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Article ; Online: Design and synthesis of 6-methylpyridin-2-one derivatives as novel and potent GluN2A positive allosteric modulators for the treatment of cognitive impairment.

Yukawa, Takafumi / Yamashita, Tohru / Imaeda, Toshihiro / Kakei, Hiroyuki / Hashizume, Shogo / Nakamura, Minoru / Daini, Masaki / Okabe, Atsutoshi / Nakashima, Kosuke / Harada, Akina / Narita, Naohiro / Bettini, Ezio / Ugolini, Annarosa / Corsi, Mauro / Hasui, Tomoaki

Bioorganic & medicinal chemistry

2022 Volume 79, Page(s) 117150

Abstract: N-Methyl-D-aspartate receptors (NMDARs) are key regulators of synaptic plasticity in the central nervous system. Potentiation of NMDARs containing GluN2A subunit has been recently recognized as a promising therapeutic approach for neurological disorders. ...

Abstract	N-Methyl-D-aspartate receptors (NMDARs) are key regulators of synaptic plasticity in the central nervous system. Potentiation of NMDARs containing GluN2A subunit has been recently recognized as a promising therapeutic approach for neurological disorders. We identified a novel series of GluN2A positive allosteric modulator (PAM) with a pyridin-2-one scaffold. Initial lead compound 1 was discovered through in silico-based screening of virtual ligands with various monocyclic scaffolds. GluN2A PAM activity was increased by introduction of a methyl group at the 6-position of the pyridin-2-one ring and a cyano group in the side chain. Modification of the aromatic ring led to the identification of potent and brain-penetrant 6-methylpyridin-2-one 17 with a negligible binding activity for α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors (AMPARs). Oral administration of 17 significantly enhanced rat hippocampal long-term potentiation (LTP). Thus, 17 would be a useful in vivo pharmacological tool to investigate complex NMDAR functions for the discovery of therapeutics toward diseases associated with NMDAR dysfunction.
MeSH term(s)	Rats ; Animals ; Receptors, N-Methyl-D-Aspartate/metabolism ; Hippocampus/metabolism ; Cognitive Dysfunction/drug therapy ; Cognitive Dysfunction/metabolism
Chemical Substances	Receptors, N-Methyl-D-Aspartate
Language	English
Publishing date	2022-12-24
Publishing country	England
Document type	Journal Article
ZDB-ID	1161284-8
ISSN	1464-3391 ; 0968-0896
ISSN (online)	1464-3391
ISSN	0968-0896
DOI	10.1016/j.bmc.2022.117150
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Article ; Online: Structure-Activity Relationship Studies of Antimalarial

Zhang, Hao / Ginn, John / Zhan, Wenhu / Leung, Annie / Liu, Yi J / Toita, Akinori / Okamoto, Rei / Wong, Tzu-Tshin / Imaeda, Toshihiro / Hara, Ryoma / Michino, Mayako / Yukawa, Takafumi / Chelebieva, Sevil / Tumwebaze, Patrick K / Vendome, Jeremie / Beuming, Thijs / Sato, Kenjiro / Aso, Kazuyoshi / Rosenthal, Philip J /

Cooper, Roland A / Liverton, Nigel / Foley, Michael / Meinke, Peter T / Nathan, Carl F / Kirkman, Laura A / Lin, Gang

Journal of medicinal chemistry

2023 Volume 66, Issue 2, Page(s) 1484–1508

Abstract: With increasing reports of resistance to artemisinins and artemisinin-combination therapies, targeting ... ...

Abstract	With increasing reports of resistance to artemisinins and artemisinin-combination therapies, targeting the
MeSH term(s)	Humans ; Animals ; Mice ; Antimalarials/pharmacology ; Antimalarials/chemistry ; Proteasome Endopeptidase Complex/metabolism ; Plasmodium ; Structure-Activity Relationship ; Plasmodium falciparum/metabolism ; Proteasome Inhibitors/pharmacology ; Proteasome Inhibitors/chemistry
Chemical Substances	Antimalarials ; Proteasome Endopeptidase Complex (EC 3.4.25.1) ; Proteasome Inhibitors
Language	English
Publishing date	2023-01-11
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.2c01651
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Article: Identification of a selective DDX3X inhibitor with newly developed quantitative high-throughput RNA helicase assays

