Cholestenone

Manufactured by Merck Group

Cholestenone is a laboratory chemical used as a research tool in various scientific applications. It is a steroid compound that serves as a precursor or intermediate in the synthesis and study of other steroids and related molecules. The core function of Cholestenone is to provide a building block for further chemical transformations and investigations, without making claims about its specific intended uses.

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Lab products found in correlation

4 protocols using cholestenone

Virus Entry Assay Protocol

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HOS cells expressing CD4/CCR5 were acquired from the NIH AIDS Reagent Program from Dr. Nathaniel Landau. DNA sequences encoding BaL.01 Env and NL4-3 R⁻ E⁻ Luc⁺ core were also obtained from the NIH AIDS Reagent Program from Dr. John Mascola and Dr. Nathaniel Landau, respectively. The plasmid encoding JR-FL gp160 was a kind gift of Dr. Simon Cocklin, while the plasmid encoding YU2 gp160 was a kind gift of Drs. Alon Herschorn and Joseph Sodroski. Methyl β-cyclodextrin (MβCD), cholesterol, cholestanol (5α-cholestan-3β-ol), 7-dehydrocholesterol (3β-hydroxy-5,7-cholestadiene), coprostan-3-ol (5β-cholestan-3β-ol), cholestenone (3-oxo-4-cholestene), 5α-cholestane, dehydroergosterol (Ergosta-5,7,9(11),22-tetraen-3β-ol) and Triton X-100 were purchased from Sigma–Aldrich. Laurdan dye was purchased from Invitrogen. Rabbit and mouse anti-p24 and CD45 antibodies were purchased from Abcam. D7324 anti-gp120 antibody was purchased from Aalto.

Sundaram R.V., Li H., Bailey L., Rashad A.A., Aneja R., Weiss K., Huynh J., Bastian A.R., Papazoglou E., Abrams C., Wrenn S, & Chaiken I. (2016). Impact of HIV-1 Membrane Cholesterol on Cell-Independent Lytic Inactivation and Cellular Infectivity. Biochemistry, 55(3), 447-458.

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Radiolabeled Lipid Extraction and TLC

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Mycobacterial cells labeled with [1-¹⁴C]palmitic acid, [4-¹⁴C]cholesterol, or [26-¹⁴C]cholesterol for various times were pelleted by centrifugation. The conditioned medium was also collected for extraction of lipids. The bacterial cells were washed three times with PBS-Ty. Bacterial cells and conditioned medium were extracted with chloroform-methanol (2:1) (24 (link)), and the extracts were dried under N₂ after two washes (25 (link)). Radiolabeled compounds were resolved by thin-layer chromatography (TLC) using silica gel G60 TLC plates (Millipore, Temecula, CA) developed three times in chloroform-ethyl acetate (97:3) or once in chloroform-methanol (95:5) and detected using a PhosphorImager (Typhoon 9400 scanner; GE Amersham, Sunnyvale, CA). Lipid extracts were also spiked with 2 μg of authentic cholesterol or cholestenone (both from Sigma-Aldrich) and loaded on TLC plates, which were developed with chloroform-methanol-acetic acid (95:4:1) or chloroform-methanol-ammonium hydroxide (95:4:1). After the TLC plates had been to the phosphorimaging screen overnight, they were sprayed with a charring solution consisting of 5% phosphomolybdic acid in 100% ethanol or anisaldehyde solution (26 (link)) and heated to visualize the lipids.

Marques M.A., Berrêdo-Pinho M., Rosa T.L., Pujari V., Lemes R.M., Lery L.M., Silva C.A., Guimarães A.C., Atella G.C., Wheat W.H., Brennan P.J., Crick D.C., Belisle J.T, & Pessolani M.C. (2015). The Essential Role of Cholesterol Metabolism in the Intracellular Survival of Mycobacterium leprae Is Not Coupled to Central Carbon Metabolism and Energy Production. Journal of Bacteriology, 197(23), 3698-3707.

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Phytosterol Mixture Characterization

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4‐Androstene‐3,17‐dione was purchased from TCI America. Chloroform and glycerol were purchased from Merck. Cholesterol, cholestenone, N,O‐bis(trimethylsilyl) trifluoroacetamide (BSTFA), gentamicin, pyridine, Tween 80 and tyloxapol were from Sigma. Oligonucleotides were from Sigma‐Genosys. Phytosterols were provided by Gadea Biopharma containing a mixture of different sterols (w/w percentage): brassicasterol (2.16%), stigmasterol (8.7%), campesterol (36.8%) and β‐sitosterol (54.4%).

Hernández‐Fernández G., Acedos M.G., García J.L, & Galán B. (2023). Identification of the aldolase responsible for the production of 22‐hydroxy‐23,24‐bisnorchol‐4‐ene‐3‐one from natural sterols in Mycolicibacterium smegmatis. Microbial Biotechnology, 17(1), e14270.

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Lipid Composition and Fluorescent Probes

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All lipids were from Avanti Polar Lipids (Alabaster, AL). 1,1′-dioctadecyl-3,3,3′,3′-tetramethylindodicarbocyanine perchlorate (DiD), aminonaphthalene-1,3,6-trisulfonic acid (ANTS) and p-xylene-bis-pyridinium bromide (DPX) were from Molecular Probes (Invitrogen, Carlsbad, CA). Cholesterol, lanosterol, cholestenone and coprostanol were purchased from Sigma (St Louis, MO). 1,2-dimyristoyl-phosphatidylethanolamine-N-(polyethylene glycol-triethoxysilane (DPS) and the HIV-FP with the sequence AVGIGALFLGFLGAAGSTMGAASGGGKKKKK were custom synthesized by Shearwater Polymers (Huntsville, AL) and by the Yale WM Keck Biomolecular Research Facility (New Haven, CT), respectively.

Yang S.T., Kiessling V, & Tamm L.K. (2016). Line tension at lipid phase boundaries as driving force for HIV fusion peptide-mediated fusion. Nature Communications, 7, 11401.

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