Antibacterial activity and optical characteristics of films based on 4-aminoazobenzene pyridine derivatives
https://doi.org/10.29235/1561-8331-2025-61-4-315-326
Abstract
Various (E,E)-azoazomethines were synthesized by condensation of nicotinic/isonicotinic acid esters with 4-aminoazobenzene in methanol. The corresponding iodomethylates were obtained by quaternization of aldehyde esters and (E,E)-azoazomethines in di-chloromethane in the presence of excess iodomethane. The optical characteristics of polyvinyl alcohol (PVA) films based on synthe-sized pyridine derivatives of 4-aminoazobenzene have been studied. Antibacterial activity against Staphylococcus aureus and Escherichia coli was assessed using the agar diffusion method.
About the Authors
E. A. DikusarBelarus
Dikusar Evgenij A. – Ph. D. (Chemistry), Senior Resear- cher
13, Surganov Str., 220072, Minsk
L. N. Filippovich
Belarus
Filippovich Liudmila N. – Ph. D. (Chemistry), Associate Professor, Senior Researcher
13, Surganov Str., 220072, Minsk
N. V. Bogdanova
Belarus
Bogdanova Natalia V. – Senior Lecturer
23A, Dolgbrodskaya Str., 220070, Minsk
E. E. Skidan
Belarus
Skidan Elizaveta E. – Student
23A, Dolgbrodskaya Str., 220070, Minsk
A. A. Muravsky
Belarus
Muravsky Anatoli A. – Ph. D. (Physics and Mathema- tics), Head of the Laboratory
36, F. Skorina Str., 220084, Minsk
E. A. Akishina
Belarus
Akishina Ekaterina A. – Researcher
13, Surganov Str., 220072, Minsk
S. N. Shahab
Belarus
Shahab Siyamak N. – Dr. Sc. (Chemistry), Associate Professor, Head of the Department
23A, Dolgbrodskaya Str., 220070, Minsk
V. I. Potkin
Belarus
Potkin Vladimir I. – Academician, Dr. Sc. (Chemistry), Professor, Head of the Laboratory
13, Surganov Str., 220072, Minsk
References
1. Han G., Guo R., Yu Zh., Chen G. Progress on biodegradable films for antibacterial food packaging. E3S Web of Conferences, 2020, vol. 145, no. 01036. https://doi.org/10.1051/e3sconf/202014501036.
2. Han Y., Xu Y., Tian L., Zhou J., Zhou X., Kamoun E.A., Kenawy E.S., Chen X. A review on polymeric hydrogel membranes for wound dressing applications: PVA-based hydrogel dressings. Journal of Advanced Research, 2017, vol. 8, no. 3, pp. 217–233. https://doi.org/10.1016/j.jare.2017.01.005
3. Zhongguo Yi., Liao Qi., Xie Za Zhi. Research Progress of Polyvinyl Alcohol (PVA) Based on Hydrogel Dressings. Zhongguo yi Liao qi xie za zhi = Chinese Journal of Medical Instrumentation, 2018, vol. 42, no. 6, pp. 437–439 (in Chinese). https://doi.org/10.3969/j.issn.1671-7104.2018.06.013
4. Nikolaev A. F., Mosyagina L. P. Polyvinyl alcohol and vinyl alcohol copolymers in medicine. Journal of Russian Plastics, 2000, no. 3, pp. 34–42 (in Russian).
5. Yudanova T. N. Polymer wound dressings with enzymatic and antimicrobial action. Moscow, 2004. 32 p. (in Russian).
6. Chang J. B., Namgoong J. W., Kim S. H., Park S. H., Hwang B. H., Kim J. P. Effect of dye structure on orientational behavior and transition dipole moments in coatable guest–host polarizers. Dyes and Pigments, 2015, vol. 121, pp. 30–37. https://doi.org/10.1016/j.dyepig.2015.05.007
7. Shahab S., Yahyaei H., Sheikhi M., Filippovich L., Zhou H., Kaviani S., Alnajjar R., Potkin V., Dikusar E., Petkevich S., Agabekov V. Two new dichroic dyes: Quantum chemical modeling, synthesis, optical properties and their application in polarizing films. Journal of Molecular Structure, 2021, vol. 1239, pp. 130353. https://doi.org/10.1016/j.molstruc.2021.130353
8. Almodarresiyeh H. A., Shahab S. N., Agabekov V. E., Ariko N. G. Spectral properties of polarizing films containing mixture of dichroic dyes. Vescі Nacyanal’naj akademіі navuk Belarusі. Serya hіmіchnyh navuk = Proceedings of the National Academy of Sciences of Belarus. Chemical Series, 2013, no. 3, pp. 55–59.
9. Pikhler I., Lauk U. Azo dyes, method of their preparation and their use in dyeing or printing on hydrophobic fibrous materials : patent RU2288243C2. Publ. date 27 November 2006 (in Russian).
10. Overdahl K. E., Gooden D., Bobay B., Getzinger G.J., Stapleton H. M., Ferguson P. L. Characterizing azobenzene disperse dyes in commercial mixtures and children’s polyester clothing. Environmental Pollution, 2021, vol. 287, pp. 117299. https://doi.org/10.1016/j.envpol.2021.117299.
11. Zatsepin T. S., Abrosimova L. A., Monakhova M. V., Le Thi Hien, Pingoud A., Kubareva E. A., Oretskaya T. S. Design of photocontrolled biomolecules based on azobenzene derivatives. Russian Chemical Reviews, 2013, vol. 82, no. 10, pp. 942–963. https://doi.org/10.1070/RC2013v082n10ABEH004355.
12. Agabekov V. E., Ariko N. G., Filippovich L. N., Malashko P. M., Shakhab S. N., Almodarresie Kh. A 6-Amino-4-hydroxy-3-{[4-((phenyl)azo)phenyl]azo}-2-naphthalene sulfonic acid and its application : patent BY18134. Publ. date 30 April 2014 (in Russian).
