852818-04-3

Basic information

• Product Name: 5-Carboxy-2,3,3-triMethyl-1-(4-sulfobutyl)-3H-indoliuM
• Synonyms: 5-Carboxy-1-(4-sulfobutyl)-2,3,3-triMethyl-3H-indoliuM;5-Carboxy-2,3,3-triMethyl-1-(4-sulfobutyl)-3H-indoliuM
• CAS NO: 852818-04-3
• Molecular Formula: C16H22NO5S+
• Molecular Weight: 340.41458
• Product Categories: Chiral Reagents;Cyanine Dyes;Fluorescent Labels & Indicators;Labeling and Diagnostics Reagents
• Mol File: 852818-04-3.mol

Chemical Properties

• Appearance: /
• Solubility: Methanol
• CAS DataBase Reference: 5-Carboxy-2,3,3-triMethyl-1-(4-sulfobutyl)-3H-indoliuM(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Carboxy-2,3,3-triMethyl-1-(4-sulfobutyl)-3H-indoliuM(852818-04-3)
• EPA Substance Registry System: 5-Carboxy-2,3,3-triMethyl-1-(4-sulfobutyl)-3H-indoliuM(852818-04-3)

Safety Data

• Hazardous Substances Data: 852818-04-3(Hazardous Substances Data)

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 1633-83-6 1,4-butane sultone 
• 84100-84-5 2,3,3-trimethyl-5-carboxy-3H-indole 
• 619-67-0 4-Hydrazinobenzoic acid 

Relevant articles and documents

A novel colorimetric and ratiometric pH sensor with a notably large Stokes shift for sensing extremely alkaline solution

In this work, a facile hemicyanine-naphthalene-based fluorescent sensor for colorimetric and ratiometric sensing of pH was constructed via a simple synthesis process. Significantly, sensor 3 showed a high sensitivity to extremely alkaline solution and had a notably large Stokes shift (145 nm). Its absorbance and fluorescence enhanced or quenched obviously in the pH range of 5.0–12.0, accompanying with colour change. In addition, the fluorescence intensity increased 727-fold (F440/F710) when the pH was adjusted to 12, indicating that sensor 3 showed great potential in the detection of extremely alkaline solution.

Ligand taking indocyanine green derivative as carrier as well as preparation method and application of ligand

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NIR/PET bimodal contrast agent, and preparation method and application thereof

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NIR/MRI bimodal contrast agent, and preparation method and application thereof

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MODIFIED CYANINE DYES AND CONJUGATES THEREOF

The present invention relates to the field of optical imaging. More particularly, it relates to compounds of the cyanine family characterized by improved physico-chemical and biological properties and to their conjugates with biological ligands thereof. The invention also relates to the use of these compounds as optical diagnostic agents in imaging or therapy of solid tumors, to the methods for their preparation and to the compositions comprising them.

Probing two PESIN-indocyanine-dye-conjugates: Significance of the used fluorophore

Peptide-dye-conjugates hold a great promise in application for biological and medical imaging of cellular processes and in delineation and characterization of human tumors. In particular, indocyanine dyes are of great interest due to their reported superior properties such as absorption and emission in the near-infrared (NIR) spectral range, favorable Stokes shifts and their well-studied safety profile in humans. In this study, we investigated and describe the influence of indocyanine dyes on different properties of the final peptide-dye-conjugates. As a target peptide, PESIN, a bombesin derivative, was used as a model peptide which addresses GRP receptors overexpressed on different malignancies. Here, we map similarities and differences of the fluorescent conjugates and by this elucidate the influence of the dyes on different properties of the formed conjugates. We performed the dye syntheses, subsequent bioconjugation reactions and in the following investigated the optical properties, water/octanol distribution coefficients and target receptor affinities by in vitro competitive binding studies on PC-3 cells. The obtained results give a handrail to medical and biological researchers planning studies involving indocyanine dye biomolecule conjugates.

Heptamethine carboxyl indocyanine dye, preparation method and application thereof

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Accessing Structurally Diverse Near-Infrared Cyanine Dyes for Folate Receptor-Targeted Cancer Cell Staining

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A polyamine-modified near-infrared fluorescent probe for selective staining of live cancer cells

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Targeting tumor hypoxia: A third generation 2-nitroimidazole-indocyanine dye-conjugate with improved fluorescent yield

Tumor hypoxia is associated with the rapid proliferation and growth of malignant tumors, and the ability to detect tumor hypoxia is important for predicting tumor response to anti-cancer treatments. We have developed a class of dye-conjugates that are related to indocyanine green (ICG, 1) to target tumor hypoxia, based on in vivo infrared fluorescence imaging using nitroimidazole moieties linked to indocyanine fluorescent dyes. We previously reported that linking 2-nitroimidazole to an indocyanine dicarboxylic acid dye derivative (2) using an ethanolamine linker (ethanolamine-2-nitroimidazole-ICG, 3), led to a dye-conjugate that gave promising results for targeting cancer hypoxia in vivo. Structural modification of the dye conjugate replaced the ethanolamine unit with a piperazineacetyl unit and led a second generation dye conjugate, piperzine-2-nitroimidazole-ICG (4). This second generation dye-conjugate showed improved targeting of tumor hypoxia when compared with 3. Based on the hypothesis that molecules with more planar and rigid structures have a higher fluorescence yield, as they could release less absorbed energy through molecular vibration or collision, we have developed a new 2-nitroimidazole ICG conjugate, 12, with two carbon atoms less in the polyene linker. Dye-conjugate 12 was prepared from our new dye (8), and coupled to 2-nitroimidazole using a piperazine linker to produce this third-generation dye-conjugate. Spectral measurements showed that the absorption/emission wavelengths of 657/670 were shifted ～100 nm from the second-generation hypoxia dye of 755/780 nm. Its fluorescence quantum yield was measured to be 0.467, which is about 5 times higher than that of 4 (0.083). In vivo experiments were conducted with balb/c mice and 12 showed more than twice the average in vivo fluorescence intensity in the tumor beyond two hours post retro-orbital injection as compared with 4. These initial results suggest that 12 may significantly improve in vivo tumor hypoxia targeting.