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Journal articles on the topic 'Steroid enantiomers'

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1

Li, Wenjun, Douglas F. Covey, Juha-Matti Alakoskela, Paavo K. J. Kinnunen, and Joe Henry Steinbach. "Enantiomers of Neuroactive Steroids Support a Specific Interaction with the GABA-C Receptor as the Mechanism of Steroid Action." Molecular Pharmacology 69, no. 6 (2006): 1779–82. http://dx.doi.org/10.1124/mol.106.022863.

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2

Sheikh, Sana U., and Joseph C. Touchstone. "Effect of subambient temperatures on separation of steroid enantiomers by high-performance liquid chromatography." Analytical Chemistry 59, no. 10 (1987): 1472–73. http://dx.doi.org/10.1021/ac00137a022.

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3

Walle, UK, TC Fagan, MJ Topmiller, EC Conradi, and T. Walle. "The influence of gender and sex steroid hormones on the plasma binding of propranolol enantiomers." British Journal of Clinical Pharmacology 37, no. 1 (1994): 21–25. http://dx.doi.org/10.1111/j.1365-2125.1994.tb04233.x.

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4

Liu, Ya-Ping, Sheng-Tao Fang, Zhen-Zhen Shi, Bin-Gui Wang, Xiao-Nian Li, and Nai-Yun Ji. "Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus Penicillium oxalicum." Marine Drugs 19, no. 1 (2020): 9. http://dx.doi.org/10.3390/md19010009.

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Three new phenylhydrazones, penoxahydrazones A–C (compounds 1–3), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and mass spectroscopic data, and the absolute configurations of 1, 4, and 5 were established on the basis of X-ray crystallography or ECD calculations. Compound 1 represents the first natural phenylhydrazone-bearing steroid, while compounds 2 and 3 are rarely occur
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5

Sneitz, Nina, Kathiresan Krishnan, Douglas F. Covey та Moshe Finel. "Glucuronidation of the steroid enantiomers ent-17β-estradiol, ent-androsterone and ent-etiocholanolone by the human UDP-glucuronosyltransferases". Journal of Steroid Biochemistry and Molecular Biology 127, № 3-5 (2011): 282–88. http://dx.doi.org/10.1016/j.jsbmb.2011.08.008.

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6

Audia, James E., David E. Lawhorn та Jack B. Deeter. "Synthesis of the individual enantiomers of the benzoquinolinone human type 1 steroid 5-α-reductase inhibitors LY191704 and LY266111". Tetrahedron Letters 34, № 44 (1993): 7001–4. http://dx.doi.org/10.1016/s0040-4039(00)61581-2.

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7

NAGAMINE, Sachiko, Eri HORISAKA, Yukari FUKUYAMA, et al. "Stereoselective Reductive Metabolism of Metyrapone and Inhibitory Activity of Metyrapone Metabolites, Metyrapol Enantiomers, on Steroid 11.BETA.-Hydroxylase in the Rat." Biological & Pharmaceutical Bulletin 20, no. 2 (1997): 188–92. http://dx.doi.org/10.1248/bpb.20.188.

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8

AUDIA, J. E., D. E. LAWHORN та J. B. DEETER. "ChemInform Abstract: Synthesis of the Individual Enantiomers of the Benzoquinolinone Human Type 1 Steroid 5-α-Reductase Inhibitors LY191704 and LY266111." ChemInform 25, № 4 (2010): no. http://dx.doi.org/10.1002/chin.199404178.

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9

Krishnan, Kathiresan, Brad D. Manion, Amanda Taylor та ін. "Neurosteroid Analogues. 17. Inverted Binding Orientations of Androsterone Enantiomers at the Steroid Potentiation Site on γ-Aminobutyric Acid Type A Receptors". Journal of Medicinal Chemistry 55, № 3 (2012): 1334–45. http://dx.doi.org/10.1021/jm2014925.

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10

Kravchenko, Anastasia, Ekaterina Kolobova, and Liudmila Kartsova. "Multifunction covalent coatings for separation of amino acids, biogenic amines, steroid hormones, and ketoprofen enantiomers by capillary electrophoresis and capillary electrochromatography." SEPARATION SCIENCE PLUS 3, no. 4 (2020): 102–11. http://dx.doi.org/10.1002/sscp.201900098.