13. Zhu J., Guo T., Wang Zh., Zhao Y. Triggered azobenzene-based prodrugs and drug delivery systems. Journal of Controlled Release, 2022, vol. 345, pp. 475–493. https://doi.org/10.1016/j.jconrel.2022.03.041.
14. Cerón-Carrasco J. P., Jacquemin D. Using Theory to Extend the Scope of Azobenzene Drugs in Chemotherapy: Novel Combinations for a Specific Delivery. ChemMedChem, 2021, vol. 16, no. 11, pp. 1765–1775. https://doi.org/10.1002/cmdc.202100046
15. Li S., Jiang X., Zheng R., Zuo S., Zhao L., Fan G., Fan J., Liao Y., Yu X., Cheng, H. An azobenzene-based hetero- meric prodrug for hypoxia-activated chemotherapy by regulating subcellular localization. Chemical Communications, 2018, vol. 54, pp. 7983–7986. https://doi.org/10.1039/C8CC03430C
16. Piotto S., Concilio S., Sessa L., Porta A., Calabrese E.C., Zanfardino A., Varcamonti M., Iannelli P. Small azobenzene derivatives active against bacteria and fungi. European Journal of Medicinal Chemistry, 2013, vol. 68, pp. 178–184. https://doi.org/10.1016/j.ejmech.2013.07.030
17. Martino M. Di, Sessa L., Matteo M. Di, Panunzi B., Piotto S., Concilio S. Azobenzene as Antimicrobial Molecules. Molecules, 2022, vol. 27, no. 17, pp. 5643. https://doi.org/10.3390/molecules27175643.
18. Akishina E. A., Kazak D. V., Dikusar Е. А. Synthesis of functionally substituted esters of nicotinic and isonicotinic acid. Vestsi Natsyyanal’nai akademii navuk Belarusi. Seryya khimichnykh navuk = Proceedings of the National Academy of Sciences of Belarus. Chemical Series, 2020, vol. 56, no. 3, pp. 301–310 (in Russian). https://doi.org/10.29235/1561-83312020-56-3-301-310
19. Dikusar E. A., Filippovich L. N., Shahab S. N., Petkevich S. K., Stepin S. G. Synthesis of (E,E)-azoazomethines based on 4-aminoazobenzene. Vestsi Natsyianal’nai akademii navuk Belarusi. Seryia khimichnykh navuk=Proceedings of the National Academy of Sciences of Belarus. Chemical series, 2018, vol. 54, no. 1, pp. 58–71 (in Russian). https://doi.org/10.29235/1561-8331-2018-54-1-58-71
20. Shahab S., Sheikhi M., Filippovich L., Dikusar E., Yahyaei H., Kumar R., Khaleghian M. Design of geometry, synthe- sis, spectroscopic (FT-IR, UV/Vis, excited state, polarization) and anisotropy (thermal conductivity and electrical) properties of new synthesized derivatives of (E,E)-azomethines in colored stretched poly (vinyl alcohol) matrix. Journal of Molecular Structure, 2018, vol. 1157, pp. 536–550. https://doi.org/10.1016/j.molstruc.2017.12.094
21. Rzheusskij S. Je., Stepin S. G., Dikusar E. A., Man’kova Ju. S. Synthesis and study of antimicrobial and antiviral activity of 4-benzoylpyridine iodomethylate. Fiziko-khimicheskaya biologiya kak osnova sovremennoi meditsiny: tez. dokl. Mezhdunar. nauch. konf., posvyashch. 75-letiyu so dnya rozhdeniya prof. E. V. Barkovskogo, Minsk, 21 maya 2021 g. [Physico- chemical biology as the basis of modern medicine: Abstracts of the reports of the international scientific conference dedicated to the 75th anniversary of the birth of Professor E. V. Barkovsky, Minsk, May 21, 2021]. Minsk, 2021, pp. 238–240 (in Russian).
22. Sowmiah S., Esperança J. M. S. S., Rebelo, L. P. N., Afonso, C. A. M. Pyridinium salts: from synthesis to reactivity and applications. Organic Chemistry Frontiers, 2018, vol. 5, no. 3, pp. 453-493. https://doi.org/10.1039/C7QO00836H
23. Vinyukova G. N. Dye chemistry. Moscow, Khimiya Publ., 1979. 296 p. (in Russian).
24. Stepanov B. I. Introduction to the chemistry and technology of organic dyes. Moscow, Khimiya Publ., 1971. 447 p. (in Russian).
25. Kiprianov A. I., Dyadyusha G. G., Mikhailenko F. A. The colour of dyes and steric hindrance in their molecules. Russian Chemical Reviews, 1966, vol. 35, no. 5, pp. 361–373. https://doi.org/10.1070/rc1966v035n05abeh001477
26. Almodarresie H. A. Polarizing films of a wide spectral range based on polyvinyl alcohol, dichroic dyes and nanoparticles. Minsk, 2015. 23 p. (in Russian).
27. Han S. E., Hwang I. S. Modeling of the optical anisotropy of a dye polarizer. Journal of Polymer Science Part B: Polymer Physics, 2002, vol. 40, no. 13, pp. 1363–1370. https://doi.org/10.1002/polb.10198
28. Potkin V. I., Bumagin N. A., Dikusar E. A., Petkevich S. K., Kurman P. V. Functional Derivatives of 4-Formyl-2methoxyphenyl Pyridine-4-carboxylate. Russian Journal of Organic Chemistry, 2019, vol. 55, no. 10, pp. 1483–1494. https://doi.org/10.1134/s1070428019100063


























