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25-NBD Cholesterol

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Category	Cholesterol
Catalog NO.	BPG-3267
Product Name	25-NBD Cholesterol
CAS	105539-27-3
Molecular Formula	C33H48N4O4
Molecular Weight	564.76

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Description	25-NBD Cholesterol, a renowned fluorescent cholesterol analog, serves as a pivotal tool in investigations concerning lipid metabolism, membrane dynamics, and cholesterol transport pathways. Moreover, its profound significance extends to the realm of atherosclerosis and Niemann-Pick disease research, exhibiting profound potential for elucidating intricate pathological mechanisms.
Synonyms	25-Nbd-mnc; 25-[N-[(7-nitro-2-1,3-benzoxadiazol-4-yl)methyl]amino]-27-norcholesterol; 25-Nbd-methylamino-27-norcholesterol; 25-((7-Chloro-4-nitrobenz-2-oxa-1,3-diazole)methylamino)-27-norcholesterol
IUPAC Name	(3S,8S,9S,10R,13R,14S,17S)-10,13-dimethyl-17-[(2R)-6-[methyl-(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]heptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Canonical SMILES	CC(CCCC(C)N(C)C1=CC=C(C2=NON=C12)[N+](=O)[O-])C3CCC4C3(CCC5C4CC=C6C5(CCC(C6)O)C)C
InChI	InChI=1S/C33H48N4O4/c1-20(7-6-8-21(2)36(5)28-13-14-29(37(39)40)31-30(28)34-41-35-31)25-11-12-26-24-10-9-22-19-23(38)15-17-32(22,3)27(24)16-18-33(25,26)4/h9,13-14,20-21,23-27,38H,6-8,10-12,15-19H2,1-5H3/t20-,21?,23+,24+,25+,26+,27+,32+,33-/m1/s1
InChIKey	RMGLSQAGXRZCPZ-OVHOIDCTSA-N
Boiling Point	682.6°C at 760 mmHg
Purity	>99%
Density	1.2 g/cm3
Appearance	Powder
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	564.368
Hygroscopic	Yes
Light Sensitive	Yes
Percent Composition	C 70.18%, H 8.57%, N 9.92%, O 11.33%

References

1. Tornmalm J, Piguet J, Chmyrov V, Widengren J. Imaging of intermittent lipid-receptor interactions reflects changes in live cell membranes upon agonist-receptor binding. Sci Rep. 2019 Dec 2;9(1):18133. doi: 10.1038/s41598-019-54625-w. PMID: 31792325; PMCID: PMC6889430. PubMed ID: 31792325.
2. Xiao L, Luo G, Guo X, Jiang C, Zeng H, Zhou F, Li Y, Yu J, Yao P. Macrophage iron retention aggravates atherosclerosis: Evidence for the role of autocrine formation of hepcidin in plaque macrophages. Biochim Biophys Acta Mol Cell Biol Lipids. 2019 Oct 27:158531. doi: 10.1016/j.bbalip.2019.158531. [Epub ahead of print]...PubMed ID: 31666189.
3. Syakila RN, Lim SM, Agatonovic-Kustrin S, Lim FT, Ramasamy K. In vitro assessment of pediococci- and lactobacilli-induced cholesterol-lowering effect using digitally enhanced high-performance thin-layer chromatography and confocal microscopy. Anal Bioanal Chem. 2019 Feb;411(6):1181-1192. doi: 10.1007/s00216-018-1544-2. Epub 2019 Jan 24. PubMed ID: 30680424.
4. Zhang Y, Bush X, Yan B, Chen JA. Gemcitabine nanoparticles promote antitumor immunity against melanoma. Biomaterials. 2019 Jan;189:48-59. doi: 10.1016/j.biomaterials.2018.10.022. Epub 2018 Oct 20. PubMed ID: 30388589.
5. Iwamoto M, Oiki S. Constitutive boost of a K+ channel via inherent bilayer tension and a unique tension-dependent modality. Proc Natl Acad Sci U S A. 2018 Dec 18;115(51):13117-13122. doi: 10.1073/pnas.1812282115. Epub 2018 Dec 3. PubMed ID: 30509986.

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