Research Article
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Year 2022, , 47 - 53, 28.04.2022
https://doi.org/10.26650/IstanbulJPharm.2022.958484

Abstract

References

  • Almoughrabie, S., Ngari, C., Guillier, L., Briandet, R., Poulet, V., & Dubois-Brissonnet, F. (2020). Rapid assessment and prediction of the efficiency of two preservatives against S. aureus in cosmetic products using High Content Screening—Confocal Laser Scan- ning Microscopy. PLoS ONE, 15, 7, e0236059.
  • Beata, Z., Anna, C., & Anna, B. (2014). Development studies on determination of preservatives decomposition products. Acta Poloniae Pharmaceutica-Drug Research, 71(4), 563-573.
  • Bozdogan, B., & Appelbaum, P. C. (2004). Oxazolidinones: Activ- ity, Mode of action, and Mechanism of Resistance. International Journal of Antimicrobial Agents, 23(2), 113-119.
  • Cheng, F., Li, W., Zhou, Y., Shen, J., Wu, Z., Liu, G., & Tang, Y. (2012). admetSAR: A comprehensive source and free tool for assessment of chemical ADMET properties. Journal of Chemical Information and Modeling, 52(11), 3099-3105.
  • Durante-Mangoni, E., Grammatikos, A., Utili, R., & Falagas M., E. (2009). Do we still need the aminoglycosides? International Jour- nal of Antimicrobial Agents, 33(3), 201-205.
  • European Committee for Antimicrobial Susceptibility Testing (EU- CAST) of the European Society of Clinical Microbiology and Infec- tious Diseases (ESCMID). Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by broth dilution. EUCAST Discussion Document E.Dis 5.1, March 2003.
  • Gaussian 09, Revision E.01, Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., & Petersson, G. A. Gaussian, Inc., Wallingford CT, 2009.
  • Giamarellos-Bourboulis, E. J. (2008). Macrolides beyond the conventional antimicrobials: A Class of Potent Immunomodula- tors. International Journal of Antimicrobial Agents, 31(1), 12-20.
  • Gonzalo-Garijo, M. A., Rodriguez-Nevado, I., & de Argila, D. (2006). Patch tests for diagnosis of delayed hypersensitivity to cephalo- sporins. Allergologia et Immunopathologia, 34(1), 39-41.
  • Imanirampa, L., & Alele, P. E. (2016). Antifungal activity of Cleome gynandra L. aerial parts for topical treatment of Tinea capitis: an in vitro evaluation. BMC Complementary and Alternative Medi- cine, 16, 1, 1-8
  • Koushlesh, K., M., Chanchal, D., K., Anil, K., S., Rajnikant, P., Pankaj, K., Saraswati, P., M., & Shweta, D. (2020). Medicinal Plants Having Antifungal Properties. In Bassam Hassan (Ed.), Medicinal Plants Use in Prevention and Treatment of Diseases. IntechOpen.
  • Leeson, P., D., & Springthorpe, B. (2007). The influence of drug- like concepts on decision-making in medicinal chemistry. Nature Reviews Drugs Discovery, 6(11), 881–890.
  • Lim, E. J., Kang, H. J., Jung, H. J., Song, Y. S., Lim C. J., & Park, E. H. (2008). Anti-angiogenic, anti-inflammatory and anti-nociceptive activities of vanillin in ICR mice. Biomolecules and Therapeutics, 16, 132-136.
  • Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (2001). Experimental and computational approaches to estimate solubil- ity and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 46, 3–26.
  • Singh, R., Dar, S. A., & Sharma, P. (2012). Antibacterial Activity and Toxicological Evaluation of Semi Purified Hexane Extract of Urtica dioica Leaves. Research Journal of Medicinal Plants, 6, 123-135.
  • Veber, D. F., Johnson, S. R., Cheng, H.-Y., Smith, B. R., Ward, K. W., & Kopple, K. D. (2002). Molecular properties that influence the oral bioavailability of drug candidates. Journal of Medicinal Chemistry, 45, 2615–2623.
  • Wei, A., & Shibamoto, T. (2007). Antioxidant activities and volatile constituents of various essential oils. Journal of Agricultural and Food Chemistry, 55(5), 1737-1742.
  • Wang, C., Liu, Y., Bao, C., Xue, Y., Zhou, Y., Zhang, D., Lin, Q., & Zhu, L. (2020). Phototriggered labeling and crosslinking by 2-nitrobenzyl alcohol derivatives with amine selectivity. Chemical Communica- tions, 56(15), 2264-2267.

