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Boronic acid recognition of non-interacting carbohydrates for biomedical applications: increasing fluorescence signals of minimally interacting aldoses and sucralose
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2017-11-13 00:00:00 , DOI: 10.1039/c7ob01893b
Angel Resendez 1, 2, 3, 4 , Md Abdul Halim 5, 6, 7, 8, 9 , Jasmeet Singh 1, 2, 3, 4 , Dominic-Luc Webb 5, 6, 7, 8, 9 , Bakthan Singaram 1, 2, 3, 4
Affiliation  

To address carbohydrates that are commonly used in biomedical applications with low binding affinities for boronic acid based detection systems, two chemical modification methods were utilized to increase sensitivity. Modified carbohydrates were analyzed using a two component fluorescent probe based on boronic acid-appended viologen–HPTS (4,4′-o-BBV). Carbohydrates normally giving poor signals (fucose, L-rhamnose, xylose) were subjected to sodium borohydride (NaBH4) reduction in ambient conditions for 1 h yielding the corresponding sugar alcohols from fucose, L-rhamnose and xylose in essentially quantitative yields. Compared to original aldoses, apparent binding affinities were increased 4–25-fold. The chlorinated sweetener and colon permeability marker sucralose (Splenda), otherwise undetectable by boronic acids, was dechlorinated to a detectable derivative by reactive oxygen and hydroxide intermediates by the Fenton reaction or by H2O2 and UV light. This method is specific to sucralose as other common sugars, such as sucrose, do not contain any carbon–chlorine bonds. Significant fluorescence response was obtained for chemically modified sucralose with the 4,4′-o-BBV–HPTS probe system. This proof of principle can be applied to biomedical applications, such as gut permeability, malabsorption, etc.

中文翻译:

硼酸对生物医学应用中非相互作用碳水化合物的识别:增加最小相互作用的醛糖和三氯蔗糖的荧光信号

为了解决在生物医学应用中通常用于基于硼酸的检测系统具有低结合亲和力的碳水化合物,采用了两种化学修饰方法来提高灵敏度。使用基于硼酸的紫精-HPTS(4,4' - o -BBV)的两组分荧光探针分析了修饰的碳水化合物。正常情况下信号较差的碳水化合物(岩藻糖,L-鼠李糖,木糖)在环境条件下经过硼氢化钠(NaBH 4)还原处理1小时,从岩藻糖L中得到相应的糖醇-鼠李糖和木糖的产量基本定量。与原始醛糖相比,表观结合亲和力提高了4-25倍。氯化甜味剂和结肠通透性标记三氯蔗糖(Splenda)原本无法用硼酸检测到,但通过Fenton反应或H 2 O 2和紫外光通过活性氧和氢氧化物中间体脱氯成可检测的衍生物。此方法是针对三氯蔗糖的,因为其他常见的糖(例如蔗糖)不含任何碳-氯键。用4,4'- o -BBV-HPTS探针系统对化学修饰的三氯半乳蔗糖获得了显着的荧光响应。该原理证明可以应用于生物医学应用,例如肠通透性,吸收不良
更新日期:2017-11-13
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