3 years ago

Two 3-hydroxyflavone derivatives as two-photon fluorescence turn-on chemosensors for cysteine and homocysteine in living cells

Two 3-hydroxyflavone derivatives as two-photon fluorescence turn-on chemosensors for cysteine and homocysteine in living cells
Two 3-hydroxyflavone derivatives as one- and two-photon fluorescent chemosensors for cysteine (Cys) and homocysteine (Hcy) were synthesized. The recognition properties and mechanism of the chemosensors for Cys and Hcy were investigated systematically. The experiment results indicate that 3-hydroxyflavone compound 1 (6-bromo-2-(9-ethyl-9H-carbazol-3-yl)-3-hydroxy-chromen-4-one) after the addition of nickel ions exhibits good recognition properties for Cys and Hcy with fluorescence enhancement and 65nm absorption peak blue shift based on nickel displacement reaction mechanism. The detection limits (DL) with fluorescence as detected signal are 4.06 × 10−3 µM (Cys, linear range of 10–80µM) and 5.8 × 10−3 µM (Hcy, linear range of 10–100µM), respectively. But acrylate substituted 3-hydroxyflavone compound 2 (4-oxo-2-(4-diethylamino-phenyl)-4H-chromen-3-yl acrylate) can specially identify Cys with fluorescence turn-on (DL = 1.87 × 10−3 µM, linear range of 4–22µM) based on Cys leading to acrylate hydrolysis mechanism and succedent excited-state intramolecular proton transfer process of 3-hydroxyflavone compound. Then Cys and Hcy biological thiols can be recognized at one time by these two 3-hydroxyflavone derivatives. The bioimaging experiment indicates that both the compounds can be successfully applied to the detection of Cys/Hcy in living cells and compound 2 also can be applied to bioimaging Cys in zebrafish by one- and two-photon fluorescence mode. Then these two compounds have a potential in the application of biological sample analysis.

Publisher URL: www.sciencedirect.com/science

DOI: S0039914017312651

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.