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甘露糖修饰的环糊精囊泡:多价性和表面密度在凝集素-碳水化合物识别中的相互作用。

Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin-carbohydrate recognition.

机构信息

Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster, Correnstraße 40, 48149 Münster, Germany.

出版信息

Beilstein J Org Chem. 2012;8:1543-51. doi: 10.3762/bjoc.8.175. Epub 2012 Sep 17.

DOI:10.3762/bjoc.8.175
PMID:23209484
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3510984/
Abstract

Cyclodextrin vesicles are versatile models for biological cell membranes since they provide a bilayer membrane that can easily be modified by host-guest interactions with functional guest molecules. In this article, we investigate the multivalent interaction of the lectin concanavalin A (ConA) with cyclodextrin vesicles decorated with mannose-adamantane conjugates with one, two or three adamantane units as well as one or two mannose units. The carbohydrate-lectin interaction in this artificial, self-assembled glycocalyx was monitored in an agglutination assay by the increase of optical density at 400 nm. It was found that there is a close relation between the carbohydrate density at the cyclodextrin vesicle surface and the multivalent interaction with ConA, and the most efficient interaction (i.e., fastest agglutination at lowest concentration) was observed for mannose-adamantane conjugates, in which both the cyclodextrin-adamantane and the lectin-mannose interaction is inherently multivalent.

摘要

环糊精囊泡是生物细胞膜的多功能模型,因为它们提供了一个双层膜,通过与功能客体分子的主客体相互作用很容易进行修饰。在本文中,我们研究了甘露糖-金刚烷偶联物修饰的环糊精囊泡与带有一个、两个或三个金刚烷单元以及一个或两个甘露糖单元的凝集素伴刀豆球蛋白 A (ConA) 的多价相互作用。通过在 400nm 处的吸光度增加,在凝集测定中监测了这种人工自组装糖萼中的碳水化合物-凝集素相互作用。结果发现,环糊精囊泡表面的碳水化合物密度与 ConA 的多价相互作用密切相关,并且在甘露糖-金刚烷偶联物中观察到最有效的相互作用(即在最低浓度下最快凝集),其中环糊精-金刚烷和凝集素-甘露糖相互作用都是多价的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/2355839f4e60/Beilstein_J_Org_Chem-08-1543-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/cf3b0dffcece/Beilstein_J_Org_Chem-08-1543-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/e4b56580f4a4/Beilstein_J_Org_Chem-08-1543-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/d80c8c5df6e4/Beilstein_J_Org_Chem-08-1543-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/bea6f4911029/Beilstein_J_Org_Chem-08-1543-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/65fe435f2786/Beilstein_J_Org_Chem-08-1543-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/232ecbf07b5d/Beilstein_J_Org_Chem-08-1543-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/1ad6c51cb919/Beilstein_J_Org_Chem-08-1543-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/26142f9b657f/Beilstein_J_Org_Chem-08-1543-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/2355839f4e60/Beilstein_J_Org_Chem-08-1543-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/cf3b0dffcece/Beilstein_J_Org_Chem-08-1543-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/e4b56580f4a4/Beilstein_J_Org_Chem-08-1543-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/d80c8c5df6e4/Beilstein_J_Org_Chem-08-1543-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/bea6f4911029/Beilstein_J_Org_Chem-08-1543-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/65fe435f2786/Beilstein_J_Org_Chem-08-1543-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/232ecbf07b5d/Beilstein_J_Org_Chem-08-1543-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/1ad6c51cb919/Beilstein_J_Org_Chem-08-1543-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/26142f9b657f/Beilstein_J_Org_Chem-08-1543-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a98/3510984/2355839f4e60/Beilstein_J_Org_Chem-08-1543-g010.jpg

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