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2-[2-[2-Chloro-3-[2-[1,3-dihydro-3,3-dimethyl-1-(4-sulfobutyl)-2H-indol-2-ylidene]-ethylidene]-1-cyclohexen-1-yl]-ethenyl]-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium

2-[2-[2-Chloro-3-[2-[1,3-dihydro-3,3-dimethyl-1-(4-sulfobutyl)-2H-indol-2-ylidene]-ethylidene]-1-cyclohexen-1-yl]-ethenyl]-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium

Kam Leung

PMID: 21028751

Abstract:

Optical fluorescence imaging is increasingly being used to monitor biological functions of specific targets (1-3). However, the intrinsic fluorescence of biomolecules poses a problem when fluorophores that absorb visible light (350-700 nm) are used. Near-infrared (NIR) fluorescence (700-1,000 nm) detection avoids the natural background fluorescence interference of biomolecules, which provides a high contrast between target and background tissues in small animals. NIR fluorophores have a wider dynamic range and minimal background fluorescence as a result of reduced scattering compared with visible fluorescence detection. NIR fluorophores also have high sensitivity, attributable to low background fluorescence, and high extinction coefficients, which provide high quantum yields. The NIR region is also compatible with solid-state optical components such as diode lasers and silicon detectors. NIR fluorescence imaging is a non-invasive complement to radionuclide imaging in small animals.
Among the various NIR agents, only indocyanine green (ICG), with absorption at 780 nm and emission at 820 nm, is approved by the United States Food and Drug Administration for clinical applications in angiography, blood flow evaluation, and liver function assessment (4). It is also under evaluation in several clinical trials for other applications. However, ICG has a plasma half-life of 2-4 min because it forms aggregates in the blood and is rapidly cleared from blood circulation (5). ICG is prone to photobleaching and non-specific quenching via its extensive binding to proteins. On the other hand, the fluorescence efficiency of some cyanine dyes can increase by ~1,000-fold upon binding to proteins and nucleic acids (6).
Organic anion transporters (OATPs) are responsible for the transport of a diverse group of substances (hormones, xenobiotics, and bile acids) (7). Some OATPs have been shown to be overexpressed in various human cancer tissues and cancer cell lines (8, 9). Lysosomes are membranous vesicles found in most mammalian cells (10). Lysosomes contain various types of proteases, which have been implicated in migration, invasion, and metastasis of malignant cancer cells by degradation of extracellular matrix (11). Lysosomes are found to be larger in malignant cancer cells than in benign cancer cells (12). 2-[2-[2-Chloro-3-[2-[1,3-dihydro-3,3-dimethyl-1-(4-sulfobutyl)-2H-indol-2-ylidene]-ethylidene]-1-cyclohexen-1-yl]-ethenyl]-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium (IR-783) has been shown to accumulate in the mitochondria and lysosomes of cancer cells (13). Uptake of IR-783 may be dependent upon OATPs. Yang et al. (13) have evaluated the usefulness of IR-783 as a probe for NIR imaging of tumors.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP7453261	1,3-Dimethyl-1,1,3,3-tetraphenyldisilazane		7453-26-1	Price

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