Synthetic and Receptor Signaling Explorations of the Mitragyna Alkaloids: Mitragynine as an Atypical Molecular Framework for Opioid Receptor Modulators.

PubWeight™: 0.84‹?›

🔗 View Article (PMID 27192616)

Published in J Am Chem Soc on May 18, 2016

Authors

Andrew C Kruegel, Madalee M Gassaway, Abhijeet Kapoor1, András Váradi2, Susruta Majumdar2, Marta Filizola1, Jonathan A Javitch3, Dalibor Sames

Author Affiliations

1: Department of Structural and Chemical Biology, Icahn School of Medicine at Mount Sinai , New York, New York 10029, United States.
2: Department of Neurology, Memorial Sloan Kettering Cancer Center , New York, New York 10065, United States.
3: Division of Molecular Therapeutics, New York State Psychiatric Institute , New York, New York 10032, United States.

Articles cited by this

AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem (2009) 23.19

Crystal structure of the β2 adrenergic receptor-Gs protein complex. Nature (2011) 13.92

Crystal structure of the µ-opioid receptor bound to a morphinan antagonist. Nature (2012) 6.18

The dysphoric component of stress is encoded by activation of the dynorphin kappa-opioid system. J Neurosci (2008) 3.54

Antidepressant-like effects of kappa-opioid receptor antagonists in the forced swim test in rats. J Pharmacol Exp Ther (2003) 3.48

An opioid agonist that does not induce mu-opioid receptor--arrestin interactions or receptor internalization. Mol Pharmacol (2006) 2.06

Crystal structure of venus, a yellow fluorescent protein with improved maturation and reduced environmental sensitivity. J Biol Chem (2002) 1.87

Clinical pharmacology of opioids for pain. Clin J Pain (2002) 1.85

Structural insights into µ-opioid receptor activation. Nature (2015) 1.77

Mu opioids and their receptors: evolution of a concept. Pharmacol Rev (2013) 1.66

A G protein-biased ligand at the μ-opioid receptor is potently analgesic with reduced gastrointestinal and respiratory dysfunction compared with morphine. J Pharmacol Exp Ther (2013) 1.62

Functional selectivity at the μ-opioid receptor: implications for understanding opioid analgesia and tolerance. Pharmacol Rev (2011) 1.61

Crystal structures of the luciferase and green fluorescent protein from Renilla reniformis. J Mol Biol (2007) 1.44

Buprenorphine treatment of refractory depression. J Clin Psychopharmacol (1995) 1.37

Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa. Chem Pharm Bull (Tokyo) (2004) 1.35

Self-treatment of opioid withdrawal using kratom (Mitragynia speciosa korth). Addiction (2008) 1.32

kappa-Opioid receptor signaling and brain reward function. Brain Res Rev (2009) 1.32

Crystal structure of arrestin-3 reveals the basis of the difference in receptor binding between two non-visual subtypes. J Mol Biol (2011) 1.31

Spinal or systemic TY005, a peptidic opioid agonist/neurokinin 1 antagonist, attenuates pain with reduced tolerance. Br J Pharmacol (2010) 1.30

Central antinociceptive effects of mitragynine in mice: contribution of descending noradrenergic and serotonergic systems. Eur J Pharmacol (1996) 1.29

A New Indole Alkaloid, 7 alpha-Hydroxy-7H-mitragynine, from Mitragyna speciosa in Thailand. Planta Med (1994) 1.20

Antinociceptive effect of 7-hydroxymitragynine in mice: Discovery of an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa. Life Sci (2004) 1.17

Tramadol induces antidepressant-type effects in mice. Life Sci (1998) 1.15

Antidepressant-like effects of tramadol and other central analgesics with activity on monoamines reuptake, in helpless rats. Life Sci (2002) 1.13

Ligand-directed signalling within the opioid receptor family. Br J Pharmacol (2012) 1.13

Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands. J Med Chem (2002) 1.11

Molecular insights into mu opioid pharmacology: From the clinic to the bench. Clin J Pain (2010) 1.10

Safety, tolerability, and clinical effect of low-dose buprenorphine for treatment-resistant depression in midlife and older adults. J Clin Psychiatry (2014) 1.08

Biased agonism of the μ-opioid receptor by TRV130 increases analgesia and reduces on-target adverse effects versus morphine: A randomized, double-blind, placebo-controlled, crossover study in healthy volunteers. Pain (2014) 1.05

Possible antidepressive effects of opioids: action of buprenorphine. Ann N Y Acad Sci (1982) 1.04

Fulfilling the Promise of "Biased" G Protein-Coupled Receptor Agonism. Mol Pharmacol (2015) 1.01

Antinociceptive action of mitragynine in mice: evidence for the involvement of supraspinal opioid receptors. Life Sci (1996) 1.01

