810255 | TopFluor® Cholesterol

23-(dipyrrometheneboron difluoride)-24-norcholesterol

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10mg 810255P-10mg 810255P-10mg 1 x 10mg $992.40
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TopFluor® Cholesterol

TopFluor® Cholesterol

23-(dipyrrometheneboron difluoride)-24-norcholesterol

Hygroscopic
Yes
Light Sensitive
Yes
Molecular Formula
C36H51BF2N2O
Percent Composition
C 74.99%, H 8.92%, B 1.87%, F 6.59%, N 4.86%, O 2.77%
Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
878557-19-8
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
576.611
Exact Mass
576.406
Synonyms
Bodipy Cholesterol
Bdp-Chol

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Ferraz-Amaro I, Hernández-Hernández MV, Armas-González E, Sánchez-Pérez H, Machado JD, Díaz-González F. HDL cholesterol efflux capacity is related to disease activity in psoriatic arthritis patients. Clin Rheumatol. 2020 Jan 28:10.1007/s10067-020-04961-4. doi: 10.1007/s10067-020-04961-4. Epub ahead of print. PMID: 31993889.

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Yamashita K, Ito K, Endo J, Matsuhashi T, Katsumata Y, Yamamoto T, Shirakawa K, Isobe S, Kataoka M, Yoshida N, Goto S, Moriyama H, Kitakata H, Mitani F, Fukuda K, Goda N, Ichihara A, Sano M. Adrenal cortex hypoxia modulates aldosterone production in heart failure. Biochem Biophys Res Commun. 2020 Jan 23:S0006-291X(20)30157-1. doi: 10.1016/j.bbrc.2020.01.088. Epub ahead of print. PMID: 31982132.

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Oshita T, Toh R, Nagano Y, Kuroda K, Nagasawa Y, Harada A, Murakami K, Kiriyama M, Yoshikawa K, Miwa K, Kubo T, Iino T, Nagao M, Irino Y, Hara T, Shinohara M, Otake H, Shinke T, Nakajima K, Ishida T, Hirata KI. Association of cholesterol uptake capacity, a novel indicator for HDL functionality, and coronary plaque properties: An optical coherence tomography-based observational study. Clin Chim Acta. 2020 Jan 21;503:136-144. doi: 10.1016/j.cca.2020.01.001. Epub ahead of print. PMID: 31972150.

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Ruwisch J, Sehlmeyer K, Roldan N, Garcia-Alvarez B, Perez-Gil J, Weaver TE, Ochs M, Knudsen L, Lopez-Rodriguez E. Air Space Distension Precedes Spontaneous Fibrotic Remodeling and Impaired Cholesterol Metabolism in the Absence of Surfactant Protein C. Am J Respir Cell Mol Biol. 2020 Jan 10:10.1165/rcmb.2019-0358OC. doi: 10.1165/rcmb.2019-0358OC. Epub ahead of print. PMID: 31922895.

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Kim HY, Cheon JH, Lee SH, Min JY, Back SY, Song JG, Kim DH, Lim SJ, Han HK. Ternary nanocomposite carriers based on organic clay-lipid vesicles as an effective colon-targeted drug delivery system: preparation and in vitro/in vivo characterization. J Nanobiotechnology. 2020 Jan 21;18(1):17. doi: 10.1186/s12951-020-0579-7. PMID: 31964393; PMCID: PMC6975051.

 PubMed ID: 31964393

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 PubMed ID: 31941372

Feng M, Darabi M, Tubeuf E, Canicio A, Lhomme M, Frisdal E, Lanfranchi-Lebreton S, Matheron L, Rached F, Ponnaiah M, Serrano CV Jr, Santos RD, Brites F, Bolbach G, Gautier E, Huby T, Carrie A, Bruckert E, Guerin M, Couvert P, Giral P, Lesnik P, Le Goff W, Guillas I, Kontush A. Free cholesterol transfer to high-density lipoprotein (HDL) upon triglyceride lipolysis underlies the U-shape relationship between HDL-cholesterol and cardiovascular disease. Eur J Prev Cardiol. 2019 Dec 15;2047487319894114. doi: 10.1177/2047487319894114. [Epub ahead of print]. PMID: 31840535.

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Khattib A, Atrahimovich D, Dahli L, Vaya J, Khatib S. Lyso-diacylglyceryltrimethylhomoserine (lyso-DGTS) isolated from Nannochloropsis microalgae improves high-density lipoprotein (HDL) functions. Biofactors. 2019 Oct 29. doi: 10.1002/biof.1580. [Epub ahead of print]

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Lim CY, Davis OB, Shin HR, Zhang J, Berdan CA, Jiang X, Counihan JL, Ory DS, Nomura DK, Zoncu R. ER-lysosome contacts enable cholesterol sensing by mTORC1 and drive aberrant growth signalling in Niemann-Pick type C. Nat Cell Biol. 2019 Oct;21(10):1206-1218. doi: 10.1038/s41556-019-0391-5. Epub 2019 Sep 23.

