Perussi J R, Yushmanov V E, Monte S C, Imasato H, Tabak M
Instituto de Química de São Carlos, Universidade de São Paulo, Brazil.
Physiol Chem Phys Med NMR. 1995;27(1):1-15.
The characteristics of binding of primaquine (PQ) and chloroquine (CQ) to micelles of surfactants with different charge of headgroups were studied by 1H-NMR and optical absorption spectroscopy. Cetyltrimethylammonium chloride (CTAC) was used as a cationic surfactant, sodium dodecylsulfate (SDS) as an anionic surfactant and N-hexadecyl-N,N-dimethyl-3-ammonio-1-propane-sulfonate (HPS) as zwitterionic. The pK values and binding constants were estimated. Interaction with SDS significantly increases an apparent pK of PQ and CQ. However, chemical shift patterns and values of binding constants in the presence of different surfactants show that mode of interaction of charged drugs with micelles is nonspecific, since the complexes formed are similar for different types of surfactants. Electrostatic forces alter the affinity between drugs and micelles bearing charged groups. Interaction of drugs with cationic micelles is prevented if the drug has two positive charges. HPS interacts with charged drugs in the same manner as CTAC rather than SDS.
通过1H-NMR和光学吸收光谱研究了伯氨喹（PQ）和氯喹（CQ）与具有不同头基电荷的表面活性剂胶束的结合特性。十六烷基三甲基氯化铵（CTAC）用作阳离子表面活性剂，十二烷基硫酸钠（SDS）用作阴离子表面活性剂，N-十六烷基-N，N-二甲基-3-铵基-1-丙烷磺酸盐（HPS）用作两性离子表面活性剂。估算了pK值和结合常数。与SDS的相互作用显著提高了PQ和CQ的表观pK值。然而，在不同表面活性剂存在下的化学位移模式和结合常数的值表明，带电药物与胶束的相互作用模式是非特异性的，因为不同类型表面活性剂形成的复合物相似。静电力改变了药物与带电荷基团胶束之间的亲和力。如果药物带有两个正电荷，则会阻止药物与阳离子胶束的相互作用。HPS与带电药物的相互作用方式与CTAC相同，而不是与SDS相同。
