. Non-acylated Quaternary Ammonium Salts Derived from Aliphatic Amines1
Shelton R.S., Campen M.G., Tilford C.H., Lang H.C., Nisonger L., Bandelin F.J., Rubenkoenig H.L.
Journal of the American Chemical Society, 1946
.
The zwitterion effect in high-conductivity polyelectrolyte materials
Tiyapiboonchaiya C., Pringle J.M., Sun J., Byrne N., Howlett P.C., MacFarlane D.R., Forsyth M.
Nature Materials, 2003
.
Polymerizable phospholipid analogues--new stable biomembrane and cell models.
Hub H., Hupfer B., Koch H., Ringsdorf H.
Angewandte Chemie - International Edition, 1980
.
Phospholipid polymers
Nakaya T.
Progress in Polymer Science, 1999
.
Biosurfactant Producing Microbes and their Potential Applications: A Review
Shekhar S., Sundaramanickam A., Balasubramanian T.
Critical Reviews in Environmental Science and Technology, 2014
.
Biodegradability and toxicity of monorhamnolipid biosurfactant diastereomers
Hogan D.E., Tian F., Malm S.W., Olivares C., Palos Pacheco R., Simonich M.T., Hunjan A.S., Tanguay R.L., Klimecki W.T., Polt R., Pemberton J.E., Curry J.E., Maier R.M.
Journal of Hazardous Materials, 2019
.
Synthesis, structure, and biological activity of dicarboxylate phosphabetaines
Bakhtiyarova Y.V., Minnullin R.R., Morozov M.V., Bakhtiyarov D.I., Islamov D.R., Dobrynin A.B., Kataeva O.N., Cherkasov R.A., Galkin V.I., Galkina I.V.
Phosphorus, Sulfur and Silicon and the Related Elements, 2016
.
FTIR spectroscopic analyses of the pentyl {[benzyl(dibutyl)ammonio]methyl}phosphonate copper(II) complex
Davletshina N., Khabibullina A., Ushakova J., Davletshin R., Islamov D., Usachev K., Cherkasov R.
Journal of Organometallic Chemistry, 2020
.
FT-IR spectroscopic analyses of complex formation process phosphorylated betaines with metal ions
Davletshina N., Khabibullina A., Davletshin R., Ivshin K., Kataeva O., Cherkasov R.
Journal of Organometallic Chemistry, 2021
.
Membranes from Polymerizable Lipids
Zhang H., Joubert J.R., Saavedra S.S.
Advances in Polymer Science, 2009
.
Less bound cations and stable inner salt structure enhanced the salt tolerance of the bio-based zwitterionic surfactants
He X., Wang Z., Gang H., Ye R., Yang S., Mu B.
Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2022
.
Structure and FT-IR spectroscopic analyses of complexes phosphorylated betaines with rare earth metal ions
Davletshina N., Ermakova E., Dolgova D., Davletshin R., Ivshin K., Fedonin A., Stoikov I., Cherkasov R.
Inorganica Chimica Acta, 2023
.
Membrane Transport and Extraction Properties of Hexyl [(N-Methyl-N,N-dioctylammonio)methyl]phosphonate
Davletshina N.V., Sultanova D.R., Cherkasov R.А.
Russian Journal of General Chemistry, 2022