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Article ; Online: Effects of Repeated Treatment with the Monoacylglycerol Lipase Inhibitor MJN110

Diester, Clare M / Balint, Hallie / Gillespie, James C / Lichtman, Aron H / Sim-Selley, Laura J / Selley, Dana E / Negus, S Stevens

The Journal of pharmacology and experimental therapeutics

2024

Abstract: MJN110 inhibits the enzyme monoacylglycerol lipase (MAGL) to increase levels of the endocannabinoid (eCB) 2-arachidonoylglycerol (2-AG), an endogenous high-efficacy agonist of cannabinoid 1 and 2 receptors ( ... ...

Abstract	MJN110 inhibits the enzyme monoacylglycerol lipase (MAGL) to increase levels of the endocannabinoid (eCB) 2-arachidonoylglycerol (2-AG), an endogenous high-efficacy agonist of cannabinoid 1 and 2 receptors (CB
Language	English
Publishing date	2024-01-23
Publishing country	United States
Document type	Journal Article
ZDB-ID	3106-9
ISSN	1521-0103 ; 0022-3565
ISSN (online)	1521-0103
ISSN	0022-3565
DOI	10.1124/jpet.123.001940
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Article ; Online: Exploring naltrexamine derivatives featuring azaindole moiety via nitrogen-walk approach to investigate their in vitro pharmacological profiles at the mu opioid receptor.

Ma, Hongguang / Wang, Huiqun / Gillespie, James C / Mendez, Rolando E / Selley, Dana E / Zhang, Yan

Bioorganic & medicinal chemistry letters

2021 Volume 41, Page(s) 127953

Abstract: In the present work, we reported the application of a nitrogen-walk approach on developing a series of novel opioid ligands containing an azaindole moiety at the C6-position of the epoxymorphinan skeleton. In vitro study results showed that introducing a ...

Abstract	In the present work, we reported the application of a nitrogen-walk approach on developing a series of novel opioid ligands containing an azaindole moiety at the C6-position of the epoxymorphinan skeleton. In vitro study results showed that introducing a nitrogen atom around the indole moiety not only retained excellent binding affinity, but also led to significant functional switch at the mu opioid receptor (MOR). Further computational investigations provided corroborative evidence and plausible explanations of the results of the in vitro studies. Overall, our current work implemented a series of novel MOR ligands with high binding affinity and considerably low efficacy, which may shed light on rational design of low efficacy MOR ligands for opioid use disorder therapeutics.
MeSH term(s)	Binding Sites ; Humans ; Ligands ; Models, Molecular ; Molecular Docking Simulation ; Naltrexone/analogs & derivatives ; Naltrexone/chemical synthesis ; Naltrexone/pharmacology ; Nitrogen/chemistry ; Opioid-Related Disorders/drug therapy ; Protein Conformation ; Receptors, Opioid, mu/drug effects
Chemical Substances	Ligands ; Receptors, Opioid, mu ; Naltrexone (5S6W795CQM) ; Nitrogen (N762921K75)
Language	English
Publishing date	2021-03-22
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2021.127953
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Article ; Online: Role of efficacy as a determinant of locomotor activation by mu-opioid receptor (MOR) ligands in female and male mice. II. Effects of novel MOR-selective phenylmorphans with high-to-low MOR efficacy.

Santos, Edna J / Nassehi, Nima / Bow, Eric W / Chambers, Dana R / Gutman, Eugene S / Jacobson, Arthur E / Lutz, Joshua A / Marsh, Samuel A / Rice, Kenner C / Sulima, Agnieszka / Selley, Dana E / Negus, S Stevens

Pharmacology research & perspectives

2023 Volume 11, Issue 4, Page(s) e01111

Abstract: Low-efficacy mu-opioid receptor (MOR) agonists represent promising therapeutics, but existing compounds (e.g., buprenorphine, nalbuphine) span a limited range of low MOR efficacies and have poor MOR selectivity. Accordingly, new and selective low- ... ...

