Research Article
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Determination of in vitro antifungal activity of dihydroisoxazole dimethanol compound against dermatophytes obtained from clinical isolates and design of some new dihydroisoxazole dimethanol compounds

Year 2024, Volume: 8 Issue: 1, 46 - 52

Meryem Pir Fatma Budak Kemal Metiner

Abstract

In this study, the in vitro antifungal activity of (3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl) dimethanol compound (1) was investigated against two pathogenic fungi species (Trichophyton mentagrophytes and Microsporum canis) and important results were obtained. The difficulty of treating fungal diseases induced us to assess the antifungal properties of dihydroisoxazole dimethanol compound. The broth microdilution method was used to determine the minimum inhibitory concentration (MIC). The compound (1) showed an antifungal effect with MIC=12.5 µg ml-1 on M. canis and MIC=50 µg ml-1 on T. mentagrophytes, respectively. To prepare potentially more effective antifungal agents, new dihydroisoxazole derivatives (2-32) were theoretically designed. The geometrical optimization of all compounds (1-32) was performed using the semi-empirical AM-1 level. Some structural parameters of the optimized compounds (1-32) were also calculated.

Keywords

Antifungal activity dermatophyte dihydroisoxazole MIC Microsporum canis structural parameters Trichophyton mentagrophytes.

References

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  • Cabanes FJ, Abarca ML, Bragulat MR. Mycopathologia. 1997, 137, 107-113.
  • Pinter L, Jurak Z, Ukalovic M, Susic V. Veterinarski Arhiv. 1999, 69, 261-270.
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  • Sparkes AH, Gruffydd-Jones TJ, Shaw SE, Wright AI, Stokes CR. Vet. Rec. 1993, 133, 57-61.
  • Havlickova B, Czaika VA, Friedrich M. Mycoses. 2008, 51, 2-15.
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  • Yamaguchi MU, Silva APB, Ueda-Nakamura T, Filho BPD, Silva CC, Nakamura CV. Molecules. 2009, 14, 1796-1807.
  • Martinez-Rossi NM, Peres NTA, Rossi A. Mycopathologia. 2008, 166, 369-383.
  • Fontenelle ROS, Morais SM, Brito EHS, Brilhante RSN, Cordeiro RA, Lima YC, Brasil NVGPS, Monteiro A, Sidrim JJC, Rocha MFG. Molecules. 2011, 16, 6422-6431.
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  • Ouf SA, Moussa TA, Abd-Elmegeed AM, Eltahlawy SR. Braz. J. Microbiol. 2016, 47, 697-702.
  • Abdel-Shafi S, Al-Mohammadi A, Almanaa TN, Moustafa AH, Saad TMM, Ghonemey A, Anacarso I, Enan G, El-Gazzar N. Antibiotics. 2020, 9, 176.
  • Asgarpanah J, Hashemi SJ, Hashemi E, Askari K. Chin. J. Integr. Med. 2017, 23, 433-437.
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  • Tiwari N, Pandit R, Gaikwad S, Gade A, Rai M. I.E.T. Nanobiotech. 2017, 11, 205-211.
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  • Furmanek L, Czarnota P, Seaward MRD. J. Appl. Microbiol. 2019, 127, 308-325.
  • Song D, Bi F, Zhang N, Qin Y, Liu X, Teng Y, Ma S. Bioorgan. Med. Chem. 2020, 28, 1-16.
  • Gabriela ADB, Aguiar AP, Martins CE, Maria RNJ. Lett Drug Des Discov. 2019, 16, 364-369.
  • Sowdari J, Thata S, Gudi Y, Venkatapuram P, Adiviredd P. J. Heterocyclic Chem. 2020, 57, 1882-1892.
  • Pir M, Agirbas H, Budak F, Sahin O. Heteroatom Chem. 2017, 28, e21363.
  • CLSI (formerly NCCLS). Clinical Laboratory Standards Institute. Reference method for broth dilution antifungal susceptibility testing of filamentous fungi. Approved Standard, CLSI document M38-A2, 2nd ed. Wayne: PA, USA, 2008.
  • Fernandez-Torres B, Cabanes FJ, Carillo-Munoz AJ, Esteban A, Inza I, Abarca, L, Guarro J. J. Clin. Microbiol. 2002, 40, 3999-4003.
  • HyperChem 7.2 for Windows. Hypercube Inc. Gainesville, FL, ABD, 2002.
  • Ferreira AM, Krishnamurthy M, Moore BM, Finkelstein D, Bashford D. Bioorgan. Med. Chem. 2009, 17, 2598-2606.
  • Akı-Şener E, Yalçın İ. Farmasötik/Medisinal Kimyada İlaç Etken Madde Tasarım Yöntemleri-1: Kantitatif Yapı-Etki İlişkileri Analizleri (QSAR). Ankara Üniversitesi Eczacılık Fakültesi Yayınları. Ankara, 2002, 58-109.
  • Ajdacic V, Senerovic L, Vranic M, Pekmezovic M, Arsic-Arsnijevic V, Veselinovic A, Veselinovic J, Solaja BA, Nikodinovic-Runic J, Opsenica IM. Bioorgan. Med. Chem. 2016, 24, 1277-1291.
  • Ercan S, Pir M. ChemistrySelect. 2023, 8, e202303543, 1-14.
  • Pir M, Budak F. Düzce University Journal of Science & Technology. 2022, 10, 815-822.

