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D0250

Sigma-Aldrich

α-Dansyl-L-arginine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C18H25N5O4S · HCl
CAS Number:
28217-22-3
Molecular Weight:
443.95
EC Number:
248-904-6
MDL number:
MFCD00037733
UNSPSC Code:
12352200
PubChem Substance ID:
24893219
NACRES:
NA.26

assay

≥98% (TLC)

form

powder

color

yellow to green

storage temp.

−20°C

SMILES string

CN(C)c1cccc2c(cccc12)S(=O)(=O)NC(CCCNC(N)=N)C(O)=O

InChI

1S/C18H25N5O4S/c1-23(2)15-9-3-7-13-12(15)6-4-10-16(13)28(26,27)22-14(17(24)25)8-5-11-21-18(19)20/h3-4,6-7,9-10,14,22H,5,8,11H2,1-2H3,(H,24,25)(H4,19,20,21)

InChI key

HRBPBWKDJGGGCX-UHFFFAOYSA-N

Biochem/physiol Actions

α-Dansyl-L-arginine contains an N-terminal fluorophore (dansyl) making it useful as fluorescent marker/probe. α-Dansyl-L-arginine is used as a site specific marker for drug binding pockets on proteins. α-Dansyl-L-arginine, dansyl-l-asparagine, and dansyl-l-glutamate are specific for the site 1 drug binding site on albumin (HSA).

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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P J McIlroy et al.
Endocrinology, 113(1), 222-227 (1983-07-01)
The effects of dansyl-arginyl-(4'-ethyl)-piperidine amide (DAPA) on the binding of gonadotropins has been investigated. The compound inhibited the binding of hCG, human LH, and porcine LH to rat luteal membranes with an ED50 of 70 microM and the binding of
J M Mesaros et al.
Analytical chemistry, 68(19), 3441-3449 (1996-10-01)
Continuous zone electrophoretic separations in narrow channels coupled to small-bore capillaries have been demonstrated and characterized previously. Presented here is the use of this new technique to monitor dynamic chemical changes occurring in a flow injection analysis system. The fundamental
Ali J Ryan et al.
Journal of structural biology, 174(1), 84-91 (2010-10-14)
Human serum albumin (HSA) has two primary binding sites for drug molecules. These sites selectively bind different dansylated amino acid compounds, which-due to their intrinsic fluorescence-have long been used as specific markers for the drug pockets on HSA. We present
N Muller et al.
The Journal of pharmacy and pharmacology, 46(4), 300-304 (1994-04-01)
Human serum albumin is known to have two major and selective drug binding sites, termed sites I and II. The fluorescent probes, dansylamide and dansylsarcosine selectively interact with sites I and II, respectively. However, the binding site of the fluorescent

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