Abstract	Low-efficacy mu-opioid receptor (MOR) agonists represent promising therapeutics, but existing compounds (e.g., buprenorphine, nalbuphine) span a limited range of low MOR efficacies and have poor MOR selectivity. Accordingly, new and selective low-efficacy MOR agonists are of interest. A novel set of chiral C9-substituted phenylmorphans has been reported to display improved MOR selectivity and a range of high-to-low MOR efficacies under other conditions; however, a full opioid receptor binding profile for these drugs has not been described. Additionally, studies in mice will be useful for preclinical characterization of these novel compounds, but the pharmacology of these drugs in mice has also not been examined. Accordingly, the present study characterized the binding selectivity and in vitro efficacy of these compounds using assays of opioid receptor binding and ligand-stimulated [
MeSH term(s)	Animals ; Female ; Male ; Mice ; Analgesics, Opioid/pharmacology ; Buprenorphine/pharmacology ; Guanosine 5'-O-(3-Thiotriphosphate) ; Ligands ; Receptors, Opioid, mu/agonists
Chemical Substances	Analgesics, Opioid ; Buprenorphine (40D3SCR4GZ) ; Guanosine 5'-O-(3-Thiotriphosphate) (37589-80-3) ; Ligands ; phenylmorphan (91190-14-6) ; tianeptine (0T493YFU8O) ; Receptors, Opioid, mu
Language	English
Publishing date	2023-06-28
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, N.I.H., Intramural
ZDB-ID	2740389-0
ISSN	2052-1707 ; 2052-1707
ISSN (online)	2052-1707
ISSN	2052-1707
DOI	10.1002/prp2.1111
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Article ; Online: Molecular Pharmacology Profiling of Phenylfentanil and Its Analogues to Understand the Putative Involvement of an Adrenergic Mechanism in Fentanyl-Induced Respiratory Depression.

Li, Mengchu / Pagare, Piyusha P / Ma, Hongguang / St Onge, Celsey M / Mendez, Rolando E / Gillespie, James C / Stevens, David L / Dewey, William L / Selley, Dana E / Zhang, Yan

Journal of medicinal chemistry

2023 Volume 67, Issue 1, Page(s) 603–619

Abstract: While there are approved therapeutics to treat opioid overdoses, the need for treatments to reverse overdoses due to ultrapotent fentanyls remains unmet. This may be due in part to an adrenergic mechanism of fentanyls in addition to their stereotypical ... ...

Abstract	While there are approved therapeutics to treat opioid overdoses, the need for treatments to reverse overdoses due to ultrapotent fentanyls remains unmet. This may be due in part to an adrenergic mechanism of fentanyls in addition to their stereotypical mu-opioid receptor (MOR) effects. Herein, we report our efforts to further understanding of the functions these distinct mechanisms impart. Employing the known MOR neutral antagonist phenylfentanil as a lead, 17 analogues were designed based on the concept of isosteric replacement. To probe mechanisms of action, these analogues were pharmacologically evaluated in vitro and in vivo, while in silico modeling studies were also conducted on phenylfentanil. While it did not indicate MOR involvement in vivo, phenylfentanil yielded respiratory minute volumes similar to those caused by fentanyl. Taken together with molecular modeling studies, these results indicated that respiratory effects of fentanyls may also correlate to inhibition of both α1A- and α1B-adrenergic receptors.
MeSH term(s)	Fentanyl/pharmacology ; Adrenergic Agents ; Receptors, Opioid, mu ; Narcotic Antagonists ; Analgesics, Opioid/pharmacology
Chemical Substances	Fentanyl (UF599785JZ) ; Adrenergic Agents ; Receptors, Opioid, mu ; Narcotic Antagonists ; Analgesics, Opioid
Language	English
Publishing date	2023-12-29
Publishing country	United States
Document type	Journal Article
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.3c01801
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Article ; Online: Amphetamine maintenance differentially modulates effects of cocaine, methylenedioxypyrovalerone (MDPV), and methamphetamine on intracranial self-stimulation and nucleus accumbens dopamine in rats.

Johnson, Amy R / Banks, Matthew L / Selley, Dana E / Negus, S Stevens

Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology

2018 Volume 43, Issue 8, Page(s) 1753–1762

Abstract: Amphetamine maintenance is effective clinically to reduce the consumption of the monoamine uptake inhibitor cocaine but not of the monoamine releaser methamphetamine, and its effectiveness in treating the abuse of other psychostimulants is not known. The ...