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11

Wouters, Walter, Roland de Coster, Jacky van Dun, et al. "Comparative effects of the aromatase inhibitor R76713 and of its enantiomers R83839 and R83842 on steroid biosynthesis in vitro and in vivo." Journal of Steroid Biochemistry and Molecular Biology 37, no. 6 (1990): 1049–54. http://dx.doi.org/10.1016/0960-0760(90)90464-v.

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12

Chisari, Mariangela, Lawrence N. Eisenman, Kathiresan Krishnan, et al. "The Influence of Neuroactive Steroid Lipophilicity on GABAA Receptor Modulation: Evidence for a Low-Affinity Interaction." Journal of Neurophysiology 102, no. 2 (2009): 1254–64. http://dx.doi.org/10.1152/jn.00346.2009.

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Anesthetic steroids with actions at γ-aminobutyric acid type A receptors (GABAARs) may access transmembrane domain binding site(s) directly from the plasma cell membrane. Accordingly, the effective concentration in lipid phase and the ability of the steroid to meet pharmacophore requirements for activity will both contribute to observed steady-state potency. Furthermore, onset and offset of receptor effects may be rate limited by lipid partitioning. Here we show that several GABA-active steroids, including naturally occurring neurosteroids, of different lipophilicity differ in kinetics and pot
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13

Hudson, Cook, Grimes, Muller, Adams, and Wandinger-Ness. "Dual Actions of Ketorolac in Metastatic Ovarian Cancer." Cancers 11, no. 8 (2019): 1049. http://dx.doi.org/10.3390/cancers11081049.

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Cytoreductive surgery and chemotherapy are cornerstones of ovarian cancer treatment, yet disease recurrence remains a significant clinical issue. Surgery can release cancer cells into the circulation, suppress anti-tumor immunity, and induce inflammatory responses that support the growth of residual disease. Intervention within the peri-operative window is an under-explored opportunity to mitigate these consequences of surgery and influence the course of metastatic disease to improve patient outcomes. One drug associated with improved survival in cancer patients is ketorolac. Ketorolac is a ch
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14

Biellmann, Jean-Francois. "Enantiomeric Steroids: Synthesis, Physical, and Biological Properties." Chemical Reviews 103, no. 5 (2003): 2019–34. http://dx.doi.org/10.1021/cr020071b.

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15

Yuan, Xucan, Xianhui Li, Ping Guo, Zhili Xiong, and Longshan Zhao. "Simultaneous enantiomeric analysis of chiral non-steroidal anti-inflammatory drugs in water, river sediment, and sludge using chiral liquid chromatography-tandem mass spectrometry." Analytical Methods 10, no. 36 (2018): 4404–13. http://dx.doi.org/10.1039/c8ay01417e.

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16

Kano, Koji, Naofumi Tsujino, and Myounghee Kim. "Mechanisms for steroid-induced conformational enantiomerism of bilirubin in protic solvents." Journal of the Chemical Society, Perkin Transactions 2, no. 10 (1992): 1747. http://dx.doi.org/10.1039/p29920001747.

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17

Kluess, Brigitte, Wolfgang Kreiser, Tony Sukri, Wolfgang Poll, and Hartmut Wunderlich. "(R)-5-[(1R,2R)-1-Ethyl-2- (4-oxocyclohexyl)butyl]oxepan-2-one, an Enantiopure ‘Pseudosteroid′." Zeitschrift für Naturforschung B 61, no. 1 (2006): 111–12. http://dx.doi.org/10.1515/znb-2006-0122.

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The title compound C18H30O3 represents an optically pure member of a class of ‘pseudosteroids’, i. e. perhydrostilbene derivatives which mimic steroidal androgens (in the way like hexestrols or stilbestrols serve to substitute natural estrogens). The molecule 2 is characterized by three consecutive chiral centers leading to eight possible stereoisomers including four diastereomers. All enantiomers have been separated and their biological profile has been determined. As the result of the crystal structure presented here the two symmetry independent molecules display the configuration R,R,R at t
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18

Brownholland, David P., та Douglas F. Covey. "Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ 22 steroids". Steroids 121 (травень 2017): 22–31. http://dx.doi.org/10.1016/j.steroids.2017.03.002.

