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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:
12352108
PubChem Substance ID:
57652412
NACRES:
NA.32

product line

BioReagent

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL9005
BCCK1334
BCCH1276
BCCC9453
BCBX5425

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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
C E Kung et al.
Biochemistry, 28(16), 6678-6686 (1989-08-08)
9-(Dicyanovinyl)julolidine (DCVJ) is a fluorescent dye whose intramolecular rotational relaxation is solvent dependent. Since its quantum yield increases with decreasing free volume, this molecule has been very useful in monitoring synthetic polymer reactions and measuring local microviscosity changes in phospholipid
Dexter N Dean et al.
Biochemistry, 55(15), 2238-2250 (2016-03-26)
Oligomers of amyloid-β (Aβ) have emerged as the primary toxic agents responsible for early synaptic dysfunction and neuronal death in Alzheimer's disease (AD). Characterization of oligomers is an important step in the progress toward delineating the complex molecular mechanisms involved
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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