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BODIPY-Cholesterol

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Category	Glycerolipids
Catalog NO.	BPG-3268
Product Name	BODIPY-Cholesterol
CAS	878557-19-8
Molecular Formula	C36H51BF2N2O
Molecular Weight	576.61

Scheme Design
Custom Synthesis
cGMP Manufacturing
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Product Information
Application
References
Documents
Reviews

Product Information

Description	BODIPY-cholesterol is a cell-permeable analog of cholesterol that is tagged with BODIPY group. BODIPY-cholesterol mimics the membrane partitioning and trafficking of cholesterol, and it is often used to study the sterol distribution and transport in living cells.
Synonyms	TopFluor Cholesterol; BCh2; (T-4)-[(3β)-24-(3,5-dimethyl-1H-pyrrol-2-yl-κN)-24-(3,5-dimethyl-2H-pyrrol-2-ylidene-κN)chol-5-en-3-olato]difluoro-boron
IUPAC Name	(10R,13R)-17-[4-(2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)butan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Canonical SMILES	[B-]1(N2C(=CC(=C2C(=C3[N+]1=C(C=C3C)C)CCC(C)C4CCC5C4(CCC6C5CC=C7C6(CCC(C7)O)C)C)C)C)(F)F
InChI	InChI=1S/C36H51BF2N2O/c1-21(8-10-29-33-22(2)18-24(4)40(33)37(38,39)41-25(5)19-23(3)34(29)41)30-12-13-31-28-11-9-26-20-27(42)14-16-35(26,6)32(28)15-17-36(30,31)7/h9,18-19,21,27-28,30-32,42H,8,10-17,20H2,1-7H3/t21-,27+,28+,30-,31+,32+,35+,36-/m1/s1
InChIKey	CFFWELDLDWZNRO-ZVEUZXBYSA-N
Purity	≥98%
Appearance	Red Solid
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	576.406
Hygroscopic	Yes
Light Sensitive	Yes
Percent Composition	C 74.99%, H 8.92%, B 1.87%, F 6.59%, N 4.86%, O 2.77%

References

1. Bernecic NC, Gadella BM, de Graaf SP, Leahy T. Synergism between albumin, bicarbonate and cAMP upregulation for cholesterol efflux from ram sperm. Reproduction. 2020 Aug;160(2):269-280. doi: 10.1530/REP-19-0430. PMID: 32460237. PubMed ID: 32460237.
2. Carro MLM, Peñalva DA, Antollini SS, Hozbor FA, Buschiazzo J. Cholesterol and desmosterol incorporation into ram sperm membrane before cryopreservation: Effects on membrane biophysical properties and sperm quality. Biochim Biophys Acta Biomembr. 2020 Sep 1;1862(9):183357. doi: 10.1016/j.bbamem.2020.183357. Epub 2020 May 13. PMID: 32416195. PubMed ID: 32416195.
3. Sibold J, Tewaag VE, Vagedes T, Mey I, Steinem C. Phase separation in pore-spanning membranes induced by differences in surface adhesion. Phys Chem Chem Phys. 2020 May 6;22(17):9308-9315. doi: 10.1039/d0cp00335b. PMID: 32309836. PubMed ID: 32309836.
4. Lee HR, You DG, Kim HK, Sohn JW, Kim MJ, Park JK, Lee GY, Yoo YD. Romo1-Derived Antimicrobial Peptide Is a New Antimicrobial Agent against Multidrug-Resistant Bacteria in a Murine Model of Sepsis. mBio. 2020 Apr 14;11(2):e03258-19. doi: 10.1128/mBio.03258-19. PMID: 32291307; PMCID: PMC7157825. PubMed ID: 32291307.
5. Navdaev AV, Sborgi L, Wright SD, Didichenko SA. Nascent HDL (High-Density Lipoprotein) Discs Carry Cholesterol to HDL Spheres: Effects of HDL Particle Remodeling on Cholesterol Efflux. Arterioscler Thromb Vasc Biol. 2020 May;40(5):1182-1194. doi: 10.1161/ATVBAHA.120.313906. Epub 2020 Mar 5. PMID: 32131613. PubMed ID: 32131613.
6. Lin M, Grandinetti G, Hartnell LM, Bliss D, Subramaniam S, Rikihisa Y. Host membrane lipids are trafficked to membranes of intravacuolar bacterium Ehrlichia chaffeensis. Proc Natl Acad Sci U S A. 2020 Apr 7;117(14):8032-8043. doi: 10.1073/pnas.1921619117. Epub 2020 Mar 19. PMID: 32193339; PMCID: PMC7149431. PubMed ID: 32193339.
7. Hayakawa EH, Yamaguchi K, Mori M, Nardone G. Real-time cholesterol sorting in Plasmodium falciparum-erythrocytes as revealed by 3D label-free imaging. Sci Rep. 2020 Feb 17;10(1):2794. doi: 10.1038/s41598-020-59552-9. PMID: 32066816; PMCID: PMC7026401. PubMed ID: 32066816.
8. Lee HR, Lee GY, You DG, Kim HK, Yoo YD. Hepatitis C Virus p7 Induces Membrane Permeabilization by Interacting with Phosphatidylserine. Int J Mol Sci. 2020 Jan 30;21(3):897. doi: 10.3390/ijms21030897. PMID: 32019133; PMCID: PMC7037181. PubMed ID: 32019133.
9. Sánchez-Pérez H, Quevedo-Abeledo JC, de Armas-Rillo L, Rua-Figueroa Í, Tejera-Segura B, Armas-González E, Machado JD, García-Dopico JA, Jimenez-Sosa A, Rodríguez-Lozano C, Díaz-González F, González-Gay MA, Ferraz-Amaro I. Impaired HDL cholesterol efflux capacity in systemic lupus erythematosus patients is related to subclinical carotid atherosclerosis. Rheumatology (Oxford). 2020 Feb 17:keaa038. doi: 10.1093/rheumatology/keaa038. Epub ahead of print. PMID: 32065639. PubMed ID: 32065639.
10. Plewes MR, Hou X, Talbott HA, Zhang P, Wood JR, Cupp AS, Davis JS. Luteinizing hormone regulates the phosphorylation and localization of the mitochondrial effector dynamin-related protein-1 (DRP1) and steroidogenesis in the bovine corpus luteum. FASEB J. 2020 Feb 20. doi: 10.1096/fj.201902958R. Epub ahead of print. PMID: 32077149. PubMed ID: 32077149.

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