title: Boronic Acid: A Bio-Inspired Strategy To Increase the Sensitivity and Selectivity of Fluorescent NADH Probe.
abstract: Fluorescent probes have emerged as an essential tool in the molecular recognition events in biological systems; however, due to the complex structures of certain biomolecules, it remains a challenge to design small-molecule fluorescent probes with high sensitivity and selectivity. Inspired by the enzyme-catalyzed reaction between biomolecule and probe, we present a novel combination-reaction two-step sensing strategy to improve sensitivity and selectivity. Based on this strategy, we successfully prepared a turn-on fluorescent reduced nicotinamide adenine dinucleotide (NADH) probe, in which boronic acid was introduced to bind with NADH and subsequently accelerate the sensing process. This probe shows remarkably improved sensitivity (detection limit: 0.084 μM) and selectivity to NADH in the absence of any enzymes. In order to improve the practicality, the boronic acid was further modified to change the measurement conditions from alkalescent (pH 9.5) to physiological environment (pH 7.4). Utilizing these probes, we not only accurately quantified the NADH weight in a health care product but also evaluated intracellular NADH levels in live cell imaging. Thus, these bio-inspired fluorescent probes offer excellent tools for elucidating the roles of NADH in biological systems as well as a practical strategy to develop future sensitive and selective probes for complicated biomolecules.
authors: Department of Chemistry and Medicinal Chemistry Program, National University of Singapore , Singapore 117543.
authors: Lu
authors: L
authors: Wang
authors: Key Laboratory of Smart Drug Delivery, Ministry of Education, School of Pharmacy, Fudan University , Shanghai 201203, P. R. China.
authors: Jingye
authors: J
authors: Zhang
authors: Laboratory of Bioimaging Probe Development, Singapore Bioimaging Consortium , Singapore 117543.
authors: Beomsue
authors: B
authors: Kim
authors: Laboratory of Bioimaging Probe Development, Singapore Bioimaging Consortium , Singapore 117543.
authors: Juanjuan
authors: J
authors: Peng
authors: Laboratory of Bioimaging Probe Development, Singapore Bioimaging Consortium , Singapore 117543.
authors: Stuart N
authors: SN
authors: Berry
authors: Laboratory of Bioimaging Probe Development, Singapore Bioimaging Consortium , Singapore 117543.
authors: Yong
authors: Y
authors: Ni
authors: Laboratory of Bioimaging Probe Development, Singapore Bioimaging Consortium , Singapore 117543.
authors: Dongdong
authors: D
authors: Su
authors: Department of Chemistry and Medicinal Chemistry Program, National University of Singapore , Singapore 117543.
authors: Jungyeol
authors: J
authors: Lee
authors: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha 410082, P. R. China.
authors: Lin
authors: L
authors: Yuan
authors: Department of Chemistry and Medicinal Chemistry Program, National University of Singapore , Singapore 117543.|Laboratory of Bioimaging Probe Development, Singapore Bioimaging Consortium , Singapore 117543.
authors: Young-Tae
authors: YT
authors: Chang
mesh_terms: D032701:Biomimetics; D001897:Boronic Acids / Q000737:chemistry / Q000378:metabolism*; D045744:Cell Line, Tumor; D005456:Fluorescent Dyes / Q000378:metabolism*; D006801:Humans; D006863:Hydrogen-Ion Concentration; D057230:Limit of Detection; D009243:NAD / Q000378:metabolism*
chemical_list: D001897:Boronic Acids; D005456:Fluorescent Dyes; D009243:NAD