Antinociceptive effects of herkinorin, a MOP receptor agonist derived from salvinorin A in the formalin test in rats: new concepts in mu opioid receptor pharmacology: from a symposium on new concepts in mu-opioid pharmacology. Drug Alcohol Depend (2011) 1.00

Mitragyna speciosa, a psychoactive tree from Southeast Asia with opioid activity. Curr Top Med Chem (2011) 0.99

Antidepressant-like effect of mitragynine isolated from Mitragyna speciosa Korth in mice model of depression. Phytomedicine (2011) 0.98

Treatment of refractory major depression with tramadol monotherapy. J Clin Psychiatry (2001) 0.97

Open-label pilot study of tramadol hydrochloride in treatment-refractory obsessive-compulsive disorder. Depress Anxiety (1997) 0.95

Depressive symptoms during buprenorphine vs. methadone maintenance: findings from a randomised, controlled trial in opioid dependence. Eur Psychiatry (2004) 0.94

Total synthesis of ent-dihydrocorynantheol by using a proline-catalyzed asymmetric addition reaction. Org Lett (2006) 0.93

Some observations on the pharmacology of mitragynine. Arch Int Pharmacodyn Ther (1972) 0.90

Antidepressant-like effect of endomorphin-1 and endomorphin-2 in mice. Neuropsychopharmacology (2006) 0.88

beta-Endorphin. Intravenous infusion causes behavioral change in psychiatric inpatients. Arch Gen Psychiatry (1980) 0.87

Phytochemical characterization of the leaves of Mitragyna speciosa grown in U.S.A. Nat Prod Commun (2009) 0.87

Pharmacologic characterization in the rat of a potent analgesic lacking respiratory depression, IBNtxA. J Pharmacol Exp Ther (2014) 0.85

Orally active opioid compounds from a non-poppy source. J Med Chem (2013) 0.84

Proline-catalyzed asymmetric addition reaction of 9-tosyl-3,4-dihydro-beta-carboline with ketones. Org Lett (2003) 0.84

Treatment augmentation with opiates in severe and refractory major depression. Am J Psychiatry (1999) 0.83

Mutation of three residues in the third intracellular loop of the dopamine D2 receptor creates an internalization-defective receptor. J Biol Chem (2014) 0.82

Antagonists of the kappa opioid receptor. Bioorg Med Chem Lett (2014) 0.82

The atypical antidepressant and neurorestorative agent tianeptine is a μ-opioid receptor agonist. Transl Psychiatry (2014) 0.80

Effects of morphine, naloxone and their interaction in the learned-helplessness paradigm in rats. Psychopharmacology (Berl) (1996) 0.79

Orally active opioid μ/δ dual agonist MGM-16, a derivative of the indole alkaloid mitragynine, exhibits potent antiallodynic effect on neuropathic pain in mice. J Pharmacol Exp Ther (2013) 0.79

The mixed-action delta/mu opioid agonist MMP-2200 does not produce conditioned place preference but does maintain drug self-administration in rats, and induces in vitro markers of tolerance and dependence. Pharmacol Biochem Behav (2015) 0.77

Articles by these authors

C-H bond functionalization in complex organic synthesis. Science (2006) 3.76

Direct palladium-catalyzed C-2 and C-3 arylation of indoles: a mechanistic rationale for regioselectivity. J Am Chem Soc (2005) 1.82

sp3 C-H bond arylation directed by amidine protecting group: alpha-arylation of pyrrolidines and piperidines. J Am Chem Soc (2006) 1.40

Fluorescent false neurotransmitters visualize dopamine release from individual presynaptic terminals. Science (2009) 1.39

Fully synthetic carbohydrate-based vaccines in biochemically relapsed prostate cancer: clinical trial results with alpha-N-acetylgalactosamine-O-serine/threonine conjugate vaccine. J Clin Oncol (2003) 1.37

C-C bond formation via C-H bond activation: synthesis of the core of teleocidin B4. J Am Chem Soc (2002) 1.35

Direct C-arylation of free (NH)-indoles and pyrroles catalyzed by Ar-Rh(III) complexes assembled in situ. J Am Chem Soc (2005) 1.32

Room temperature hydroalkylation of electron-deficient olefins: sp3 C-H functionalization via a lewis acid-catalyzed intramolecular redox event. J Am Chem Soc (2005) 1.31

Pt(IV)-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation. Org Lett (2003) 1.29

Catalytic C-H arylation of SEM-protected azoles with palladium complexes of NHCs and phosphines. Org Lett (2006) 1.25

Reactivity of functional groups on the protein surface: development of epoxide probes for protein labeling. J Am Chem Soc (2003) 1.25