Abstract	Amphetamine maintenance is effective clinically to reduce the consumption of the monoamine uptake inhibitor cocaine but not of the monoamine releaser methamphetamine, and its effectiveness in treating the abuse of other psychostimulants is not known. The mechanisms for differential amphetamine-maintenance effectiveness to treat different types of psychostimulant abuse are also not known. Accordingly, the present study compared the effects of amphetamine maintenance on abuse-related behavioral and neurochemical effects of cocaine, methamphetamine, and the "bath salts" constituent 3,4-methylenedioxypyrovalerone (MDPV) in rats. In behavioral studies, rats were trained to lever press for electrical brain stimulation in an intracranial self-stimulation (ICSS) procedure. In neurochemical studies, nucleus accumbens (NAc) levels of dopamine (DA) and serotonin (5-HT) were monitored by in vivo microdialysis. Cocaine, methamphetamine, and MDPV each produced dose-dependent ICSS facilitation and increases in NAc DA; cocaine and methamphetamine also increased NAc 5-HT. Amphetamine maintenance (0.32 mg/kg/h × 7 days) produced (1) sustained increases in basal ICSS and NAc DA with no change in NAc 5-HT, (2) blockade of cocaine but not methamphetamine effects on ICSS and NAc DA, and (3) no blockade of cocaine- or methamphetamine-induced increases in NAc 5-HT. Amphetamine maintenance blocked the increases in NAc DA produced by the selective DA uptake inhibitor MDPV, but it did not block MDPV-induced ICSS facilitation. These results show different effects of amphetamine maintenance on behavioral and neurochemical effects of different psychostimulants. The selective effectiveness of amphetamine maintenance to treat cocaine abuse may reflect attenuation of cocaine-induced increases in NAc DA while preserving cocaine-induced increases in NAc 5-HT.
MeSH term(s)	Amphetamine/pharmacology ; Animals ; Benzodioxoles/pharmacology ; Central Nervous System Agents/pharmacology ; Cocaine/pharmacology ; Dopamine/metabolism ; Male ; Methamphetamine/pharmacology ; Nucleus Accumbens/drug effects ; Nucleus Accumbens/metabolism ; Pyrrolidines/pharmacology ; Rats, Sprague-Dawley ; Self Stimulation ; Serotonin/metabolism
Chemical Substances	Benzodioxoles ; Central Nervous System Agents ; Pyrrolidines ; Serotonin (333DO1RDJY) ; Methamphetamine (44RAL3456C) ; Amphetamine (CK833KGX7E) ; 3,4-methylenedioxypyrovalerone (E7LD6JMR0L) ; Cocaine (I5Y540LHVR) ; Dopamine (VTD58H1Z2X)
Language	English
Publishing date	2018-04-19
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	639471-1
ISSN	1740-634X ; 0893-133X
ISSN (online)	1740-634X
ISSN	0893-133X
DOI	10.1038/s41386-018-0071-3
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Zs.A 2379: Show issues

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Article ; Online: Exploring the putative mechanism of allosteric modulations by mixed-action kappa/mu opioid receptor bitopic modulators.

Wang, Huiqun / Cao, Danni / Gillespie, James C / Mendez, Rolando E / Selley, Dana E / Liu-Chen, Lee-Yuan / Zhang, Yan

Future medicinal chemistry

2021 Volume 13, Issue 6, Page(s) 551–573

Abstract: The modulation and selectivity mechanisms of seven mixed-action kappa opioid receptor (KOR)/mu opioid receptor (MOR) bitopic modulators were explored. Molecular modeling results indicated that the 'message' moiety of seven bitopic modulators shared the ... ...

