Cyano Derivatives of 7‐Aminoquinoline That Are Highly Emissive in Water: Potential for Sensing Applications. Issue 30 (27th April 2021)

• Record Type: Journal Article
• Authors: Chang, Kai‐Hsin; Chao, Wei‐Chih; Yang, Yu‐Hsuan; Wu, Cheng‐Ham; Li, Zhi‐Bin; Chen, Hung‐Che; Chou, Yi‐Te; Annie Ho, Ja‐an; Li, Xin‐Cheng; Peng, Yu‐Chiang; Liao, Yu‐Chan; Liu, Kuan‐Miao; Chao, Chi‐Min; Chou, Pi‐Tai
• Is Part Of: Chemistry. Volume 27:Issue 30(2021)
• Page Start: 8040
• Page End: 8047
• Publication Date: 2021-04-27
• Subjects: 7-aminoquinoline -- azides -- bioimaging -- fluorescent probes -- hydrogen sulfide probes; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202100413
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 6‐Cyano‐7‐aminoquinoline (6CN−7AQ ) and 3‐cyano‐7‐aminoquinoline (3CN−7AQ ) were synthesized and found to exhibit intense emission with quantum yield as high as 63 % and 85 %, respectively, in water. Conversely, their derivatives 6‐cyano‐7‐azidoquinoline (6CN−7N3 Q ) and 3‐cyano‐7‐azidoquinoline (3CN−7N3 Q ) show virtually no emission, which makes them suitable to be used as recognition agents in azide reactions based on fluorescence recovery. Moreover, conjugation of 6CN−7AQ with a hydrophobic biomembrane‐penetration peptide PFVYLI renders a nearly non‐emissive 6CN−7AQ‐PFVYLI composite, which can be digested by proteinase K, recovering the highly emissive 6CN−7AQ with ∼200‐fold enhancement. The result provides an effective early confirmation for RT‐qPCR in viral detection. Abstract : 6‐Cyano‐7‐azidoquinoline was synthesized and found to be non‐emissive in water, while the amino derivative 6CN−7AQ exhibits intense emission, making the azido/amino pair excellent in sensing H2 S. Moreover, conjugation of 6CN−7AQ with peptide renders a nearly non‐emissive composite that can be digested by proteinase‐K, recovering intense 6CN−7AQ emission with ∼200‐fold enhancement.