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19

Alakoskela, Juha-Matti, Douglas F. Covey, and Paavo K. J. Kinnunen. "Lack of enantiomeric specificity in the effects of anesthetic steroids on lipid bilayers." Biochimica et Biophysica Acta (BBA) - Biomembranes 1768, no. 1 (2007): 131–45. http://dx.doi.org/10.1016/j.bbamem.2006.07.011.

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20

Kummer, Matthias, H. J. Palme, and G. Werner. "Resolution of enantiomeric steriod by high-performance liquid chromatography on chiral stationary phases." Journal of Chromatography A 749, no. 1-2 (1996): 61–68. http://dx.doi.org/10.1016/0021-9673(96)00364-0.

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21

Al-Judaibi, B., N. Chande, G. K. Dresser, N. Sultan, and J. C. Gregor. "Gastric Acid-Related Diseases: Focus on Esomeprazole." Clinical Medicine Insights: Therapeutics 2 (January 2010): CMT.S4500. http://dx.doi.org/10.4137/cmt.s4500.

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Esomeprazole (S-omeprazole) is a single optical enantiomer proton-pump inhibitor (PPI) approved for the management of gastro-oesophageal reflux disease, the prevention and treatment of Non-Steroidal Anti-Inflammatory Drugs (NSAID) associated gastric ulcer disease, treatment of duodenal ulcer disease associated with Helicobacter pylori infection, and the treatment of Zollinger-Ellison syndrome. Esomeprazole has been shown to be safe and effective during pregnancy and was introduced to the market in 2001. PPI therapy may interact with clopidogrel by cytocrome 2C19. Clopidogrel is a prodrug which
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22

Melnik, M. G. "Choice of optimal non-steroidal anti-inflammatory drug from position of cardiologist." Medical alphabet, no. 36 (January 13, 2021): 55–60. http://dx.doi.org/10.33667/2078-5631-2020-36-55-60.

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Non-steroidal anti-inflammatory drugs (NSAIDs) are a large and extremely heterogeneous group of drugs that have a single mechanism of action and therapeutic activity. The article lists their main subgroups by chemical structure and selectivity of action, describes the most typical side effects due to the pharmacodynamic characteristics of drugs, explains the reasons for their formation, and describes the cardiovascular complications they cause. Taking into account the lack of the desired safety of classical NSAIDs for cardiological practice, the possibility of optimizing their tolerance with t
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23

Mahmud, T., S. Somasundaram, G. Sigthorsson, et al. "Enantiomers of flurbiprofen can distinguish key pathophysiological steps of NSAID enteropathy in the rat." Gut 43, no. 6 (1998): 775–82. http://dx.doi.org/10.1136/gut.43.6.775.

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Background—Non-steroidal anti-inflammatory drugs (NSAIDs) cause gastrointestinal damage by a non-prostaglandin (PG) dependent “topical” action and by inhibiting cyclooxygenase.Aims—To discriminate between these two effects by studying some key pathophysiological steps in NSAID enteropathy following administration of (R)- and (S)-flurbiprofen, the racemic mixture, and an uncoupler, dinitrophenol.Methods—The effects of dinitrophenol, racemic, (R)-, and (S)-flurbiprofen on mitochondria were assessed in vitro and on key pathophysiological features of small intestinal damage in vivo (ultrastructure
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24

Patel, Mitul P., Nathaneal T. Green, Jacob K. Burch, Kimberly A. Kew, and Robert M. Hughes. "Screening of Biocatalysts for Synthesis of the Wieland–Miescher Ketone." Catalysts 10, no. 9 (2020): 1063. http://dx.doi.org/10.3390/catal10091063.

