Antimalarial drugs and heme in detergent micelles: An NMR study.
Proton nuclear magnetic resonance relaxation times were measured for the protons of micelles formed by the detergents sodium dodecyl sulfate, dodecyltrimethyl ammonium bromide, and polyethylene glycol sorbitan monolaureate in the presence of ferriprotoporphyrin IX and the antimalarial drugs chloroquine, 7-chloro-4-quinolyl 4-N,N-diethylaminobutyl sulfide, and primaquine. Diffusion coefficients were extracted from pulsed gradient NMR experiments to evaluate the degree of association of these drugs with the detergent micelles. Results indicate that at low or neutral pH when the quinolyl N is protonated, chloroquine does not associate with neutral or cationic detergent micelles. For this reason, chloroquine's interaction with heme perturbs the partitioning of heme between the aqueous medium and detergent micelles.
Casabianca
Leah B
LB
Department of Chemistry, Georgetown University, NW Washington, DC 20057, United States.
Kallgren
Joye B
JB
Natarajan
Jayakumar K
JK
Alumasa
John N
JN
Roepe
Paul D
PD
Wolf
Christian
C
de Dios
Angel C
AC
D000962:Antimalarials / Q000737:chemistry*; D003902:Detergents / Q000737:chemistry*; D006418:Heme / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008823:Micelles; D015394:Molecular Structure; D011319:Primaquine / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D012967:Sodium Dodecyl Sulfate / Q000737:chemistry
D000962:Antimalarials; D003902:Detergents; D008823:Micelles; D000644:Quaternary Ammonium Compounds; D012967:Sodium Dodecyl Sulfate; D006418:Heme; C022806:dodecyltrimethylammonium; D011319:Primaquine