Abstract	The modulation and selectivity mechanisms of seven mixed-action kappa opioid receptor (KOR)/mu opioid receptor (MOR) bitopic modulators were explored. Molecular modeling results indicated that the 'message' moiety of seven bitopic modulators shared the same binding mode with the orthosteric site of the KOR and MOR, whereas the 'address' moiety bound with different subdomains of the allosteric site of the KOR and MOR. The 'address' moiety of seven bitopic modulators bound to different subdomains of the allosteric site of the KOR and MOR may exhibit distinguishable allosteric modulations to the binding affinity and/or efficacy of the 'message' moiety. Moreover, the 3-hydroxy group on the phenolic moiety of the seven bitopic modulators induced selectivity to the KOR over the MOR.
MeSH term(s)	Allosteric Regulation ; Allosteric Site ; Binding Sites ; Humans ; Ligands ; Molecular Docking Simulation ; Morphinans/chemistry ; Morphinans/metabolism ; Naltrexone/analogs & derivatives ; Naltrexone/chemistry ; Naltrexone/metabolism ; Protein Binding ; Receptors, Opioid, kappa/chemistry ; Receptors, Opioid, kappa/metabolism ; Receptors, Opioid, mu/chemistry ; Receptors, Opioid, mu/metabolism ; Spiro Compounds/chemistry ; Spiro Compounds/metabolism ; Thermodynamics
Chemical Substances	Ligands ; Morphinans ; Receptors, Opioid, kappa ; Receptors, Opioid, mu ; Spiro Compounds ; TRK 820 (25CC4N0P8J) ; Naltrexone (5S6W795CQM) ; beta-funaltrexamine (72782-05-9)
Language	English
Publishing date	2021-02-16
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural
ISSN	1756-8927
ISSN (online)	1756-8927
DOI	10.4155/fmc-2020-0308
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Article ; Online: Novel bivalent ligands carrying potential antinociceptive effects by targeting putative mu opioid receptor and chemokine receptor CXCR4 heterodimers.

Ma, Hongguang / Li, Mengchu / Pagare, Piyusha P / Wang, Huiqun / Nassehi, Nima / Santos, Edna J / Stevens Negus, S / Selley, Dana E / Zhang, Yan

Bioorganic chemistry

2022 Volume 120, Page(s) 105641

Abstract: The functional interactions between opioid and chemokine receptors have been implicated in the pathological process of chronic pain. Mounting studies have indicated the possibility that a MOR-CXCR4 heterodimer may be involved in nociception and related ... ...

Abstract	The functional interactions between opioid and chemokine receptors have been implicated in the pathological process of chronic pain. Mounting studies have indicated the possibility that a MOR-CXCR4 heterodimer may be involved in nociception and related pharmacologic effects. Herein we have synthesized a series of bivalent ligands containing both MOR agonist and CXCR4 antagonist pharmacophores with an aim to investigate the functional interactions between these two receptors. In vitro studies demonstrated reasonable recognition of designed ligands at both respective receptors. Further antinociceptive testing in mice revealed compound 1a to be the most promising member of this series. Additional molecular modeling studies corroborated the findings observed. Taken together, we identified the first bivalent ligand 1a showing promising antinociceptive effect by targeting putative MOR-CXCR4 heterodimers, which may serve as a novel chemical probe to further develop more potent bivalent ligands with potential application in analgesic therapies for chronic pain management.
MeSH term(s)	Analgesics/pharmacology ; Analgesics/therapeutic use ; Animals ; Ligands ; Mice ; Models, Molecular ; Receptors, Opioid, mu ; Signal Transduction
Chemical Substances	Analgesics ; Ligands ; Receptors, Opioid, mu
Language	English
Publishing date	2022-01-24
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	120080-x
ISSN	1090-2120 ; 0045-2068
ISSN (online)	1090-2120
ISSN	0045-2068
DOI	10.1016/j.bioorg.2022.105641
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Zs.A 4207: Show issues

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Article ; Online: Characterization of a Potential KOR/DOR Dual Agonist with No Apparent Abuse Liability via a Complementary Structure-Activity Relationship Study on Nalfurafine Analogues.

Li, Mengchu / Stevens, David L / Arriaga, Michelle / Townsend, E Andrew / Mendez, Rolando E / Blajkevch, Nadejda A / Selley, Dana E / Banks, Matthew L / Negus, S Stevens / Dewey, William L / Zhang, Yan

ACS chemical neuroscience

2022 Volume 13, Issue 24, Page(s) 3608–3628

Abstract: Discovery of analgesics void of abuse liability is critical to battle the opioid crisis in the United States. Among many strategies to achieve this goal, targeting more than one opioid receptor seems promising to minimize this unwanted side effect while ... ...

