NIR-Thiol dinitrobenzenesulfonate has both absorption and emission in the NIR region. NIR-Thiol dinitrobenzenesulfonate responds to thiol with a large turn-on NIR fluorescence signal upon excitation in the NIR region. NIR-Thiol dinitrobenzenesulfonate is capable of imaging endogenously produced thiol in living cells and mice.

Product information

Molecular Weight: 875.83

Formula: C39H33N5O15S2

Chemical Name: 2, 4-dinitrobenzenesulfonate;[5-[(E)-2-(1-ethyl-3, 3-dimethylindol-1-ium-2-yl)ethenyl]-7, 8-dihydro-6H-xanthen-3-yl] 2, 4-dinitrobenzenesulfonate

Smiles: CC[N+]1C2=CC=CC=C2C(C)(C)C=1/C=C/C1CCCC2=CC3=CC=C(C=C3OC=12)OS(=O)(=O)C1=CC=C(C=C1[N+]([O-])=O)[N+]([O-])=O.[O-]S(=O)(=O)C1=CC=C(C=C1[N+]([O-])=O)[N+]([O-])=O

InChiKey: LKUGARKBEIHOQY-IWSIBTJSSA-M

InChi: InChI=1S/C33H30N3O8S.C6H4N2O7S/c1-4-34-27-11-6-5-10-26(27)33(2,3)31(34)17-13-21-8-7-9-23-18-22-12-15-25(20-29(22)43-32(21)23)44-45(41,42)30-16-14-24(35(37)38)19-28(30)36(39)40;9-7(10)4-1-2-6(16(13,14)15)5(3-4)8(11)12/h5-6,10-20H,4,7-9H2,1-3H3;1-3H,(H,13,14,15)/q+1;/p-1/b17-13+;

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

NIR-Thiol dinitrobenzenesulfonate is highly selective to typical small molecular weight biological thiols (Cys, Hcy, and GSH) over other biorelevant species, such as Phe, Gly, Arg, Lys, Tyr, Leu, glucose, Ser, and Val. To assess the ability of the sensor NIR-Thiol dinitrobenzenesulfonate for NIR imaging of thiols in living cells, the sensor is incubated with living HeLa or Bel 7702 cells, and bright fluorescence is observed. Thus, the sensor appears to be cell membrane permeable and capable of NIR imaging of thiols in living cell. NIR-Thiol dinitrobenzenesulfonate has some prominent features, includinf NIR absorption and emission, rapid response, high sensitivity, excellent selectivity, good cell membrane permeability, and low cytotoxicity.

In Vivo:

A different amount (0, 20, 40, or 160 nanomoles) of NIR-Thiol dinitrobenzenesulfonate is injected into the ip cavity of mice. Strong fluorescence is noted for the mice injected with 20 nanomoles of NIR-Thiol dinitrobenzenesulfonate, whereas almost no fluorescence is observed in the control mice without being injected with the sensor. In addition, the mice injected with a higher amount (40 or 160 nanomoles) of NIR-Thiol dinitrobenzenesulfonate provids brighter fluorescence. A very large signal-to-noise contrast ratio (ca. 700-fold enhancement) is observed for the mice injected with 20 nanomoles of NIR-Thiol dinitrobenzenesulfonate. In addition, the signal-to-noise contrast ratio jumped to ca. 2900- or 7400-fold enhancement when the mice are injected with 40 or 160 nanomoles of NIR-Thiol dinitrobenzenesulfonate, respectively.

Products are for research use only. Not for human use.