Thermodynamic Origin of Molecular Selective Binding of Bile Salts by Aminated β-Cyclodextrins

化学 疏水效应 分子结合 范德瓦尔斯力 等温微量热法 分子 水溶液 滴定法 位阻效应 选择性 环糊精 等温滴定量热法 化学稳定性 结晶学 物理化学 立体化学 有机化学 热力学 物理 催化作用
作者
Yu Liu,Ying‐Wei Yang,Rui Cao,Shi-Hui Song,Heng‐Yi Zhang,Lihua Wang
出处
期刊:Journal of Physical Chemistry B [American Chemical Society]
卷期号:107 (50): 14130-14139 被引量:50
标识
DOI:10.1021/jp036366q
摘要

To elucidate quantitatively the sidearm effects on the molecular selective binding of aminated β-cyclodextrins (β-CD), microcalorimetry titration has been performed in aqueous phosphate buffer solution (pH = 7.20) at 298.15 K to give the complex stability constants (Ks) and the standard free energy (ΔG°), enthalpy (ΔH°), and entropy changes (ΔS°) for the 1:1 inclusion complexation of β-CD (1), mono(6-amino-6-deoxy)-β-CD (2), mono(6-carboxymethylamino-6-deoxy)-β-CD (3), and mono[6-(R(−)-1-hydroxymethylpropylamino)-6-deoxy]-β-CD (4) with representative bile salts, deoxycholate, cholate, glycocholate, and taurocholate. The results obtained indicate that the aminated β-CDs could alter significantly the original molecular binding ability and selectivity of parent β-CD through the cooperative electrostatic interaction, van der Waals, and hydrophobic interactions between hosts and guests. As compared with parent 1 and aminated β-CD 2, glycine-modified β-CD 3 possessing a hydrophilic carboxylic group at the sidearm shows a lower binding ability toward bile salts, attributed to the relatively weaker hydrophobic interactions and the electrostatic repulsion between host and guest to some extent. However, the R(−)-2-amino-1-butanol-modified β-CD 4 possessing additional binding sites at the chiral sidearm could significantly orient the guest molecules to be included in cavity and thus evidently enhances the molecular binding ability and selectivity through steric interactions. Thermodynamically, the higher complex stability for inclusion complexation of aminated β-CDs is mainly resulting from enthalpy gain with smaller entropy loss. The combination of calorimetric titration experiments and ROESY spectra establishes the correlation between the thermodynamic parameters and the conformation of the resulting complex, and reveals the factors governing the molecular binding ability and selectivity of bile salts by aminated β-CDs.
最长约 10秒,即可获得该文献文件

科研通智能强力驱动
Strongly Powered by AbleSci AI
更新
PDF的下载单位、IP信息已删除 (2025-6-4)

科研通是完全免费的文献互助平台,具备全网最快的应助速度,最高的求助完成率。 对每一个文献求助,科研通都将尽心尽力,给求助人一个满意的交代。
实时播报
4秒前
4秒前
8R60d8应助烟酒不离生采纳,获得10
6秒前
8R60d8应助烟酒不离生采纳,获得10
6秒前
8R60d8应助烟酒不离生采纳,获得10
6秒前
6秒前
量子星尘发布了新的文献求助10
7秒前
橡树果完成签到 ,获得积分10
8秒前
完美小蘑菇应助潇湘雪月采纳,获得10
8秒前
张wx_100完成签到,获得积分10
10秒前
chenjingjing发布了新的文献求助10
10秒前
13秒前
illi发布了新的文献求助10
14秒前
16秒前
17秒前
Ava应助大青山采纳,获得10
18秒前
18秒前
2116564发布了新的文献求助10
20秒前
21秒前
婵婵发布了新的文献求助10
22秒前
ASZXDW发布了新的文献求助20
22秒前
23秒前
Orange应助1235656646采纳,获得10
24秒前
2311发布了新的文献求助10
25秒前
EDSS完成签到,获得积分10
25秒前
勤奋大地完成签到,获得积分10
27秒前
29秒前
2311完成签到,获得积分20
32秒前
共享精神应助小木安华采纳,获得10
34秒前
q1356478314应助2116564采纳,获得10
34秒前
34秒前
刘佳冉完成签到,获得积分10
34秒前
星期八发布了新的文献求助10
35秒前
万能图书馆应助潇湘雪月采纳,获得10
37秒前
黑石完成签到,获得积分10
37秒前
zpc发布了新的文献求助10
38秒前
小郭完成签到,获得积分10
39秒前
41秒前
41秒前
43秒前
高分求助中
A new approach to the extrapolation of accelerated life test data 1000
ACSM’s Guidelines for Exercise Testing and Prescription, 12th edition 500
‘Unruly’ Children: Historical Fieldnotes and Learning Morality in a Taiwan Village (New Departures in Anthropology) 400
Indomethacinのヒトにおける経皮吸収 400
Phylogenetic study of the order Polydesmida (Myriapoda: Diplopoda) 370
基于可调谐半导体激光吸收光谱技术泄漏气体检测系统的研究 350
Robot-supported joining of reinforcement textiles with one-sided sewing heads 320
热门求助领域 (近24小时)
化学 材料科学 医学 生物 工程类 有机化学 生物化学 物理 内科学 纳米技术 计算机科学 化学工程 复合材料 遗传学 基因 物理化学 催化作用 冶金 细胞生物学 免疫学
热门帖子
关注 科研通微信公众号,转发送积分 3989390
求助须知:如何正确求助?哪些是违规求助? 3531487
关于积分的说明 11254109
捐赠科研通 3270153
什么是DOI,文献DOI怎么找? 1804887
邀请新用户注册赠送积分活动 882087
科研通“疑难数据库(出版商)”最低求助积分说明 809174