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Cyano Derivatives of 7-Aminoquinoline That Are Highly Emissive in Water: Potential for Sensing Applications |
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| Authors: | Dr. Kai-Hsin Chang Dr. Wei-Chih Chao Yu-Hsuan Yang Dr. Cheng-Ham Wu Zhi-Bin Li Hung-Che Chen Dr. Yi-Te Chou Prof. Ja-an Annie Ho Xin-Cheng Li Yu-Chiang Peng Yu-Chan Liao Prof. Kuan-Miao Liu Prof. Chi-Min Chao Prof. Pi-Tai Chou |
| Affiliation: | 1. Department of Chemistry, National Taiwan University, Taipei, 10617 Taiwan, R.O.C. These authors contributed equally.;2. Department of Chemistry, National Taiwan University, Taipei, 10617 Taiwan, R.O.C. Department of Medical Applied Chemistry, Chung Shan Medical University, Taichung, 40201 Taiwan, R.O.C. Department of Medical Education, Chung Shan Medical University Hospital, Taichung, 40201 Taiwan, R.O.C. These authors contributed equally.;3. Department of Chemistry, National Taiwan University, Taipei, 10617 Taiwan, R.O.C.;4. Department of Medical Applied Chemistry, Chung Shan Medical University, Taichung, 40201 Taiwan, R.O.C. Department of Medical Education, Chung Shan Medical University Hospital, Taichung, 40201 Taiwan, R.O.C.;5. BioAnalytical Chemistry and Nanobiomedicine Laboratory, Department of Biochemical Science and Technology, National Taiwan University, Taipei, 10617 Taiwan, R.O.C.;6. BioAnalytical Chemistry and Nanobiomedicine Laboratory, Department of Biochemical Science and Technology, National Taiwan University, Taipei, 10617 Taiwan, R.O.C. Department of Chemistry, National Taiwan University, Taipei, 10617 Taiwan, R.O.C. Center for Emerging Materials and Advanced Devices, National Taiwan University, Taipei, 10617 Taiwan, R.O.C. Center for Biotechnology, National Taiwan University, Taipei, 10617 Taiwan, R.O.C.;7. Department of Medical Applied Chemistry, Chung Shan Medical University, Taichung, 40201 Taiwan, R.O.C. |
| 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−7N3Q ) and 3-cyano-7-azidoquinoline ( 3CN−7N3Q ) 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 |
