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Langmuir monolayers of the long-chain alkyl derivatives of a nucleoside analogue and the formation of self-assembled nanoparticles
Jin, YG1; Qiao, YX1; Li, M1; Ai, P1; Hou, XP1
关键词Self-assembly Langmuir Monolayers Nanoparticles Acyclovir Nucleoside Analogues
刊名COLLOIDS AND SURFACES B-BIOINTERFACES
2005-04-25
DOI10.1016/j.colsurfb.2005.02.001
42期:1页:45-51
收录类别SCI
文章类型Article
WOS标题词Science & Technology
类目[WOS]Biophysics ; Chemistry, Physical ; Materials Science, Biomaterials
研究领域[WOS]Biophysics ; Chemistry ; Materials Science
关键词[WOS]LIPOPHILIC DEOXYGUANOSINE ; SUPRAMOLECULAR CHEMISTRY ; CHOLESTEROL ; PHOSPHOLIPIDS ; ACYCLOVIR ; DESIGN
英文摘要

The long-chain alkyl derivatives of a nucleoside analogue-acyclovir were prepared in the paper. One is stearyl-glycero-succinyl-acyclovir (SGSA) with a single 18-carbon length (C18) alkyl chain. Another is dioctadecyl-aspartate-succinyl-acyclovir (DASA) with double C18 alkyl chains. They were prepared by the esterification of succirryl-acyclovir with the lipids, and sodium salts of them were also prepared. Guanine moieties and alkyl moieties bring the derivatives intermolecular hydrogen bonding and hydrophobic interaction in water separately. The forces are influenced by the number of alkyl chains and the charged state, and determine the solubility and the self-assembly behavior of the derivatives. The double alkyl-chain derivatives (DASA and DASA-Na) formed rigid Langmuir monolayers on air/water surface, while the single alkyl chain derivatives (SGSA and SGSA-Na) did not. However, cholesterol (Chol) could assist SGSA to form rigid monolayers through inserting into the alkyl chains of SGSA to mimic the second alkyl chain. SGSA self-aggregates in water were prepared by the injection method with tetrahydrofuran as solvent. Cuboid-like shape and nanoscale size demonstrated that SGSA self-aggregates were self-assembled nanoparticles. Shape, particle size, zeta potential and phase transition of the nanoparticles were characterized. And they showed an average size of 83.2-mV, a negative surface charge of -31.3-mV zeta potential and a gel-liquid crystalline phase transition of 50.38 degrees C. The formation mechanism of self-assembled nanoparticles was analyzed. Hydrophobic interaction of alkyl chains improves SGSA molecules to form bilayers, and then cuboid-like nanoparticles were obtained by layer-by-layer aggregation based on inter-bilayers hydrogen bonding. However, the charged guanine moieties make SGSA-Na lose the function of hydrogen bonding so that SGSA-Na only forms vesicles in water based on hydrophobic interaction. Strong hydrophobicity and wide-open rigid double alkyl chains of DASA and DASA-Na restrict self-assembly in water media, and no homogeneous suspensions were obtained. Therefore, the molecular self-assembly behavior of the long-chain alkyl derivatives of nucleoside analogues on water surface or in water media is determined by the number of alkyl chains and the charged state. (c) 2005 Elsevier B.V. All rights reserved.

语种英语
WOS记录号WOS:000228264300005
引用统计
被引频次:20[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/51830
专题北京大学药学院
作者单位1.Beijing Inst Radiat Med, Dept Pharmaceut Chem, Beijing 100850, Peoples R China
2.Peking Univ, Dept Phys Pharm, Sch Pharmaceut Sci, Beijing 100083, Peoples R China
推荐引用方式
GB/T 7714
Jin, YG,Qiao, YX,Li, M,et al. Langmuir monolayers of the long-chain alkyl derivatives of a nucleoside analogue and the formation of self-assembled nanoparticles[J]. COLLOIDS AND SURFACES B-BIOINTERFACES,2005,42(1):45-51.
APA Jin, YG,Qiao, YX,Li, M,Ai, P,&Hou, XP.(2005).Langmuir monolayers of the long-chain alkyl derivatives of a nucleoside analogue and the formation of self-assembled nanoparticles.COLLOIDS AND SURFACES B-BIOINTERFACES,42(1),45-51.
MLA Jin, YG,et al."Langmuir monolayers of the long-chain alkyl derivatives of a nucleoside analogue and the formation of self-assembled nanoparticles".COLLOIDS AND SURFACES B-BIOINTERFACES 42.1(2005):45-51.
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