An in-depth study of the antimicrobial spectrum activity of a number of new phosphonium derivatives of naphthalene
DOI:
https://doi.org/10.14739/2310-1210.2019.3.169099Keywords:
phosphonium salts, antimicrobial activity, naphtalenes, antibacterial agentsAbstract
An intensive use of antibiotics and antiseptics is a part of modern principles of treatment and prevention of infectious diseases. Excessive and uncontrolled use leads to the emergence of antibiotic-resistant strains of microorganisms, which necessitates the search for new antimicrobial alternatives. The study of phosphonium derivatives of naphthalene is one of the promising directions for the detection of new highly active antimicrobial agents.
Objective – to determine the antimicrobial effect of phosphonium derivatives of naphthalene on the extended spectrum of archival test strains.
Materials and methods. The phosphonium derivatives of naphthalene were investigated. For a detailed study of their antibacterial and antifungal activity, 14 test-cultures of archival strains of Gram-positive and Gram-negative bacteria belonging to different taxonomic groups and yeast-like fungi of the genus Candida were selected. Experiments for the biological activity of phosphonium derivatives of naphthalene determination were carried out by using a micromethod with disposable polystyrene plates and Takatsy microtitrator.
Result. Phosphonium derivatives of naphthalene showed high antimicrobial activity against Gram-positive microorganisms and vegetative cells of spore-forming bacilli. Their minimal inhibitory concentrations (MIC) for Gram-positive bacteria (S. aureus 209, M. luteus ATCC 3941) ranged from 0.97 mcg/ml to 3.90 mcg/ml, and for vegetative cells of spore-forming bacilli (B. cereus ATCC 10 702) was 3.90 mcg/ml. They showed a slightly lower antimicrobial activity against Gram-negative strains of microorganisms (MIC ranged from 31.2 mcg/ml to 250.0 mcg/ml). The tested compounds showed a moderate antifungal activity against C. utilis LIA-01 (MIC ranged from 31.2 mcg/ml to 62.5 mcg/ml).
Conclusions. It has been established that investigated phosphonium derivatives of naphthalene revealed high biological activity against Gram-positive microorganisms. Both studied compounds showed moderate antimicrobial activity against Gram-negative microorganisms and yeast-like fungi of the genus Candida.
References
Cassir, N., Rolain, J.M., & Brouqui, P. (2014). A new strategy to fight antimicrobial resistance: the revival of old antibiotics. Frontiersin Microbiology, 5, 551. doi: 10.3389/fmicb.2014.00551
Aziz, A. M. (2013). The role of healthcare strategies in controlling antibiotic resistance. British Journal of Nursing, 22(18), 1066–1074. doi: 10.12968/bjon.2013.22.18.1066
Cully, M. (2014). Antibacterial drugs: Redesigned antibiotic combats drug-resistant tuberculosis. Nature Reviews. Drug Discovery, 13(4), 256. doi: 10.1038/nrd4287
Humenna, A. V. (2016). Khimioterapevtychna efektyvnist heterotsyklichnoi fosfoniievoi spoluky z pirymidynovym tsyklom na modeli heneralizovanoi stafilokokovoi infektsii [Chemotheraphy efficiency of phosphonium heterocyclic compounds with pyrimidine cycle in models of generalized staph infection]. Aktual'naya infektologiya, 1, 29-31. [in Ukrainian].
Shevchuk, N. M. (2013). Doslidzhennia formuvannia stiikosti u stafilokokiv ta esherykhii do antyseptykiv [Research of formation of resistance of staphylococci and escherichia to antiseptics]. Visnyk Vinnytskoho natsionalnoho medychnoho universytetu, 17(1), 33–36.[in Ukrainian].
Desai, Sh., Laddi, U., Bennur, R., & Bennur, Sh.(2013). Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives. Indian Journal of Chemistry, 52(8), 1176–1181.
