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Статті в журналах з теми "6β-naltrexol"

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Автор: Grafiati
Опубліковано: 10 грудня 2022
Оновлено: 28 січня 2023

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1

Sadee, Wolfgang, John Oberdick, and Zaijie Wang. "Biased Opioid Antagonists as Modulators of Opioid Dependence: Opportunities to Improve Pain Therapy and Opioid Use Management." Molecules 25, no. 18 (September 11, 2020): 4163. http://dx.doi.org/10.3390/molecules25184163.

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Анотація:
Opioid analgesics are effective pain therapeutics but they cause various adverse effects and addiction. For safer pain therapy, biased opioid agonists selectively target distinct μ opioid receptor (MOR) conformations, while the potential of biased opioid antagonists has been neglected. Agonists convert a dormant receptor form (MOR-μ) to a ligand-free active form (MOR-μ*), which mediates MOR signaling. Moreover, MOR-μ converts spontaneously to MOR-μ* (basal signaling). Persistent upregulation of MOR-μ* has been invoked as a hallmark of opioid dependence. Contrasting interactions with both MOR-μ and MOR-μ* can account for distinct pharmacological characteristics of inverse agonists (naltrexone), neutral antagonists (6β-naltrexol), and mixed opioid agonist-antagonists (buprenorphine). Upon binding to MOR-μ*, naltrexone but not 6β-naltrexol suppresses MOR-μ*signaling. Naltrexone blocks opioid analgesia non-competitively at MOR-μ*with high potency, whereas 6β-naltrexol must compete with agonists at MOR-μ, accounting for ~100-fold lower in vivo potency. Buprenorphine’s bell-shaped dose–response curve may also result from opposing effects on MOR-μ and MOR-μ*. In contrast, we find that 6β-naltrexol potently prevents dependence, below doses affecting analgesia or causing withdrawal, possibly binding to MOR conformations relevant to opioid dependence. We propose that 6β-naltrexol is a biased opioid antagonist modulating opioid dependence at low doses, opening novel avenues for opioid pain therapy and use management.
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2

Li, Jun-Xu, Lance R. McMahon та Charles P. France. "Comparison of naltrexone, 6α-naltrexol, and 6β-naltrexol in morphine-dependent and in nondependent rhesus monkeys". Psychopharmacology 195, № 4 (16 вересня 2007): 479–86. http://dx.doi.org/10.1007/s00213-007-0914-9.

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3

Ko, M. C. Holden, Mary F. Divin, Heeseung Lee, James H. Woods та John R. Traynor. "Differential in Vivo Potencies of Naltrexone and 6β-Naltrexol in the Monkey". Journal of Pharmacology and Experimental Therapeutics 316, № 2 (28 жовтня 2005): 772–79. http://dx.doi.org/10.1124/jpet.105.094409.

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4

Yancey-Wrona, Janet E., Tyler J. Raymond, Hannah K. Mercer, Wolfgang Sadée та Edward J. Bilsky. "6β-naltrexol preferentially antagonizes opioid effects on gastrointestinal transit compared to antinociception in mice". Life Sciences 85, № 11-12 (вересень 2009): 413–20. http://dx.doi.org/10.1016/j.lfs.2009.06.016.

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5

Porter, Susan J., Andrew A. Somogyi та Jason M. White. "Kinetics and inhibition of the formation of 6β-naltrexol from naltrexone in human liver cytosol". British Journal of Clinical Pharmacology 50, № 5 (листопад 2000): 465–71. http://dx.doi.org/10.1046/j.1365-2125.2000.00281.x.

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6

Bayron, Jennifer A., Amy M. Deveau та John M. Stubbs. "Conformational Analysis of 6α- and 6β-Naltrexol and Derivatives and Relationship to Opioid Receptor Affinity". Journal of Chemical Information and Modeling 52, № 2 (20 січня 2012): 391–95. http://dx.doi.org/10.1021/ci200405u.

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7

Ferrari, Anna, Marco Bertolotti, Alessandra Dell'Utri, Ustik Avico та Emilio Sternieri. "Serum time course of naltrexone and 6β-naltrexol levels during long term treatment in drug addicts". Drug and Alcohol Dependence 52, № 3 (листопад 1998): 211–20. http://dx.doi.org/10.1016/s0376-8716(98)00098-2.