Year 2024, Volume: 8 Issue: 1, 46 - 52

Meryem Pir Fatma Budak Kemal Metiner

Abstract

References

  • A, Saniç A, Yenigün A, Ekinci B, Atilla S, Kosif E, Özcan F. J. Exp. Clin. Med. 2000, 17, 45-49.
  • Schmutz JL, Barbaud A, Contet-Audonneau N. Rev. Prat. 1996, 46, 1617-1622.
  • Elewski BE. Clin. Microbiol. Rev. 1998, 11, 415-429.
  • Tanış H, Cihangir N. F.Ü. Sağ. Bil. Tıp Derg. 2009, 23, 137-144.
  • Ünal ZÖ, Erdal B. Namık Kemal Tıp Derg. 2020, 8, 515-522.
  • Dilek N, Yücel AY, Dilek AR, Saral Y, Toraman ZA. Türk Dermatoloji Derg. 2009, 3, 27-31.
  • Chermette R, Ferreiro L, Guillot J. Mycopathologia. 2008, 166, 385-405.
  • Hanedan B, Bilgili A, Uysal MH. Icontech International Journal. 2021, 5, 10-17.
  • Yu RJ, Harmon SR, Blank F. J. Bacteriol. 1968, 96, 1435-1436.
  • Özekinci T, Özbek E, Gedik M, Toğçu M, Tekay F, Mete M. Dicle Tıp Derg. 2006, 33, 19-22.
  • Friedrich J, Gradisar H, Mandin D, Chaumont JP. Lett. Appl. Microbiol. 1999, 28, 127-130.
  • Tümbay E. Mantar Laboratuvarında Uygulanan Yöntemler. Pratik Tıp Mikoloji Kitabı. Bilgihan Basımevi. İzmir, 1983, 7-30.
  • Willke TA, Söyletir G, Doğanay M. İnfeksiyon Hastalıklarında İstanbul. Nobel Tıp Kitapevleri. 2002, 1785-1797.
  • Tel OY, Akan M. Ankara Üniv. Vet. Fak. Derg. 2008, 55, 167-171.
  • Cabanes FJ, Abarca ML, Bragulat MR. Mycopathologia. 1997, 137, 107-113.
  • Pinter L, Jurak Z, Ukalovic M, Susic V. Veterinarski Arhiv. 1999, 69, 261-270.
  • Scott DW, Horn RT. Vet. Clin. North. Am. Small. Anim. Pract. 1987, 17, 117-144.
  • Sparkes AH, Gruffydd-Jones TJ, Shaw SE, Wright AI, Stokes CR. Vet. Rec. 1993, 133, 57-61.
  • Havlickova B, Czaika VA, Friedrich M. Mycoses. 2008, 51, 2-15.
  • Willke TA, Söyletir G, Doğanay M. İnfeksiyon Hastalıkları ve Mikrobiyolojisi. Nobel Kitapevi. Cilt 2. Adana, 2002.
  • Alan EM, Or ME, Dokuzeylül B. Türk Mikrobiyol. Cem. Derg. 2019, 49, 55-60.
  • Yamaguchi MU, Silva APB, Ueda-Nakamura T, Filho BPD, Silva CC, Nakamura CV. Molecules. 2009, 14, 1796-1807.
  • Martinez-Rossi NM, Peres NTA, Rossi A. Mycopathologia. 2008, 166, 369-383.
  • Fontenelle ROS, Morais SM, Brito EHS, Brilhante RSN, Cordeiro RA, Lima YC, Brasil NVGPS, Monteiro A, Sidrim JJC, Rocha MFG. Molecules. 2011, 16, 6422-6431.
  • Gezer AH, Acar A. Turk J. Vet. Anim. Sci. 2020, 44, 258-265.
  • Ouf SA, Moussa TA, Abd-Elmegeed AM, Eltahlawy SR. Braz. J. Microbiol. 2016, 47, 697-702.
