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700147P

Avanti

PhotoClick Cholesterol

Hex-5′-ynyl 3β-hydroxy-6-diazirinyl-5α-cholan-24-oate, powder

Synonym(s):

hex-5-yn-1-yl 4-((3S,5S)-3-hydroxy-10, 13-dimethyl-1,2,3,4,5,7,8,9,10,11,12,13,14,15,16,17-hexadecahydrospiro[cyclopenta[a]phenanthrene-6,3′-diazirin]-17-yl)pentanoate

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About This Item

Empirical Formula (Hill Notation):
C30H46N2O3
CAS Number:
1485490-47-8
Molecular Weight:
482.70
UNSPSC Code:
12352211
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 100 μg (with stopper and crimp cap (700147P-100ug))
pkg of 1 × 250 μg (with stopper and crimp cap (700147P-250ug))

manufacturer/tradename

Avanti Research™ - A Croda Brand 700147P

lipid type

click reagents

shipped in

dry ice

storage temp.

−20°C

General description

PhotoClick Cholesterol is a clickable, photoreactive sterol probe for use in combination with quantitative mass spectrometry to globally map cholesterol-protein interactions directly in living cells. In addition to the UV-activatable cross-linking diazirine group that reacts with proteins, the sterol contains an alkyne group for incorporation of reporter and affinity tags through click-chemistry.
PhotoClick Cholesterol is a synthetic analog of cholesterol and is photoreactive. It comprises the alkyne group.

Application

PhotoClick Cholesterol has been used:
  • in lysosome-associated membrane protein 1 (LAMP1) crosslinking studies
  • as an analog of cholesterol in binding and competition assay of sterol binding proteins from yeast
  • as a conjugate with the ectodomain of lysosomal integral membrane protein-2 (LIMP-2)

Biochem/physiol Actions

PhotoClick Cholesterol serves as a probe for tracking cholesterol-binding proteins. The copper-catalyzed azide-alkyne cycloaddition is the basis for its probe functionality. The alkyne group is essential for the click chemistry property. Its binding to partners is mediated by photocrosslinking.

Packaging

2 mL Amber Serum Vial with Stopper and Crimp Cap (700147P-100ug)
2 mL Amber Serum Vial with Stopper and Crimp Cap (700147P-250ug)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

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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May Kwang-Mei Wang et al.
PLoS pathogens, 14(9), e1007322-e1007322 (2018-09-29)
Lassa fever virus (LASV) is endemic in West Africa and causes severe hemorrhagic fever and sensorineural hearing loss. We identified a small molecule inhibitor of LASV and used it to analyze the mechanism of entry. Using a photo-reactive analog that
Neha Chauhan et al.
Yeast (Chichester, England), 37(1), 15-25 (2019-11-24)
Ergosterol is a prominent component of the yeast plasma membrane and essential for yeast cell viability. It is synthesized in the endoplasmic reticulum and transported to the plasma membrane by nonvesicular mechanisms requiring carrier proteins. Oxysterol-binding protein homologues and yeast
Jonathan J Hulce et al.
Nature methods, 10(3), 259-264 (2013-02-12)
Cholesterol is an essential structural component of cellular membranes and serves as a precursor for several classes of signaling molecules. Cholesterol exerts its effects and is, itself, regulated in large part by engagement in specific interactions with proteins. The full
Saskia Heybrock et al.
Nature communications, 10(1), 3521-3521 (2019-08-08)
The intracellular transport of cholesterol is subject to tight regulation. The structure of the lysosomal integral membrane protein type 2 (LIMP-2, also known as SCARB2) reveals a large cavity that traverses the molecule and resembles the cavity in SR-B1 that

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