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Pregnenolone

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https://www.readbyqxmd.com/read/27917709/synthesis-of-some-steroidal-derivatives-with-side-chain-of-20-and-22-hydrazone-aromatic-heterocycles-and-their-antiproliferative-acitivity
#1
Chunfang Gan, Liang Liu, Jianguo Cui, Zhiping Liu, Haixin Shi, Qifu Lin, Haibing Sheng, Chunhui Yang, Yanmin Huang
BACKGROUND: The modification of steroidal structure is commonly used to change the biological activity of steroids in medicinal chemistry. Some steroids containing heterocycles exhibit distinct cytotoxicity against various cancer cell lines and have been gotten wide attention over the years by medicinal chemists for drug discovery. METHODS: Using pregnenolone and stigmasterol as starting materials, via different chemical reaction, two series of heterosteroids with side chain of 20- and 22-hydrazone aromatic cycles or heterocycles in their structures were synthesized and characterized by IR, NMR and HRMS...
December 5, 2016: Medicinal Chemistry
https://www.readbyqxmd.com/read/27914864/serum-dhea-s-concentration-correlates-with-clinical-symptoms-and-neurocognitive-function-in-patients-with-bipolar-ii-disorder-a-case-controlled-study
#2
Sheng-Yu Lee, Liang-Jen Wang, Cheng-Ho Chang, Chih-Ching Wu, Hsing-Ling Chen, Shih-Hsien Lin, Chin-Liang Chu, Ti Lu, Ru-Band Lu
OBJECTIVES: Dysregulation of the neuroendocrine system including dehydroepiandrosterone (DHEA), dehydroepiandrosterone sulfate (DHEA-S), and pregnenolone may play a role in the pathophysiology of bipolar II disorder (BP-II). The aims of the current study are to determine (a) the differences in DHEA, DHEA-S and pregnenolone in patients with BP-II and controls; and (b) the correlation of levels of the above hormones, cognitive function, and clinical symptoms. METHODS: Patients diagnosed with BP-II and healthy controls were recruited from psychiatric department...
November 30, 2016: Progress in Neuro-psychopharmacology & Biological Psychiatry
https://www.readbyqxmd.com/read/27913096/a-sensitive-and-accurate-lc-ms-ms-assay-with-the-derivatization-of-1amino4methylpiperazine-applied-to-serum-allopregnanolone-pregnenolone-and-androsterone-in-pre-and-postmenopausal-women
#3
Yuyong Ke, Renaud Gonthier, Fernand Labrie
The concentrations of allopregnanolone (Allopreg), pregnenolone (Preg) and androsterone (ADT) are very low in the circulation, especially in postmenopausal women, resulting in a considerable challenge for their accurate measurements in serum or plasma. In this report, a sensitive and reliable LC-MS/MS assay method has been developed using a simple sample preparation and the 1-Amino-4-methylpiperazine (AMP) derivatization procedure. A 5pg/ml (0.1pg on column) of low limit of quantitation has been achieved for Allopreg, Preg and ADT, with a sensitivity comparable to data obtained with the commercial reagent...
November 29, 2016: Steroids
https://www.readbyqxmd.com/read/27890531/short-term-effects-of-diabetes-on-neurosteroidogenesis-in-the-rat-hippocampus
#4
Simone Romano, Nico Mitro, Silvia Diviccaro, Roberto Spezzano, Matteo Audano, Luis Miguel Garcia-Segura, Donatella Caruso, Roberto Cosimo Melcangi
Diabetes may induce neurophysiological and structural changes in the central nervous system (i.e., diabetic encephalopathy). We here explored whether the levels of neuroactive steroids (i.e., neuroprotective agents) in the hippocampus may be altered by short-term diabetes (i.e., one month). To this aim, by liquid chromatography-tandem mass spectrometry we observed that in the experimental model of the rat raised diabetic by streptozotocin injection, one month of pathology induced changes in the levels of several neuroactive steroids, such as pregnenolone, progesterone and its metabolites (i...
