Development of a Silicon-Rhodamine Based Near-Infrared Emissive Two-Photon Fluorescent Probe for Nitric Oxide

Abstract

Two-photon (TP) fluorescent probes are potential candidates for near-infrared (NIR) imaging which holds great promise in biological research. However, currently, most TP probes emit at wavelength <600 nm, which impedes their practical applications. In this work, we explored the TP properties of a silicon-rhodamine (SiR) derivative and hence developed the first SiR scaffold based "NIR-to-NIR" TP probe (SiRNO) for nitric oxide (NO). SiRNO exhibited high sensitivity and specificity, as well as fast response for NO detection. It was able to track the subtle variation of intracellular NO content in live cells. Owing to the NIR excitation and emission, SiRNO enabled the detection of NO in situ in the xenograft tumor mouse model, revealing the NO generation during the tumor progression. This work indicates that SiR can be an ideal platform for the development of NIR emissive TP probe and may thus promote the advancement of NIR imaging.

Molecular Fluorophores for Deep-Tissue Bioimaging

“…Molecular probes based on rhodamines have been studied for a long time, 53 , 54 but few have been explored for 2P imaging, 55 especially under NIR-II excitation. Nevertheless, 1P and 2P probes share a common mechanism for fluorescence response, that is, a photoinduced electron transfer (PeT) mechanism between fluorophore and electronic donor.…”

Red-emissive azabenzanthrone derivatives for photodynamic therapy irradiated with ultralow light power density and two-photon imaging

“…4-(1,2,2-Triphenylethenyl)- N -[4-(1,2,2-triphenylethenyl)phenyl]-benzenamine 10 was synthesized according to the literature. 30 …”

Small-molecule fluorescent probes for imaging gaseous signaling molecules: current progress and future implications

“…The rst "NIR-to-NIR" probe based on a silicon-rhodamine (SiR) scaffold for the detection of NO with 4-methoxy-N-methylaniline as the NO recognition group was designed by Liu in 2017 (probe 20). 35 The main absorption band of the probe was centered at 651 nm and the emission wavelength aer reaction with NO was 672 nm. The absorption and emission of the probe were in the NIR region, which enabled the probe to visualize NO in situ in a mouse model of xenogra tumor and reveal the process of NO production in tumor development.…”