Formation of anhydrotetracycline during a high-temperature treatment of animal-derived feed contaminated with tetracycline

Kühne, Michael; Hamscher, Gerd; Körner, Ute; Schedl, Dagmar; Wenzel, Siegfried

doi:10.1016/s0308-8146(01)00230-8

Cited by 31 publications

(12 citation statements)

References 13 publications

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“…The anhydro form can also reversibly epimerize at the C4 position as well. Anhydrotetracycline and 4-epianhydrotetracycline are reported to be toxic in vivo [2] and have been implicated in the development of Fanconi's Syndrome from use of degraded tetracycline medication. [3] For this reason, it is crucial to have a reliable analytical method for discriminating amongst tetracycline and its major degradation products.…”

Section: Introductionmentioning

confidence: 99%

Separation Differences Among Phenyl Hydride, Udc Cholesterol, and Bidentate C8 Stationary Phases for Stability Indicating Methods of Tetracyclines

Young¹,

Matyska

Azad

et al. 2013

Journal of Liquid Chromatography & Related Technologies

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Formulation extracts of tetracycline hydrochloride (HCl), minocycline hydrochloride (HCl), and doxycycline hyclate were degraded by strong acidic conditions and heating. Subsequently, components of the extracts were separated by Bidentate C8, Phenyl Hydride and Cholesterol (UDC) HPLC columns operating in the reverse phase mode. The Phenyl Hydride column was able to baseline separate minocycline from the observed degradant, while partial or total co-elution was observed with the other two columns using otherwise identical method conditions. For both the degraded tetracycline HCl and doxycycline hyclate extracts, the UDC column gave the best resolution for the critical pair. The findings suggest that the postulated secondary retention mechanisms of π–π interactions from the Phenyl Hydride and shape selectivity from the UDC can provide superior resolution for structurally similar analytes compared to hydrophobic interactions alone.

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Section: Introductionmentioning

confidence: 99%

Separation Differences Among Phenyl Hydride, Udc Cholesterol, and Bidentate C8 Stationary Phases for Stability Indicating Methods of Tetracyclines

Young¹,

Matyska

Azad

et al. 2013

Journal of Liquid Chromatography & Related Technologies

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“…8) AHTC can be produced by dehydration in acid media, 5,8) by photolysis in mild reducing conditions 6,9,10) or during high-temperature treatments. 11) Removal of a water molecule from the C5a-C6 positions of TC by treatment with warm mineral acid gives the anhydroderivative (Fig. 1).…”

mentioning

confidence: 99%

Binding of the Highly Toxic Tetracycline Derivative, Anhydrotetracycline, to Bovine Serum Albumin

Burgos

Fernández

Celej

et al. 2011

Biological & Pharmaceutical Bulletin

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Tetracycline (TC) derivatives comprise a group of bacteriostatic antibiotics extensively used in human and veterinary medicine and in acquaculture, and as animal growth promoters due to their safe toxicological profile.1) More recently, they have been proposed as anti-amyloidogenic drugs since they can interfere with protein conformational changes and self-assemblies associated with protein misfolding and deposition diseases. 2-4)Despite their popular use, TC derivatives are highly unstable and some degradation products formed during the storage or normal use of the drugs are pharmacologically toxic or inactive compounds.5) Anhydrotetracycline (AHTC) is one of the major degradation products of TC that has been linked to several side effects of the drug, e.g., cutaneous phototoxicity 6) and Fanconi-type syndrome. 7) AHTC has also proven to be more toxic than TC against environmentally relevant bacteria. 8)AHTC can be produced by dehydration in acid media, 5,8) by photolysis in mild reducing conditions 6,9,10) or during high-temperature treatments.11) Removal of a water molecule from the C5a-C6 positions of TC by treatment with warm mineral acid gives the anhydroderivative (Fig. 1).12) Dehydration leads to significant changes in aromatization and planarity of the tetracyclic moiety, 13,14) showing variations in potency, 15) mechanism of action 1) and lipophilicity 16,17) as compared to the parent compound. Changes in chemical configuration can also modulate the interaction of drugs with serum proteins. 18)Serum albumins are the main carriers of physiological metabolites and pharmacological drugs in blood. Protein binding has a significant impact on the pharmacokinetics and biological activity of drugs and modulates the toxicity of bound substances, attenuates adverse reactions and prolongs the in vivo half-life of therapeutic agents. 18-21)The facts outlined above prompted us to investigate the interaction of AHTC with bovine serum albumin (BSA) using three biophysical techniques. Binding affinity and number of interacting ligands were assessed by fluorimetric titration. . Drug binding was enthalpically and entropically driven and seemed to involve hydrophobic interactions. AHTC fluorescence enhancement and hypsochromic shifts observed upon binding suggested a low-polarity location excluded from water for the bound drug. Our data are useful for evaluating the biodisponibility of the pharmacophore and the dynamic distribution of the toxic derivative.

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“…The degradation product ATC is much more toxic than the parent TC. The non‐observed‐effect levels for ATC in different tests for embryotoxicity, immuno‐depressive action, and teratogenic effects were 4.8 to 100 times lower than that of parent TC . As reported by Sarmah et al , the degradation product ATC had an EC 50 value for sewage sludge bacteria lower (approximately three times) than the EC 50 value of TC.…”

Section: Resultsmentioning

confidence: 62%

Determination and Monitoring of Tetracycline and Degradation Products in Landfill Leachate

Topal

2016

CLEAN Soil Air Water

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Tetracyclines (TCs) have importance because of their common usage, high potential to reach the receiving environments, and toxicity for the organisms. The aim of this study is the determination of concentrations of TC and degradation products (DPs) as anhydrotetracycline (ATC), 4‐epitetracycline (ETC), and 4‐epianhydrotetracycline (EATC) in the leachate basin of landfill located in Elazığ City, Turkey. For this aim, leachate samples are taken from the leachate basin every week (wk) during March and April 2014. Maximum TC, ETC, EATC, and ATC concentrations in leachate samples are 2.47 ± 0.12 (wk 3), 10.3 ± 0.5 (wk 3), 37.1 ± 1.8 (wk 1), and 6.43 ± 0.32 μg/L (wk 8). The concentrations of TC and DPs followed the decreasing order of EATC > ETC > ATC > TC. As a result, it is determined that the concentrations of TC and DPs are at μg/L levels in the leachate basin of landfill.

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Formation of anhydrotetracycline during a high-temperature treatment of animal-derived feed contaminated with tetracycline

Cited by 31 publications

References 13 publications

Separation Differences Among Phenyl Hydride, Udc Cholesterol, and Bidentate C8 Stationary Phases for Stability Indicating Methods of Tetracyclines

Separation Differences Among Phenyl Hydride, Udc Cholesterol, and Bidentate C8 Stationary Phases for Stability Indicating Methods of Tetracyclines

Binding of the Highly Toxic Tetracycline Derivative, Anhydrotetracycline, to Bovine Serum Albumin

Determination and Monitoring of Tetracycline and Degradation Products in Landfill Leachate

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