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810250C

Avanti

25-NBD Cholesterol

Avanti Polar Lipids 810250C

Synonym(s):
25-[N-[(7-nitro-2-1,3-benzoxadiazol-4-yl)methyl]amino]-27-norcholesterol
Empirical Formula (Hill Notation):
C33H48N4O4
CAS Number:
Molecular Weight:
564.76
NACRES:
NA.25

assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 1 mL (810250C-10mg)
pkg of 1 × 1 mL (810250C-1mg)
pkg of 1 × 1 mL (810250C-5mg)

manufacturer/tradename

Avanti Polar Lipids 810250C

concentration

1 mg/mL (810250C-1mg)
10 mg/mL (810250C-10mg)
5 mg/mL (810250C-5mg)

shipped in

dry ice

storage temp.

−20°C

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

InChI key

RMGLSQAGXRZCPZ-OVHOIDCTSA-N

General description

25-NBD Cholesterol is a fluorescent derivative of cholesterol. Its fluorescent property is due to presence of NBD (2-(4-nitro-2,1,3-benzoxadiazol-7-yl) aminoethyl) group.

Application

25-NBD Cholesterol can be used as a labeling agent for confocal microscopy in studying endosomal trafficking and vesicle formation.

Biochem/physiol Actions

Cholesterol is synthesized via a cascade of enzymatic reactions known as the mevalonate pathway. Cholesterol plays a major role in the architecture and stability of the plasma membrane and is also involved in the synthesis of cholecalciferol (Vitamin D3). Cholesterol build up on the walls or arteries causes obstruction of blood flow leading to a serious condition called artherosclerosis. It is a precursor for bile acid and for the synthesis of steroid hormones like progesterone, testosterone, cortisol, and aldosterone.

Packaging

5 mL Clear Glass Sealed Ampule (810250C-1mg)
5 mL Clear Glass Sealed Ampule (810250C-5mg)
5 mL Clear Glass Sealed Ampule (810250C-10mg)

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

does not flash

Flash Point(C)

does not flash

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Anita H Payne et al.
Endocrine reviews, 25(6), 947-970 (2004-12-08)
Significant advances have taken place in our knowledge of the enzymes involved in steroid hormone biosynthesis since the last comprehensive review in 1988. Major developments include the cloning, identification, and characterization of multiple isoforms of 3beta-hydroxysteroid dehydrogenase, which play a
Fluorescent and Luminescent Probes for Biological Activity (1999)
Cholesterol in health and disease.
Ira Tabas
The Journal of clinical investigation, 110(5), 583-590 (2002-09-05)
Pedro M R Cruz et al.
Frontiers in pharmacology, 4, 119-119 (2013-10-05)
While the unique metabolic activities of malignant tissues as potential targets for cancer therapeutics has been the subject of several recent reviews, the role of cholesterol metabolism in this context is yet to be fully explored. Cholesterol is an essential
Johan Tornmalm et al.
Scientific reports, 9(1), 18133-18133 (2019-12-04)
Protein-lipid interactions in cellular membranes modulate central cellular functions, are often transient in character, but occur too intermittently to be readily observable. We introduce transient state imaging (TRAST), combining sensitive fluorescence detection of fluorophore markers with monitoring of their dark

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