head JofIMAB
Journal of IMAB - Annual Proceeding (Scientific Papers)
Publisher: Peytchinski Publishing Ltd.
ISSN: 1312-773X (Online)
Issue: 2020, vol. 26, issue3
Subject Area: Medicine
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DOI: 10.5272/jimab.2020263.3328
Published online: 21 September 2020

Original article

J of IMAB. 2020 Jul-Sep;26(3):3328-3332
ANTIFUNGAL ACTIVITY OF A PHOSPHORYLATED 3-(α-HYDROXYALKYL) ALLENES ETHANOL EXTRACTS
Sevginar Ibryamova1ORCID logo, Hasan Hasanov2ORCID logo, Tsveteslava Ignatova-Ivanova1ORCID logo Corresponding Autoremail,
1) Department of Biology, Shumen University, Shumen, Bulgaria.
2) Department of Chemistry, Shumen University, Shumen, Bulgaria.

ABSTRACT:
Antifungal effects of a 4-(Diphenylphosphinoyl)-2-methyl-4-phenylbuta-2,3-dien-1-ol (PA-2) on pathogenic yeast and fungi had been established. PA-2 (50mg/ml, 25mg/ml, 12.5mg/ml, 6.25mg/ml and 3.125mg/ml) exerted different inhibitory effect on different yeast and fungi cells in vitro. The effects of PA-2 on eukaryotic cells have not been studied yet. The present study was aimed to assess the antifungal activity of PA-2on pathogenic yeast and fungi. Experimental approach: In vitro antifungal test: Aspergillus niger, Penicillium claviforme, Saccharomyces cerevisae, Candida albicans 8673 and Candida glabrata 72 were treated for 24 hours with PA-2(50mg/ml, 25mg/ml, 12.5mg/ml, 6.25mg/ml and 3.125mg/ml), Fluconazole (150 mg/ml). The antifungal activity was assayed by the gootiffusion method with a digitalaliper. Determination of minimum inhibitory concentrations (MICs): The MIC of PA-2, that shows antifungal activity wasetermined by 2-fold dilution methodsnd MICs were read in μg/ml after overnight incubation at 37ºC. Determination of Minimum fungal concentration (MFC): The MFC was carried out to check whether the test microbes were killed or only their growth was inhibited. Potato Dextrose Agar (PDA, Oxoid, Hampshire, UK) was prepared and sterilized at 121ºC for 15 minutes, the medium was poured into sterile petri dishesnd was allowed to cool and solidify. The contents of the MIC in the serial dilution were then subcultured onto the prepared medium, incubation was made at 37ºC for 24 h, after which each plate was observed for colony growth. All experiments were performed in triplicate.
The lowest concentration of the PA-2 without a colony growth was recorded as the MFC. PA-2 had higher antifungal activity than the tested antibiotic (Fluconazole).

Keywords: 4-(Diphenylphosphinoyl)-2-methyl-4-phenylbuta-2,3-dien-1-ol, Antibacterial activity, Antibiotic,

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Please cite this article as: Ibryamova S, Hasanov H, Ignatova-Ivanova T. Antifungal Activity of a Phosphorylated 3-(α-Hydroxyalkyl) allenes ethanol extracts. J of IMAB. 2020 Jul-Sep;26(3):3328-3332. DOI: 10.5272/jimab.2020263.3328

Corresponding AutorCorrespondence to: Tsveteslava Ignatova-Ivanova, Department of Biology, Shumen University “Konstantin Preslavski”; 115, Universitetska Str., Shumen, Bulgaria; E-mail: ts.ignatovaivanova@shu.bg

