TY - JOUR
T1 - Emergent Molecular Recognition through Self-Assembly
T2 - Unexpected Selectivity for Hyaluronic Acid among Glycosaminoglycans
AU - Noguchi, Takao
AU - Roy, Bappaditya
AU - Yoshihara, Daisuke
AU - Sakamoto, Junji
AU - Yamamoto, Tatsuhiro
AU - Shinkai, Seiji
PY - 2016/5/4
Y1 - 2016/5/4
N2 - Oligophenylenevinylene (OPV)-based fluorescent (FL) chemosensors exhibiting linear FL responses toward polyanions were designed. Their application to FL sensing of glycosaminoglycans (heparin: HEP, chondroitin 4-sulfate: ChS, and hyaluronic acid: HA) revealed that the charge density encoded as the unit structure directs the mode of OPV self-assembly: H-type aggregate for HEP with 16-times FL increase and J-type aggregate for HA with 93-times FL increase, thus unexpectedly achieving the preferential selectivity for HA in contrast to the conventional HEP selective systems. We have found that the integral magnitude of three factors consisting of binding mechanism, self-assembly, and FL response can amplify the structural information on the target input into the characteristic FL output. This emergent property has been used for a novel molecular recognition system that realizes unconventional FL sensing of HA, potentially applicable to the clinical diagnosis of cancer-related diseases. An unexpectedly selective fluorescent (FL) chemosensor for hyaluronic acid (HA) was developed, where structural information on the target critically directs the mode of chemosensor self-assembly leading to the characteristic FL response (see picture). This system is potentially applicable to the clinical diagnosis of functional disorders such as cancer-related diseases involving the overexpression of HA.
AB - Oligophenylenevinylene (OPV)-based fluorescent (FL) chemosensors exhibiting linear FL responses toward polyanions were designed. Their application to FL sensing of glycosaminoglycans (heparin: HEP, chondroitin 4-sulfate: ChS, and hyaluronic acid: HA) revealed that the charge density encoded as the unit structure directs the mode of OPV self-assembly: H-type aggregate for HEP with 16-times FL increase and J-type aggregate for HA with 93-times FL increase, thus unexpectedly achieving the preferential selectivity for HA in contrast to the conventional HEP selective systems. We have found that the integral magnitude of three factors consisting of binding mechanism, self-assembly, and FL response can amplify the structural information on the target input into the characteristic FL output. This emergent property has been used for a novel molecular recognition system that realizes unconventional FL sensing of HA, potentially applicable to the clinical diagnosis of cancer-related diseases. An unexpectedly selective fluorescent (FL) chemosensor for hyaluronic acid (HA) was developed, where structural information on the target critically directs the mode of chemosensor self-assembly leading to the characteristic FL response (see picture). This system is potentially applicable to the clinical diagnosis of functional disorders such as cancer-related diseases involving the overexpression of HA.
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U2 - 10.1002/anie.201511564
DO - 10.1002/anie.201511564
M3 - Article
C2 - 27060601
AN - SCOPUS:84979723580
VL - 55
SP - 5708
EP - 5712
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 19
ER -