126
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

Evaluation of antifungal activity, mechanisms of action and toxicological profile of the synthetic amide 2-chloro-N-phenylacetamide

, ORCID Icon, , ORCID Icon, , ORCID Icon, , , , , ORCID Icon & show all
Pages 191-202 | Received 20 Jul 2022, Accepted 10 Dec 2022, Published online: 20 Feb 2023

References

  • Abreu, P. A., 2008. NMDA receptor: molecular modeling by homology and SAR analysis of antagonists of a potential therapeutic target in neurodegenerative diseases. Dissertation. Fluminense Federal University.
  • Arendrup, M.C., et al., 2010. Development of azole resistance in Aspergillus fumigatus during azole therapy associated with change in virulence. PLoS One, 5 (4), e10080–19.
  • Aschale, M., 2012. Synthesis and Antimicrobial Evaluation of Some Novel Substituted 2-chloroacetanalides. International Journal of ChemTech Research, 4 (4), 1437–1441.
  • Bellmann, R., 2013. Pharmacodynamics and pharmacokinetics of antifungals for treatment of invasive aspergillosis. Current Pharmaceutical Design, 19 (20), 3629–3647.
  • Blatzer, M., et al., 2015. Blocking Hsp70 enhances the efficiency of amphotericin B treatment against resistant Aspergillus terreus strains. Antimicrobial Agents and Chemotherapy, 59 (7), 3778–3788.
  • Blum, G., et al., 2013. New insight into Amphotericin B resistance in Aspergillus terreus. Antimicrobial Agents and Chemotherapy, 57 (4), 1583–1588.
  • Bonapace, C.R., et al., 2002. Comparison of methods of interpretation of checkerboard synergy testing. Diagnostic Microbiology and Infectious Disease, 44 (4), 363–366.
  • Borman, A.M., et al., 2017. MIC distributions and evaluation of fungicidal activity for amphotericin B, itraconazole, voriconazole, posaconazole and caspofungin and 20 species of pathogenic filamentous fungi determined using the CLSI broth microdilution method. Journal of Fungi, 3 (2), 27.
  • Brandão, R., et al., 2005. Hemolytic effect of sodium selenite and mercuric chloride in human blood. Drug and Chemical Toxicology, 28 (4), 397–407.
  • Butt, A.R.S., et al., 2019. Synthesis and structure-activity relationship of tyrosinase inhibiting novel bi-heterocyclic acetamides: mechanistic insights through enzyme inhibition, kinetics and computational studies. Bioorganic Chemistry, 86, 459–472.
  • Cairns, T.C., et al., 2018. How a fungus shapes biotechnology: 100 years of Aspergillus niger research. Fungal Biology and Biotechnology, 5 (1), 1–14.
  • Carrard, V.C., et al., 2007. Teste dos Micronúcleos: Um biomarcador de dano genotóxico em células descamadas da mucosa bucal. Revista da Faculdade de Odontologia de Porto Alegre, 48 (1/3), 77–81.
  • Chowdhary, A., et al., 2015. Prevalence and mechanism of triazole resistance in Aspergillus fumigatus in a referral chest hospital in Delhi, India and an update of the situation in Asia. Frontiers in Microbiology, 06, 1–10.
  • CLSI (Clinical and Laboratory Standards Institute), formely NCCLS (National Committee for Clinical Laboratory Standards) 2008. Reference method for broth dilution antifungal susceptibility testing of filamentous fungi. (2rd ed., Vol. 37). Wayne: CSLI Standart M38. p. 11.
  • Cordeiro, L., et al., 2020. Potential of 2-Chloro-N-(4-fluoro-3-nitrophenyl) acetamide against Klebsiella pneumoniae and in vitro toxicity analysis. Molecules, 25 (17), 3959–19.
  • Cowen, L.E., et al., 2005. Hsp90 potentiates the rapid evolution of new traits: drug resistance in diverse fungi. Science (New York, N.Y.), 309 (5744), 2185–2189.
  • Dacie, J. V., 2001. Investigation of haemostasis. In: S. M. Lewis, ed. Practical Haematology. (9th ed.). London: Harcourt Pubilshers Limited.
  • Daina, A., et al., 2017. Swiss ADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Science Report, 7, 1–13.
  • Dhingra, S., et al., 2017. Regulation of sterol biosynthesis in the human fungal pathogen Aspergillus fumigatus: opportunities for therapeutic development. Frontiers in Microbiology, 8 (2), 92.
  • Diniz, D.S.F., et al., 2013. Vantagens do Midazolam Intravenoso em Relação à Premedicação Via Oral em Crianças. Revista de Ciências da Saúde, 3 (1), 1–18.
  • Douglas, L.M., et al., 2014. Fungal membrane organization: the eisosome concept. Annual Review of Microbiology, 68 (3), 377–393.
  • Drago, L., et al., 2007. In vitro evaluation of antibiotics for emprirical therapy of suspected methicilin resistant Staphylococcus aureus severe respiratory infections. BMC Infectious Diseases, 7, (111–117.