REFERENCES:
1. Howard SJ, Catchpole M, Watson J, Davies SC. Antibiotic resistance: global response needed. Lancet Infect Dis. 2013 Dec;13(12):1001-3. [PubMed] [Crossref]
2. Klompas M. Overuse of Broad-Spectrum Antibiotics for Pneumonia. JAMA Intern Med. 2020 Feb 17.  [PubMed] [Crossref]
3. Laxminarayan R, Duse A, Wattal C, Zaidi AKM, Wertheim HFL, Sumpradit N, et al. Antibiotic resistance-the need for global solutions. Lancet Infect Dis. 2013 Dec;13(12):1057-98. [PubMed]
4. Gajdбcs M. The Concept of an Ideal Antibiotic: Implications for Drug Design. Molecules. 2019 Mar 3;24(5):892. [PubMed]
5. Hasanov HH, Ivanov IK, Christov VC. Bifunctionalized allenes. Part XX. A convenient and efficient regioselective synthesis of phosphorylated 3-(a-hydroxyalkyl)allenes. Bulgarian Chemical Communications.  2017; 49(Special Edition B):25-32. [Internet]
6. Akl MA, Mostafa MM, Abdel Hamid AI, Hassanin EE, Abdel-Raouf M. Assessment of The Antimicrobial Activities of Trioctylphosphine Oxide Modified Silica Nanoparticles. Egypt J Chem. 2020 Apr;63(4):1325-1339.  [Crossref]
7. Ignatova-Ivanova Ts, Stefanova I, Ismailov I E, Ivanov IK, Christov VCh. In Vitro Studies of antifungal activity of a bifunctionalized allene ethanol extracts. Int J Recent Sci Res. 2015; 6(5):4352-4355. 
8. Al-Abdalall AHA. Effect of plants extracts on the growth of Candida albicans and Staphylococcus aureus. Afr J Pharm Pharmacol. 2016 Apr;10(16): 337-345. [Crossref]
9. Gajdбcs M. The Concept of an Ideal Antibiotic: Implications for Drug Design. Molecules. 2019 Mar;24(5), 892. [PubMed]
10. Lin J, Nishino K, Roberts MC, Tolmasky M, Aminov RI, Zhang L. Mechanisms of antibiotic resistance. Front Microbiol. 2015 Feb 5;6:34.  [PubMed]
11.  Konda S, Raparthi S, Bhaskar K, Munaganti RK, Guguloth V, Nagarapu L, et al. Synthesis and antimicrobial activity of novel benzoxazine sulfonamide derivatives. Bioorg Med Chem Lett. 2015 Apr 1;25(7):1643-6. [PubMed]
12. Zhao C, Rakesh KP, Ravidar L, Fang W-Y, Qin H-L. Pharmaceutical and medicinal significance of sulfur (S VI)-Containing motifs for drug discovery: A critical review. Eur J Med Chem. 2019 Jan 15;162:679-734. [PubMed]
13. Ismailov IE, Ivanov IK, Christov VCh. Bifunctionalized allenes. Part XIII. A convenient and efficient method for regioselective synthesis of phosphorylated α-hydroxyallenes with protected and unprotected hydroxy group. Molecules. 2014 May 16;19(5):6309-29. [PubMed]
14. Ismailov IE, Ivanov IK,  Christov VCh. Bifunctionalized allenes. Part XV. Synthesis of 2,5-dihydro-1,2-oxaphospholes by electrophilic cyclization reaction of phosphorylated α-hydroxyallenes. Molecules. 2014 Jul 29;19(8):11056-76. [PubMed]
15. Ismailov IE, Ivanov IK, Christov VC. Bifunctionalized allenes. Part XIV. A convenient and efficient regioselective synthesis of phosphorylated b-hydroxyallenes with protected and unprotected hydroxy group. Bulgarian Chemical Communications. 2014; 46(Special Issue A):39-46. [Internet]
16. Christov VC, Ismailov IE, Ivanov IK. Bifunctionalized Allenes. Part XVI. Synthesis of 3-Phosphoryl-2,5-dihydrofurans by Coinage Metal-Catalyzed Cyclo-isomerization of Phosphorylated α-Hydroxyallenes. Molecules. 2015 Apr 21;20(4):7263-75. [PubMed]
