Construction of a fluorine substituted chromenylium-cyanine near-infrared fluorophore for ratiometric sensing
Abstract Near-infrared (NIR) fluorescent probes have been considered as powerful tools for exploring bioactive species and biological processes in living systems by virtue of the substantial merits of the NIR window (such as minimal photo-toxicity, deep tissue penetration, and low background interference). However, the development of effective NIR fluorescent probes for biological application is still facing great challenges due to some weakness (for example, pH sensitivity, poor chemical and photo-stability) of mainly current NIR fluorophores. Herein, we synthesized a novel fluorine atom substituted NIR chromenylium-cyanine fluorophore, termed CCF-OH , with an optically tunable hydroxyl group. Compound CCF-OH possess several optical advantages, including high chemical stability, high photo-stability, and high fluorescence quantum yield (Φ = 0.47). Significantly, a low pK a value (6.3) of CCF-OH was obtained, making its fluorescence signal steady around the pH ranging from 6.8 to 8.1. To demonstrate the practicability of CCF-OH , a mitochondria-targeted near-infrared fluorescent probe, N-Cys , was developed by masking the hydroxyl group of CCF-OH with an acrylate group as the recognition unit for cysteine (Cys). N-Cys responded to Cys with an obvious ratiometric signal. Furthermore, N-Cys has also been successfully applied for ratiometric NIR imaging of Cys in living cells, suggesting the great potential of the new NIR fluorophore, CCF-OH , for practical applications in living systems. Highlights A novel fluorine atom substituted NIR chromenylium-cyanine fluorophore (termed CCF-OH ) was proposed. CCF-OH exhibited high fluorescence quantum yield, high chemical and photo-stability, and stable fluorescence signal around the pH range from 6.8 to 8.1. To demonstrate the practicability of CCF-OH , a mitochondria-targeted near-infrared fluorescent probe, N-Cys , was developed by using CCF-OH as the fluorescent reporter. Probe N-Cys displayed excellent selectivity, high sensitivity, and ratiometric response to Cys. Probe N-Cys has also been successfully applied for ratiometric NIR imaging of Cys in living cells, suggesting the great potential of the new NIR fluorophore, CCF-OH , for practical applications in living systems. Graphical abstract [DISPLAY OMISSION]
유료 다운로드의 경우 해당 사이트의 정책에 따라 신규 회원가입, 로그인, 유료 구매 등이 필요할 수 있습니다. 해당 사이트에서 발생하는 귀하의 모든 정보활동은 NDSL의 서비스 정책과 무관합니다.
원문복사신청을 하시면, 일부 해외 인쇄학술지의 경우 외국학술지지원센터(FRIC)에서
무료 원문복사 서비스를 제공합니다.
NDSL에서는 해당 원문을 복사서비스하고 있습니다. 위의 원문복사신청 또는 장바구니 담기를 통하여 원문복사서비스 이용이 가능합니다.
- 이 논문과 함께 출판된 논문 + 더보기