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 PubMed ID: 31381343

Bernecic NC, Zhang M, Gadella BM, Brouwers JFHM, Jansen JWA, Arkesteijn GJA, de Graaf SP, Leahy T. BODIPY-cholesterol can be reliably used to monitor cholesterol efflux from capacitating mammalian spermatozoa. Sci Rep. 2019 Jul 8;9(1):9804. doi: 10.1038/s41598-019-45831-7.

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Doll F, Keckeis P, Scheel P, Cölfen H. Visualizing Cholesterol Uptake by Self-Assembling Rhodamine B-Labeled Polymer Inside Living Cells via FLIM-FRET Microscopy. Macromol Biosci. 2019 Jun 21:e1900081. doi: 10.1002/mabi.201900081. [Epub ahead of print]

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Laraia L, Friese A, Corkery DP, Konstantinidis G, Erwin N, Hofer W, Karatas H, Klewer L, Brockmeyer A, Metz M, Schölermann B, Dwivedi M, Li L, Rios-Munoz P, Köhn M, Winter R, Vetter IR, Ziegler S, Janning P, Wu YW, Waldmann H. The cholesterol transfer protein GRAMD1A regulates autophagosome biogenesis. Nat Chem Biol. 2019 Jul;15(7):710-720. doi: 10.1038/s41589-019-0307-5. Epub 2019 Jun 20.

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Králová J, Král V. Fluorescent Probes for Monitoring Cholesterol Trafficking in Cells. Folia Biol (Praha). 2019;65(1):1-10.

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Zhou Y, Miles JR, Tavori H, Lin M, Khoshbouei H, Borchelt D, Bazick H, Landreth GE, Lee S, Fazio S, Notterpek L. PMP22 regulates cholesterol trafficking and ABCA1-mediated cholesterol efflux. J Neurosci. 2019 May 6. pii: 2942-18. doi: 10.1523/JNEUROSCI.2942-18.2019. [Epub ahead of print]

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Stumpf SK, Berghoff SA, Trevisiol A, Spieth L, Düking T, Schneider LV, Schlaphoff L, Dreha-Kulaczewski S, Bley A, Burfeind D, Kusch K, Mitkovski M, Ruhwedel T, Guder P, Röhse H, Denecke J, Gärtner J, Möbius W, Nave KA, Saher G. Ketogenic diet ameliorates axonal defects and promotes myelination in Pelizaeus-Merzbacher disease. Acta Neuropathol. 2019 Mar 27. doi: 10.1007/s00401-019-01985-2. [Epub ahead of print]

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Cockburn CL, Green RS, Damle SR, Martin RK, Ghahrai NN, Colonne PM, Fullerton MS, Conrad DH, Chalfant CE, Voth DE, Rucks EA, Gilk SD, Carlyon JA. Functional inhibition of acid sphingomyelinase disrupts infection by intracellular bacterial pathogens. Life Sci Alliance. 2019 Mar 22;2(2). pii: e201800292. doi: 10.26508/lsa.201800292. Print 2019 Apr.

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Otis JP, Shen MC, Caldwell BA, Reyes Gaido OE, Farber SA. Dietary cholesterol and apolipoprotein A-I are trafficked in endosomes and lysosomes in the live zebrafish intestine. Am J Physiol Gastrointest Liver Physiol. 2019 Mar 1;316(3):G350-G365. doi: 10.1152/ajpgi.00080.2018. Epub 2019 Jan 10.

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Dergunov AD, Litvinov DY, Bazaeva EV, Dmitrieva VG, Nosova EV, Rozhkova AV, Dergunova LV. Relation of High-Density Lipoprotein Charge Heterogeneity, Cholesterol Efflux Capacity, and the Expression of High-Density Lipoprotein-Related Genes in Mononuclear Cells to the HDL-Cholesterol Level. Lipids. 2018 Oct;53(10):979-991. doi: 10.1002/lipd.12104. Epub 2018 Nov 15.

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 PubMed ID: 23326230

Lund, F.W., M.A. Lomholt, L.M. Solanko, R. Bittman, and D. Wustner. (2012). Two-photon time-lapse microscopy of BODIPY-cholesterol reveals anomalous sterol diffusion in chinese hamster ovary cells. BMC Biophys. 2012 Oct 18;5:20. doi: 10.1186/2046-1682-5-20.

