Capreomycin is an important therapeutic agent having intriguing and diverse molecular features. Its polypeptidic structure rich in nitrogen donors makes the drug a promising chelating agent for a number of transition metal ions, especially for copper(II). The results of the model investigational studies suggest that capreomycin anchors Cu(2+) ion with an amino function of the alpha,beta-diaminopropionic acid residue at pH around 5. At physiological pH copper(II) ion is coordinated by two deprotonated amide nitrogen atoms of the alpha,beta-diaminopropionic acid, the serine residue as well as the amino function deriving from the beta-lysine. Above that pH value we observe a rearrangement within the coordination sphere leading to movement of Cu(2+) to the center of the peptide ring with concurrent coordination of four nitrogen donors. Spin-lattice relaxation enhancements and potentiometric measurements clearly indicate that deprotonated amide nitrogen atom from the beta-ureidodehydroalanine moiety is the fourth donor atom.

Stokowa, K., Szczepanik, W., Gaggelli, E., Gaggelli, N., Valensin, G., Jezowska Bojczuk, M. (2012). Capreomycin - A polypeptide antitubercular antibiotic with unusual binding properties toward copper(II). JOURNAL OF INORGANIC BIOCHEMISTRY, 106(1), 111-116 [10.1016/j.jinorgbio.2011.08.021].

Capreomycin - A polypeptide antitubercular antibiotic with unusual binding properties toward copper(II)

GAGGELLI, ELENA;GAGGELLI, NICOLA;VALENSIN, GIANNI;
2012-01-01

Abstract

Capreomycin is an important therapeutic agent having intriguing and diverse molecular features. Its polypeptidic structure rich in nitrogen donors makes the drug a promising chelating agent for a number of transition metal ions, especially for copper(II). The results of the model investigational studies suggest that capreomycin anchors Cu(2+) ion with an amino function of the alpha,beta-diaminopropionic acid residue at pH around 5. At physiological pH copper(II) ion is coordinated by two deprotonated amide nitrogen atoms of the alpha,beta-diaminopropionic acid, the serine residue as well as the amino function deriving from the beta-lysine. Above that pH value we observe a rearrangement within the coordination sphere leading to movement of Cu(2+) to the center of the peptide ring with concurrent coordination of four nitrogen donors. Spin-lattice relaxation enhancements and potentiometric measurements clearly indicate that deprotonated amide nitrogen atom from the beta-ureidodehydroalanine moiety is the fourth donor atom.
2012
Stokowa, K., Szczepanik, W., Gaggelli, E., Gaggelli, N., Valensin, G., Jezowska Bojczuk, M. (2012). Capreomycin - A polypeptide antitubercular antibiotic with unusual binding properties toward copper(II). JOURNAL OF INORGANIC BIOCHEMISTRY, 106(1), 111-116 [10.1016/j.jinorgbio.2011.08.021].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/24321
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