Lee, Jaeseok Choi, Sang -Kee Aslam, Adil S. Lim, Woojeong Lee, Juyong Ko, Junsu Ryu, Chan Hee Lee, Kang Mun Jung, Young Mee Yoo, Hyuk Sang Park, Ju Hyun Lee, Sanghee Choi, Junwon Kim, Eunha Park, Jongmin 2024-01-19T10:03:56Z 2024-01-19T10:03:56Z 2023-03-10 2023-02 0143-7208 https://pubs.kist.re.kr/handle/201004/114023 Fluorescent molecules have been used for various applications in biological system monitoring. Considering the complexity of cellular systems, there is a huge demand for diverse fluorescent organic molecular scaffolds. However, only a limited number of fluorescent scaffolds have been reported due to the lack of a rational design strategy. We serendipitously discovered N4-phenylquinazoline-4,6-diamine as a fluorescent scaffold with turn-on characteristics. To improve the photophysical property of the initial fluorescence molecule, we synthesized derivatives of the N4-phenylquinazoline-4,6-diamine and found systematic correlation between electronic den-sity of the phenyl substituent of the scaffold and fluorescence intensity. Through tuning the photophysical property of the scaffold and a rational design strategy, we developed N4-dichlorophenylquinazoline-4,6-diamine as a potential fluorophore for various biological applications. To prove the value of the developed fluorescent scaffold, we devised formaldehyde (FA) fluorescent sensor by tailoring amine on 6-position of N4-dichlorophenylquinazoline-4,6-diamine to employ a 2-aza-Cope rearrangement as the molecular detection mechanism with double-digit nanomolar detection limits. FA level in live HeLa cells were successfully visualized with the probe, exhibiting that N4-dichlorophenylquinazoline-4,6-diamine can serve as a useful molecular scaffold for offering various fluorescent sensors toward the investigation of physiological and pathological processes in live cells. English Elsevier BV N4-phenylquinazoline-4,6-diamine as a tunable fluorescent scaffold for the development of fluorescent probes Article 10.1016/j.dyepig.2022.110987 1 Dyes and Pigments, v.210 Dyes and Pigments 210 N scie scopus 000916948200002 2-s2.0-85145603973 Chemistry, Applied Engineering, Chemical Materials Science, Textiles Chemistry Engineering Materials Science Article PHOTOPHYSICAL PROPERTIES DESIGN DERIVATIVES SENSORS DYES Quinazoline Fluorogenic Structure photophysical property relationship Fluorescent sensor Formaldehyde