DAUDA (Dansyl-11-aminoundecanoic acid)

Product ID: M1249



Unit SizePriceQuantity 
25mg
$44.08
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Availability: In stock


Description

Ambiphilic probe with a polar, environmentally-sensitive dansyl fluorophore attached to a long chain fatty acid. The polar dansyl headgroup partitions to the surface of lipid bilayer membranes while the fatty acid portion embeds into lipid bilayers or can attach to fatty acid carrier protein lipidic environments.

It has been found that dansyl-11-aminoundecanoic acid exhibits up to a 60-fold fluorescence enhancement and a shift to shorter emission wavelengths on binding to certain proteins (EX 335 nm; EM 519 nm). This property has been exploited to analyze fatty acid binding proteins and also to develop several fluorometric lipase assays, including phospholipase assays based on competitive fatty acid displacement from fatty acid binding proteins.

Technical Data
SKU M1249
CAS Number 73025-02-2
Unit Size 25mg
Alternative Names 11-[5-(Dimethylamino)-1-naphthalenesulfonylamino]undecanoic acid; DAUDA
Absorption 335nm
Emission Wavelength 519
Detection Method Fluorescence
Molecular Formula C₂₃H₃₄N₂O₄S;
Molecular Weight 434.59
Soluble In CHCl3, CH2Cl2, DMSO, DMF
Storage Conditions 2-8C, Desiccated

References and Citations

References:

  • Moules IK, Rooney EK, Lee AG. (1982) "Binding of amphipathic drugs and probes to biological membranes." FEBS Lett 138: 95-100.
  • Rooney EK, East JM, Jones OT. (1983) "Interaction of Fatty Acids with Lipid Bilayers." Biochim Biophys Acta 728:159.
  • Stubbs CD, Meech SR, Lee AG, Phillips D. (1985) "Solvent relaxation in lipid bilayers with dansyl probes." Biochim Biophys Acta 815: 351-360.
  • Wilkinson TC, Wilton DC. (1986) "Studies on fatty acid-binding proteins. The detection and quantification of the protein from rat liver by using a fluorescent fatty acid analogue." Biochem J 238: 419-424
  • Wilton DC (1990) "The fatty acid analogue 11-(dansylamino)undecanoic acid is a fluorescent probe for the bilirubin-binding sites of albumin and not for the high-affinity fatty acid-binding sites." Biochem J 270, 163-166.
  • Wilton DC (1990) "A continuous fluorescence displacement assay for the measurement of phospholipase A2 and other lipases that release long-chain fatty acids." Biochem J 266, 435-439.
  • Wilton DC (1991) "A continuous fluorescence-displacement assay for triacylglycerol lipase and phospholipase C that also allows the measurement of acylglycerols." Biochem J 276:129-133.
  • Worrall AF, Evans C, Wilton DC (1991) "Synthesis of a gene for rat liver fatty-acid-binding protein and its expression in Escherichia coli." Biochem J 278:365-368.
  • Thumser AE, Voysey J, Wilton DC (1997) "A fluorescence displacement assay for the measurement of arachidonoyl ethanolamide (anandamide) and oleoyl amide (octadecenoamide) hydrolysis." Biochem Pharmacol 53: 433-435.
  • Buckland AG, Heeley EL, Wilton DC (2000) "Bacterial cell membrane hydrolysis by secreted phospholipases A(2): a major physiological role of human group IIa sPLA(2) involving both bacterial cell wall penetration and interfacial catalysis." Biochim Biophys Acta 1484:195-206.
  • Gasymov OK, Abduragimov AR, Yusifov TN, Glasgow BJ (2001) "Site-directed tryptophan fluorescence reveals the solution structure of tear lipocalin: evidence for features that confer promiscuity in ligand binding." Biochemistry 40: 14754-14762.
  • Bezzine S, Bollinger JG, Singer AG, Veatch SL, Keller SL, Gelb MH (2002) "On the Binding Preference of Human Groups IIA and X Phospholipases A2 for Membranes with Anionic Phospholipids." J Biol Chem 277: 48523-48534.
  • Ramos CR, Figueredo RC, Pertinhez TA, Vilar MM, do Nascimento AL, Tendler M, Raw I, Spisni A, Ho PL (2003) "Gene structure and M20T polymorphism of the Schistosoma mansoni Sm14 fatty acid-binding protein. Molecular, functional, and immunoprotection analysis." J. Biol. Chem. 278: 12745-12751.
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