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Lipases, a versatile class of biocatalysts, have been shown to function in non-aqueous media/organic solvents and to possess “promiscuous” catalytic activity for a wide range of organic transformations. In this study, we explored the biocatalytic properties of a library of commercially available lipases by screening them for catalysis of a one-pot synthesis of Wieland–Miescher ketone, an important intermediate in the synthesis of biologically active compounds such as steroids and terpenoids, from methyl vinyl ketone and 2-methyl-1,3-cyclohexanedione. As a direct outgrowth of this screen, we cr
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25

Sánchez-López, Elena, Gerard Esteruelas, Alba Ortiz, et al. "Dexibuprofen Biodegradable Nanoparticles: One Step Closer towards a Better Ocular Interaction Study." Nanomaterials 10, no. 4 (2020): 720. http://dx.doi.org/10.3390/nano10040720.

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Ocular inflammation is one of the most prevalent diseases in ophthalmology, which can affect various parts of the eye or the surrounding tissues. Non-steroidal anti-inflammatory drugs (NSAIDs) such as ibuprofen, are commonly used to treat ocular inflammation in the form of eye-drops. However, their bioavailability in ocular tissues is very low (less than 5%). Therefore, drug delivery systems such as biodegradable polymeric PLGA nanoparticles constitute a suitable alternative to topical eye administration, as they can improve ocular bioavailability and simultaneously reduce drug induced side ef
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26

Dean, Pamela M. "Structural and Thermal Characterization of Cyclodextrin - Suprofen Complexes." Australian Journal of Chemistry 60, no. 2 (2007): 133. http://dx.doi.org/10.1071/ch06371.

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Suprofen, α-methyl-4-(2-thienylcarbonyl)benzeneacetic acid, a non-steroidal anti-inflammatory drug (NSAID), forms an inclusion complex with β-cyclodextrin of formula (β-cyclodextrin)2·(suprofen)·20H2O 1 and with TRIMEB (a permethylated β-cyclodextrin) of formula (β-cyclodextrin)·(suprofen)·0H2O 2. These species were investigated by thermal analysis techniques (HSM, TGA, DSC), powder X-ray diffraction (PXRD), and single-crystal X-ray diffraction at 173 K. Thermal analysis of 1 revealed dehydration followed by decomposition at 311.0°C, and only melting at 161.0°C for 2. The host-to-drug stoichio
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27

Kummer, Matthias, and G. Werner. "Chiral resolution of enantiomeric steroids by high-performance liquid chromatography on amylose tris(3,5-dimethylphenylcarbamate) under reversed-phase conditions." Journal of Chromatography A 825, no. 2 (1998): 107–14. http://dx.doi.org/10.1016/s0021-9673(98)00719-5.

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28

Rinchard, J., K. J. Lee, K. Dabrowski, A. Ciereszko, J. H. Blom, and J. S. Ottobre. "Influence of gossypol from dietary cottonseed meal on haematology, reproductive steroids and tissue gossypol enantiomer concentrations in male rainbow trout (Oncorhynchus mykiss )." Aquaculture Nutrition 9, no. 4 (2003): 275–82. http://dx.doi.org/10.1046/j.1365-2095.2003.00253.x.

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29

Hugo F. Miranda, Viviana Noriega, Fernando Sierralta, Ramón Sotomayor-Zárate, and Juan Carlos Prieto. "Adrenergic modulation of dexketoprofen antinociception in murine formalin orofacial pain." World Journal of Advanced Research and Reviews 9, no. 2 (2021): 172–78. http://dx.doi.org/10.30574/wjarr.2021.9.2.0063.

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Non-steroidal anti-inflammatory drugs (NSAIDs) are widely used in pain whose mechanism of action is the inhibition of cyclooxygenase enzymes (COXs), however, there are evidence of other mechanisms of action, such as the inhibition of substance P, interaction with systems NO, monoaminergic and others. The objective of the present work was to study the participation of a-1 (prazosin) and a-2 (yohimbine) adrenoceptors antagonists in the antinociception of dexketoprofen, the S (+) enantiomer of ketoprofen. The antinociception evaluation was thru the mice orofacial formalin assay. Dexketoprofen (DE
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30

Hu, Yuefei, Lisa L. Wittmer, Melissa Kalkbrenner, Alex S. Evers, Charles F. Zorumski, and Douglas F. Covey. "Neurosteroid analogues. Part 5.1 Enantiomers of neuroactive steroids and benz[e]indenes: total synthesis, electrophysiological effects on GABAA receptor function and anesthetic actions in tadpoles." Journal of the Chemical Society, Perkin Transactions 1, no. 24 (1997): 3665–72. http://dx.doi.org/10.1039/a703212i.

