Isolation, structural elucidation and in vitro activity of 2-acetyl-2-decarboxamido-oxytetracycline against environmental relevant bacteria, including tetracycline-resistant bacteria

Anne Kruse Lykkeberg; Gitte Sengeløv; Claus Cornett; Jens Tjørnelund; Steen Honoré Hansen; Bent Halling-Sørensen

doi:10.1016/S0731-7085(03)00629-0

Isolation, structural elucidation and in vitro activity of 2-acetyl-2-decarboxamido-oxytetracycline against environmental relevant bacteria, including tetracycline-resistant bacteria

Anne Kruse Lykkeberg, Gitte Sengeløv, Claus Cornett, Jens Tjørnelund, Steen Honoré Hansen, Bent Halling-Sørensen

Technical University of Denmark

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

2-Acetyl-2-decarboxamido-oxytetracycline (ADOTC) is a major impurity of oxytetracycline (OTC) produced as a side product during fermentation. ADOTC was isolated from OTC and other impurities using preparative HPLC. The preparative column was an Xterra MS. C-18 chromatographic column (100 mm x 19 turn W., 5 mum), and the mobile phase contained methanol-water (27:73 (v/v)) with 0.08 M formic acid added. The flow rate was 9.0 ml/min. It was possible to isolate few milligram ADOTC in a day. The compound was unambiguously identified using NMR and MS-MS. The anti-microbial activity against activated sludge bacteria was deter-mined giving a potency of only 3% of that of OTC. With tetracycline-resistant bacteria, no anti-microbial activity was observed, indicating a mode of action similar to that of OTC.

Original language	English
Journal	Journal of Pharmaceutical and Biomedical Analysis
Volume	34
Issue number	3
Pages (from-to)	559-567
ISSN	0731-7085
DOIs	https://doi.org/10.1016/S0731-7085(03)00629-0
Publication status	Published - 2004

Keywords

preparative HPLC
tandem mass spectrometry
resistance
microbial testing
NMR
2-acetyl-2-decarboxamido-oxytetracycline

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Lykkeberg, A. K., Sengeløv, G., Cornett, C., Tjørnelund, J., Hansen, S. H., & Halling-Sørensen, B. (2004). Isolation, structural elucidation and in vitro activity of 2-acetyl-2-decarboxamido-oxytetracycline against environmental relevant bacteria, including tetracycline-resistant bacteria. Journal of Pharmaceutical and Biomedical Analysis, 34(3), 559-567. https://doi.org/10.1016/S0731-7085(03)00629-0

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abstract = "2-Acetyl-2-decarboxamido-oxytetracycline (ADOTC) is a major impurity of oxytetracycline (OTC) produced as a side product during fermentation. ADOTC was isolated from OTC and other impurities using preparative HPLC. The preparative column was an Xterra MS. C-18 chromatographic column (100 mm x 19 turn W., 5 mum), and the mobile phase contained methanol-water (27:73 (v/v)) with 0.08 M formic acid added. The flow rate was 9.0 ml/min. It was possible to isolate few milligram ADOTC in a day. The compound was unambiguously identified using NMR and MS-MS. The anti-microbial activity against activated sludge bacteria was deter-mined giving a potency of only 3% of that of OTC. With tetracycline-resistant bacteria, no anti-microbial activity was observed, indicating a mode of action similar to that of OTC.",

keywords = "preparative HPLC, tandem mass spectrometry, resistance, microbial testing, NMR, 2-acetyl-2-decarboxamido-oxytetracycline",

author = "Lykkeberg, {Anne Kruse} and Gitte Sengel{\o}v and Claus Cornett and Jens Tj{\o}rnelund and Hansen, {Steen Honor{\'e}} and Bent Halling-S{\o}rensen",