  • Abdel-Shafi S, Al-Mohammadi A, Almanaa TN, Moustafa AH, Saad TMM, Ghonemey A, Anacarso I, Enan G, El-Gazzar N. Antibiotics. 2020, 9, 176.
  • Asgarpanah J, Hashemi SJ, Hashemi E, Askari K. Chin. J. Integr. Med. 2017, 23, 433-437.
  • Khayyat S, Al-Kattan M, Basudan N. Int. J. Pharmacol. 2018, 14, 802-810.
  • Soković M, Ristić M, Grubišić D. Pharm. Biol. 2004, 42, 328-331.
  • Tiwari N, Pandit R, Gaikwad S, Gade A, Rai M. I.E.T. Nanobiotech. 2017, 11, 205-211.
  • Mousavi SAA, Salari S, Hadizadeh S. Iran J. Biotech. 2015, 13, e1302.
  • Kazemi M, Akbari A, Zarrinfar H, Soleimanpour S, Sabouri Z, Khatami M, Darroudi M. J. Inorg. Organomet. Polym. 2020, 30, 3036-3044.
  • Furmanek L, Czarnota P, Seaward MRD. J. Appl. Microbiol. 2019, 127, 308-325.
  • Song D, Bi F, Zhang N, Qin Y, Liu X, Teng Y, Ma S. Bioorgan. Med. Chem. 2020, 28, 1-16.
  • Gabriela ADB, Aguiar AP, Martins CE, Maria RNJ. Lett Drug Des Discov. 2019, 16, 364-369.
  • Sowdari J, Thata S, Gudi Y, Venkatapuram P, Adiviredd P. J. Heterocyclic Chem. 2020, 57, 1882-1892.
  • Pir M, Agirbas H, Budak F, Sahin O. Heteroatom Chem. 2017, 28, e21363.
  • CLSI (formerly NCCLS). Clinical Laboratory Standards Institute. Reference method for broth dilution antifungal susceptibility testing of filamentous fungi. Approved Standard, CLSI document M38-A2, 2nd ed. Wayne: PA, USA, 2008.
  • Fernandez-Torres B, Cabanes FJ, Carillo-Munoz AJ, Esteban A, Inza I, Abarca, L, Guarro J. J. Clin. Microbiol. 2002, 40, 3999-4003.
  • HyperChem 7.2 for Windows. Hypercube Inc. Gainesville, FL, ABD, 2002.
  • Ferreira AM, Krishnamurthy M, Moore BM, Finkelstein D, Bashford D. Bioorgan. Med. Chem. 2009, 17, 2598-2606.
  • Akı-Şener E, Yalçın İ. Farmasötik/Medisinal Kimyada İlaç Etken Madde Tasarım Yöntemleri-1: Kantitatif Yapı-Etki İlişkileri Analizleri (QSAR). Ankara Üniversitesi Eczacılık Fakültesi Yayınları. Ankara, 2002, 58-109.
  • Ajdacic V, Senerovic L, Vranic M, Pekmezovic M, Arsic-Arsnijevic V, Veselinovic A, Veselinovic J, Solaja BA, Nikodinovic-Runic J, Opsenica IM. Bioorgan. Med. Chem. 2016, 24, 1277-1291.
  • Ercan S, Pir M. ChemistrySelect. 2023, 8, e202303543, 1-14.
  • Pir M, Budak F. Düzce University Journal of Science & Technology. 2022, 10, 815-822.
There are 46 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Research Articles
Authors