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31

Sonawane, Dipti R., Jugalkishor B. Jaju, Ganesh R. Pawar, and Punam A. Gosavi. "Evaluation of analgesic and anti-inflammatory activity of Levocetirizine in albino rats." International Journal of Basic & Clinical Pharmacology 8, no. 8 (2019): 1805. http://dx.doi.org/10.18203/2319-2003.ijbcp20193182.

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Background: Levocetirizine, the R-enantiomer of Cetirizine has pharmacokinetically and pharmacodynamically favourable characteristics, with rapid onset of action, high bioavailability, high affinity for and occupancy of the H1-receptor, limited distribution, minimal hepatic metabolism together with minimal side effects. Non-steroidal anti-inflammatory drugs (NSAIDs) have been used for many years for analgesic, anti-inflammatory, and more recently in the case of aspirin, antithrombotic purposes. Because of the significant side effect profiles of steroidal and NSAID medications, there is a great
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32

Liu, Jay, Catherine C. Y. Chang, Emily J. Westover, Douglas F. Covey, and Ta-Yuan Chang. "Investigating the allosterism of acyl-CoA:cholesterol acyltransferase (ACAT) by using various sterols: in vitro and intact cell studies." Biochemical Journal 391, no. 2 (2005): 389–97. http://dx.doi.org/10.1042/bj20050428.

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ACAT1 (acyl-CoA:cholesterol acyltransferase 1) is thought to have two distinct sterol-binding sites: a substrate-binding site and an allosteric-activator site. In the present work, we investigated the structural features of various sterols as substrates and/or activators in vitro. The results show that without cholesterol, the plant sterol sitosterol is a poor substrate for ACAT. In the presence of cholesterol, ACAT1-mediated esterification of sitosterol is highly activated while ACAT2-mediated esterification of sitosterol is only moderately activated. For ACAT1, we show that the stereochemist
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33

HU, Y., L. L. WITTMER, M. KALKBRENNER, A. S. EVERS, C. F. ZORUMSKI, and D. F. COVEY. "ChemInform Abstract: Neurosteroid Analogues. Part 5. Enantiomers of Neuroactive Steroids and Benz[e]indenes: Total Synthesis, Electrophysiological Effects on GABAA Receptor Function and Anesthetic Actions in Tadpoles." ChemInform 29, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199818209.

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34

Feng, Rentian, Gulsum Anderson, Guozhi Xiao та ін. "SDX-308, a Structural Analog of Etodolac, Inhibits NF-κB Activity Resulting in Significant Inhibition of Osteoclast Formation/Activity and Multiple Myeloma Cell Growth." Blood 108, № 11 (2006): 3456. http://dx.doi.org/10.1182/blood.v108.11.3456.3456.

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Abstract Multiple myeloma (MM) is characterized by increased osteoclast activity resulting in bone destruction and the development of lytic bone lesions. Current treatment modalities have resulted in an increased overall survival in MM patients and new drugs are required that specifically inhibit bone destruction. Etodolac is a non-steroidal anti-inflammatory drug that is approved for treatment of degenerative joint disease and rheumatoid arthritis. SDX-101, an R-enantiomer of Etodolac, was recently demonstrated to induce cytotoxicity, overcome drug resistance, and enhance the activity of dexa
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35

Kravchenko, Anastasia, Ekaterina Kolobova, and Liudmila Kartsova. "Back Cover: Multifunction covalent coatings for separation of amino acids, biogenic amines, steroid hormones, and ketoprofen enantiomers by capillary electrophoresis and capillary electrochromatography." SEPARATION SCIENCE PLUS 3, no. 4 (2020). http://dx.doi.org/10.1002/sscp.202070010.