Abstract	Discovery of analgesics void of abuse liability is critical to battle the opioid crisis in the United States. Among many strategies to achieve this goal, targeting more than one opioid receptor seems promising to minimize this unwanted side effect while achieving a reasonable therapeutic profile. In the process of understanding the structure-activity relationship of nalfurafine, we identified a potential analgesic agent, NMF, as a dual kappa opioid receptor/delta opioid receptor agonist with minimum abuse liability. Further characterizations, including primary in vitro ADMET studies (hERG toxicity, plasma protein binding, permeability, and hepatic metabolism), and in vivo pharmacodynamic and toxicity profiling (time course, abuse liability, tolerance, withdrawal, respiratory depression, body weight, and locomotor activity) further confirmed NMF as a promising drug candidate for future development.
MeSH term(s)	Humans ; Analgesics, Opioid/chemistry ; Receptors, Opioid, kappa/agonists ; Morphinans/pharmacology ; Analgesics/pharmacology ; Structure-Activity Relationship ; Receptors, Opioid, mu/agonists
Chemical Substances	TRK 820 (25CC4N0P8J) ; Analgesics, Opioid ; Receptors, Opioid, kappa ; Morphinans ; Analgesics ; Receptors, Opioid, mu
Language	English
Publishing date	2022-11-30
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ISSN	1948-7193
ISSN (online)	1948-7193
DOI	10.1021/acschemneuro.2c00526
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Article ; Online: A Journey through Diastereomeric Space: The Design, Synthesis, In Vitro and In Vivo Pharmacological Activity, and Molecular Modeling of Novel Potent Diastereomeric MOR Agonists and Antagonists.

Chambers, Dana R / Sulima, Agnieszka / Luo, Dan / Prisinzano, Thomas E / Goldberg, Alexander / Xie, Bing / Shi, Lei / Paronis, Carol A / Bergman, Jack / Nassehi, Nima / Selley, Dana E / Imler, Gregory H / Jacobson, Arthur E / Rice, Kenner C

Molecules (Basel, Switzerland)

2022 Volume 27, Issue 19

Abstract: Four sets of diastereomeric C9-alkenyl 5-phenylmorphans, varying in the length of the C9-alkenyl chain, were designed to examine the effect of these spatially distinct ligands on opioid receptors. Functional activity was obtained by forskolin-induced ... ...

Abstract	Four sets of diastereomeric C9-alkenyl 5-phenylmorphans, varying in the length of the C9-alkenyl chain, were designed to examine the effect of these spatially distinct ligands on opioid receptors. Functional activity was obtained by forskolin-induced cAMP accumulation assays and several compounds were examined in the [
MeSH term(s)	Animals ; CHO Cells ; Colforsin ; Cricetinae ; Ligands ; Mice ; Morphine/pharmacology ; Naltrexone ; Receptors, Opioid/metabolism ; Receptors, Opioid, delta/metabolism ; Receptors, Opioid, mu/metabolism ; Respiratory Insufficiency
Chemical Substances	Ligands ; Receptors, Opioid ; Receptors, Opioid, delta ; Receptors, Opioid, mu ; Colforsin (1F7A44V6OU) ; Naltrexone (5S6W795CQM) ; Morphine (76I7G6D29C)
Language	English
Publishing date	2022-09-30
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules27196455
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Article ; Online: Structural Alterations of the "Address" Moiety of NAN Leading to the Discovery of a Novel Opioid Receptor Modulator with Reduced hERG Toxicity.

Ma, Hongguang / Pagare, Piyusha P / Li, Mengchu / Neel, Logan T / Mendez, Rolando E / Gillespie, James C / Stevens, David L / Dewey, William L / Selley, Dana E / Zhang, Yan

Journal of medicinal chemistry

2022 Volume 66, Issue 1, Page(s) 577–595

Abstract: The search for selective opioid ligands with desired pharmacological potency and improved safety profile has always been an area of interest. Our previous effort yielded a potent opioid modulator, NAN, a 6α- ...

Abstract	The search for selective opioid ligands with desired pharmacological potency and improved safety profile has always been an area of interest. Our previous effort yielded a potent opioid modulator, NAN, a 6α-
MeSH term(s)	Humans ; Receptors, Opioid ; Analgesics, Opioid/pharmacology ; Ether-A-Go-Go Potassium Channels ; Ligands
Chemical Substances	Receptors, Opioid ; compound 21 (RC2V4W0EYC) ; Analgesics, Opioid ; Ether-A-Go-Go Potassium Channels ; Ligands
Language	English
Publishing date	2022-12-20
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.2c01499
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