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53846

Sigma-Aldrich

1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine, 7-nitrobenzofurazan-labeled

BioReagent, suitable for fluorescence, ammonium salt, ≥98.0% (TLC)

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Synonym(s):
L-β,γ-Dioleoyl-α-cephaline, 7-nitrobenzofurazan-labeled, N-(7-Nitrobenzofurazan-4-yl)-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine, Phosphatidylethanolamine 18:1, NBD-labeled
Empirical Formula (Hill Notation):
C47H79N4O11P
CAS Number:
137819-86-4
Molecular Weight:
907.12
MDL number:
MFCD06798191
UNSPSC Code:
12352200
PubChem Substance ID:
57651455

product line

BioReagent

Assay

≥98.0% (TLC)

form

powder

fluorescence

λex 461 nm; λem 529 nm in methanol

suitability

suitable for fluorescence

functional group

ester

storage temp.

−20°C

SMILES string

CCCCCCCC\C=C\CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCNc1ccc([N+]([O-])=O)c2nonc12)OC(=O)CCCCCCC\C=C\CCCCCCCC

InChI

1S/C47H79N4O11P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-44(52)58-39-41(61-45(53)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)40-60-63(56,57)59-38-37-48-42-35-36-43(51(54)55)47-46(42)49-62-50-47/h17-20,35-36,41,48H,3-16,21-34,37-40H2,1-2H3,(H,56,57)/b19-17+,20-18+/t41-/m1/s1

InChI key

RKWFXILULDJZBB-JJYVMECISA-N

Application

1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine, 7-nitrobenzofurazan-labeled (DOPE,NBD) may be used as a fluorescence label for lipid membranes in studies of membrane structures such as liposomes and lipid rafts.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Ligand-based targeted delivery of a peptide modified nanocarrier to endothelial cells in adipose tissue.
Hossen MN, Kajimoto K, Akita H, et al.
J. Controlled Release, 147, 261-268 (2010)
André E P Bastos et al.
Chemistry and physics of lipids, 165(5), 577-588 (2012-06-19)
In this work, binary mixtures of phospholipid/ergosterol (erg) were studied using three fluorescent membrane probes. The phospholipid was either saturated (1,2-dipalmitoyl-sn-glycero-3-phosphocholine, DPPC) or monounsaturated (1-palmitoyl-2-dioleoyl-sn-glycero-3-phosphocholine, POPC) phosphatidylcholine, to evaluate the fluorescence properties of the probes in gel, liquid ordered (l(o))
Huai-Ying Zhang et al.
Journal of the Royal Society, Interface, 8(54), 127-143 (2010-05-28)
Self-diffusion coefficients of poly(ethylene glycol)2k-derivatized lipids (DSPE-PEG2k-CF) in glass-supported DOPC phospholipid bilayers are ascertained from quantitative fluorescence recovery after photobleaching (FRAP). We developed a first-order reaction-diffusion model to ascertain the bleaching constant, mobile fraction and lipopolymer self-diffusion coefficient D(s) at
Michela Pisani et al.
The journal of physical chemistry. B, 115(34), 10198-10206 (2011-07-28)
Neutral lipids have received up to now a little attention as genetic material carriers, despite some valuable features, such as the absence of toxicity and the high stability in serum of their complexes with DNA. We have prepared two quaternary

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