The metabolism of the fluorescent probe cholesta-5,7,9(11)-trien-3 beta-ol by rat liver.
Ontology highlight
ABSTRACT:
SUBMITTER: Wilton DC
PROVIDER: S-EPMC1153994 | biostudies-other | 1982 Nov
REPOSITORIES: biostudies-other
Similar Datasets
Project description:Cholesta-5,7,9(11)-trien-3β-ol (9,11-dehydroprovitamin D3, CTL) is used as a fluorescent probe to track the presence and migration of cholesterol in vivo. We recently described the photochemistry and photophysics of CTL in degassed and air-saturated tetrahydrofuran (THF) solution, an aprotic solvent. The zwitterionic nature of the singlet excited state, 1CTL* is revealed in ethanol, a protic solvent. In ethanol, the products observed in THF are accompanied by ether photoadducts and by photoreduction of the triene moiety to four dienes, including provitamin D3. The major diene retains the conjugated s-trans-diene chromophore and the minor is unconjugated, involving 1,4-addition of H at the 7 and 11 positions. In the presence of air, peroxide formation is a major reaction channel as in THF. X-ray crystallography confirmed the identification of two of the new diene products as well as of a peroxide rearrangement product.
| S-EPMC10222123 | biostudies-literature
Project description:1. [3alpha-(3)H]Cholesta-7,9-dien-3beta-ol is converted in high yield into cholesterol by a 10000g(av.) supernatant fraction of rat liver homogenate. 2. Incubation of cholesta-7,9-dien-3beta-ol with [4-(3)H]NADPH and rat liver microsomal fractions under anaerobic conditions resulted in (3)H being incorporated into the 14alpha-position of cholest-7-en-3beta-ol. 3. Under anaerobic conditions in the absence of NADPH cholesta-7,9-dien-3beta-ol was isomerized into cholesta-8,14-dien-3beta-ol by rat liver microsomal fractions.
| S-EPMC1174072 | biostudies-other
Project description:The biosynthesis of cholesterol from squalene and tritiated water is described. Degradation of the cholesterol indicated that C-15 may be involved in cholesterol biosynthesis. In accordance with this view it is shown that in the conversion of [2RS-(3)H(2)]mevalonic acid into cholesterol one of the hydrogen atoms at C-15 is removed. A mechanism for the removal of the 14alpha-methyl group in steroid biosynthesis that involves the labilization of a C-15 hydrogen atom is outlined. In accordance with the requirement of this scheme it is shown that 4,4'-dimethyl-cholesta-8,14-dien-3beta-ol is converted into cholesterol.
| S-EPMC1187605 | biostudies-other
Project description:The ability to image and ultimately quantitate beta-cell mass in vivo will likely have far reaching implications in the study of diabetes biology, in the monitoring of disease progression or response to treatment, and for drug development. Here, using animal models, we report on the synthesis, characterization, and intravital microscopic imaging properties of a near-infrared fluorescent exendin-4 analogue with specificity for the GLP-1 receptor on beta cells (E4(K12)-Fl). The agent demonstrated subnanomolar EC(50) binding concentrations, with high specificity and binding that could be inhibited by GLP-1R agonists. Following intravenous administration to mice, pancreatic islets were readily distinguishable from exocrine pancreas, achieving target-to-background ratios within the pancreas of 6:1, as measured by intravital microscopy. Serial imaging revealed rapid accumulation kinetics (with initial signal within the islets detectable within 3 min and peak fluorescence within 20 min of injection), making this an ideal agent for in vivo imaging.
| S-EPMC2912453 | biostudies-literature
Project description:1. The conversion of cholest-5-en-3beta-ol (cholesterol) into cholesta-5,7-dien-3beta-ol by axenic Calliphora erythrocephala larvae was demonstrated. 2. The transformation is probably direct (Delta(5)-->Delta(5,7)) and does not involve a Delta(0) intermediate (Delta(5)-->Delta(0)-->Delta(7)--> Delta(5,7)). 3. Delta(7)-bond formation involves the stereospecific elimination of the 7beta hydrogen atom. 4. The relative amounts of free and esterified sterols were determined in larvae grown on cholesterol as sole sterol source and on 5alpha-cholestan-3beta-ol supplemented with minimal amounts of cholesterol. 5. The significance of the results is assessed in relation to the probable role of cholesta-5,7-dien-3beta-ol as an intermediate in the biosynthesis of ecdysones.
| S-EPMC1172472 | biostudies-other
Project description:There are two independent mol-ecules (A and B) in the asymmetric unit of the title compound, C(19)H(23)NOS. In each mol-ecule, the seven-membered thiepine ring is bent into a slightly twisted V-shape. The dihedral angles between the mean planes of the two benzene rings fused to the thiepine ring are 75.7 (5) in mol-ecule A and 73.8 (4)° in mol-ecule B. In both mol-ecules, an intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, weak inter-molecular C-H⋯O and C-H⋯π-ring inter-actions are observed.
