4-(5-Dimethylamino-Phenyl-2-Oxazolyl)Benzenesulfonamide
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Cat. No.: D0005 4-(5-dimethylamino-phenyl-2-oxazolyl)benzenesulfonamide
Data:
Introduction:
Use: this fluorescent sulfonamide is used with carbonic anhydrase-based zinc biosensors to measure free zinc ion concentrations in aqueous media and inside cells. To use, dissolve in dimethylformamide or dimethylsulfoxide at millimolar concentration and add this stock solution to cell culture medium or other aqueous solution (containing the fluorescent-labeled carbonic anhydrase) to give final concentration of 3 – 10 micromolar. The compound rapidly penetrates prokaryotic and eukaryotic cells; zinc is measured by measuring or imaging fluorescence intensity at λemiss = 617 nm with λexc = 365 nm and λexc = 540 nm or other suitable wavelengths; the concentration is proportional to the ratio of intensities measured at the two excitation wavelengths: I@365 nm / I@540 nm in comparison to known free zinc concentrations in our MetalloBufferTM calibration buffer sets (see Figure). Note that it also stains most cell membranes with bluish fluorescence, which does not interfere.
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Specifications:
Product Type: Fluorescent sulfonamide for use with carbonic anhydrase-based biosensor
Name: D-0005 4-(5-dimethylamino-phenyl-2-oxazolyl)benzenesulfonamide
Description: This cell-permeant 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. Its use with suitably fluorescent labeled hCA II for excitation ratiometric zinc determination is illustrated above.
The sensor consists of suitably fluorescent-labeled apoCAII, together with D-0005; the protein may be expressed in a cell or enter the cell membrane if it contains a cell-penetrant peptide such as TAT.
Molecular Weight : 331
Format: Dry powder
Purity: 95+%
Tested Application: 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: Frozen
Provider:
Pokegama Technologies, Inc. (KeraFast Partner)
References:
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
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
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 Biomembranes44(2) 253 - 263 (2012). DOI: 10.1007/s10863-012-9427-2 PMID 22430627NIHMS382081
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 .