Chloroacetamide derivatives as a promising topical treatment for fungal skin infections

LITERATURE CITED

• Abd E, Yousef SA, Pastore MN, Telaprolu K, Mohammed YH, Namjoshi S, Grice JE, Roberts MS. 2016. Skin models for the testing of transdermal drugs. Clinical Pharmacology: Advances and Applications 8:163–176.
   PubMedGoogle Scholar
• Alcazar-Fuoli L, Mellado E, Alastruey-Izquierdo A, Cuenca-Estrella M, Rodriguez-Tudela JL. 2009. Species identification and antifungal susceptibility patterns of species belonging to Aspergillus section Nigri. Antimicrobial Agents and Chemotherapy 53:4514–4517.
   PubMed Web of Science ®Google Scholar
• Ammar HO, Ghorab M, Mahmoud AA, Makram TS, Ghoneim AM. 2013. Rapid pain relief using transdermal film forming polymeric solution of ketorolac. Pharmaceutical Development and Technology 18:1005–1016.
   PubMed Web of Science ®Google Scholar
• Aschale M. 2012. Synthesis and antimicrobial evaluation of some novel substituted 2-chloroacetanilides. International Journal of ChemTech Research 4:1437–1441.
   Google Scholar
• Badiee P, Hashemizadeh Z. 2014. Opportunistic invasive fungal infections: diagnosis and clinical management. The Indian Journal of Medical Research 139:195–204.
   PubMed Web of Science ®Google Scholar
• Been RA, Bernatchez SF, Conrad-Vlasak DM, Asmus RA, Ekholm BP, Parks PJ. 2016. In vivo methods to evaluate a new skin protectant for loss of skin integrity. Wound Repair and Regeneration 24:851–859.
   Web of Science ®Google Scholar
• Boger P. 2003. Mode of action of chloroacetamides and functionally retaled compounds. Journal of Pesticide Science 28:324–329.
   Web of Science ®Google Scholar
• Bowman JC, Hicks PS, Kurtz MB, Rosen H, Schmatz DM, Liberator PA, Douglas CM. 2002. The antifungal echinocandin caspofungin acetate kills growing cells of Aspergillus fumigatus in vitro. Antimicrobial Agents and Chemotherapy 46:3001–3012.
   PubMed Web of Science ®Google Scholar
• Bowmann SM, Free SJ. 2006. The structure and synthesis of the fungal cell wall. BioEssays 28:799–808.
   Web of Science ®Google Scholar
• Carrillo-Muñoz AJ, Tur-Tur C, Cardenes D, Rojas F, Giusiano G. 2012. Sertaconazole antifungal profile determined by a microdilution method versus nine topical substances against dermatophyte fungi. Chemotherapy 58:399–404.
   Web of Science ®Google Scholar
• Cheng KC, Demirci A, Catchmark JM. 2011. Pullulan: biosynthesis, production, and applications. Applied Microbiology and Biotechnology 92:29–44.
   PubMed Web of Science ®Google Scholar
• (CLSI) Clinical and Laboratory Standards Institute. 2008a. Reference method for broth dilution antifungal susceptibility testing of yeasts; approved standard, 3rd ed. CLSI Document M27-A3. Wayne, Pennsylvania: Clinical Laboratory Standards Institute.
   Google Scholar
• (CLSI) Clinical and Laboratory Standards Institute. 2008b. Reference method for broth dilution antifungal susceptibility testing of filamentous fungi; approved standard, 2nd ed. CLSI Document M38-A2. Wayne, Pennsylvania: Clinical Laboratory Standards Institute.
   Google Scholar
• Corrêa JCR, Salgado HRN. 2011. Review of fluconazole properties and analytical for its determination. Critical Reviews in Analytical Chemistry 41:270–279.
   Google Scholar
• Crowley PD, Gallagher HC. 2014. Clotrimazole as a pharmaceutical: past, present and future. Journal of Applied Microbiology 117:611–617.
