2207602-75-1
Chemical Structure
APNO-5
- CAS No.: 2207602-75-1
- Formula:C48H54BF2IN8O5
- Molecular Weight:998.71
InChIKey: RKQOVBRKXAFEOW-UHFFFAOYSA-M
SMILES: CNC1=C(C=C(C=C1)C2=CC(C3=CC=CC=C3)=C4N=C5C(C6=CC=CC=C6)=CC(C7=CC=C(C=C7)OCC8=CN(N=N8)CCOCCOCCOCC[N+](C)(C)C)=[N]5B(F)(N24)F)OC.[I-]
Biological Activity: APNO-5 is a photoacoustic probe for in vivo nitric oxide (NO) detection. APNO-5 contains a PEGylated tetraalkylammonium group, which reduces aggregation and promotes tissue and cellular uptake. APNO-5 rapidly reacts with NO via N-nitrosation in the presence of O2 to generate the N-nitroso product tAPNO-5, causing a 91 nm blueshift in the maximum absorption wavelength (from 764 nm to 673 nm), thereby enabling ratiometric photoacoustic imaging at excitation wavelengths of 770 nm (APNO-5) and 680 nm (tAPNO-5). APNO-5 exhibits high selectivity for NO over other reactive nitrogen species, oxidants, and biological carbonyl species[1][2][3][4].
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APNO-5 | APNO-5 is a photoacoustic probe for in vivo nitric oxide (NO) detection. APNO-5 contains a PEGylated tetraalkylammonium group, which reduces aggregation and promotes tissue and cellular uptake. APNO-5 rapidly reacts with NO via N-nitrosation in the presence of O2 to generate the N-nitroso product tAPNO-5, causing a 91 nm blueshift in the maximum absorption wavelength (from 764 nm to 673 nm), thereby enabling ratiometric photoacoustic imaging at excitation wavelengths of 770 nm (APNO-5) and 680 nm (tAPNO-5). APNO-5 exhibits high selectivity for NO over other reactive nitrogen species, oxidants, and biological carbonyl species. | |||||||||||||||||||||
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References
- [1]. Reinhardt CJ, et al. A Ratiometric Acoustogenic Probe for in Vivo Imaging of Endogenous Nitric Oxide. Journal of the American Chemical Society. 2018 Jan 24;140(3):1011-1018.
- [2]. Lee MC, et al. Activity-Based Photoacoustic Probes for Detection of Disease Biomarkers beyond Oncology. ACS bio & med chem Au. 2023 Jun 21;3(3):223-232.
- [3]. Li J, et al. Detection and Imaging of Active Substances in Early Atherosclerotic Lesions Using Fluorescent Probes. Chembiochem : a European journal of chemical biology. 2023 Aug 01;24(15):e202300105.
- [4]. Qing Shen, et al. Stimuli-Responsive Organic Near-Infrared Photoacoustic Probes. Adv. Funct. Mater. 2023, 33, 2300023.
