Fluorescent molecules are widely utilized in various fields such as analytical chemistry and chemical biology. Molecules, whose fluorescent properties are changed by interaction or reaction with the analyte, could be utilized as fluorescent sensors. We have searched novel fluorescent molecules from natural source such as various plants, and found amarastelline A and nigakinone with unique fluorescent properties. Amarastelline A could stain cytoplasmic region of living cells for relatively long time. At present, the relationship between structure and fluorescent properties was not clarified. In this study, we planned to synthesize the derivatives of amarastelline A and nigakinone, and study their fluorescent properties in order to develop novel fluorescent sensors. Both amarastelline A and nigakinone consist of canthin-6-one skeleton, and the substituents on 3 and 4 positions are different. Thus, we designed and synthesized various canthin-6-one derivatives 1. Further, compounds 2 that consists of substructure of canthin-6-one were synthesized. Analysis of their fluorescent properties revealed the effects of each substituted group on fluorescent properties. For example, substituents on 3-position could regulate solvent-dependent fluorescent change. Tautomerization between a-hydroxyketone and 5,6-diketone forms would involve for 3-unsubstituted derivatives, which would result in the solvent-dependent properties. In addition, some fluorescent sensor candidate molecules were obtained. Compound 3 exhibited ‘OFF-ON-OFF’ fluorescence change by the increase of pH, so it could be utilized for the fluorescent sensor for the specific pH range. Substructure-based compound 4 showed strong and bathochromic shifted fluorescence in polar and protic solvents.

Development of novel fluorescent sensors based on fluorescent natural compounds

252nd National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.