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Merck
CN

SML4163

BODIPY 558/568 C12, Red

new

≥98% (HPLC), (Powder, film, or oil)

Synonym(s):

3-(11-Carboxyundecyl)-5,5-difluoro-7-(thiophen-2-yl)-5H-6l4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-5-uide, (T-4)-difluoro[5-[[5-(2-thienyl)-2H-pyrrol-2-ylidene-κN]methyl]-1H-pyrrole-2-dodecanoato(2-)-κN1]-borate(1-) monohydrogen, Hydrogen (T-4)-difluoro[5-[[5-(2-thienyl)-2H-pyrrol-2-ylidene-κN]methyl]-1H-pyrrole-2-dodecanoato(2-)-κN1]borate(1-), BDP 558/568 C12

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Quality Level

100

Assay

≥98% (HPLC)

form

(Powder, film, or oil)

storage condition

desiccated

color

red to black

storage temp.

-10 to -25°C

SMILES string

F[B-]1([N+]2=C(C3=CC=CS3)C=CC2=CC4=CC=C(CCCCCCCCCCCC(O)=O)N14)F

Biochem/physiol Actions

Stable orange-red fluorescent fatty acid analog monitors lipid flux/fatty acid trafficking in live cells and fixed cells.


BODIPY 558/568 C12, also known as BODIPY-red C12, is an orange-red fluorescent saturated fatty acid analog structurally resembling an 18-carbon fatty acid. In cells, red-C12 probe primarily localizes in neutral lipids within lipid droplets (LDs) and to the endoplasmic reticulum (ER), tracing lipid accumulation in these structures as well as in mitochondria and peroxisomes. BDP 558/568 C12 reveals fatty acid transfer from lipid droplet triacylglycerides (TAGs) to mitochondria and demonstrates how these fatty acids are esterified and stored in lipid droplets within the cytotrophoblast layer. Red C12 features a sharp fluorescence peak and high quantum yield, maintaining stable fluorescence across various physiological conditions and resisting changes in environmental polarity and pH. Excites at ~558 nm and emits at ~568 nm. BODIPY = boron dipyrromethene.

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Hygroscopic Store with dessicant

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Certificates of Analysis (COA)

Lot/Batch Number
0000459703
0000459703

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Hongyan Chen et al.
Molecular biology reports, 51(1), 320-320 (2024-02-23)
The aim of this study was to investigate whether ischemia/hypoxia conditions induce fatty acid transport from neurons to astrocytes and whether this mechanism is affected by ApoE isoforms. A neonatal rat model of hypoxic-ischemic brain damage was established. Excessive accumulation
Paul Targett-Adams et al.
The Journal of biological chemistry, 278(18), 15998-16007 (2003-02-20)
Neutral lipid is stored in spherical organelles called lipid droplets that are bounded by a coat of proteins. The protein that is most frequently found at the surface of lipid droplets is adipocyte differentiation-related protein (ADRP). In this study, we
Daria Korotkova et al.
Nature communications, 15(1), 4314-4314 (2024-05-22)
Peroxisomes are eukaryotic organelles that are essential for multiple metabolic pathways, including fatty acid oxidation, degradation of amino acids, and biosynthesis of ether lipids. Consequently, peroxisome dysfunction leads to pediatric-onset neurodegenerative conditions, including Peroxisome Biogenesis Disorders (PBD). Due to the

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