  • Dutta, N.K., et al., 2004. Antimycobacterial activity of the anti-inflammatory agent diclofenac sodium, and its synergism with streptomycin. Brazilian Journal of Microbiology, 35 (4), 316–323.
  • Egan, W.J., et al., 2000. Prediction of drug absorption using multivariate statistics. Journal of Medicinal Chemistry, 43 (21), 3867–3877.
  • Escarlante, A., et al., 2008. Evidence for the mechanism of action of the antifungal phytolaccoside B isolate from Phytolacca tetramera Hauman. Journal of Natural Products, 71 (10), 720–725.
  • Falci, D.R., et al., 2015. Amphotericina B: uma revisão sobre suas diferentes formulações, efeitos adversos e toxicidade. Clinical & Biomedical Research, 35 (2), 65–82.
  • Ferreira, E.S., et al., 2021. Antifungal activity and mechanism of action of 2-chloro-N-phenylacetamide: a new molecule with activity against strains of Aspergillus flavus. Anais da Academia Brasileira de Ciências, 93 (Suppl 3), 1–15.
  • Filippin, F.B., et al., 2006. Eficiência terapêutica das formulações lipídicas de amphotericin B. Revista Brasileira de Ciências Farmacêuticas, 42 (2), 167–194.
  • Flockhart, D.A., 2007. Drug interactions: cytochrome P450 drug interaction table. https://drug-interactions.medicine.iu.edu/MainTable.aspx.Acessoem22demarçode2021.
  • Frost, D.J., et al., 1995. A whole-cell Candida albicans assay for the detection of inhibitors towards fungal cell wall synthesis and assembly. The Journal of Antibiotics, 48 (4), 306–310.
  • Gabriel, H.E., et al., 2006. Chronic cigarette smoking is associated with diminished folate status, altered folate form distribution, and increased genetic damage in the buccal mucosa of healthy adults. The American Journal of Clinical Nutrition, 83 (4), 835–841.
  • Gaddis, G.M., et al., 2002. Drug interactions in atrisk emergency department patients. Academic Emergency Medicine : official Journal of the Society for Academic Emergency Medicine, 9 (11), 1162–1167.
  • Ghose, A.K., et al., 1999. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. Journal of Combinatorial Chemistry, 1 (1), 55–68.
  • Guerra, F.S.Q., et al., 2015. Evaluation of antifungal activity and mode of action of new coumarin derivative, 7-Hydroxy-6-nitro-2H-1-benzopyran-2-one, against Aspergillus spp. Evidence-Based Complementary and Alternative Medicine, 2015, 1–8.
  • Hagiwara, D., et al., 2016. Epidemiological and genomic landscape of azole resistance mechanisms in Aspergillus fungi. Frontiers in Microbiology, 7, (1382–14.
  • Hashimoto, A., et al., 2017. Drug Sensitivity and Resistance Mechanism in Aspergillus Section Nigri Strains from Japan. Antimicrobial Agents and Chemotherapy, 61 (8), 1–10.
  • Hazen, K.C., 1998. The fungicidal versus fungistatic activity of terbinafine and itraconazole: An in vitro comparison. Journal of the American Academy of Dermatology, 38 (5), S37–S41.
  • Holetz, F.B., et al., 2002. Screening of some plants used in the Brazilian folk medicine for the treatment of infectious diseases. Memorias do Instituto Oswaldo Cruz, 97 (7), 1027–1031.
  • Huang, M. F. N., 2016. Síntese de novos compostos organosselênicos com potencial atividade antimicrobiana e antitumoral. Dissertation, Universidade Federal da Paraíba.
  • Huang, S., et al., 2008. New era in drug interaction evaluation: US Food and Drug Administration update on CYP enzymes, transporters, and the guidance process. Journal of Clinical Pharmacology, 48 (6), 662–670.
  • Jukic, E., et al., 2017. Oxidative stress response tips the balance in Aspergillus terreus amphotericin B resistance. Antimicrobials Agents and Chemotherapy, 61 (10), 1–14.
  • Kassie, F., et al., 2001. Khat (Catha edulis) consumption causes genotoxic effects in humans. International Journal of Cancer, 92 (3), 329–332.
  • Katke, S.A., et al., 2011. Synthesis of biologically active 2-chloro-N-alkyl/aryl acetamide derivatives. International Journal of Pharma Sciences and Research, 2 (7), 148–156.
  • Korzeniowska, K.M., et al., 1990. Pulmonary aspergillosis caused by Aspergillus niger. Pneumonology Polska, 58 (3), 328–333.
  • Lipinski, C.A., et al., 2001. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 23 (1-3), 3–25.
  • Lunde, C.S., et al., 2000. Effect of polygodial on the mitochondrial ATPase of Saccharomyces cerevisiae. Antimicrobial Agents and Chemotherapy, 44 (7), 1943–1953.
  • Martinez-Rossi, M., et al., 2008. Antifungal resistance mechanisms in dermathophytes. Mycopathologia, 166 (5-6), 369–383.