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8

Zuccaro, Piergiorgio, Ilaria Altieri, Peppino Betto, Roberta Pacifici, Giuseppe Ricciarello, Luigi Alberto Pini, Emilio Sternieri та Simona Pichini. "Determination of naltrexone and 6β-naltrexol in plasma by high-performance liquid chromatography with coulometric detection". Journal of Chromatography B: Biomedical Sciences and Applications 567, № 2 (липень 1991): 485–90. http://dx.doi.org/10.1016/0378-4347(91)80156-7.

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9

Brünen, Sonja, Nina Kim Bekier, Christoph Hiemke, Felix Korf, Klaus Wiedemann, Holger Jahn та Falk Kiefer. "Therapeutic Drug Monitoring of Naltrexone and 6β-Naltrexol During Anti-craving Treatment in Alcohol Dependence: Reference Ranges". Alcohol and Alcoholism 54, № 1 (27 вересня 2018): 51–55. http://dx.doi.org/10.1093/alcalc/agy067.

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10

Pelotte, Andrea L., Ryan M. Smith, Mario Ayestas, Christina M. Dersch, Edward J. Bilsky, Richard B. Rothman та Amy M. Deveau. "Design, synthesis, and characterization of 6β-naltrexol analogs, and their selectivity for in vitro opioid receptor subtypes". Bioorganic & Medicinal Chemistry Letters 19, № 10 (травень 2009): 2811–14. http://dx.doi.org/10.1016/j.bmcl.2009.03.095.

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11

Yancey-Wrona, Janet, Brian Dallaire, Edward Bilsky, Brad Bath, John Burkart, Lynn Webster, Dan Magiera, Xiaoxia Yang, Mitch Phelps та Wolfgang Sadee. "6β-Naltrexol, a Peripherally Selective Opioid Antagonist that Inhibits Morphine-Induced Slowing of Gastrointestinal Transit: An Exploratory Study". Pain Medicine 12, № 12 (грудень 2011): 1727–37. http://dx.doi.org/10.1111/j.1526-4637.2011.01279.x.

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12

Divin, Mary F., M. C. Holden Ko та John R. Traynor. "Comparison of the opioid receptor antagonist properties of naltrexone and 6β-naltrexol in morphine-naïve and morphine-dependent mice". European Journal of Pharmacology 583, № 1 (березень 2008): 48–55. http://dx.doi.org/10.1016/j.ejphar.2008.01.004.

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13

Divin, MF, FA Bradbury, FI Carroll та JR Traynor. "Neutral antagonist activity of naltrexone and 6β-naltrexol in naïve and opioid-dependent C6 cells expressing a µ-opioid receptor". British Journal of Pharmacology 156, № 7 (31 березня 2009): 1044–53. http://dx.doi.org/10.1111/j.1476-5381.2008.00035.x.

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14

Ferrari, A., M. Bertolotti, M. C. Vecchi, T. Trenti та S. Sternieri. "Plasma concentrations of naltrexone and 6β-naltrexol in patients with liver cirrhosis and drug addicts in chronic treatment with naltrexone". Pharmacological Research 26 (вересень 1992): 315. http://dx.doi.org/10.1016/1043-6618(92)91339-i.

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15

Sadee, Wolfgang, та John C. McKew. "Ligand-Free Signaling of G-Protein-Coupled Receptors: Relevance to μ Opioid Receptors in Analgesia and Addiction". Molecules 27, № 18 (8 вересня 2022): 5826. http://dx.doi.org/10.3390/molecules27185826.

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Анотація:
Numerous G-protein-coupled receptors (GPCRs) display ligand-free basal signaling with potential physiological functions, a target in drug development. As an example, the μ opioid receptor (MOR) signals in ligand-free form (MOR-μ*), influencing opioid responses. In addition, agonists bind to MOR but can dissociate upon MOR activation, with ligand-free MOR-μ* carrying out signaling. Opioid pain therapy is effective but incurs adverse effects (ADRs) and risk of opioid use disorder (OUD). Sustained opioid agonist exposure increases persistent basal MOR-μ* activity, which could be a driving force for OUD and ADRs. Antagonists competitively prevent resting MOR (MOR-μ) activation to MOR-μ*, while common antagonists, such as naloxone and naltrexone, also bind to and block ligand-free MOR-μ*, acting as potent inverse agonists. A neutral antagonist, 6β-naltrexol (6BN), binds to but does not block MOR-μ*, preventing MOR-μ activation only competitively with reduced potency. We hypothesize that 6BN gradually accelerates MOR-μ* reversal to resting-state MOR-μ. Thus, 6BN potently prevents opioid dependence in rodents, at doses well below those blocking antinociception or causing withdrawal. Acting as a ‘retrograde addiction modulator’, 6BN could represent a novel class of therapeutics for OUD. Further studies need to address regulation of MOR-μ* and, more broadly, the physiological and pharmacological significance of ligand-free signaling in GPCRs.
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16