   PubMed Web of Science ®Google Scholar
• Dalla Lana DF, Batista BG, Alves SH, Fuentefria AM. 2016. Dermatophytoses: etiologic agents, clinical forms, therapy and new perspectives of treatment. Clinical and Biomedical Research 36:230–241.
   Google Scholar
• Debeer S, Le Luduec JB, Kaiserlian D, Laurent P, Nicolas JF, Dubois B, Kanitakis J. 2013. Comparative histology and immunohistochemistry of porcine versus human skin. European Journal of Dermatology 23:456–466.
   Web of Science ®Google Scholar
• Eckermann C, Matthes B, Nimtz M, Reiser V, Lederer B, Boger P, Schroder P. 2003. Covalent binding of chloroacetamide herbicides to the active site cysteine of plant type III polyketide synthases. Phytochemistry 64:1045–1054.
   Web of Science ®Google Scholar
• Fortwendel JR, Juvvadi PR, Perfect BZ, Rogg LE, Perfect JR, Steinbach WJ. 2010. Transcriptional regulation of chitin synthases by calcineurin controls paradoxical growth of Aspergillus fumigatus in response to caspofungin. Antimicrobial Agents and Chemotherapy 54:1555–1563.
   PubMed Web of Science ®Google Scholar
• Frederiksen K, Guy RH, Petersson P. 2016. The potential of polymeric film-forming systems as sustained delivery platforms for topical drugs. Expert Opinion on Drug Delivery 13:349–360.
   PubMed Web of Science ®Google Scholar
• Fuentefria AM, Andrade SF, Silveira GP, Kulkamp I, Pippi B, Machado MM, De Oliveira LFS, Cruz L, Frizzo C, Martins AF. 2016. Caracterização do perfil de susceptibilidade a antifúngicos azólicos de uma micoteca como embasamento para estratégias de combate à candidemias. Journal of Infection Control 5:1–11.
   Google Scholar
• Fukuda EK, Vasconcelos AFD, Matias AC, Barbosa ADM, Dekker RF, Da Silva MLC. 2009. Fungal cell wall polysaccharides: purification and characterization. Semina: Ciências Agrárias 30:117–134.
   Web of Science ®Google Scholar
• Harte AJ, Gunnlaugsson T. 2006. Synthesis of α-chloroamides in water. Tetrahedron Letters 47:6321–6324.
   Web of Science ®Google Scholar
• Hayette MP, Sacheli R. 2015. Dermatophytosis, trends in epidemiology and diagnostic approach. Current Fungal Infection Reports 9:164–179.
   Web of Science ®Google Scholar
• Ingham CJ, Schneeberger PM. 2012. Microcolony Imaging of Aspergillus fumigatus treated with echinocandins reveals both fungistatic and fungicidal activities. PLoS ONE 7:e35478.
   Web of Science ®Google Scholar
• (ICCVMA) Interagency Coordinating Committee on the Validation of Alternative Methods. 2010. The hen’s egg test–chorioallantoic membrane (HET-CAM) test method. Research Triangle Park, North Carolina: National Toxicology Program.
   Google Scholar
• Jablonkai I. 2003. Alkylating reactivity and herbicidal activity of chloroacetamides. Pest Management Science 59:443–450.
   Web of Science ®Google Scholar
• Jampilek J. 2016. Potential of agricultural fungicides for antifungal drug discovery. Expert Opinion on Drug Discovery 11:1–9.
   PubMed Web of Science ®Google Scholar
• Joubert LM, Ferreira JAG, Stevens DA, Cegelski L. 2015. Aspergillus fumigates biofilms: a comparison of processing techniques for scanning electron microscopy of fungal mycelium and extracellular matrix. Microscopy and Microanalysis 21:935–936.
   Google Scholar
• Junior JAO, Shiota LM, Chiavacci LA. 2014. Development of organic-inorganic polymeric film formers for controlled drug release and wound care. Matéria 19:24–32.
   Google Scholar
• Karier P, Kraus G, Kolbe I. 2017. Metazachlor traces in the main drinking water reservoir in Luxembourg: a scientific and political discussion. Environmental Sciences Europe 29:25.
