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Materials Science Photo-oxidation of Tetracycline Adsorbed on Hydroxyapatite in Relation to the Light-induced Staining of Teeth

Department of Chemistry and Applied Chemistry

R.B. Cundall

Department of Biological Sciences

Y. Dandiker

Department of Biological Sciences

M.A. Slifkin

Department of Electronic and Electrical Engineering, University of Salford, Salford, M5 4WT, United Kingdom

In an attempt to understand the chemistry of the light-induced staining of children's teeth by tetracycline, we studied the photochemical behavior of tetracycline adsorbed on hydroxyapatite, as a simple model of enamel. Tetracycline was strongly bound by hydroxyapatite to give a pale yellow material which, under ultraviolet light, showed a bright yellow fluorescence (_max 525 nm). On exposure of this material to the radiation from a medium-pressure mercury lamp, the fluorescence gradually disappeared, and a red-purple product was formed. Photo-acoustic spectroscopy was employed to follow the disappearance of tetracycline and the concomitant formation of the red-purple product, the spectrum of which (_max 530 nm) led to the conclusion that it was 4, 12-anhydro-4-oxo-4-dedimethylaminotetracycline (AODTC). This assignment was supported by the observation that 1 mole of oxygen was absorbed per mole of adsorbed tetracycline converted to the red-purple product.

It is suggested that the formation of AODTC on hydroxyapatite probably takes place by a mechanism of photo-oxidation similar to that already proposed for solutions of tetracycline, and that the formation of AODTC in children's teeth is responsible for the light-induced staining caused by tetracycline.

REFERENCES

• Bennick, A.; Cannon, M.; and Madapallimattam, G. (1979): The Nature of the Hydroxyapatite Binding Site in Salivary Acidic Proline-Rich Proteins, Biochem J 183:115-126.[Medline] [Order article via Infotrieve]
• Davies, A.K.; McKellar, J.F.; Phillips, G.O.; and Reid, A.G. (1979): Photochemical Oxidation of Tetracycline in Aqueous Solution, J Chem Soc Perkin Trans II:369-375.
• Hlavka, J.J. and Bitha, P. (1966): Photochemistry IV. A Photodeamination, Tetrahedron Lett:3843-3846.
• Ibsen, K.H.; Urist, M.R.; and Sognnaes, R.F. (1965): Differences among Tetracyclines with Respect to the Staining of Teeth, J Pediatr 67:459462.
• Johnson, R.H. and Mitchell, D.F. (1966): The Effects of Tetracyclines on Teeth and Bones, J Dent Res 45:86-93.[Free Full Text]
• Lambrou, D.B.; Tahos, B.S.; and Lambrou, K.D. (1977): In Vitro Studies of the Phenomenon of Tetracycline Incorporation into Enamel, J Dent Res 56:1527-1532.[Abstract/Free Full Text]
• Reid, J.S. and Newman, P. (1977): Bleaching Tetracycline Stained Vital Teeth: Results of a Pilot Study, J Dent Res 56: D102.
• Renson, R.E., quoted in Health Shock by Martin Weitz, Newton Abbot, London: David and Charles, 1980, p. 184.
• Rosencwaig, A.: Photoacoustics and Photoacoustic Spectroscopy. In: Chemical Analysis: A Series of Monographs on Analytical Chemistry and its Applications, Vol. 57, Elving, P.J., Winefordner, J.D., and Kolthoff, I.M., Eds., New York: John Wiley and Sons, 1980, pp. 132-136.
• Wallman, I.S. and Hilton, H.B. (1962): Teeth Pigmented by Tetracycline, Lancet 1:827-829.[CrossRef][Medline] [Order article via Infotrieve]
• Wiebe, J.A. and Moore, D.E. (1977): Oxidation Photosensitised by Tetracyclines, J Pharm Sci 66:186-189.[CrossRef][Medline] [Order article via Infotrieve]
• Wilkes, P.D. and Leach, S.A. (1979): Adsorption of Human Submandibular Salivary Proteins to Hydroxyapatite, J Dent Res 58:1249.
• Witkop, C.J. and Wolf, R.O. (1963): Hypoplasia and Intrinsic Staining of Enamel Following Tetracycline Therapy, JAMA 185:100-103.[Abstract/Free Full Text]

Journal of Dental Research, Vol. 64, No. 6, 936-939 (1985)
DOI: 10.1177/00220345850640061701


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This Article Abstract Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Add to Saved Citations Download to citation manager Request Permissions Request Reprints Add to My Marked Citations Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Citing Articles via Scopus Google Scholar Articles by Davies, A.K. Articles by Slifkin, M.A. Search for Related Content PubMed PubMed Citation Articles by Davies, A.K. Articles by Slifkin, M.A. Pubmed/NCBI databases Compound via MeSH Substance via MeSH Hazardous Substances DB CALCIUM COMPOUNDS HYDROXYAPATITE TETRACYCLINE Social Bookmarking                         What's this?