November 23, 2016: Journal of Steroid Biochemistry and Molecular Biology
https://www.readbyqxmd.com/read/27888513/decreased-allopregnanolone-levels-in-cerebrospinal-fluid-obtained-during-status-epilepticus
#5
Stefano Meletti, Chiara Lucchi, Giulia Monti, Giada Giovannini, Roberta Bedin, Tommaso Trenti, Cecilia Rustichelli, Giuseppe Biagini
Neuroactive steroids are increasingly considered as relevant modulators of neuronal activity. Especially allopregnanolone (AP) and pregnenolone sulfate (PS) have been shown to possess, respectively, anticonvulsant or proconvulsant properties. In view of the potential role of these steroids, we aimed at evaluating AP and PS levels in cerebrospinal fluid (CSF) and blood samples obtained from patients with status epilepticus (SE). To this purpose, we enrolled 41 patients affected by SE and 41 subjects investigated for nonepileptic neurologic disorders...
November 26, 2016: Epilepsia
https://www.readbyqxmd.com/read/27884493/initial-genetic-dissection-of-serum-neuroactive-steroids-following-chronic-intermittent-ethanol-across-bxd-mouse-strains
#6
Patrizia Porcu, Todd K O'Buckley, Marcelo F Lopez, Howard C Becker, Michael F Miles, Robert W Williams, A Leslie Morrow
Neuroactive steroids modulate alcohol's impact on brain function and behavior. Ethanol exposure alters neuroactive steroid levels in rats, humans, and some mouse strains. We conducted an exploratory analysis of the neuroactive steroids (3α,5α)-3-hydroxypregnan-20-one (3α,5α-THP), (3α,5α)-3,21-dihydroxypregnan-20-one (3α,5α-THDOC), and pregnenolone across 126-158 individuals and 19 fully inbred strains belonging to the BXD family, which were subjected to air exposure, or chronic intermittent ethanol (CIE) exposure...
November 10, 2016: Alcohol
https://www.readbyqxmd.com/read/27855232/novel-scc-mutation-in-a-patient-of-mexican-descent-with-sex-reversal-salt-losing-crisis-and-adrenal-failure
#7
Jasmeet Kaur, Alan M Rice, Elizabeth O'Connor, Anil Piya, Bradley Buckler, Himangshu S Bose
: Congenital adrenal hyperplasia (CAH) is caused by mutations in cytochrome P450 side chain cleavage enzyme (CYP11A1 and old name, SCC). Errors in cholesterol side chain cleavage by the mitochondrial resident CYP11A1 results in an inadequate amount of pregnenolone production. This study was performed to evaluate the cause of salt-losing crisis and possible adrenal failure in a pediatric patient whose mother had a history of two previous stillbirths and loss of another baby within a week of birth...
2016: Endocrinology, Diabetes & Metabolism Case Reports
https://www.readbyqxmd.com/read/27815506/plasma-membrane-origin-of-the-steroidogenic-pool-of-cholesterol-used-in-hormone-induced-acute-steroid-formation-in-leydig-cells
#8
Sathvika Venugopal, Daniel Benjamin Martinez-Arguelles, Seimia Chebbi, Françoise Hullin-Matsuda, Toshihide Kobayashi, Vassilios Papadopoulos
Hormone-sensitive acute steroid biosynthesis requires trafficking of cholesterol from intracellular sources to the inner mitochondrial membrane. The precise location of the intracellular cholesterol and its transport mechanism are uncertain. Perfringolysin O, produced by Clostridium perfringens, binds cholesterol. Its fourth domain, D4, retains cholesterol-binding properties but not cytotoxicity. We transfected steroidogenic MA-10 cells of mouse Leydig-cell tumors with the mCherry-D4 plasmid. Tagged D4 with fluorescent proteins enabled us to track cholesterol...