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Lykkeberg, AK, Sengeløv, G, Cornett, C, Tjørnelund, J, Hansen, SH & Halling-Sørensen, B 2004, 'Isolation, structural elucidation and in vitro activity of 2-acetyl-2-decarboxamido-oxytetracycline against environmental relevant bacteria, including tetracycline-resistant bacteria', Journal of Pharmaceutical and Biomedical Analysis, vol. 34, no. 3, pp. 559-567. https://doi.org/10.1016/S0731-7085(03)00629-0

Isolation, structural elucidation and in vitro activity of 2-acetyl-2-decarboxamido-oxytetracycline against environmental relevant bacteria, including tetracycline-resistant bacteria. / Lykkeberg, Anne Kruse; Sengeløv, Gitte; Cornett, Claus et al.
In: Journal of Pharmaceutical and Biomedical Analysis, Vol. 34, No. 3, 2004, p. 559-567.

Research output: Contribution to journal › Journal article › Research › peer-review

TY - JOUR

T1 - Isolation, structural elucidation and in vitro activity of 2-acetyl-2-decarboxamido-oxytetracycline against environmental relevant bacteria, including tetracycline-resistant bacteria

AU - Lykkeberg, Anne Kruse

AU - Sengeløv, Gitte

AU - Cornett, Claus

AU - Tjørnelund, Jens

AU - Hansen, Steen Honoré

AU - Halling-Sørensen, Bent

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N2 - 2-Acetyl-2-decarboxamido-oxytetracycline (ADOTC) is a major impurity of oxytetracycline (OTC) produced as a side product during fermentation. ADOTC was isolated from OTC and other impurities using preparative HPLC. The preparative column was an Xterra MS. C-18 chromatographic column (100 mm x 19 turn W., 5 mum), and the mobile phase contained methanol-water (27:73 (v/v)) with 0.08 M formic acid added. The flow rate was 9.0 ml/min. It was possible to isolate few milligram ADOTC in a day. The compound was unambiguously identified using NMR and MS-MS. The anti-microbial activity against activated sludge bacteria was deter-mined giving a potency of only 3% of that of OTC. With tetracycline-resistant bacteria, no anti-microbial activity was observed, indicating a mode of action similar to that of OTC.

AB - 2-Acetyl-2-decarboxamido-oxytetracycline (ADOTC) is a major impurity of oxytetracycline (OTC) produced as a side product during fermentation. ADOTC was isolated from OTC and other impurities using preparative HPLC. The preparative column was an Xterra MS. C-18 chromatographic column (100 mm x 19 turn W., 5 mum), and the mobile phase contained methanol-water (27:73 (v/v)) with 0.08 M formic acid added. The flow rate was 9.0 ml/min. It was possible to isolate few milligram ADOTC in a day. The compound was unambiguously identified using NMR and MS-MS. The anti-microbial activity against activated sludge bacteria was deter-mined giving a potency of only 3% of that of OTC. With tetracycline-resistant bacteria, no anti-microbial activity was observed, indicating a mode of action similar to that of OTC.

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KW - tandem mass spectrometry

KW - resistance

KW - microbial testing

KW - NMR

KW - 2-acetyl-2-decarboxamido-oxytetracycline

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DO - 10.1016/S0731-7085(03)00629-0

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SN - 0731-7085

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EP - 567

JO - Journal of Pharmaceutical and Biomedical Analysis

JF - Journal of Pharmaceutical and Biomedical Analysis

IS - 3

ER -

Lykkeberg AK, Sengeløv G, Cornett C, Tjørnelund J, Hansen SH, Halling-Sørensen B. Isolation, structural elucidation and in vitro activity of 2-acetyl-2-decarboxamido-oxytetracycline against environmental relevant bacteria, including tetracycline-resistant bacteria. Journal of Pharmaceutical and Biomedical Analysis. 2004;34(3):559-567. doi: 10.1016/S0731-7085(03)00629-0

Isolation, structural elucidation and in vitro activity of 2-acetyl-2-decarboxamido-oxytetracycline against environmental relevant bacteria, including tetracycline-resistant bacteria

Abstract

Keywords

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