N-辛基-N’-(2-羧基环己甲酰基)-壳聚糖的制备、表征与pH敏感性  

Synthesis,Characterization and pH Sensitivity of N-octyl-N'-(2-carboxyl-cyclohexamethenyl) Chitosan

作　　者：李红霞[1] 董晓燕[1] 陈清[1] 张业旺[1] 张灿[2] 

机构地区：[1]江苏大学药学院,江苏镇江212013 [2]中国药科大学药学院,南京210009

出　　处：《中国现代应用药学》2012年第2期137-141,共5页Chinese Journal of Modern Applied Pharmacy

基　　金：江苏省高校自然科学基金(09KJB530001);江苏大学高级专业人才科研启动基金(11JDG056);江苏大学学生科研立项(10A248)

摘　　要：目的以pH敏感的酰胺键为连接臂，制备两亲性壳聚糖衍生物。方法通过在壳聚糖2-NH2上引入疏水辛基和pH敏感的酰胺键，制备两亲性壳聚糖接枝共聚物，用FTIR、1H—NMR和13C—NMR对其结构进行表征，使用XRD、DSC对其物理性质进行分析，采用紫外．可见分光光度计和粒径仪评价其pH敏感性。结果合成了7种取代度的N-辛基-N＇-（2一羧基环己甲酰基）．壳聚糖，在pH5．0～6．0内具有pH敏感性。结论合成的pH敏感衍生物有望用于智能型药物释放系统，在体内特定部位（肿瘤、梗塞）或细胞内（内涵体、细胞质）释放包载的难溶性药物。OBJECTIVE To synthesize a series of amphiphilic chitosan derivatives using pH-sensitive amide as spacer. METHODS The pH-sensitive chitosan graft copolymers with octyl and carboxylbenzoyl groups as hydrophobic and hydrophilic moieties were synthesized. The chemical structure of galactosylated chitosan was characterized by FTIR, 1H-NMR and 13C-NMR. The physical properties were measured by XRD and DSC. RESULTS Seven pH-sensitive N-octyl-N＇-（2-carboxyl-cyclohexamethenyl） chitosan derivatives were synthesized. The micelles formed by N-octyl-N＇-（2-carboxyl-cyclohexamethenyl） chitosan were found to be highly sensitive to mildly acidic pH and reasonably stable at physiologic pH by UV-visible spectrophotometer. CONCLUSION This pH-sensitive polymeric micelle with controlled pH sensitivity may applied in ＂smart＂ drug delivery systems for constructing pharmaceutical nanocarriers capable of specific release of their cargo at certain pathological sites in the body （tumors, infarcts） or intracellular compartments （endosomes, cytoplasm） demonstrating decreased pH.

关 键 词：壳聚糖 酰胺 PH敏感 聚合物胶束 

分 类 号：O636.1[理学—高分子化学]