VALIVETI, S., B. NALLURI, D. HAMMELL, K. PAUDEL та A. STINCHCOMB. "Development and validation of a liquid chromatography–mass spectrometry method for the quantitation of naltrexone and 6β-naltrexol in guinea pig plasma". Journal of Chromatography B 810, № 2 (25 жовтня 2004): 259–67. http://dx.doi.org/10.1016/s1570-0232(04)00660-9.

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17

Brünen, Sonja, Ralf Krüger, Susann Finger, Felix Korf, Falk Kiefer, Klaus Wiedemann, Karl J. Lackner та Christoph Hiemke. "Determination of naltrexone and 6β-naltrexol in human blood: comparison of high-performance liquid chromatography with spectrophotometric and tandem-mass-spectrometric detection". Analytical and Bioanalytical Chemistry 396, № 3 (28 листопада 2009): 1249–57. http://dx.doi.org/10.1007/s00216-009-3301-z.

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18

Raehal, Kirsten M., John J. Lowery, Castigliano M. Bhamidipati, Ryan M. Paolino, Jennifer R. Blair, Danxin Wang, Wolfgang Sadée та Edward J. Bilsky. "In Vivo Characterization of 6β-Naltrexol, an Opioid Ligand with Less Inverse Agonist Activity Compared with Naltrexone and Naloxone in Opioid-Dependent Mice". Journal of Pharmacology and Experimental Therapeutics 313, № 3 (16 лютого 2005): 1150–62. http://dx.doi.org/10.1124/jpet.104.082966.

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19

Hamad, Mohamed O., Paul K. Kiptoo, Audra L. Stinchcomb та Peter A. Crooks. "Synthesis and hydrolytic behavior of two novel tripartate codrugs of naltrexone and 6β-naltrexol with hydroxybupropion as potential alcohol abuse and smoking cessation agents". Bioorganic & Medicinal Chemistry 14, № 20 (жовтень 2006): 7051–61. http://dx.doi.org/10.1016/j.bmc.2006.06.018.

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20

Kim, Seon Yeong, Dong Won Shin, SungIll Suh, Jae Chul Cheong та Jin Young Kim. "Monitoring alcohol-use-disorder medication compliance by LC-MS/MS determination of urinary ethyl glucuronide, acamprosate, naltrexone, and 6β-naltrexol using zirconia-based hybrid solid-phase extraction". Journal of Pharmaceutical and Biomedical Analysis 212 (квітень 2022): 114615. http://dx.doi.org/10.1016/j.jpba.2022.114615.

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21

CLAVIJO, C., J. BENDRICKPEART, Y. ZHANG, G. JOHNSON, A. GASPARIC та U. CHRISTIANS. "An automated, highly sensitive LC-MS/MS assay for the quantification of the opiate antagonist naltrexone and its major metabolite 6β-naltrexol in dog and human plasma". Journal of Chromatography B 874, № 1-2 (15 жовтня 2008): 33–41. http://dx.doi.org/10.1016/j.jchromb.2008.08.021.

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22

Dodou, Kalliopi, Andrew Armstrong, Ivan Kelly, Simon Wilkinson, Kevin Carr, Paul Shattock та Paul Whiteley. "Ex vivostudies for the passive transdermal delivery of low-dose naltrexone from a cream; detection of naltrexone and its active metabolite, 6β-naltrexol, using a novel LC Q-ToF MS assay". Pharmaceutical Development and Technology 20, № 6 (2 травня 2014): 694–701. http://dx.doi.org/10.3109/10837450.2014.915569.

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23

Sadee, Wolfgang, та John Oberdick. "Low‐Dose 6β‐Naltrexol Prevents Opioid Dependence Without Affecting Antinociception". FASEB Journal 36, S1 (травень 2022). http://dx.doi.org/10.1096/fasebj.2022.36.s1.r6225.

