Cyano Derivatives of 7-Aminoquinoline That Are Highly Emissive in Water: Potential for Sensing Applications

Kai-Hsin Chang; Wei-Chih Chao; Yu-Hsuan Yang; Cheng-Ham Wu; Zhi-Bin Li; Hung-Che Chen; Yi-Te Chou; Ja-An Annie Ho; Xin-Cheng Li; Yu-Chiang Peng; Yu-Chan Liao; Kuan-Miao Liu; Chi-Min Chao; Pi-Tai Chou

doi:10.1002/chem.202100413

Cyano Derivatives of 7-Aminoquinoline That Are Highly Emissive in Water: Potential for Sensing Applications

Chemistry. 2021 May 26;27(30):8040-8047. doi: 10.1002/chem.202100413. Epub 2021 Apr 27.

Authors

Kai-Hsin Chang¹, Wei-Chih Chao¹, Yu-Hsuan Yang^{1

2

3}, Cheng-Ham Wu¹, Zhi-Bin Li^{2

3}, Hung-Che Chen^{2

3}, Yi-Te Chou⁴, Ja-An Annie Ho^{4

1

5

6}, Xin-Cheng Li^{2

3}, Yu-Chiang Peng^{2

3}, Yu-Chan Liao¹, Kuan-Miao Liu^{2

3}, Chi-Min Chao^{2

3}, Pi-Tai Chou¹

Affiliations

¹ Department of Chemistry, National Taiwan University, Taipei, 10617, Taiwan, R.O.C.
² Department of Medical Applied Chemistry, Chung Shan Medical University, Taichung, 40201, Taiwan, R.O.C.
³ Department of Medical Education, Chung Shan Medical University Hospital, Taichung, 40201, Taiwan, R.O.C.
⁴ BioAnalytical Chemistry and Nanobiomedicine Laboratory, Department of Biochemical Science and Technology, National Taiwan University, Taipei, 10617, Taiwan, R.O.C.
⁵ Center for Emerging Materials and Advanced Devices, National Taiwan University, Taipei, 10617, Taiwan, R.O.C.
⁶ Center for Biotechnology, National Taiwan University, Taipei, 10617, Taiwan, R.O.C.

PMID: 33904607
DOI: 10.1002/chem.202100413

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.

Keywords: 7-aminoquinoline; azides; bioimaging; fluorescent probes; hydrogen sulfide probes.

Abstract

Grants and funding