November 3, 2016: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/27790795/development-and-application-of-an-uhplc-ms-ms-method-for-the-simultaneous-determination-of-17-steroidal-hormones-in-equine-serum
#9
Michele Genangeli, Giovanni Caprioli, Manuela Cortese, Fulvio Laus, Mara Matteucci, Riccardo Petrelli, Massimo Ricciutelli, Gianni Sagratini, Stefano Sartori, Sauro Vittori
A new, fast and simple analytical method that is able to identify and quantify simultaneously 17 steroid hormones and metabolites (Pregnenolone, 17-OH-Pregnenolone, Progesterone, 17-OH Progesterone, Androsterone, Androstenedione, DHEA, DHEAS, Testosterone, Cortisol, Corticosterone, Aldosterone, 11-Deoxycortisol, 11-Deoxycorticosterone, Dihydrotestosterone, Estrone, Estradiol) has been developed in equine serum using the UHPLC-MS/MS technique. 400 μL of sample were deproteinized with 1000 µl of acetonitrile, evaporated, restored with 50 µl of a solution of 25% methanol and injected in UHPLC-MS/MS triple quadrupole...
October 27, 2016: Journal of Mass Spectrometry: JMS
https://www.readbyqxmd.com/read/27737514/presence-of-sex-steroid-metabolizing-enzymes-in-the-olfactory-mucosa-of-rats
#10
Sawa Horie, Akiko Yamaki, Shigeru Takami
Although several lines of evidence have suggested that sex steroids influence olfaction, little is known about the cellular basis of steroid-metabolizing enzymes in the olfactory system. Thus, we aimed to examine gene expression and immunolocalization of four sex steroid-metabolizing enzymes in the olfactory mucosa (OM) of albino rats; steroid side chain-cleaving enzyme (P450scc), 17β -hydroxysteroid dehydrogenase type 1 (17β -HSD-1), 17β -HSD type 2 (17β -HSD-2), and aromatase. P450scc is known to catalyze conversion from cholesterol to pregnenolone...
October 13, 2016: Anatomical Record: Advances in Integrative Anatomy and Evolutionary Biology
https://www.readbyqxmd.com/read/27717154/application-of-testosterone-to-epitestosterone-ratio-to-horse-urine-a-complimentary-approach-to-detect-the-administrations-of-testosterone-and-its-pro-drugs-in-thoroughbred-geldings
#11
Marjaana Viljanto, James Scarth, Pamela Hincks, Lynn Hillyer, Adam Cawley, Craig Suann, Glenys Noble, Christopher J Walker, Andrew T Kicman, Mark C Parkin
Detection of testosterone and/or its pro-drugs in the gelding is currently regulated by the application of an international threshold for urinary testosterone of 20 ng/mL. The use of steroid ratios may provide a useful supplementary approach to aid in differentiating between the administration of these steroids and unusual physiological conditions that may result in atypically high testosterone concentrations. In the current study, an ultra high performance liquid chromatography tandem mass spectrometry (UHPLC-MS/MS) method was developed to quantify testosterone (T) and epitestosterone (E)...
October 7, 2016: Drug Testing and Analysis
https://www.readbyqxmd.com/read/27702589/electrochemistry-of-cytochrome-p450-17%C3%AE-hydroxylase-17-20-lyase-p450c17
#12
Lisandra L Martin, Clemens Kubeil, Alexandr N Simonov, Vladimir L Kuznetsov, C Jo Corbin, Richard J Auchus, Alan J Conley, Alan M Bond, Raymond J Rodgers
Within the superfamily of cytochrome P450 enzymes (P450s), there is a small class which is functionally employed for steroid biosynthesis. The enzymes in this class appear to have a small active site to accommodate the steroid substrates specifically and snuggly, prior to the redox transformation or hydroxylation to form a product. Cytochrome P450c17 is one of these and is also a multi-functional P450, with two activities, the first 17α-hydroxylation of pregnenolone is followed by a subsequent 17,20-lyase transformation to dehydroepiandrosterone (DHEA) as the dominant pathways to cortisol precursors or androgens in humans, respectively...
