4-(5-dimethylamino-phenyl-2-oxazolyl) benzenesulfonamide

This fluorescent sulfonamide is used together with a fluorescent-labeled apocarbonic anhydrase sensor to measure and image free zinc ion in aqueous solution by wavelength ratio. These Fierke-Thompson sensors offer high sensitivity and selectivity, rapid response, ratiometric quantitation, cell penetration or expressibility in cells, targeting to desired organelles, and tunable zinc range and kinetics.

This cell-permeante fluorescent aryl sulfonamide is a component of excitation ratiometric fluorescence-based zinc biosensors employing human carbonic anhydrase II (CA II). It binds significantly more tightly to human CA II in the holo-form (Zn2+ in the active site) than in the apo-form; upon binding to holo-CA II it exhibits a 20-fold increase in fluorescence quantum yield and 60 nm emission blue shift (600 nm to 540 nm) compared to when free in aqueous solution. Extinction coefficient 21, 000 M-1 cm-1 at 370 nm. Its use with suitably fluorescent labeled hCA II for excitation ratiometric zinc determination is illustrated above. The sensor consists of suitably fluorescent-labeled apoCA II, (TAT-H36C-FLX-hCA wt-apoCA-tagRFP) together with this product; the protein may be expressed in a cell, or enter the cell membrane if it contains a cell-penetrant peptide such as TAT.

Catalog Number Product Size AVAILABILITY Price Qty
KPG001
4-(5-dimethylamino-phenyl-2-oxazolyl) benzenesulfonamide
5mg In stock
Regular Price:$250.00
Specifications

Product Type: Small Molecule
Molecular Weight: 344.1
Variant MPN: D-0005
Format: Yellow Solid
Purity: 95%
Tested Applications: Fluorescent zinc ion sensor
Solubility: DMF, DMSO
Storage: Store frozen, dry, and tightly closed; millimolar solutions in DMF or DMSO generally are stable for months in the freezer
Shipped: Room Temperature

Data
Compound
References
  1. R. B. Thompson, M. L. Cramer, R. Bozym, and C. A. Fierke, "Excitation ratiometric fluorescent biosensor for zinc ion at picomolar levels". J. Biomed. Optics7 (4), 555 - 506 (2002). PMID 12421121.
  2. R. A. Bozym, A. K. Stoddard, C. A. Fierke, and R. B. Thompson, "Measuring picomolar exchangeable zinc in PC-12 cells using a ratiometric fluorescence biosensor". ACS Chemical Biology1(2) 103 -111 (2006) PMID: 17163650.
  3. B. J. McCranor, R. A. Bozym, M. Vitolo, C. A. Fierke, L. Bambrick, B. Polster, G. Fiskum, and R. B. Thompson, "Quantitative imaging of mitochondrial and cytosolic free zinc levels in an in vitro model of ischemia/reperfusion" Journal of Bioenergetics and Biomembranes 44(2) 253 - 263 (2012). DOI: 10.1007/s10863-012-9427-2 PMID 22430627 NIHMS382081.
  4. D. Wang, T. K. Hurst, R. B. Thompson, and C. A. Fierke "Genetically Encoded Ratiometric Biosensors to Measure Intracellular Exchangeable Zinc in Escherichia coli".J. Biomed. Opt. 16(8) 087011/1-11 (2011) [DOI: 10.1117/1.3613926. PMID: 21895338 PMCID: PMC3166341 .

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