«IZVESTIYA IRKUTSKOGO GOSUDARSTVENNOGO UNIVERSITETA». SERIYA «BIOLOGIYA. ECOLOGIYA»
«THE BULLETIN OF IRKUTSK STATE UNIVERSITY». SERIES «BIOLOGY. ECOLOGY»
ISSN 2073-3372 (Print)

List of issues > Series «Biology. Ecology». 2017. Vol. 22

Estimation of Antibacterial Activity of some Representatives of a New Family of Phosphorus-Nitrogen Containing Ionenes

Author(s)
V. L. Mikhailenko, S. I. Verkhoturova, O. F. Vyatchina, М. А. Коzik, V. N. Kizhnyaev
Abstract
The synthesis of antibacterial and antiviral drugs using of polyelectrolytes of natural or synthetic origin is being actively developed. Polycations containing nitrogen and phosphorus atoms in the main chain can be used for interpolymer interactions with cell membranes or other biopolymers. The antibacterial activity of the first synthesized phosphorus-nitrogen-containing ionenes was studied towards to Escherichia coli and Staphylococcus aureus. The growth of microorganisms has been suppressed at an ionene concentration of 0.01-0.1%. Synthesis of new objects of this ionenes class was realized by the polycondensation reaction of bis[2-(4-pyridyl)ethyl]phenylethyl- and bis[2-(4-pyridyl)ethyl](2-cyanoethyl)phosphinoxides with 1,4-dihalobutanes. Water-soluble ionenes of linear structure bearing a phenylethyl and pharmacophoric 2-cyanoethyl group were prepared. It was shown that the nature of the halide ion influences on exhibition of microbicidal properties of synthesized ionenes. Ionene containing iodide anion, posseses antibacterial activity against both strains. In this case, the opportunistic bacterium Staphylococcus aureus was more sensitive to the impact of this polymer than Escherichia coli.
Keywords
antibacterial activity, phosphorus-nitrogen-containing ionenes, polycondensation, Escherichia coli, Staphylococcus aureus
UDC
547.34541.64536.7+579.0+579.6
References

1. Afinogenov G.E. Antimikrobnye polimery [Antimicrobial polymers]. St.-Petersburg, Gippokrat Publ., 1993, 264 p. (in Russian).

2. Plate N.A. Fiziologicheski aktivnye polimery [Physiologically Active Polymers]. Moscow, Khimiya Publ., 1986, 296 p. (in Russian).

3. Polimery v biologii i meditsine [Polymers in Biology and Medicine]. Moscow, Nauchnyi mir Publ., 2011, 247 p. (in Russian).

4. Mikhailenko V.L., Kizhnyaev V.N., Verkhoturova S.I., Apartsin K.A., Gusarova N.K., Grigor'ev E.G., Trofimov B.A. Sintez i svoistva novogo semeistva fosfor-azotsoderzhashchikh ionenov [Synthesis and Properties of New Family of Phosphorous-containing ionenes]. Doklady Akademii nauk [Doklady Chemistry], 2015, vol. 465, no. 4, pp. 446-450. (in Russian). DOI: 10.7868/S0869565215340150

5. Tatarinov D.A., Kostin A.A., Baronova T.A., Dobrynin A.B., Mironova E.V., Krivolapov D.B., Buzykin B.I., Mironov V.F. 3,3,5-Trimetil-2-khlor-1,2-oksafosfolen-2-oksid – prekursor v novom metode sinteza dialkil(diaril)(2-metil-4-oksopent-2-il)fosfinoksidov [3,3,5-Trimethyl-2-Chlor-1,2-Oxsafosfolene-2-oxyde – Prekursor to New Dialkil(diaril)(2-methyl-4-oxopent-2-yl)fosfinoxyides Synthesis Method]. Zhurnal Organicheskoi Khimii [Russian Journal of Organic Chemistry], 2013, vol. 49, no. 4, pp. 534-542. (in Russian). DOI: 10.1134/S1070428013040040.

6. Mikhailenko V.L., Kizhnyaev V.N., Verkhoturova S.I., Apartsin K.A., Gusarova N.K., Grigor'ev E.G., Trofimov B.A. Fosforsoderzhashchie ioneny [Phosphorous-containing ionenes]. Fundamental'nye nauchnye issledovaniya: teoreticheskie i prakticheskie aspekty [Fundamental Researsh: Theoretical and Practical Aspekts]. Abstract of Paper. II Int. conf. 29.09.2016. Kemerovo, 2016, vol. II, pp. 83-86. (in Russian).

7. Caporali M., Serrano-Ruiz M., Peruzzini M. Benign Chlorine-Free Approaches to Organophosphorus Compounds. Chemistry Beyond Chlorine, Springer Publ., 2016, 97 p. DOI: 10.1007/978-3-319-30073-3.

8. Carmona-Ribeiro A.M., de Melo Carrasco L.D. Cationic Antimicrobial Polymers and Their Assemblies. Int. J. Mol. Sci., 2013, vol. 14, no. 5, pp. 9906–9946.

9. Gusarova N.K., Arbuzova S.N., Trofimov B.A. Novel general halogen-free methodology for the synthesis of organophosphorus compounds. Pure Appl. Chem., 2012, vol. 84, no. 3, pp. 439-459.

10. Hollis C.G., Jacquess P.A. Ionene polymers as microbicides. Buckman Lab. International, Inc., U.S. Pat. No. 5681862 A, MKI A 01 N 33/12, 1997.

11. Mattheis C., Zheng M., Agarwal S. Closing One of the Last Gaps in Polyionene Compositions: Alkyloxyethylammonium Ionenes as Fast-Acting Biocides. Macromolecular bioscience, 2012, vol. 12, no. 3, pp. 341-349.

12. Trofimov B.A., Gusarova N.K. Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free ‘green’ organophosphorus chemistry. Mendeleev Commun., 2009, vol. 19, no. 6, pp. 295-302.


Full text (russian)