Fluorescent dopamine tracer resolves individual dopaminergic synapses and their activity in the brain. Proc Natl Acad Sci U S A (2012) 1.20

Retracted C-C bond formation via C-H bond activation: catalytic arylation and alkenylation of alkane segments. J Am Chem Soc (2002) 1.18

C-H bond functionalization via hydride transfer: Lewis acid catalyzed alkylation reactions by direct intramolecular coupling of sp3 C-H bonds and reactive alkenyl oxocarbenium intermediates. J Am Chem Soc (2009) 1.14

Room temperature intramolecular hydro-O-alkylation of aldehydes: sp3 C-H functionalization via a Lewis acid catalyzed tandem 1,5-hydride transfer/cyclization. Org Lett (2005) 1.13

Principles of mucin architecture: structural studies on synthetic glycopeptides bearing clustered mono-, di-, tri-, and hexasaccharide glycodomains. J Am Chem Soc (2002) 1.13

Cross-coupling of sp(3) C-H bonds and alkenes: catalytic cyclization of alkene-amide substrates. J Am Chem Soc (2004) 1.09

Total synthesis of (-)-rhazinilam: asymmetric C[bond]H bond activation via the use of a chiral auxiliary. J Am Chem Soc (2002) 1.05

Ru(III)-catalyzed cyclization of arene-alkene substrates via intramolecular electrophilic hydroarylation. Org Lett (2004) 1.04

Retracted Oxidative C-arylation of free (NH)-heterocycles via direct (sp3) C-H bond functionalization. J Am Chem Soc (2004) 1.03

Direct C-H bond arylation: selective palladium-catalyzed C2-arylation of N-substituted indoles. Org Lett (2004) 1.00

Retracted Selective and catalytic arylation of N-phenylpyrrolidine: sp3 C-H bond functionalization in the absence of a directing group. J Am Chem Soc (2005) 0.99

Phosphine-free palladium-catalyzed C-H bond arylation of free (N-H)-indoles and pyrroles. J Org Chem (2007) 0.99

C-H bond functionalization via hydride transfer: synthesis of dihydrobenzopyrans from ortho-vinylaryl akyl ethers. Org Lett (2009) 0.97

Selective and catalytic arylation of N-phenylpyrrolidine: (sp3) C-H bond functionalization in the absence of a directing group [J. Am. Chem. Soc. 2005, 127, 5284-5285]. J Am Chem Soc (2006) 0.97

Oxidative C-arylation of free (NH)-heterocycles via direct sp3 C-H bond functionalization [J. Am. Chem. Soc. 2004, 126, 13244-13246]. J Am Chem Soc (2006) 0.96

Development of pH-responsive fluorescent false neurotransmitters. J Am Chem Soc (2010) 0.94

Imaging induction of cytoprotective enzymes in intact human cells: coumberone, a metabolic reporter for human AKR1C enzymes reveals activation by panaxytriol, an active component of red ginseng. J Am Chem Soc (2008) 0.93

Retracted Diversity synthesis via C-H bond functionalization: concept-guided development of new C-arylation methods for imidazoles. J Am Chem Soc (2003) 0.93

A luminescent sensor for tyrosine phosphorylation. Org Lett (2007) 0.90

C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring. J Am Chem Soc (2011) 0.90

Design of optical switches as metabolic indicators: new fluorogenic probes for monoamine oxidases (MAO A and B). J Am Chem Soc (2005) 0.90

Retracted Selective C-arylation of free (NH)-heteroarenes via catalytic C-H bond functionalization. J Am Chem Soc (2003) 0.89

Complementation of biotransformations with chemical C-H oxidation: copper-catalyzed oxidation of tertiary amines in complex pharmaceuticals. J Am Chem Soc (2013) 0.88

C-H bond functionalization via hydride transfer: direct coupling of unactivated alkynes and sp(3) C-H bonds catalyzed by platinum tetraiodide. J Am Chem Soc (2009) 0.88

Cocktails of Tb(3+) and Eu(3+) complexes: a general platform for the design of ratiometric optical probes. J Am Chem Soc (2007) 0.87

Ruthenium catalyzed decarbonylative arylation at sp3 carbon centers in pyrrolidine and piperidine heterocycles. J Am Chem Soc (2007) 0.87

C-H bonds as ubiquitous functionality: a general approach to complex arylated pyrazoles via sequential regioselective C-arylation and N-alkylation enabled by SEM-group transposition. J Am Chem Soc (2009) 0.87

New tools for molecular imaging of redox metabolism: development of a fluorogenic probe for 3 alpha-hydroxysteroid dehydrogenases. J Am Chem Soc (2004) 0.86

