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pH-Dependent Spectroscopy of Tetracycline and Its Analogs

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Abstract

Tetracyclines (TCs), broad spectrum antibiotics widely used in the prevention and treatment of infectious diseases, are amphoteric molecules containing several ionizable functional groups that exist predominantly as zwitterions at a given pH value. TCs are reported to undergo a wide variety of reactions at different pH values i.e. TCs form to anhydrotetracyclines at low pH, 4-epitetracyclines at pH 3–5 and isotetracyclines at high pH values. The pH-dependent absorbance and emission properties of tetracycline and its 10 analogs (4-epitetracycline, doxycyline, oxytetracycline, chlortetracycline, 4-epichlortetracycline, isochlortetracycline, methacycline, rolitetracycline, minocycline, and demeclocycline) were investigated and reported in this paper. The main focus of the study was on the pH dependent transformation of epichlortetracycline, chlortetracycline and isotetracycline at basic pH. Absorption, emission and time resolved spectroscopy were used to determine the behavior of the three TC derivatives at this condition. Increasing the buffer’s ionic concentration leads to faster transformation to iCTC. A pH dependent transformation of CTC to iCTC was observed and the lifetimes of CTC and iCTC were determined to be 3.0 and 5.89 ns respectively. The distribution factor of CTC to iCTC at basic pH was also reported for the first time.

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Acknowledgments

This material is based upon the work supported by the National Science Foundation (NSF) under Grant No. 0750321.

Any opinions and conclusion or recommendations expressed in this material are those of the author and do not necessarily reflect the views of the NSF. The author thanks Diana Aga of the Department of Chemistry, University at Buffalo for the use of the LC-MS instrument.

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Authors and Affiliations

  1. Department of Chemistry and Physical Sciences, Pace University, One Pace Plaza, New York, NY, 10038, USA

    Elmer-Rico E. Mojica, Eric Nguyen & Mariya Rozov

  2. Department of Chemistry, Natural Sciences Complex, University at Buffalo, The State University of New York, Buffalo, NY, 14260-3000, USA

    Frank V. Bright

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  1. Elmer-Rico E. Mojica
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  2. Eric Nguyen
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  3. Mariya Rozov
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Correspondence to Elmer-Rico E. Mojica.

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Mojica, ER.E., Nguyen, E., Rozov, M. et al. pH-Dependent Spectroscopy of Tetracycline and Its Analogs. J Fluoresc 24, 1183–1198 (2014). https://doi.org/10.1007/s10895-014-1399-7

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  • DOI: https://doi.org/10.1007/s10895-014-1399-7

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