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36

Biellmann, Jean-Francois. "Enantiomeric: Steroids: Synthesis, Physical, and Biological Properties." ChemInform 34, no. 32 (2003). http://dx.doi.org/10.1002/chin.200332248.

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37

Creemers, Sara G., Richard A. Feelders, Frank H. de Jong, et al. "Levoketoconazole, the 2S,4R Enantiomer of Ketoconazole, a New Steroidogenesis Inhibitor for Cushing’s Syndrome Treatment." Journal of Clinical Endocrinology & Metabolism, January 5, 2021. http://dx.doi.org/10.1210/clinem/dgaa989.

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Abstract Introduction Racemic ketoconazole (RK) is a steroidogenesis inhibitor used for treatment of Cushing’s syndrome. Levoketoconazole (COR-003), the pure 2S,4R enantiomer, is potentially more potent and safe compared to RK. We compared in vitro effects of levoketoconazole and RK on adrenocortical and pituitary adenoma cells. Materials and methods HAC15 cells and 15 primary human neoplastic adrenocortical cultures (+/- ACTH), and murine (AtT20) and human corticotroph adenoma cultures were incubated with levoketoconazole or RK (0.01-10µM). Cortisol and ACTH were measured using a chemilumines
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38

Grimes, Martha M., S. Ray Kenney, Dayna R. Dominguez, et al. "The R-enantiomer of ketorolac reduces ovarian cancer tumor burden in vivo." BMC Cancer 21, no. 1 (2021). http://dx.doi.org/10.1186/s12885-020-07716-1.

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Abstract Background Rho-family GTPases, including Ras-related C3 botulinum toxin substrate 1 (Rac1) and cell division control protein 42 (Cdc42), are important modulators of cancer-relevant cell functions and are viewed as promising therapeutic targets. Based on high-throughput screening and cheminformatics we identified the R-enantiomer of an FDA-approved drug (ketorolac) as an inhibitor of Rac1 and Cdc42. The corresponding S-enantiomer is a non-steroidal anti-inflammatory drug (NSAID) with selective activity against cyclooxygenases. We reported previously that R-ketorolac, but not the S-enan
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39

Khramtsova, Ekaterina A., Alexandra A. Ageeva, Alexander A. Stepanov, Viktor F. Plyusnin, and Tatyana V. Leshina. "Photoinduced Electron Transfer in Dyads with (R)-/(S)-Naproxen and (S)-Tryptophan." Zeitschrift für Physikalische Chemie 231, no. 3 (2017). http://dx.doi.org/10.1515/zpch-2016-0842.

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AbstractShort-lived intermediates arising from the donor-acceptor interaction of non-steroidal anti-inflammatory drug (NSAID) – (S)-naproxen (NPX) and its (R)-enantiomer with the tryptophan amino acid residue (Trp) have been studied by spin chemistry and photochemistry methods. The donor-acceptor interaction has caried out in a model linked system – dyad under the UV-irradiation. Interest in the NPX-Trp dyad diastereomers is connected with the possibility of using them as models of ligand-enzyme binding as long as amino acid residues are located at the enzyme’s active centers. It is these resi
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40

Noriega, Viviana, Fernando Sierralta, Nicolás Aranda, et al. "Isobolographic Antinociception of Nonsteroidal Anti-inflammatory Drugs in Rodent Formalin Orofacial Pain." Pharmaceutical and Biomedical Research, November 17, 2020. http://dx.doi.org/10.18502/pbr.v6i3.4647.

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Background: Diverse studies suggest that non-steroidal anti-inflammatory drugs (NSAIDs) induce antinociception through the inhibition of cyclooxygenases.
 Objectives: This study evaluated the effect of NSAIDs in inducing antinociception either alone or in combination in mice formalin orofacial pain.
 Methods: Male mice were injected intraperitoneally with dexibuprofen, dexketoprofen, diclofenac meloxicam, metamizole and piroxicam. Then from a dose-response curve the ED50 (dose that produce 50% of maximum effect) was obtained from each drug.
 Results: The administration of NSAIDs
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