146368-07-2 | - Indole Building Blocks

Mujumdar, Ratnakar B. et al. published their research in Bioconjugate Chemistry in 1993 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Computed Properties of C13H17NO3S

Cyanine dye labeling reagents: Sulfoindocyanine succinimidyl esters was written by Mujumdar, Ratnakar B.;Ernst, Lauren A.;Mujumdar, Swati R.;Lewis, Christopher J.;Waggoner, Alan S.. And the article was included in Bioconjugate Chemistry in 1993.Computed Properties of C13H17NO3S This article mentions the following:

The synthesis and properties of a series of new fluorescent labeling reagents based on sulfoindocyanine dyes are described. They contain succinimidyl ester reactive groups and can be readily conjugated to antibodies, avidin, DNA, lipids, polymers, and other amino-group-containing materials. The labeling reagents are water soluble, pH insensitive, and show much reduced dye aggregation under labeling conditions. One of the reagents, Cy3, can be excited with the 488-, 514-, and 532-nm laser lines and is optimally excited with the 546-nm mercury arc line. Another, Cy5, can be excited with the 633-nm HeNe and 647-nm Kr laser lines available with many flow cytometers and confocal laser-scanning microscopes. New laser diodes emitting near 650 nm should also be excellent excitation sources for Cy5. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Computed Properties of C13H17NO3S).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zheng, Hong et al. published their research in Gaodeng Xuexiao Huaxue Xuebao in 1999 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Reference of 146368-07-2

Synthesis of a new near-IR fluorescent reagent and study on its in-situ dimer’s interaction with DNA was written by Zheng, Hong;Li, Dong-Hui;Wu, Min;Chen, Qiu-Ying;Xu, Jin-Gou. And the article was included in Gaodeng Xuexiao Huaxue Xuebao in 1999.Reference of 146368-07-2 This article mentions the following:

A new anionic Near-IR fluorescent cyanine dye was synthesized and its absorption and fluorescence spectra in water and in the solution of cationic surfactant-hexadecyltrimethyl-ammonium bromide (CTAB) were studied. The results showed that the maximum excitation wavelength and emission wavelength were 765 nm and 795 nm in water, resp. In the presence of low concentration of CTAB, the dye formed ionic associate with CTAB was made higher to form the pre-micellar aggregation, the fluorescence intensity decreased dramatically because of forming a low-fluorescent in-situ dimeric dye. When the concentration of CTAB was above the critical micelle concentration (cmc), the dimeric dye dissociated, and the fluorescence intensity of Near-IR cyanine was restored, and the maximum emission wavelength was bathochromated from 795 nm to 812 nm. The possibility of using low-fluorescent in-situ dimeric dye as a Near-IR region fluorescent probe for DNA was also studied. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Reference of 146368-07-2).

Tatarets, Anatoliy L. et al. published their research in Analytica Chimica Acta in 2006 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Reference of 146368-07-2

Synthesis of water-soluble, ring-substituted squaraine dyes and their evaluation as fluorescent probes and labels was written by Tatarets, Anatoliy L.;Fedyunyayeva, Irina A.;Dyubko, Tatyana S.;Povrozin, Yevgeniy A.;Doroshenko, Andrey O.;Terpetschnig, Ewald A.;Patsenker, Leonid D.. And the article was included in Analytica Chimica Acta in 2006.Reference of 146368-07-2 This article mentions the following:

A series of ring-substituted squaraines absorbing and emitting in the red and NIR spectral region was synthesized and their spectral and photophys. properties (quantum yields, fluorescence lifetimes) and photostabilities were measured and compared to Cy5, a commonly used fluorescent label. The absorption maxima in aqueous media were between 628 and 667 nm and the emission maxima are between 642 and 685 nm. Squaraine dyes exhibit high extinction coefficients (163,000-265,000 M^-1 cm^-1) and lower quantum yields (2-7%) in aqueous buffer but high quantum yields (up to 45%) and long fluorescence lifetimes (up to 3.3 ns) in presence of BSA. Dicyanomethylene- and thio-substituted squaraines exhibit an addnl. absorption around 400 nm with extinction coefficients between 21,500 and 44,500 M^-1 cm^-1. These dyes are excitable not only with red but also with blue diode lasers or light emitting diodes. Due to the favorable spectral and photophys. properties these dyes can be used as fluorescent probes and labels for intensity- and fluorescence lifetime-based biomedical applications. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Reference of 146368-07-2).

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Reference of 146368-07-2

Park, Jin Woo et al. published their research in Bioconjugate Chemistry in 2012 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Formula: C13H17NO3S

Novel Cyanine Dyes with Vinylsulfone Group for Labeling Biomolecules was written by Park, Jin Woo;Kim, YoungSoo;Lee, Kee-Jung;Kim, Dong Jin. And the article was included in Bioconjugate Chemistry in 2012.Formula: C13H17NO3S This article mentions the following:

Novel vinylsulfone cyanine dyes (em. 550-850 nm) were designed and synthesized for fluorescent labeling of biomols. via 1,2-addition reaction in aqueous conditions. Due to the virtue of chem. structures of both fluorophore and reactive group, these dyes could be significantly stable and reactive in various aqueous/organic conditions. A wide variety of pH, temperature, buffer concentration, and protein were tested for the optimal labeling condition. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Formula: C13H17NO3S).

Song, Bo et al. published their research in Dyes and Pigments in 2009 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Safety of 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate

The synthesis and photostability of novel squarylium indocyanine dyes was written by Song, Bo;Zhang, Qian;Ma, Wen-Hui;Peng, Xiao-Jun;Fu, Xin-Mei;Wang, Bing-Shuai. And the article was included in Dyes and Pigments in 2009.Safety of 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate This article mentions the following:

Novel, water-soluble, squarylium indocyanine dyes with various N-substituents on 3H-indolenine were synthesized. The maxima of absorption and emission wavelengths of the dyes in different solvents were in the range 628-670 nm and exhibited neg. solvatochromism with increasing solvent polarity in protic solvents. Dyes with N-benzyl rings (such as N-benzyl, N-carboxylbenzyl and N-fluorobenzyl) displayed greater photostability than dyes containing N-alkyl groups (such as N-Et and N-carboxylpentanyl) in aqueous solution The electron-withdrawing group (such as carboxyl and fluoro group) on the N-benzyl group of cyanine dyes improved photostability compared to dyes that contained an electron-donating group (such as methyl). The fading constant k of the N-carboxylbenzyl dye was considerably lower than that of the N-carboxylpentanyl dye. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Safety of 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate).

Shao, Fangwei et al. published their research in Dyes and Pigments in 2011 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Category: indole-building-block

Facile synthesis of monofunctional pentamethine carbocyanine fluorophores was written by Shao, Fangwei;Yuan, Hushan;Josephson, Lee;Weissleder, Ralph;Hilderbrand, Scott A.. And the article was included in Dyes and Pigments in 2011.Category: indole-building-block This article mentions the following:

A high-yield route to sym., conjugatable pentamethine carbocyanine dyes with far-red/near IR (NIR) emission between 650 and 700 nm is reported. The dyes are prepared via condensation of indolium or benz[e]indolium inner salts with an alkyl carboxylic acid derivatized malonaldehyde dianil or alternatively in a one-pot reaction without isolation of the malonaldehyde intermediate. The fluorophores are water-soluble, have bright fluorescence emission, are easily prepared in good yield, and are promising candidates for use in a variety of biochem. and in vivo imaging applications. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Category: indole-building-block).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles