Interaction of three pradimicin derivatives with divalent cations in aqueous solution.
This study focused on further analysis of the aggregation behavior of pradimicin derivatives and their interaction with cations in aqueous solution. BMY was compared with two other pradimicin antibiotics (T2 and FB) with the same aglycone moiety but consisting of different substitute groups. The surface tension measurement showed a clear critical micelle concentration at 1-2 mM of the BMY aqueous solution. The role of Zn2+ in replacing the Ca2+ was examined using 1H nuclear magnetic resonance (NMR) method. From changes in the NMR spectrum and precipitability, it was concluded that zinc ion has lower affinity and higher precipitating ability to BMY than the divalent cations of alkaline earth metal. The aggregation behavior of T2 and FB in aqueous solution was also studied using NMR method. The results suggest that the supramolecular behavior of T2 is similar to BMY whether or not Ca2+ ions are present in solution and that there are two binding sites for calcium ions in a T2 molecule. Unlike BMY and T2, the NMR spectrum of FB does not show distinct change upon Ca2+ addition. The interaction of pradimicin antibiotics with divalent metal ions was thought to be related to ionic electronegativity and to the amphoteric property of the antibiotics.
Hu
M
M
National Institute of Bioscience and Human-Technology, Tsukuba, Ibaraki, Japan. huxiaomei@hotmail.com
Ishizuka
Y
Y
Igarashi
Y
Y
Oki
T
T
Nakanishi
H
H
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000737:chemistry*; D000935:Antifungal Agents / Q000737:chemistry; D002118:Calcium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D012996:Solutions; D013500:Surface Tension; D014867:Water / Q000737:chemistry; D015032:Zinc / Q000737:chemistry*; D000095643:Pradimicins and Benanomicins
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D000935:Antifungal Agents; D002118:Calcium; D012996:Solutions; D014867:Water; D015032:Zinc; C081414:pradimicin T2; D000095643:Pradimicins and Benanomicins; C067714:N,N-dimethylpradimicin FA-2; C080895:pradimicin FB