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24

Divin, Mary F., M. C. Holden Ko та John R. Traynor. "Comparison of naltrexone and 6β‐naltrexol in morphine‐naive and morphine‐dependent mice". FASEB Journal 20, № 4 (березень 2006). http://dx.doi.org/10.1096/fasebj.20.4.a239-b.

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25

Sim, Yeong Eun, Ji Woo Kim, Beom Jun Ko та Jin Young Kim. "Rapid and simple LC–MS/MS determination of urinary ethyl glucuronide, naltrexone, 6β-naltrexol, chlordiazepoxide, and norchlordiazepoxide for monitoring alcohol abuse". Journal of Analytical Science and Technology 13, № 1 (11 лютого 2022). http://dx.doi.org/10.1186/s40543-022-00315-8.

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Анотація:
AbstractIn this study, a liquid chromatography–tandem mass spectrometry (LC–MS/MS) method was developed to detect ethyl glucuronide (EtG), which is a biomarker for monitoring alcohol consumption, and naltrexone (NTX), 6β-naltrexol (6βNTX), chlordiazepoxide (CDP), and norchlordiazepoxide (norCDP), which are analyzed to confirm the presence of medications for alcohol dependence treatment. The protein precipitation method was conducted to rapidly prepare samples. LC–MS/MS analysis was performed in the multiple-reaction monitoring mode. The analytes were separated using a Scherzo SM-C18 (2.0 × 100 mm, 3 µm) column. The calibration ranges were 5–1000 ng/mL for EtG, 6βNTX, CDP, and norCDP, and 1–100 ng/mL for NTX, with the correlation coefficients (r) being ≥ 0.994, and the weighting factor being 1/x2. The lower limit of quantification was 1–5 ng/mL. The method was also validated for precision, accuracy, selectivity, dilution integrity, recovery, matrix effect, and stability. The developed method was successfully applied for the determination of EtG, NTX, 6βNTX, CDP, and norCDP in urine samples obtained from 49 probationers who received alcohol dependence treatment orders. The method developed herein can be used to monitor the drug-based treatment of alcohol abuse and alcohol consumption during the treatment of individuals under probation.
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26

Safa, Alireza, Allison R. Lau, Sydney Aten, Karl Schilling, Karen L. Bales, Victoria A. Miller, Julie Fitzgerald, et al. "Pharmacological Prevention of Neonatal Opioid Withdrawal in a Pregnant Guinea Pig Model." Frontiers in Pharmacology 11 (February 25, 2021). http://dx.doi.org/10.3389/fphar.2020.613328.

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Анотація:
Newborns exposed to prenatal opioids often experience intense postnatal withdrawal after cessation of the opioid, called neonatal opioid withdrawal syndrome (NOWS), with limited pre- and postnatal therapeutic options available. In a prior study in pregnant mice we demonstrated that the peripherally selective opioid antagonist, 6β-naltrexol (6BN), is a promising drug candidate for preventive prenatal treatment of NOWS, and a therapeutic mechanism was proposed based on preferential delivery of 6BN to fetal brain with relative exclusion from maternal brain. Here, we have developed methadone (MTD) treated pregnant guinea pigs as a physiologically more suitable model, enabling detection of robust spontaneous neonatal withdrawal. Prenatal MTD significantly aggravates two classic maternal separation stress behaviors in newborn guinea pigs: calling (vocalizing) and searching (locomotion) - natural attachment behaviors thought to be controlled by the endogenous opioid system. In addition, prenatal MTD significantly increases the levels of plasma cortisol in newborns, showing that cessation of MTD at birth engages the hypothalamic-pituitary-adrenal (HPA) axis. We find that co-administration of 6BN with MTD prevents these withdrawal symptoms in newborn pups with extreme potency (ID50 ∼0.02 mg/kg), at doses unlikely to induce maternal or fetal withdrawal or to interfere with opioid antinociception based on many prior studies in rodents and non-human primates. Furthermore, we demonstrate a similarly high potency of 6BN in preventing opioid withdrawal in adult guinea pigs (ID50 = 0.01 mg/kg). This high potency appears to run counter to our pharmacokinetic studies showing slow 6BN transit of both the placenta and maternal blood brain barrier in guinea pigs, and calls into question the preferential delivery mechanism. Rather, it suggests a novel receptor mechanism to account for the selectively high potency of 6BN to suppress opioid dependence at all developmental stages, even in adults, as compared to its well-established low potency as a classical opioid antagonist. In conclusion, 6BN is an attractive compound for development of a preventive therapy for NOWS.
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