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IR absorption spectrophotometric analysis of the complex formed by tetracycline and synthetic hydroxyapatite

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Summary

The infrared (IR) spectra of KBr pellet preparations of tetracycline (TC) complexes with hydroxyapatite (HA) indicated that the binding of the antibiotic to bone mineral can occur independently at each of two ligands. The shifts in the IR spectrum occur for the keto-enol ligand of rings B and C and for the tricarbonylmethane grouping of ring A. Analogs that lack one or the other of these groups are able to form complexes with HA in which the common portion resembles that of the parent molecule.

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References

  1. Baud C-A, Dupont D-H (1962) Sur la bifluorescence du tissu osseux traite par les tetracyclines. Comp Rend Acad Sci Paris 254:3129–3130

    CAS  Google Scholar 

  2. Cohlan SQ, Bevelander G, Tiansic T (1963) Growth inhibition of prematures receiving tetracycline. Am J Dis Child 105:453–461

    Google Scholar 

  3. Perrin DD (1965) Binding of tetracyclines to bone. Nature 208;787–788

    CAS  PubMed  Google Scholar 

  4. Simpson MS (1981) Effects of demineralizing tetracycline — stained human dentine. Calcif Tissue Int 33:101–4

    CAS  PubMed  Google Scholar 

  5. Urist MR, Ibsen KH (1963) Chemical reactivity of mineralized tissue with oxytetracycline. Arch Pathol 76:484–496

    CAS  PubMed  Google Scholar 

  6. Tochon-Danguy H-J, Myers HM (1981) Locus of interaction of tetracycline and hydroxyapatite. Abstract of the 1st joint meeting of central Europe and Scandinavia. Division of Int. Assoc. Dent. Res. Groningen, Netherlands

    Google Scholar 

  7. Klein L, Reilly DT (1976) Concurrent exchange of45Ca and3H tetracycline from rat bones in vitro. Calcif Tissue Res 20:229–234

    CAS  Google Scholar 

  8. Lambrou DB, Tahos BS, Lambrou KD (1977) In vitro studies of the phenomenon of tetracycline incorporation into enamel. J Dent Res 56:1527–1532

    CAS  PubMed  Google Scholar 

  9. Swallow JN, DeHaller J, Young WF (1967) Side-effects to antibiotics in cystic fibrosis: dental changes in relation to antibiotic administration. Arch Dis Child 42:311–318

    Article  CAS  PubMed  Google Scholar 

  10. Primrosch RE (1980) Tetracycline discoloration, enamel defects and dental caries in patients with cystic fibrosis. Oral Surg 50:301–308

    Article  Google Scholar 

  11. Schroeder LW, Bowen RL, Ferris JS (1980) Adhesive bonding of various materials to hard tooth tissues. XX calcium to calcium distances in hydroxyapatite. J Biomed Mater Res 14:83–90

    Article  CAS  PubMed  Google Scholar 

  12. Boothe JH, Morton J H, Petisi JP, Wilkinson RG, Williams JH (1953–4) Chemistry of tetracycline. Antibiot Ann 46–48

  13. Schnarr M, Matthies M, Lohmann W (1979) The influence of different solvents on the interaction between metal ions and tetracycline. Z Naturforsch 34C:1156–1161

    CAS  Google Scholar 

  14. Kalnin'sh KK, Belen'kii BG (1964) A study of the dissociation of tetracyclines by means of infrared spectroscopy. Proc Acad USSR 157:721–723

    Google Scholar 

  15. Brion M, Berthon G, Fourillan J-B (1981) Metal iontetracyclines interaction in biological fluids. Potentiometric study of calcium complexes with tetracycline, oxytetracycline, doxycycline and minocycline and simulation of their distributions under physiological conditions. Inorg Chim Acta 55:47–56

    Article  CAS  Google Scholar 

  16. Albert A, Rees CW (1956) Avidity of tetracyclines for the cations of metals. Nature 177:433–434

    CAS  PubMed  Google Scholar 

  17. Ibsen KH, Urist MR (1962) Complexes of calcium and magnesium with oxytetracycline. Proc Soc Exp Biol Med 109:797–801

    CAS  PubMed  Google Scholar 

  18. Mitscher LA, Bonacci AC, Slater-Eng B, Hacker AK, Sokolowski TD (1969) Interaction of various tetracyclines with metallic cations in aqueous solutions as measured by circular dichroism. Antimicrob Agents and Chemother 111–115

  19. Gulbis J, Everett GW Jr (1975) A13C nuclear magnetic resonance study of the metal binding site on tetracycline. J Am Chem Soc 97:6248–6249

    Article  CAS  PubMed  Google Scholar 

  20. Gulbis J, Everett GW Jr (1976) Effect of added electrolyte on the binding of tetracycline to paramagnetic probes. A13C and1H nuclear magnetic resonance study. J Am Chem Soc 98:1280–1283

    Article  CAS  PubMed  Google Scholar 

  21. Lacher JR, Bitner JL, Park JD (1955) The infrared absorption spectra of some antibiotics in antimony trichloride solution. J Phys Chem 59:610–614

    Article  CAS  Google Scholar 

  22. Dziegielewski J, Hanuza J, Jezowska-Trzebiatowska B (1976) IR spectra and vitrational assignments for tetracycline and its analogues. Bull Acad Pol Sci 24:307–322

    CAS  Google Scholar 

  23. Donohue J, Dunitz JD, Trueblood KN, Webster MS (1963) The crystal structure of aureomycin (chlortetracycline) hydrochloride. Configuration, bond distances and conformation. J Am Chem Soc 85:851–856

    Article  CAS  Google Scholar 

  24. Myers HM (in press) Orientation of adsorbed alizarin red S on hydroxyapatite Calcif Tissue Int

  25. Kohn KW (1961) Determination of tetracyclines by extraction of fluorescent complexes. Application to biological materials. Anal Chem 33:862–866

    Article  CAS  Google Scholar 

  26. Weiss PJ, Andrew ML, Wright WW (1957) Solubility of antibiotics in twenty-four solvents. Antibiot Chemother 7:374–377

    CAS  Google Scholar 

  27. Blackwood RK, Beereboom JJ, Renhard HH, Schach von Wittenau M, Stephens CR (1963) 6-Methylene tetracyclines. III preparation and properties. J Am Chem Soc 85:3943–3948

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Pharmacology, University of Pennsylvania, School of Dental Medicine, 4001 Spruce Street, 19104, Philadelphia, Pennsylvania

    H. M. Myers

  2. the Institute of Morphology, University Medical Center, 1211, Geneva, Switzerland

    H. J. Tochon-Danguy & C. A. Baud

Authors
  1. H. M. Myers
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  2. H. J. Tochon-Danguy
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  3. C. A. Baud
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Myers, H.M., Tochon-Danguy, H.J. & Baud, C.A. IR absorption spectrophotometric analysis of the complex formed by tetracycline and synthetic hydroxyapatite. Calcif Tissue Int 35, 745–749 (1983). https://doi.org/10.1007/BF02405117

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  • DOI: https://doi.org/10.1007/BF02405117

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