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810611P

Avanti

CNO

Avanti Polar Lipids 810611P, powder

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Synonym(s):
25-doxyl-cholesterol
Empirical Formula (Hill Notation):
C30H50NO3
CAS Number:
109024-15-9
Molecular Weight:
472.72
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

composition

(contains 10-15% of the ring-opened ketone, TLC)

packaging

pkg of 1 × 1 mg (810611P-1mg)

manufacturer/tradename

Avanti Polar Lipids 810611P

lipid type

ESR probes
ESR probes

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@](CC[C@]1([C@](CC=C2C[C@H](CC[C@]32C)O)4[H])[H])([C@]1(CC[C@@]43[H])C)[C@H](C)CCCC5(OCC(C)(C)N5[O])C

InChI

1S/C30H50NO3/c1-20(8-7-15-30(6)31(33)27(2,3)19-34-30)24-11-12-25-23-10-9-21-18-22(32)13-16-28(21,4)26(23)14-17-29(24,25)5/h9,20,22-26,32H,7-8,10-19H2,1-6H3/t20-,22+,23?,24-,25?,26?,28+,29-,30?/m1/s1

InChI key

VPKXVMQRURBFJA-AQHLAHBHSA-N

General description

A new paramagnetic analogue of cholesterol as a tool for studying molecular interactions of genuine cholesterol.

Application

CNO (25-doxyl-cholesterol) has been used in 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) liposomes reconstituted with mammalian translocator protein (mTSPO) (mTSPO:DMPC molar ratio of 1:20) for nuclear magnetic resonance (NMR) experiments.
CNO has been used to study the interactions of membrane proteins with cholesterol.

Biochem/physiol Actions

CNO (25-doxyl-cholesterol) is an analog for native cholesterol. It is used in the preparation of multilamellar vesicles. It is used as a spin-labelled analog of cholesterol.

Packaging

5 mL Amber Glass Screw Cap Vial (810611P-1mg)

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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Insights into cholesterol/membrane protein interactions using paramagnetic solid-state NMR
Jaipuria G, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 24(66), 17606-17611 (2018)
Characterization of the ternary mixture of sphingomyelin, POPC, and cholesterol: support for an inhomogeneous lipid distribution at high temperatures
Bunge A, et al.
Biophysical Journal, 94(7), 2680-2690 (2008)
Influence of the bovine seminal plasma protein PDC-109 on cholesterol in the presence of phospholipids
Muller P, et al.
European Biophysics Journal, 31(6), 438-447 (2002)
Insights into Cholesterol/Membrane Protein Interactions Using Paramagnetic Solid-State NMR
Jaipuria G, et al.
Chemistry?A European Journal , 24(66), 17606-17611 (2018)
L Maurin et al.
Biochimica et biophysica acta, 900(2), 239-248 (1987-06-30)
The synthesis of a new paramagnetic (nitroxide) analogue of cholesterol is described. This compound (called CNO) contains a doxyl group in the lateral chain at position 25. Our results show that CNO retains three molecular interactions which characterize authentic cholesterol:

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