October 3, 2016: Molecular and Cellular Endocrinology
https://www.readbyqxmd.com/read/27698208/regulation-of-steroidogenesis-in-fetal-bovine-ovaries-differential-effects-of-lh-and-fsh
#13
Jeremy J Allen, Susan L Herrick, Joanne E Fortune
In cattle, primordial follicles form before birth. Fetal ovarian capacity to produce progesterone and estradiol is high before follicle formation begins and decreases around the time follicles first appear (around 90 days of gestation). However, mechanisms that regulate steroid production during this time remain unclear. We hypothesized that LH stimulates progesterone and androgen production and that FSH stimulates aromatization of androgens to estradiol. To test this, we cultured pieces from fetal bovine ovaries for 10 days without or with exogenous hormones and then measured the accumulation of steroids in the culture medium by RIA...
October 3, 2016: Journal of Molecular Endocrinology
https://www.readbyqxmd.com/read/27697863/endoplasmic-reticulum-stress-enhances-mitochondrial-metabolic-activity-in-mammalian-adrenals-and-gonads
#14
Manoj Prasad, Anna N Walker, Jasmeet Kaur, James L Thomas, Shirley A Powell, Amit V Pandey, Randy M Whittal, William E Burak, Guy Petruzzelli, Himangshu S Bose
The acute response to stress consists of a series of physiological programs to promote survival by generating glucocorticoids and activating stress response genes that increase the synthesis of many chaperone proteins specific to individual organelles. In the endoplasmic reticulum (ER), short-term stress triggers activation of the unfolded protein response (UPR) module that either leads to neutralization of the initial stress or adaptation to it; chronic stress favors cell death. UPR induces expression of the transcription factor, C/EBP homology protein (CHOP), and its deletion protects against the lethal consequences of prolonged UPR...
December 15, 2016: Molecular and Cellular Biology
https://www.readbyqxmd.com/read/27692342/per-and-polyfluoroalkyl-substances-pfass-new-endocrine-disruptors-in-polar-bears-ursus-maritimus
#15
Kathrine Eggers Pedersen, Robert J Letcher, Christian Sonne, Rune Dietz, Bjarne Styrishave
Per- and polyfluoroalkyl substances (PFASs) are emerging in the Arctic and accumulate in brain tissues of East Greenland (EG) polar bears. In vitro studies have shown that PFASs might possess endocrine disrupting abilities and therefore the present study was conducted to investigate potential PFAS induced alterations in brain steroid concentrations. The concentrations of eleven steroid hormones were determined in eight brain regions from ten EG polar bears. Pregnenolone (PRE), the dominant progestagen, was found in mean concentrations of 5-47ng/g (ww) depending on brain region...
September 27, 2016: Environment International
https://www.readbyqxmd.com/read/27690325/biotransformation-of-cholesterol-and-16-17-alpha-epoxypregnenolone-by-novel-cladosporium-sp-strain-is547
#16
Cuiping Pang, Yuting Cao, Xiangdong Zhu
Nowadays, there are a few steroid drugs or intermediates that have been obtained via the transformation of microorganisms, and many strains of transformed steroids have not been found yet. Therefore, it is very significant to screen for the strains that have the abilities to transform steroids to produce valuable products. This study has focused on the screen and identification of strains, the structural identification of converted products, and the optimization of transformation conditions, as well as the establishment of transformation systems...
