Journal article
A bifunctional molecule as an artificial flavin mononucleotide cyclase and a chemosensor for selective fluorescent detection of flavins
Journal of the American Chemical Society, Vol.131(29), pp.10107-10112
07/29/2009
Handle:
https://hdl.handle.net/2376/108125
PMID: 19569646
Abstract
Flavins, comprising flavin mononucleotide (FMN), flavin adenine dinucleotide (FAD), and riboflavin (RF, vitamin B(2)), play important roles in numerous redox reactions such as those taking place in the electron-transfer chains of mitochondria in all eukaryotes and of plastids in plants. A selective chemosensor for flavins would be useful not only in the investigation of metabolic processes but also in the diagnosis of diseases related to flavins; such a sensor is presently unavailable. Herein, we report the first bifunctional chemosensor (PTZ-DPA) for flavins. PTZ-DPA consists of bis(Zn(2+)-dipicolylamine) and phenothiazine. Bis(Zn(2+)-dipicolylamine) (referred to here as XyDPA) was found to be an excellent catalyst in the conversion of FAD into cyclic FMN (riboflavin 4',5'-cyclic phosphate, cFMN) under physiological conditions, even at pH 7.4 and 27 degrees C, with less than 1 mol % of substrate. Utilizing XyDPA's superior function as an artificial FMN cyclase and phenothiazine as an electron donor able to quench the fluorescence of an isoalloxazine ring, PTZ-DPA enabled selective fluorescent discrimination of flavins (FMN, FAD, and RF): FAD shows ON(+), FMN shows OFF(-), and RF shows NO(0) fluorescence changes upon the addition of PTZ-DPA. With this selective sensing property, PTZ-DPA is applicable to real-time fluorescent monitoring of riboflavin kinase (RF to FMN), alkaline phosphatase (FMN to RF), and FAD synthetase (FMN to FAD).
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Details
- Title
- A bifunctional molecule as an artificial flavin mononucleotide cyclase and a chemosensor for selective fluorescent detection of flavins
- Creators
- Hyun-Woo Rhee - Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, KoreaSo Jung ChoiSang Ho YooYong Oh JangHun Hee ParkRosa María PintoJosé Carlos CameselleFrancisco J SandovalSanja RojeKyungja HanDoo Soo ChungJunghun SuhJong-In Hong
- Publication Details
- Journal of the American Chemical Society, Vol.131(29), pp.10107-10112
- Academic Unit
- Biological Chemistry, Institute of
- Publisher
- United States
- Identifiers
- 99900547346601842
- Language
- English
- Resource Type
- Journal article