| S-EPMC2980032 | biostudies-literature
Project description:Herein, a coumarin fluorescent probe (Probe 1) was developed for the ratiometric detection of β-galactosidase (β-gal) activity. The detection range was 0-0.1 U mL-1 and 0.2-0.8 U mL-1, and the limit of detection (LOD) was 0.0054 U mL-1. Moreover, the luminous intensity of Probe 1 increased gradually with increase in β-gal activity. It could be observed under 254 nm UV irradiation by the naked eye. Furthermore, this method only required a small amount of sample (20 μL) and a short analytical time (30 min) for the detection of β-gal activity with a low LOD. Probe 1 was successfully used to detect β-gal activity in real fruit samples, and can be applied to the quantitative and qualitative detection of β-gal activity.
| S-EPMC8697631 | biostudies-literature
Project description:Drug-induced liver injury (DILI) is an important cause of potentially fatal liver disease. Herein, we report the development of a molecular probe (LW-OTf) for the detection and imaging of two biomarkers involved in DILI. Initially, primary reactive oxygen species (ROS) superoxide (O2˙-) selectively activates a near-infrared fluorescence (NIRF) output by generating fluorophore LW-OH. The C[double bond, length as m-dash]C linker of this hemicyanine fluorophore is subsequently oxidized by reactive nitrogen species (RNS) peroxynitrite (ONOO-), resulting in cleavage to release xanthene derivative LW-XTD, detected using two-photon excitation fluorescence (TPEF). An alternative fluorescence pathway can occur through cleavage of LW-OTf by ONOO- to non-fluorescent LW-XTD-OTf, which can react further with the second analyte O2˙- to produce the same LW-XTD fluorescent species. By combining NIRF and TPEF, LW-OTf is capable of differential and simultaneous detection of ROS and RNS in DILI using two optically orthogonal channels. Probe LW-OTf could be used to detect O2˙- or O2˙- and ONOO- in lysosomes stimulated by 2-methoxyestradiol (2-ME) or 2-ME and SIN-1 respectively. In addition, we were able to monitor the chemoprotective effects of tert-butylhydroxyanisole (BHA) against acetaminophen (APAP) toxicity in living HL-7702 cells. More importantly, TPEF and NIRF imaging confirmed an increase in levels of both O2˙- and ONOO- in mouse livers during APAP-induced DILI (confirmed by hematoxylin and eosin (H&E) staining).
| S-EPMC8179478 | biostudies-literature
Project description:Hydrogen peroxide (H2O2) is important in the regulation of a variety of biological processes and is involved in various diseases. Quantitative measurement of H2O2 levels at the subcellular level is important for understanding its positive and negative effects on biological processes. Herein, a two-photon ratiometric fluorescent probe (SHP-Cyto) with a boronate-based carbamate leaving group as the H2O2 reactive trigger and 6-(benzo[d]thiazol-2'-yl)-2-(N,N-dimethylamino) naphthalene (BTDAN) as the fluorophore was synthesized and examined for its ability to detect cytosolic H2O2 in situ. This probe, based on the specific reaction between boronate and H2O2, displayed a fluorescent color change (455 to 528 nm) in response to H2O2 in the presence of diverse reactive oxygen species in a physiological medium. In addition, ratiometric two-photon microscopy (TPM) images with SHP-Cyto revealed that H2O2 levels gradually increased from brain to kidney, skin, heart, lung, and then liver tissues. SHP-Cyto was successfully applied to the imaging of endogenously produced cytosolic H2O2 levels in live cells and various rat organs by using TPM.
| S-EPMC5754560 | biostudies-literature
Project description:Here we reported the development of the first photoinduced electron transfer (PeT) probe (1) to directly locate β-amyloid aggregates (Aβ plaques) in the brain without the need of post-washing procedures. The probe showed a high affinity for Aβ aggregates with a Kd value of 3.5nM. It is weakly emissive by itself with its fluorescence quenched by electron transfer from PeT donor to the excited fluorophore. But selective binding to Aβ plaques would attenuate the PeT process and restore the fluorescence, therefore facilitating the tracking of Aβ plaques. The probe is advantageous in that its fluorescence is environment-less-sensitive and no washing procedure is required to provide high contrast fluorescent signal when applied to stain brain tissues. As a proof of concept, its application has been exemplified by staining Aβ plaques in slices of brain tissue from double transgenic (APP/PS1) mice of Alzheimer's disease.
| S-EPMC4874256 | biostudies-literature