17. Christov VC, Ismailov IE, Ivanov IK.  Bifunctionalized allenes. Part XVII. Synthesis of 2,5-Dihydro-1,2-Oxaphospholes and 4-Phosphoryl- 3,6-Dihydro-2H-Pyrans by Electrophilic Cyclization and Coinage Metal-Catalyzed Cycloisomerization of Phosphorylated b- Hydroxyallenes. Int J Rec Sci Res. 2015 Jun;6(6):4526-4537.
18. Ismailov IE, Ivanov IK, Christov VC. Trifunctionalized Allenes. Part VI. Synthesis of 2,5-Dihydro-1,2-oxaphospholes, Furan-2(5H)-ones and 5,6-Dihydro-2H-pyrans by Electrophilic Cyclization and Cycloisomerization of 4-Phosphorylated 6-Hydroxyhepta-2,3-dienoates. Heterocycles. 2019 Sep;98(9):1236-1243. [Crossref]
19. Ismailov IE, Ivanov IK, Christov VCh. Trifunctionalized allenes. Part III. Electrophilic cyclization and cycloisomerization of 4-phosphorylated 5-hydroxypenta-2,3-dienoates: An expedient synthetic method to construct 2,5-dihydro-1,2-oxaphospholes, furan-2(5H)-ones and 2,5-dihydrofurans. Phosphorus Sulfur Silicon Relat Elem. 2020; 195(4):314-323. [Crossref]
20. Ismailov IE, Ivanov IK, Christov VC. Trifunctionalized Allenes. Part IV. Cyclization Reactions of 4-Phosphorylated 5-Hydroxyhexa-2,3-dienoates. Lett Org Chem. 2020; 17(9):726-733. [Crossref
21. Ismailov IE, Ivanov IK, Christov VCh. Trifunctionalized allenes. Part V. Competitive electrophilic cyclization and cycloisomerization of 4-phosphorylated 5-hydroxy-5-methylhexa-2,3-dienoates. Bulgarian Chemical Communications. 2020; 51(1):121-128. [Internet]
22. Pfaller MA, Diekema DJ, Turnidge JD, Castanheira M, Jones RN. Twenty Years of the SENTRY Antifungal Surveillance Program: Results for Candida Species From 1997–2016. Open Forum Infect Dis. 2019 Mar 15;6(Suppl 1):S79-S94. [PubMed]
23. Pfaller MA, Diekema DJ. Rare and emerging opportunistic fungal pathogens: concern for resistance beyond Candida albicans and Aspergillus fumigatus. J Clin Microbiol. 2004 Oct;42(10):4419-31. [PubMed]
24. Kumar A, Nair R, Kumar M, Banerjee A, Chakrabarti A, Rudramurthy SM, et al. Assessment of antifungal resistance and associated molecular mechanism in Candida albicans isolates from different cohorts of patients in North Indian state of Haryana. Folia Microbiol (Praha).  2020 Aug;65(4):747-754. [PubMed]
25. Gao Y, Li H, Liu S, Zhang X, Sun S. Synergistic effect of fluconazole and doxycycline against Candida albicans biofilms resulting from calcium fluctuation and downregulation of fluconazole-inducible efflux pump gene overexpression. J Med Microbiol. 2014 Jul;63(Pt 7):956-961. [PubMed]
26. Esfahani AN, Golestannejad Z, Khozeimeh F, Dehghan P, Maheronnaghsh M, Zarei Z. Antifungal effect of Atorvastatin against Candida species in comparison to Fluconazole and Nystatin. Med Pharm Rep. 2019 Oct;92(4):368-373. [PubMed]
27. Chassot F, Venturini TP, Piasentin FB, Santurio JM, Svidzinski TIE, Alves SH. Activity of antifungal agents alone and in combination against echinocandin-susceptible and -resistant Candida parapsilosis strains. Rev Iberoam Micol. 2019 Jan-Mar;36(1):44-47. [PubMed].

Received: 24 August 2020
Published online: 21 September 2020

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