Meryem Pir 0000-0003-4305-8838

Fatma Budak 0000-0001-8439-3881

Kemal Metiner 0000-0003-4105-5852

Early Pub Date April 6, 2024
Publication Date
Published in Issue Year 2024 Volume: 8 Issue: 1

Cite

APA Pir, M., Budak, F., & Metiner, K. (2024). Determination of in vitro antifungal activity of dihydroisoxazole dimethanol compound against dermatophytes obtained from clinical isolates and design of some new dihydroisoxazole dimethanol compounds. International Journal of Chemistry and Technology, 8(1), 46-52.
AMA Pir M, Budak F, Metiner K. Determination of in vitro antifungal activity of dihydroisoxazole dimethanol compound against dermatophytes obtained from clinical isolates and design of some new dihydroisoxazole dimethanol compounds. Int. J. Chem. Technol. April 2024;8(1):46-52.
Chicago Pir, Meryem, Fatma Budak, and Kemal Metiner. “Determination of in Vitro Antifungal Activity of Dihydroisoxazole Dimethanol Compound Against Dermatophytes Obtained from Clinical Isolates and Design of Some New Dihydroisoxazole Dimethanol Compounds”. International Journal of Chemistry and Technology 8, no. 1 (April 2024): 46-52.
EndNote Pir M, Budak F, Metiner K (April 1, 2024) Determination of in vitro antifungal activity of dihydroisoxazole dimethanol compound against dermatophytes obtained from clinical isolates and design of some new dihydroisoxazole dimethanol compounds. International Journal of Chemistry and Technology 8 1 46–52.
IEEE M. Pir, F. Budak, and K. Metiner, “Determination of in vitro antifungal activity of dihydroisoxazole dimethanol compound against dermatophytes obtained from clinical isolates and design of some new dihydroisoxazole dimethanol compounds”, Int. J. Chem. Technol., vol. 8, no. 1, pp. 46–52, 2024.
ISNAD Pir, Meryem et al. “Determination of in Vitro Antifungal Activity of Dihydroisoxazole Dimethanol Compound Against Dermatophytes Obtained from Clinical Isolates and Design of Some New Dihydroisoxazole Dimethanol Compounds”. International Journal of Chemistry and Technology 8/1 (April 2024), 46-52.
JAMA Pir M, Budak F, Metiner K. Determination of in vitro antifungal activity of dihydroisoxazole dimethanol compound against dermatophytes obtained from clinical isolates and design of some new dihydroisoxazole dimethanol compounds. Int. J. Chem. Technol. 2024;8:46–52.
MLA Pir, Meryem et al. “Determination of in Vitro Antifungal Activity of Dihydroisoxazole Dimethanol Compound Against Dermatophytes Obtained from Clinical Isolates and Design of Some New Dihydroisoxazole Dimethanol Compounds”. International Journal of Chemistry and Technology, vol. 8, no. 1, 2024, pp. 46-52.
Vancouver Pir M, Budak F, Metiner K. Determination of in vitro antifungal activity of dihydroisoxazole dimethanol compound against dermatophytes obtained from clinical isolates and design of some new dihydroisoxazole dimethanol compounds. Int. J. Chem. Technol. 2024;8(1):46-52.

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