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72335

Sigma-Aldrich

9-(2,2-Dicyanovinyl)julolidine

BioReagent, suitable for fluorescence, ≥97.0% (HPLC)

Synonym(s):

9-Julolidinylmethylenemalononitrile, DCVJ

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About This Item

Empirical Formula (Hill Notation):
C16H15N3
CAS Number:
58293-56-4
Molecular Weight:
249.31
Beilstein:
413882
MDL number:
MFCD01747392
UNSPSC Code:
12352200
PubChem Substance ID:
57652412
NACRES:
NA.32

product line

BioReagent

Quality Level

100

Assay

≥97.0% (HPLC)

form

crystals

solubility

DMSO: soluble
chloroform: soluble

fluorescence

λex 433 nm; λem 500 nm in 50 mM Tris pH 8.0; 40% glycerol

suitability

suitable for fluorescence

SMILES string

N#C\C(=C/c1cc2CCCN3CCCc(c1)c23)C#N

InChI

1S/C16H15N3/c17-10-13(11-18)7-12-8-14-3-1-5-19-6-2-4-15(9-12)16(14)19/h7-9H,1-6H2

InChI key

LROAUBRDKLVBCP-UHFFFAOYSA-N

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Fluorescent probe for binding to proteins etc., quantum yield increases by decreasing free rotation; abs at ~450 nm, em at 480-505 nm (solvent dep.)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M A Haidekker et al.
American journal of physiology. Heart and circulatory physiology, 278(4), H1401-H1406 (2000-04-06)
Fluid shear stress (FSS) has been shown to be an ubiquitous stimulator of mammalian cell metabolism. Although many of the intracellular signal transduction pathways have been characterized, the primary mechanoreceptor for FSS remains unknown. One hypothesis is that the cytoplasmic
A Bhattacharya et al.
Protein science : a publication of the Protein Society, 5(10), 2029-2036 (1996-10-01)
9-(Dicyanovinyl) julolidine (DCVJ) is a fluorescent probe, which binds to a unique site on the tubulin dimer and exhibits different properties that are dependent upon its oligomeric state (Kung & Reed, 1989). DCVJ binds to tubulin, the tubulin-colchicine complex, and
A Bhattacharyya et al.
Indian journal of biochemistry & biophysics, 32(6), 442-446 (1995-12-01)
Di(cyano vinyl)julolidine (DCVJ) is a fluorescent probe which has been used to monitor the local mobility of its binding sites on proteins. It shows a concentration dependence of its emission spectrum in water. At higher DCVJ concentrations, a longer wavelength
Andrea Hawe et al.
Pharmaceutical research, 27(2), 314-326 (2009-12-31)
The aim was to evaluate fluorescent molecular rotors (DCVJ and CCVJ), which are mainly sensitive to viscosity, for the characterization of polysorbate-containing IgG formulations and compare them to the polarity-sensitive dyes ANS, Bis-ANS and Nile Red. IgG formulations with polysorbate
Mark A Haidekker et al.
Bioorganic & medicinal chemistry, 10(11), 3627-3636 (2002-09-06)
Molecular rotors are fluorescent molecules with a viscosity-sensitive quantum yield that are often used to measure viscosity changes in cell membranes and liposomes. However, commercially available molecular rotors, such as DCVJ (1) do not localize in cell membranes but rapidly
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