PMID: 8586970Nov 15, 1995Paper

Metal complexes of anhydrotetracycline. 2. Absorption and circular dichroism study of Mg(II), Al(III), and Fe(III) complexes. Possible influence of the Mg(II) complex on the toxic side effects of tetracycline

Journal of Inorganic Biochemistry
F C MachadoH Beraldo

Abstract

Anhydrotetracycline (AHTC) is the major toxic decomposition product of the antibiotic tetracycline. The complexation of AHTC to Mg(II), Al(III), and Fe(III) was studied in aqueous medium using absorption and circular dichroism measurements. The study of the Mg(II)-AHTC interactions at pH 7 indicated the formation of the MHL and M2L species in which an Mg(II) ion is coordinated to the C11 and C12 oxygens of the BCD ring system. In the M2L species, a second metal ion coordinates to the N4 and O3 positions on ring A, inducing the ligand to adopt the "twisted" conformation. At pH 4, an MHL species is formed with Al(III) by complexation of the metal ion to O11 and O12. At pH 1, Fe(III) forms an MH2L species, probably by coordination of the metal to 012 and 01. The stability constants of all species were calculated. The possible participation of Mg(II) in the mechanism of toxicity of tetracycline is suggested.

References

May 10, 1975·Journal of the American Chemical Society·D E Williamson, G W Everett
Mar 1, 1994·Journal of Pharmaceutical Sciences·J M de SiqueiraH Beraldo

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Citations

May 4, 2006·Journal of Molecular Modeling·Olaf G OthersenTimothy Clark
Dec 22, 1999·Journal of Inorganic Biochemistry·F C de PaulaE C Pereira-Maia
Mar 9, 1999·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·K KasaharaM Takahashi
Dec 1, 2015·Environmental Science & Technology·Hui WangChing-Hua Huang
Aug 27, 2003·Medicinal Research Reviews·Li-June Ming
Oct 14, 2005·Journal of Environmental Quality·Allison A MacKay, Brian Canterbury
Dec 15, 2020·The Science of the Total Environment·Quan LiaoRandeng Wang
Jan 6, 1999·Journal of Pharmaceutical Sciences·H A DuarteA M Simas
Sep 2, 1998·Journal of Pharmaceutical Sciences·W B De AlmeidaM C Zerner
Mar 31, 1998·Journal of Pharmaceutical Sciences·H F Dos SantosM C Zerner
Sep 30, 2005·Environmental Science & Technology·Raquel A Figueroa, Allison A MacKay

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