Synthesis, antifungal activity and in silico ADMET studies of benzyl alcohol derivatives

Year 2022, , 47 - 53, 28.04.2022
https://doi.org/10.26650/IstanbulJPharm.2022.958484

Abstract

Background and Aims: Fungal infections continue to pose a serious threat to human well-being due to the increasing cases of resistance against the existing antifungal drugs. Consequently, efforts are increasingly focused towards investigating new moieties with potential activity against different fungal species. The object of this work was to synthesize and evaluate the antifungal activity of five benzyl alcohol derivatives against Candida albicans and Trichophyton rubrum and also to study the biochemical as well as the ADMET properties of the compounds in silico.
Methods: The target compounds were obtained by the reduction of the appropriate aldehyde using sodium borohydride. Subsequently the compounds were tested against the two fungal species using ketoconazole as the positive control. The biochemical activities as well as the ADMET properties were calculated at DFT/B3LYP/6-311G* basis set with the help of Gaussian09 (G09) software.
Results: The findings revealed that some of the compounds exhibited interesting inhibitory action against C. albicans while others against T. rubrum. However, the MIC and MFC results demonstrated that none of the compounds were fungicidal at the concentrations tested. In silico ADMET studies showed that all the compounds have a good cell permeability index, their human intestinal absorption values were within the recommended scale and with good plasma protein binding.
Conclusion: The benzyl alcohol derivatives studied in this work have exhibited some encouraging antifungal activity and fa- vorable biochemical as well as pharmacokinetic properties.

References

  • Almoughrabie, S., Ngari, C., Guillier, L., Briandet, R., Poulet, V., & Dubois-Brissonnet, F. (2020). Rapid assessment and prediction of the efficiency of two preservatives against S. aureus in cosmetic products using High Content Screening—Confocal Laser Scan- ning Microscopy. PLoS ONE, 15, 7, e0236059.
  • Beata, Z., Anna, C., & Anna, B. (2014). Development studies on determination of preservatives decomposition products. Acta Poloniae Pharmaceutica-Drug Research, 71(4), 563-573.
  • Bozdogan, B., & Appelbaum, P. C. (2004). Oxazolidinones: Activ- ity, Mode of action, and Mechanism of Resistance. International Journal of Antimicrobial Agents, 23(2), 113-119.
  • Cheng, F., Li, W., Zhou, Y., Shen, J., Wu, Z., Liu, G., & Tang, Y. (2012). admetSAR: A comprehensive source and free tool for assessment of chemical ADMET properties. Journal of Chemical Information and Modeling, 52(11), 3099-3105.
  • Durante-Mangoni, E., Grammatikos, A., Utili, R., & Falagas M., E. (2009). Do we still need the aminoglycosides? International Jour- nal of Antimicrobial Agents, 33(3), 201-205.
  • European Committee for Antimicrobial Susceptibility Testing (EU- CAST) of the European Society of Clinical Microbiology and Infec- tious Diseases (ESCMID). Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by broth dilution. EUCAST Discussion Document E.Dis 5.1, March 2003.
  • Gaussian 09, Revision E.01, Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., & Petersson, G. A. Gaussian, Inc., Wallingford CT, 2009.
  • Giamarellos-Bourboulis, E. J. (2008). Macrolides beyond the conventional antimicrobials: A Class of Potent Immunomodula- tors. International Journal of Antimicrobial Agents, 31(1), 12-20.
  • Gonzalo-Garijo, M. A., Rodriguez-Nevado, I., & de Argila, D. (2006). Patch tests for diagnosis of delayed hypersensitivity to cephalo- sporins. Allergologia et Immunopathologia, 34(1), 39-41.
  • Imanirampa, L., & Alele, P. E. (2016). Antifungal activity of Cleome gynandra L. aerial parts for topical treatment of Tinea capitis: an in vitro evaluation. BMC Complementary and Alternative Medi- cine, 16, 1, 1-8
  • Koushlesh, K., M., Chanchal, D., K., Anil, K., S., Rajnikant, P., Pankaj, K., Saraswati, P., M., & Shweta, D. (2020). Medicinal Plants Having Antifungal Properties. In Bassam Hassan (Ed.), Medicinal Plants Use in Prevention and Treatment of Diseases. IntechOpen.
  • Leeson, P., D., & Springthorpe, B. (2007). The influence of drug- like concepts on decision-making in medicinal chemistry. Nature Reviews Drugs Discovery, 6(11), 881–890.
  • Lim, E. J., Kang, H. J., Jung, H. J., Song, Y. S., Lim C. J., & Park, E. H. (2008). Anti-angiogenic, anti-inflammatory and anti-nociceptive activities of vanillin in ICR mice. Biomolecules and Therapeutics, 16, 132-136.
  • Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (2001). Experimental and computational approaches to estimate solubil- ity and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 46, 3–26.
  • Singh, R., Dar, S. A., & Sharma, P. (2012). Antibacterial Activity and Toxicological Evaluation of Semi Purified Hexane Extract of Urtica dioica Leaves. Research Journal of Medicinal Plants, 6, 123-135.
  • Veber, D. F., Johnson, S. R., Cheng, H.-Y., Smith, B. R., Ward, K. W., & Kopple, K. D. (2002). Molecular properties that influence the oral bioavailability of drug candidates. Journal of Medicinal Chemistry, 45, 2615–2623.
  • Wei, A., & Shibamoto, T. (2007). Antioxidant activities and volatile constituents of various essential oils. Journal of Agricultural and Food Chemistry, 55(5), 1737-1742.
  • Wang, C., Liu, Y., Bao, C., Xue, Y., Zhou, Y., Zhang, D., Lin, Q., & Zhu, L. (2020). Phototriggered labeling and crosslinking by 2-nitrobenzyl alcohol derivatives with amine selectivity. Chemical Communica- tions, 56(15), 2264-2267.
There are 18 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Original Article
Authors