   PubMed Web of Science ®Google Scholar
• Kathe K, Kathpalia H. 2017. Film forming systems for topical and transdermal drug delivery. Asian Journal of Pharmaceutial Sciences 12:487–497.
   PubMed Web of Science ®Google Scholar
• Katke SA, Amrutkar SV, Bhor RJ, Khairnar MV. 2011. Synthesis of biologically active 2-chloro-N-alkyl/arylacetamide derivatives. International Journal of Pharma Sciences and Research 2:148–156.
   Google Scholar
• Khatri PK, Kachhawa D, Maurya V, Meena S, Bora A, Rathore L, Seervi KL,Khullar S. 2017. Antifungal resistance pattern among dermatophytes in western rajasthan. International Journal of Current Microbiology and Applied Sciences 6:499–509.
   Google Scholar
• Kovacic P, Cooksy A. 2012. Novel, unifying mechanism for amphotericin B and other polyene drugs: electron affinity, radicals, electron transfer, autoxidation, toxicity, and antifungal action. MedChemComm 3:274–280.
   Web of Science ®Google Scholar
• Lane ME. Skin penetration enhancers. 2013. International Journal of Pharmaceutics 447:12–21.
   PubMed Web of Science ®Google Scholar
• Lavorato SN, Duarte MC, De Andrade PHR, Coelho EAF, Alves RJ. 2017. Synthesis, antileishmanial activity and QSAR studies of 2-chloro-N-arylacetamides. Brazilian Journal of Pharmaceutical Sciences 53:e16067.
   Web of Science ®Google Scholar
• Lee W, Lee DG. 2018. A novel mechanism of fluconazole: fungicidal activity through dose-dependent apoptotic responses in Candida albicans. Microbiology 164:194–204.
   PubMed Web of Science ®Google Scholar
• Leite MCA, Bezerra APB, De Sousa JP, Guerra FQS, Lima EO. 2014. Evaluation of antifungal activity and mechanism of action of citral against Candida albicans. Evidence Based Complementary and Alternative Medicine 2014:1–10.
   Web of Science ®Google Scholar
• Liu X, Testa B, Fahr A. 2011. Lipophilicity and its relationship with passive drug permeation. Pharmaceutical Research 28:962–977.
   PubMed Web of Science ®Google Scholar
• Machado GRM, Pippi B, Dalla Lana DF, Amaral AP, Teixeira ML, Souza KC, Fuentefria AM. 2016. Reversal of fluconazole resistance induced by a synergistic effect with Acca sellowiana in Candida glabrata strains. Pharmaceutical Biology 54:2410–2419.
   Web of Science ®Google Scholar
• Marco-Contelles J, Gomez-Sanchez E. 2005. New agents with antimycobacterial activity. Archiv der Pharmazie 338:562–563.
   Web of Science ®Google Scholar
• Martínez-Poveda B, Muñoz-Chápuli R, Rodríguez-Nieto S, Quintela JM, Fernández A, Medina MA, Quesada AR. 2007. IB05204, a dichloropyridodithienotriazine, inhibits angiogenesis in vitro and in vivo. Molecular Cancer Therapeutics 6:2675–2685.
   Web of Science ®Google Scholar
• Netea MG, Joosten LA, Van der Meer JW, Kullberg BJ, Van de Veerdonk FL. 2015. Immune defence against Candida fungal infections. Nature Reviews Immunology 15:630–642.
   PubMed Web of Science ®Google Scholar
• Pfaller MA, Castanheira M, Messer SA, Jones RN. 2015. In vitro antifungal susceptibilities of isolates of Candida spp. and Aspergillus spp. from China to nine systemically active antifungal agents: data from the SENTRY antifungal surveillance program, 2010 through 2012. Mycoses 58:209–214.
   Google Scholar
• Pianalto KM, Alspaugh JW. 2016. New horizons in antifungal therapy. Journal of Fungi 2:26.