  • Mishra, G.S., et al., 2004. Chronic bilateral otomysocis caused by Aspergillus niger. Mycoses, 47 (1-2), 82–84.
  • Mitsugui, C.S., et al., 2008. Efeito antimicrobiano in vitro da associação de polimixina B e ceftazidima em amostras clínicas de Pseudomonas aeruginosa. Ciências e Cuidado em Saúde (Online), 7 (1), 76–81.
  • Moore, M.M., et al., 2019. The food contaminant acetamide is not an in vivo clastogen, aneugen, or mutagen in rodent hematopoietic tissue. Regulatory Toxicology and Pharmacology : Rtp, 108 (8), 104451–104457.
  • Ncube, N.S., et al., 2008. Assessment techniques of antimicrobial properties of natural compounds of plant origin: current methods and future trends. African Journal of Biotechnology, 7 (12), 1797–1806.
  • Odds, F.C., Brown, A.J.P., and Gow, N.A.R., 2003. Antifungal agents: mechanisms of action. Trends in Microbiology, 11 (6), 272–279.
  • Patel, R.V., et al., 2013. Synthesis of coumarin-based 1, 3, 4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides as antimicrobial and antituberculosis agents. Medicinal Chemistry Research, 22 (1), 195–210.
  • Patterson, T.F., et al., 2016. Practice guidelines for the diagnosis and management of aspergillosis: 2016 update by the Infectious Diseases Society of America. Clinical Infectious Diseases, 63 (4), e1–e60.
  • Raja, N.S., et al., 2006. Disseminated invasive aspergillosis in an apparently immunocompetent host. Journal of Microbiology. Immunology and Infection, 39 (1), 73–77.
  • Rangel, M., et al., 1997. Hemolytic activity in extracts of the diatom Nitzschia. Toxicon : official Journal of the International Society on Toxinology, 35 (2), 305–309.
  • Santos, L., et al., 2011. Perfil das interações medicamentosas solicitadas ao centro de informações sobre medicamentos de hospital universitário. Revista do Hospital Das Clínicas de Porto Alegre, 31 (3), 326–335.
  • Saraiva, S.R.G.L., et al., 2012. Antioxidant activity and acute toxicity of Neoglaziovia variegata (Bromeliaceae). African Journal of Biotechnology, 11 (75), 13998–14006.
  • Schuster, E., et al., 2002. On the safety of Aspergillus niger – a review. Applied Microbiology and Biotechnology, 59 (4-5), 426–435.
  • Sponchiado, G., et al., 2016. Quantitative genotoxicity assays for analysis of medicinal plants: A systematic review. Journal of Ethnopharmacology, 178 (3), 289–296.
  • Svetaz, L.M.B., et al., 2007. Antifungal activity of Zuccagnia punctata Cav.: evidence for the mechanism of action. Planta Medica, 73 (10), 1074–1080.
  • Thomas, P., et al., 2008. The buccal cytome and micronucleus frequency is substantially altered in Down’s syndrome and normal ageing compared to young healthy controls. Mutation Research, 638 (1-2), 37–47.
  • Tiwari, S., et al., 2015. Role of heat-shock proteins in cellular function and in the biology of fungi. Biotechnology Research International, 2015 (2), 1–11.
  • Tolbert, P.E., et al., 1992. Micronuclei and other nuclear anomalies in buccal smears: methods development. Mutation Research/Environmental Mutagenesis and Related Subjects, 271 (1), 69–77.
  • Trajano, V.N., et al., 2012. Antifungal activity of the essential oil of Cinnamomum zeylanicum Blume and eugenol on Aspergillus flavus. Journal of Essential Oil Bearing Plants, 15 (5), 785–793.
  • Varlam, D.E., et al., 2001. Apoptosis contributes to amphotericin B-induced nephrotoxicity. Antimicrobial Agents and Chemotherapy, 45 (3), 679–685.
  • Veber, D.F., et al., 2002. Molecular properties that influence the oral bioavailability of drug candidates. Journal of Medicinal Chemistry, 45 (12), 2615–2623.
  • Veiga-Júnior, V.F., et al., 2005. Plantas medicinais: cura segura? Química Nova, 28 (3), 519–528.
  • Vennewald, I., et al., 2003. Mycological and histological investigations in humans with middle ear infections. Mycoses, 46 (1-2), 12–18.
  • Verweij, P.E., et al., 2009. Azole resistance in Aspergillus fumigatus: a side-effect of environmental fungicide use? The Lancet Infectious Diseases, 9 (12), 789–795.
  • Whalen, K., et al., 2016. Farmacologia ilustrada. Tradução da 6 edição (pp 8), Artmed.
  • Zhang, L., et al., 2019. Multivariate effects of Chinese keemun black tea grades (Camellia sinensis var. sinensis) on the phenolic composition, antioxidant, antihemolytic and cytotoxic/cytoprotection activities. Food Reseach International, 125 (3), 1–10.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.