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C. Röhrl, C. Meisslitzer-Ruppitsch, R. Bittman, Z. Li, G. Pabst, R. Prassl, W. Strobl, J. Neumüller, A. Ellinger, M. Pavelka, and H. Stangl, “Combined Light and Electron Microscopy using Diaminobenzidine Photooxidation to Monitor Trafficking of Lipids Derived from Lipoprotein Particles,” Curr. Pharm. Biotechnol. 13, 331-340 (2012).

PubMed ID: 21470121

S. Sankaranarayanan, G. Kellner-Weibel, M. de la Llera-Moya, M. C. Phillips, B. F. Asztalos, R. Bittman, and G. H. Rothblat, “A Sensitive Assay for ABCA1-Mediated Cholesterol Efflux Using Bodipy-Cholesterol," J. Lipid Res. 52, 2332-2340 (2011).

 PubMed ID: 21957199

D. Wüstner, L. Solanko, F. W. Lund, O. Garvik, Z. Li, R. Bittman, T. Korte, and A. Herrmann, “Quantitative Assessment of Sterol Traffic in Living Cells by Dual Labeling with Dehydroergosterol and BODIPY-Cholesterol,” Chem. Phys. Lipids 164, 221-235 (2011).

PubMed ID: 21291873

S. Scolari, K. Müller, R. Bittman, A. Herrmann, and P. Müller, “Interaction of Mammalian Seminal Plasma Protein PDC-109 with Cholesterol – Implications for a Putative CRAC Domain,” Biochemistry 49, 9027-9031 (2010).

PubMed ID: 20863067

K. Trajkovic, C. Hsu, S. Chianti, L. Rajendran, D. Wenzel, F. Wieland, P. Schwille, B. Brügger, and M. Simons, "Ceramide Triggers Budding of Exosome Vesicles into Multivesicular Endosomes," Science 319, 1244-1247 (2008).

PubMed ID: 18309083

S. Chiantia, J. Ries, G. Chwastek, D. Carrer, Z. Li, R. Bittman, and P. Schwille, “Role of Ceramide in Membrane Protein Organization Investigated by Combined AFM and FCS,” Biochim. Biophys. Acta Biomembranes 1778, 1356-1364 (2008).

PubMed ID: 18346453

B. Y. Baker, R. F. Epand, R. M. Epand, and W. L. Miller, "Cholesterol Binding Does Not predict Activity of the Steroidogenic Acute Regulatory Protein, StAR," Biochemistry 282, 10223-10232 (2007).

PubMed ID: 17301050

J. E. Shaw, R. F. Epand, K. Sinnathamby, Z. Li, R. Bittman, R. M. Epand, and C. M. Yip, “Tracking Peptide-Membrane Interactions: Insights from in situ Coupled Confocal-Atomic Force Microscopy Imaging of NAP-22 Peptide Insertion and Assembly,” J. Struct. Biol. 155, 458-469 (2006).

PubMed ID: 16889981

J. E. Shaw, R. F. Epand, R. M. Epand, Z. Li, R. Bittman, and C. M. Yip, “Correlated Fluorescence-Atomic Force Microscopy of Membrane Domains: Structure of Fluorescence Probes Determines Lipid Localization,” Biophys J. 90, 2170-2178 (2006).

 PubMed ID: 16361347

Z. Li and R. Bittman, “Synthesis and Spectral Properties of Cholesterol- and FTY720-containing Boron Dipyrromethene Dyes,” J. Org. Chem. 72, 8376-8382 (2007).

PubMed ID: 17914846

M. Hölttä-Vuori, R. L. Uronen, J. Repakova, E. Salonen, I. Vattulainen, P. Panula, Z. Li, R. Bittman, and E. Ikonen, “BODIPY-Cholesterol: A New Tool to Visualize Sterol Trafficking in Living Cells and Organisms,” Traffic 9, 1839-1849 (2008).

 PubMed ID: 18647169

D. L. Marks, R. Bittman, and R. E. Pagano, “Use of Bodipy-labeled Sphingolipid and Cholesterol Analogs to Examine Membrane Microdomains in Cells,” Histochem. Cell Biol. 130, 819-832 (2008).

PubMed ID: 18820942

F. S. Ariola, Z. Li, C. Cornejo, R. Bittman, and A. A. Heikal, “Membrane Fluidity and Lipid Order in Ternary Giant Unilamellar Vesicles Using a New Bodipy-Cholesterol Derivative,” Biophys J. 96, 2696-2708 (2009).

PubMed ID: 19348752

Z. Li, E. Mintzer, and R. Bittman, “First Synthesis of Free Cholesterol – BODIPY Conjugates,” J. Org. Chem. 71, 1718-1721 (2006).

PubMed ID: 16468832

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