Tang, R., Jin, L., Mou, C., Yin, J., Bai, S., Hu, D.,et al. (2013).Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety. Chemistry Central Journal, 7(1), 30. doi: 10.1186/1752-153X-7-30
Jacob, H. J., Irshaid, F. I., & Al-Soud, Y. A. (2013).Antibacterial activity of some selected 1,2,4-triazole derivatives against standard, environmental, and medicalbacterials trains. Advanced Studies in Biology, 5(6), 291–301. doi: http://dx.doi.org/10.12988/asb.2013.3418
Popiołek, Ł., Kosikowska, U., Mazur, L., Dobosz, M., & Malm, A.(2013). Synthesis and antimicrobial evaluation of some novel 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Medicinal Chemistry Research, 22(7), 3134–3147. doi: 10.1007/s00044-012-0302-9
Patil, B. S., Krishnamurthy, G., Lokesh, M. R., Shashikumar, N. D., Naik, H., Latthe, P. R., & Ghate M. (2013). Synthesis of some novel 1,2,4-triazole and 1,3,4-oxadiazole derivatives of biological interest. Medicinal Chemistry Research, 22(7), 3341–3349. doi: 10.1007/s00044-012-0332-3
Listvan, V. M., Listvan, V. V., Malishevska, A. V., Deineka, S. Ye. (2008). Fosfoniievi soli yak potentsiini antymikrobni zasoby [Phosphonium salts as a potential antimicrobial facilities]. Visnyk Zhytomyrskoho derzhavnoho universytetu, 41, 228–232. [in Ukrainian].
Xue, Y., Xiao, H., & Zhang, Y. (2015). Antimicrobial Polymeric Materials with Quaternary Ammonium and Phosphonium Salts. International Journal of Molecular Sciences, 16(2), 3626–3655. doi: 10.3390/ijms16023626
Balouiri, M., Sadiki, M., & Ibnsouda, S. K. (2016). Methods for invitro evaluatin gantimicrobial activity: A review. Journal of Pharmaceutical Analysis, 6(2), 71–79. doi: 10.1016/j.jpha.2015.11.005
Nakaz MOZ Ukrainy «Pro zatverdzhennia metodychnykh vkazivok «Vyznachennia chutlyvosti mikroorhanizmiv do antybakterialnykh preparativ» [Order of the Ministry of Health of Ukraine «Onapproval of the methodological guidelines “Determination of microorganism sensitivity to antibacterial drugs”»]. Retrieved from http://ua-info.biz/legal/baselw/ua-qmwjae/index.htm [in Ukrainian].
Gumenna, A. V., Rotar, D. V., Dejneka, S. Ye., Yakovychuk, N. D., & Blinder, О. О. (2017). Pohlyblene vyvchennia spektra antymikrobnoi aktyvnosti riadu novykh kondensovanykh bahatoiadernykh areniv [Detailed studying of the spectrum of antimicrobial activity of several new condensedpolynuclear arens]. Zaporozhye medical journal, 19(3), 369–372. [in Ukrainian]. doi: 10.14739/2310-1210.2017.3.100939
Khasiyatullina, N. R., Vazykhova, A. M., Mironov, V. F., Krivolapov, D. B., Voronina, Y. K., Voloshina, A. D., et al. (2017). Phosphonium salts with a dihydroxynaphthyl substituent: versatile synthesis and evaluation of antimicrobial activity. Mendeleev Communicationsц, 27(2), 134–136. doi 10.1016/j.mencom.2017.03.008
Pugachev, M. V., Shtyrlin, N. V., Sapozhnikov, S. V., Sysoeva, L. P., Iksanova, A. G., Nikitina, E. V., et al.. (2013). Bis-phosphonium salts of pyridoxine: the relationship between structure and antibacterial activity. Bioorg Med Chem, 21(23), 7330–7342. doi: 10.1016/j.bmc.2013.09.056
Pugachev, M. V., Shtyrlin, N. V., Sysoeva, L. P., Nikitina, E. V., Abdullin, T. I., Iksanova, A. G., et al. (2013). Synthesis and antibacterial activity of novel phosphonium salts on the basis of pyridoxine. Bioorganic and Medicinal Chemistry, 21(14), 4388–4395. doi: 10.1016/j.bmc.2013.04.051
Gorbunova, M. (2013). Novel guanidinium and phosphonium polysulfones : synthesis and antimicrobial activity. Journal of Chemical and Pharmaceutical Research, 5(1), 185–192.
Downloads
How to Cite
Issue
Section
License
Authors who publish with this journal agree to the following terms:- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access)