September 30, 2016: Journal of Basic Microbiology
https://www.readbyqxmd.com/read/27682404/simultaneous-determination-of-seven-neuroactive-steroids-associated-with-depression-in-rat-plasma-and-brain-by-high-performance-liquid-chromatography-tandem-mass-spectrometry
#17
Youqiong Wang, Lipeng Tang, Wei Yin, Jiesi Chen, Tiandong Leng, Xiaoke Zheng, Wenbo Zhu, Haipeng Zhang, Pengxin Qiu, Xiaoxiao Yang, Guangmei Yan, Haiyan Hu
Sensitive and specific biomarkers are required for the diagnosis and treatment of depression because the existing diagnostic criteria are subjective and could produce false positives or negatives. Some endogenous neuroactive steroids that have shown either antidepressant effects or concentration changes in individuals with depression could provide potential biomarkers. In this study, a simple and specific method was developed to simultaneously determine seven endogenous neuroactive steroids in biological samples: cortisone, cortisol, dehydroepiandrosterone, estradiol, progesterone, pregnenolone, and testosterone...
2016: Analytical Sciences: the International Journal of the Japan Society for Analytical Chemistry
https://www.readbyqxmd.com/read/27648966/body-fat-mass-is-associated-with-ratio-of-steroid-metabolites-reflecting-17-20-lyase-activity-in-prepubertal-girls
#18
Shin-Hye Kim, Ju-Yeon Moon, Hironobu Sasano, Man Ho Choi, Mi-Jung Park
CONTEXT: Pediatric obesity has been related to hyperandrogenism and premature adrenarche in previous studies. However, little is known regarding the association between body fat mass and steroidogenic enzyme activities in children. OBJECTIVE: To examine whether body fat mass is associated with serum steroid profiles in girls. DESIGN, PARTICIPANTS, AND SETTING: We enrolled 242 girls (125 prepubertal, 117 pubertal; aged 7-13 years). Early morning blood samples were drawn at a university hospital to measure serum steroid profiles using gas chromatography-mass spectrometry, and steroidogenic enzyme activities were assessed from the ratios of steroid metabolites...
September 20, 2016: Journal of Clinical Endocrinology and Metabolism
https://www.readbyqxmd.com/read/27623070/age-dependent-increases-in-adrenal-cytochrome-b5-and-serum-5-androstenediol-3-sulfate
#19
Juilee Rege, Shigehiro Karashima, Antonio M Lerario, Joshua M Smith, Richard J Auchus, Josephine Z Kasa-Vubu, Hironobu Sasano, Yasuhiro Nakamura, Perrin C White, William E Rainey
CONTEXT: Adrenal production of dehydroepiandrosterone sulfate (DHEA-S) increases throughout childhood owing to expansion of the zona reticularis (ZR). ZR features cells with a steroidogenic phenotype distinct from that of the adjacent zona fasciculata (ZF), with higher expression of cytochrome b5 type A (CYB5A) and steroid sulfotransferase type 2A1 (SULT2A1) but decreased 3β-hydroxysteroid dehydrogenase type 2 (HSD3B2). In addition to DHEA-S, three adrenal Δ5-steroid sulfates could provide additional tools to define adrenal maturation...
September 13, 2016: Journal of Clinical Endocrinology and Metabolism
https://www.readbyqxmd.com/read/27616978/brain-and-serum-androsterone-is-elevated-in-response-to-stress-in-rats-with-mild-traumatic-brain-injury
#20
Richard J Servatius, Christine E Marx, Swamini Sinha, Pelin Avcu, Jason D Kilts, Jennifer C Naylor, Kevin C H Pang
Exposure to lateral fluid percussion (LFP) injury consistent with mild traumatic brain injury (mTBI) persistently attenuates acoustic startle responses (ASRs) in rats. Here, we examined whether the experience of head trauma affects stress reactivity. Male Sprague-Dawley rats were matched for ASRs and randomly assigned to receive mTBI through LFP or experience a sham surgery (SHAM). ASRs were measured post injury days (PIDs) 1, 3, 7, 14, 21, and 28. To assess neurosteroids, rats received a single 2.0 mA, 0.5 s foot shock on PID 34 (S34), PID 35 (S35), on both days (2S), or the experimental context (CON)...
2016: Frontiers in Neuroscience
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