Harnessing functional plasticity of enzymes: a fluorogenic probe for imaging 17beta-HSD10 dehydrogenase, an enzyme involved in Alzheimer's and Parkinson's diseases. J Am Chem Soc (2007) 0.85

A new fluorogenic transformation: development of an optical probe for coenzyme Q. Org Lett (2005) 0.84

New fluorescent substrate enables quantitative and high-throughput examination of vesicular monoamine transporter 2 (VMAT2). ACS Chem Biol (2013) 0.84

Concise synthesis of the chemopreventitive agent (+/-)-deguelin via a key 6-endo hydroarylation. Org Lett (2003) 0.84

Transposing molecular fluorescent switches into the near-IR: development of luminogenic reporter substrates for redox metabolism. J Am Chem Soc (2007) 0.84

C-H bonds as ubiquitous functionality: a general approach to complex arylated imidazoles via regioselective sequential arylation of all three C-H bonds and regioselective N-alkylation enabled by SEM-group transposition. J Org Chem (2010) 0.83

APP+, a fluorescent analogue of the neurotoxin MPP+, is a marker of catecholamine neurons in brain tissue, but not a fluorescent false neurotransmitter. ACS Chem Neurosci (2013) 0.83

NeuO: a fluorescent chemical probe for live neuron labeling. Angew Chem Int Ed Engl (2015) 0.82

Fluorogenic metabolic probes for direct activity readout of redox enzymes: Selective measurement of human AKR1C2 in living cells. Proc Natl Acad Sci U S A (2006) 0.81

Phosphorylation state-responsive lanthanide peptide conjugates: a luminescence switch based on reversible complex reorganization. Org Lett (2006) 0.79

Catalytic coupling of arene C-H bonds and alkynes for the synthesis of coumarins: substrate scope and application to the development of neuroimaging agents. J Org Chem (2012) 0.79

Ligand-Based Discovery of a New Scaffold for Allosteric Modulation of the μ-Opioid Receptor. J Chem Inf Model (2015) 0.78

Fluoromorphic substrates for fatty acid metabolism: highly sensitive probes for mammalian medium-chain acyl-CoA dehydrogenase. Angew Chem Int Ed Engl (2006) 0.78

C-H bond functionalization via hydride transfer: formation of α-arylated piperidines and 1,2,3,4-tetrahydroisoquinolines via stereoselective intramolecular amination of benzylic C-H bonds. J Org Chem (2012) 0.78

(-)-CHANA, a fluorogenic probe for detecting amyloid binding alcohol dehydrogenase HSD10 activity in living cells. ACS Chem Biol (2010) 0.78

Paradoxical abatement of striatal dopaminergic transmission by cocaine and methylphenidate. J Biol Chem (2013) 0.77

Site-specific phenylation of pyridine catalyzed by phosphido-bridged ruthenium dimer complexes: a prototype for C-H arylation of electron-deficient heteroarenes. J Am Chem Soc (2005) 0.77

Role of Annular Lipids in the Functional Properties of Leucine Transporter LeuT Proteomicelles. Biochemistry (2016) 0.77

Two-photon induced uncaging of a reactive intermediate. Multiphoton in situ detection of a potentially valuable label for biological applications. J Org Chem (2005) 0.76

Development and Antiparkinsonian Activity of VU0418506, a Selective Positive Allosteric Modulator of Metabotropic Glutamate Receptor 4 Homomers without Activity at mGlu2/4 Heteromers. ACS Chem Neurosci (2016) 0.76

Expanding the use of fluorogenic enzyme reporter substrates to imaging metabolic flux changes: the activity measurement of 5α-steroid reductase in intact mammalian cells. ACS Chem Biol (2010) 0.76

Dopamine release at individual presynaptic terminals visualized with FFNs. J Vis Exp (2009) 0.75

Proposed Mode of Binding and Action of Positive Allosteric Modulators at Opioid Receptors. ACS Chem Biol (2016) 0.75

C-H bonds as ubiquitous functionality: preparation of multiple regioisomers of arylated 1,2,4-triazoles via C-H arylation. J Org Chem (2012) 0.75

Synthesis of luminescent heterometallic bis-lanthanide complexes via selective, sequential metallation. Chem Commun (Camb) (2006) 0.75

Cobalt-catalyzed arylation of azole heteroarenes via direct C-H bond functionalization. Org Lett (2003) 0.75

Intermolecular energy transfer from Tb3+ to Eu3+ in aqueous aggregates and on the surface of human cells. Org Lett (2011) 0.75

Identification of fluorescent small molecule compounds for synaptic labeling by image-based, high-content screening. ACS Chem Neurosci (2017) 0.75

Constructing Iboga alkaloids via C-H bond functionalization: examination of the direct and catalytic union of heteroarenes and isoquinuclidine alkenes. J Org Chem (2015) 0.75