TY - JOUR
T1 - The binding of copper ions to daunomycin and adriamycin
AU - Greenaway, F. T.
AU - Dabrowiak, J. C.
PY - 1982
Y1 - 1982
N2 - Using visible absorption, CD, 1H nmr, and epr spectroscopy, the Cu(II) binging properties of daunomycin, adriamycin, and N-trifluoroacetyl daunomycin in water and ethanol have been explored. The drugs form two water soluble complexes having Cu-drug stoichiometries of 1:1 and 1:2, and with apparent pKas of formation of 5.6 and 6.5, respectively. At pH values above ∼8, the drugs form insoluble polymeric complexes with Cu(II). Similar species are also observed in ethanol. The structure of the compounds have been interpreted in terms of binding of the deprotonated hydroxyquinone portion of the drug to the copper ion. No evidence for the binding of the amino group on daunosamine was found.
AB - Using visible absorption, CD, 1H nmr, and epr spectroscopy, the Cu(II) binging properties of daunomycin, adriamycin, and N-trifluoroacetyl daunomycin in water and ethanol have been explored. The drugs form two water soluble complexes having Cu-drug stoichiometries of 1:1 and 1:2, and with apparent pKas of formation of 5.6 and 6.5, respectively. At pH values above ∼8, the drugs form insoluble polymeric complexes with Cu(II). Similar species are also observed in ethanol. The structure of the compounds have been interpreted in terms of binding of the deprotonated hydroxyquinone portion of the drug to the copper ion. No evidence for the binding of the amino group on daunosamine was found.
UR - http://www.scopus.com/inward/record.url?scp=0020284633&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0020284633&partnerID=8YFLogxK
U2 - 10.1016/S0162-0134(00)80218-4
DO - 10.1016/S0162-0134(00)80218-4
M3 - Article
AN - SCOPUS:0020284633
SN - 0162-0134
VL - 16
SP - 91
EP - 107
JO - Journal of Inorganic Biochemistry
JF - Journal of Inorganic Biochemistry
IS - 2
ER -