Tags

Type your tag names separated by a space and hit enter

Chiral HPLC analysis of donepezil, 5-O-desmethyl donepezil and 6-O-desmethyl donepezil in culture medium: application to fungal biotransformation studies.
Anal Bioanal Chem. 2012 Jul; 404(1):257-66.AB

Abstract

An high performance liquid chromatography (HPLC) method for the enantioselective determination of donepezil (DPZ), 5-O-desmethyl donepezil (5-ODD), and 6-O-desmethyl donepezil (6-ODD) in Czapek culture medium to be applied to biotransformation studies with fungi is described for the first time. The HPLC analysis was carried out using a Chiralpak AD-H column with hexane/ethanol/methanol (75:20:5, v/v/v) plus 0.3 % triethylamine as mobile phase and UV detection at 270 nm. Sample preparation was carried out by liquid-liquid extraction using ethyl acetate as extractor solvent. The method was linear over the concentration range of 100-10,000 ng mL(-1) for each enantiomer of DPZ (r ≥ 0.9985) and of 100-5,000 ng mL(-1) for each enantiomer of 5-ODD (r ≥ 0.9977) and 6-ODD (r ≥ 0.9951). Within-day and between-day precision and accuracy evaluated by relative standard deviations and relative errors, respectively, were lower than 15 % for all analytes. The validated method was used to assess DPZ biotransformation by the fungi Beauveria bassiana American Type Culture Collection (ATCC) 7159 and Cunninghamella elegans ATCC 10028B. Using the fungus B. bassiana ATCC 7159, a predominant formation of (R)-5-ODD was observed while for the fungus C. elegans ATCC 10028B, DPZ was biotransformed to (R)-6-ODD with an enantiomeric excess of 100 %.

Authors+Show Affiliations

Departamento de Física e Química, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil. barththiago@yahoo.com.brNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Evaluation Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22644152

Citation

Barth, Thiago, et al. "Chiral HPLC Analysis of Donepezil, 5-O-desmethyl Donepezil and 6-O-desmethyl Donepezil in Culture Medium: Application to Fungal Biotransformation Studies." Analytical and Bioanalytical Chemistry, vol. 404, no. 1, 2012, pp. 257-66.
Barth T, Conti R, Pupo MT, et al. Chiral HPLC analysis of donepezil, 5-O-desmethyl donepezil and 6-O-desmethyl donepezil in culture medium: application to fungal biotransformation studies. Anal Bioanal Chem. 2012;404(1):257-66.
Barth, T., Conti, R., Pupo, M. T., Okano, L. T., & Bonato, P. S. (2012). Chiral HPLC analysis of donepezil, 5-O-desmethyl donepezil and 6-O-desmethyl donepezil in culture medium: application to fungal biotransformation studies. Analytical and Bioanalytical Chemistry, 404(1), 257-66. https://doi.org/10.1007/s00216-012-6107-3
Barth T, et al. Chiral HPLC Analysis of Donepezil, 5-O-desmethyl Donepezil and 6-O-desmethyl Donepezil in Culture Medium: Application to Fungal Biotransformation Studies. Anal Bioanal Chem. 2012;404(1):257-66. PubMed PMID: 22644152.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chiral HPLC analysis of donepezil, 5-O-desmethyl donepezil and 6-O-desmethyl donepezil in culture medium: application to fungal biotransformation studies. AU - Barth,Thiago, AU - Conti,Raphael, AU - Pupo,Mônica Tallarico, AU - Okano,Laura Tiemi, AU - Bonato,Pierina Sueli, Y1 - 2012/05/29/ PY - 2012/04/12/received PY - 2012/05/07/accepted PY - 2012/05/04/revised PY - 2012/5/31/entrez PY - 2012/5/31/pubmed PY - 2012/10/30/medline SP - 257 EP - 66 JF - Analytical and bioanalytical chemistry JO - Anal Bioanal Chem VL - 404 IS - 1 N2 - An high performance liquid chromatography (HPLC) method for the enantioselective determination of donepezil (DPZ), 5-O-desmethyl donepezil (5-ODD), and 6-O-desmethyl donepezil (6-ODD) in Czapek culture medium to be applied to biotransformation studies with fungi is described for the first time. The HPLC analysis was carried out using a Chiralpak AD-H column with hexane/ethanol/methanol (75:20:5, v/v/v) plus 0.3 % triethylamine as mobile phase and UV detection at 270 nm. Sample preparation was carried out by liquid-liquid extraction using ethyl acetate as extractor solvent. The method was linear over the concentration range of 100-10,000 ng mL(-1) for each enantiomer of DPZ (r ≥ 0.9985) and of 100-5,000 ng mL(-1) for each enantiomer of 5-ODD (r ≥ 0.9977) and 6-ODD (r ≥ 0.9951). Within-day and between-day precision and accuracy evaluated by relative standard deviations and relative errors, respectively, were lower than 15 % for all analytes. The validated method was used to assess DPZ biotransformation by the fungi Beauveria bassiana American Type Culture Collection (ATCC) 7159 and Cunninghamella elegans ATCC 10028B. Using the fungus B. bassiana ATCC 7159, a predominant formation of (R)-5-ODD was observed while for the fungus C. elegans ATCC 10028B, DPZ was biotransformed to (R)-6-ODD with an enantiomeric excess of 100 %. SN - 1618-2650 UR - https://www.unboundmedicine.com/medline/citation/22644152/Chiral_HPLC_analysis_of_donepezil_5_O_desmethyl_donepezil_and_6_O_desmethyl_donepezil_in_culture_medium:_application_to_fungal_biotransformation_studies_ L2 - https://dx.doi.org/10.1007/s00216-012-6107-3 DB - PRIME DP - Unbound Medicine ER -