TY - JOUR
T1 - Tuning the pKa of the antihistaminic drug chlorpheniramine maleate by supramolecular interactions with water-soluble polymers
AU - Moreno-Villoslada, Ignacio
AU - González, Felipe
AU - Rivas, Bernabé L.
AU - Shibue, Toshimichi
AU - Nishide, Hiroyuki
PY - 2007/1/26
Y1 - 2007/1/26
N2 - The interaction of the pharmacologically important chlorpheniramine maleate (CPM) with polyanions containing sulfonate groups such as poly(sodium 4-styrenesulfonate) (PSS), poly(sodium vinylsulfonate) (PVS), and the more hydrophobic poly(sodium 2-(N-acrylamido)-2-methyl-propanesulfonate) (PAMPS) has been studied by 1H NMR. It was found that the pKa of the low-molecular weight molecule (LMWM) may be modified by its interaction with the polyanions, changing from 3 to 5, due to electric charge compensation. Interestingly, the interaction of CPM with PSS produces changes in CPM resonances, such as a general broadening and upfield shifts of the signals, and NOE effects between the LMWM and the water-soluble polymer (WSP) that indicate the presence of π-π interactions.
AB - The interaction of the pharmacologically important chlorpheniramine maleate (CPM) with polyanions containing sulfonate groups such as poly(sodium 4-styrenesulfonate) (PSS), poly(sodium vinylsulfonate) (PVS), and the more hydrophobic poly(sodium 2-(N-acrylamido)-2-methyl-propanesulfonate) (PAMPS) has been studied by 1H NMR. It was found that the pKa of the low-molecular weight molecule (LMWM) may be modified by its interaction with the polyanions, changing from 3 to 5, due to electric charge compensation. Interestingly, the interaction of CPM with PSS produces changes in CPM resonances, such as a general broadening and upfield shifts of the signals, and NOE effects between the LMWM and the water-soluble polymer (WSP) that indicate the presence of π-π interactions.
KW - π-π interactions
KW - Chlorpheniramine maleate
KW - Water-soluble polymers
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U2 - 10.1016/j.polymer.2006.12.015
DO - 10.1016/j.polymer.2006.12.015
M3 - Article
AN - SCOPUS:33846240850
SN - 0032-3861
VL - 48
SP - 799
EP - 804
JO - Polymer (United Kingdom)
JF - Polymer (United Kingdom)
IS - 3
ER -