   Web of Science ®Google Scholar
• Pippi B, Reginatto P, Machado GRM, Bergamo VZ, Dalla Lana DF, Teixeira ML, Franco LL, Alves RJ, Andrade FA. Fuentefria AM. 2017. Evaluation of 8-hydroxyquinoline derivatives as hits for antifungal drug design. Medical Mycology 55:763–773.
   PubMed Web of Science ®Google Scholar
• Rouzaud C, Lanternier F, Puel A. 2017. Primary immunodeficiencies and dermatophytosis. In: Carvalho A, ed. Immunogenetics of fungal diseases. Cham: Springer. p. 121–133.
   Google Scholar
• Rueda C, Cuenca-Estrella M, Zaragoza O. 2014. Paradoxical Growth of Candida albicans in the presence of caspofungin is associated with multiple cell wall rearrangements and decreased virulence. Antimicrobial Agents and Chemotherapy 58:1071–1083.
   PubMed Web of Science ®Google Scholar
• Rueda C, Puig-Asensio M, Guinea J, Almirante B, Cuenca-Estrella M, Zaragoza O. 2017. Evaluation of the possible influence of trailing and paradoxical effects on the clinical outcome of patients with candidemia clinical microbiology and infection. Clinical Microbiology and Infection 23:49.e1–49.e8.
   Google Scholar
• Sheu SY, Wang WL, Fu YT, Lin CS, Lei YC, Liao JH, Tang NY, Kuo TF, Yao CH. 2014. The pig as an experimental model for mid-dermal burns research. Burns 40:1679–1688.
   Web of Science ®Google Scholar
• Sigurgeirsson B, Hay RJ. 2016. The antifungal drugs used in skin disease. In: Ólafsson J, Hay R, ed. Antibiotic and antifungal therapies in dermatology. Cham: Springer. p. 141–156.
   Google Scholar
• Singh DCP, Hashim SR, Singhal RG. 2011. Synthesis and antimicrobial activity of some new thioether derivatives of quinoxaline. E-Journal of Chemistry 8:635–642.
   Google Scholar
• Singh UP, Bhat HR, Gahtori P. 2012. Antifungal activity, SAR and physicochemical correlation of some thiazole-1,3,5-triazinederivatives. Journal de Mycologie Médicale 22:134– 141.
   PubMed Web of Science ®Google Scholar
• Souissi Y, Bouchonnet S, Bourcier S, Kusk KO, Sablier M, Andersen HR. 2013. Identification and ecotoxicity of degradation products of chloroacetamide herbicides from UV-treatment of water. The Science of the Total Environment 458–460:527–534.
   PubMed Web of Science ®Google Scholar
• Srinivasan A, Lopez-Ribot JL, Ramasubramanian AK. 2014. Overcoming antifungal resistance. Drug Discovery Today: Technologies 11:65–71.
   PubMedGoogle Scholar
• Tobudic S, Kratzer C, Presterl E. 2012. Azole-resistant Candida spp.—emerging pathogens? Mycoses 5:24–32.
   Web of Science ®Google Scholar
• Vandeputte P, Ferrari S, Coste AY. 2012. Antifungal resistance and new strategies to control fungal infections. International Journal of Microbiology 2012:1–26. Article ID 713687.
   Google Scholar
• Vena GA, Chieco P, Posa F, Garofalo A, Bosco A, Cassano N. 2012. Epidemiology of dermatophytoses: retrospective analysis from 2005 to 2010 and comparison with previous data from 1975. The New Microbiologica 35:207–213.
   PubMed Web of Science ®Google Scholar
• Wagener J, Loiko V. 2018. Recent Insights into the paradoxical effect of echinocandins. Journal of Fungi 4:5.
   Web of Science ®Google Scholar
• Whaley SG, Berkow EL, Rybak JM, Nishimoto AT, Barker KS, Rogers PD. 2017. Azole antifungal resistance in Candida albicans and emerging non-albicans Candida species. Frontiers in Microbiology 7:2173.
   PubMed Web of Science ®Google Scholar
• Williams AC, Barry BW. 2004. Penetration enhancers. Advanced Drug Delivery Reviews 56:603–618.
   PubMed Web of Science ®Google Scholar