Justina Benson Ogala This is me 0000-0001-5611-7249

Yusuf Hassan 0000-0001-6117-2357

Abdullahi Samaıla This is me 0000-0001-5261-9305

Murtala Isah Bindawa This is me 0000-0001-8883-3354

Tugba Taskın Tok 0000-0002-0064-8400

Publication Date April 28, 2022
Submission Date June 28, 2021
Published in Issue Year 2022

Cite

APA Benson Ogala, J., Hassan, Y., Samaıla, A., Isah Bindawa, M., et al. (2022). Synthesis, antifungal activity and in silico ADMET studies of benzyl alcohol derivatives. İstanbul Journal of Pharmacy, 52(1), 47-53. https://doi.org/10.26650/IstanbulJPharm.2022.958484
AMA Benson Ogala J, Hassan Y, Samaıla A, Isah Bindawa M, Taskın Tok T. Synthesis, antifungal activity and in silico ADMET studies of benzyl alcohol derivatives. iujp. April 2022;52(1):47-53. doi:10.26650/IstanbulJPharm.2022.958484
Chicago Benson Ogala, Justina, Yusuf Hassan, Abdullahi Samaıla, Murtala Isah Bindawa, and Tugba Taskın Tok. “Synthesis, Antifungal Activity and in Silico ADMET Studies of Benzyl Alcohol Derivatives”. İstanbul Journal of Pharmacy 52, no. 1 (April 2022): 47-53. https://doi.org/10.26650/IstanbulJPharm.2022.958484.
EndNote Benson Ogala J, Hassan Y, Samaıla A, Isah Bindawa M, Taskın Tok T (April 1, 2022) Synthesis, antifungal activity and in silico ADMET studies of benzyl alcohol derivatives. İstanbul Journal of Pharmacy 52 1 47–53.
IEEE J. Benson Ogala, Y. Hassan, A. Samaıla, M. Isah Bindawa, and T. Taskın Tok, “Synthesis, antifungal activity and in silico ADMET studies of benzyl alcohol derivatives”, iujp, vol. 52, no. 1, pp. 47–53, 2022, doi: 10.26650/IstanbulJPharm.2022.958484.
ISNAD Benson Ogala, Justina et al. “Synthesis, Antifungal Activity and in Silico ADMET Studies of Benzyl Alcohol Derivatives”. İstanbul Journal of Pharmacy 52/1 (April 2022), 47-53. https://doi.org/10.26650/IstanbulJPharm.2022.958484.
JAMA Benson Ogala J, Hassan Y, Samaıla A, Isah Bindawa M, Taskın Tok T. Synthesis, antifungal activity and in silico ADMET studies of benzyl alcohol derivatives. iujp. 2022;52:47–53.
MLA Benson Ogala, Justina et al. “Synthesis, Antifungal Activity and in Silico ADMET Studies of Benzyl Alcohol Derivatives”. İstanbul Journal of Pharmacy, vol. 52, no. 1, 2022, pp. 47-53, doi:10.26650/IstanbulJPharm.2022.958484.
Vancouver Benson Ogala J, Hassan Y, Samaıla A, Isah Bindawa M, Taskın Tok T. Synthesis, antifungal activity and in silico ADMET studies of benzyl alcohol derivatives. iujp. 2022;52(1):47-53.