Nakao, Shoichi / Nogami, Masahiro / Iwatani, Misa / Imaeda, Toshihiro / Ito, Masahiro / Tanaka, Toshio / Tawada, Michiko / Endo, Satoshi / Cary, Douglas R / Ohori, Momoko / Imaeda, Yasuhiro / Kawamoto, Tomohiro / Aparicio, Samuel / Nakanishi, Atsushi / Araki, Shinsuke

Biochemical and biophysical research communications. 2020 Mar. 12, v. 523, no. 3

2020

Abstract: The DEAD-box family of RNA helicases plays essential roles in both transcriptional and translational mRNA degradation; they unwind short double-stranded RNA by breaking the RNA–RNA interactions. Two DEAD-box RNA helicases, eukaryotic translation ... ...

Abstract	The DEAD-box family of RNA helicases plays essential roles in both transcriptional and translational mRNA degradation; they unwind short double-stranded RNA by breaking the RNA–RNA interactions. Two DEAD-box RNA helicases, eukaryotic translation initiation factor 4A3 (eIF4A3) and DEAD-box helicase 3 (DDX3X), show high homology in the ATP-binding region and are considered key molecules for cancer progression. Several small molecules that target eIF4A3 and DDX3X have been reported to inhibit cancer cell growth; however, more potent compounds are required for cancer therapeutics, and there is a critical need for high-throughput assays to screen for RNA helicase inhibitors. In this study, we developed novel fluorescence resonance energy transfer-based high-throughput RNA helicase assays for eIF4A3 and DDX3X. Using these assays, we identified several eIF4A3 allosteric inhibitors whose inhibitory effect on eIF4A3 ATPase showed a strong correlation with inhibitory effect on helicase activity. From 102 compounds that exhibited eIF4A3 ATPase inhibition, we identified a selective DDX3X inhibitor, C1, which showed stronger inhibition of DDX3X than of eIF4A3. Small-molecule helicase inhibitors can be valuable for clarifying the molecular machinery of DEAD-box RNA helicases. The high-throughput quantitative assays established here should facilitate the evaluation of the helicase inhibitory activity of compounds.
Keywords	DEAD-box RNA helicases ; adenosinetriphosphatase ; cell growth ; double-stranded RNA ; energy ; fluorescence ; neoplasm cells ; neoplasm progression ; research ; therapeutics ; transcription (genetics)
Language	English
Dates of publication	2020-0312
Size	p. 795-801.
Publishing place	Elsevier Inc.
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	205723-2
ISSN	0006-291X ; 0006-291X
ISSN (online)	0006-291X
ISSN	0006-291X
DOI	10.1016/j.bbrc.2019.12.094
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Article ; Online: Identification of a selective DDX3X inhibitor with newly developed quantitative high-throughput RNA helicase assays.

Biochemical and biophysical research communications

2020 Volume 523, Issue 3, Page(s) 795–801

Abstract: The DEAD-box family of RNA helicases plays essential roles in both transcriptional and translational mRNA degradation; they unwind short double-stranded RNA by breaking the RNA-RNA interactions. Two DEAD-box RNA helicases, eukaryotic translation ... ...

Abstract	The DEAD-box family of RNA helicases plays essential roles in both transcriptional and translational mRNA degradation; they unwind short double-stranded RNA by breaking the RNA-RNA interactions. Two DEAD-box RNA helicases, eukaryotic translation initiation factor 4A3 (eIF4A3) and DEAD-box helicase 3 (DDX3X), show high homology in the ATP-binding region and are considered key molecules for cancer progression. Several small molecules that target eIF4A3 and DDX3X have been reported to inhibit cancer cell growth; however, more potent compounds are required for cancer therapeutics, and there is a critical need for high-throughput assays to screen for RNA helicase inhibitors. In this study, we developed novel fluorescence resonance energy transfer-based high-throughput RNA helicase assays for eIF4A3 and DDX3X. Using these assays, we identified several eIF4A3 allosteric inhibitors whose inhibitory effect on eIF4A3 ATPase showed a strong correlation with inhibitory effect on helicase activity. From 102 compounds that exhibited eIF4A3 ATPase inhibition, we identified a selective DDX3X inhibitor, C1, which showed stronger inhibition of DDX3X than of eIF4A3. Small-molecule helicase inhibitors can be valuable for clarifying the molecular machinery of DEAD-box RNA helicases. The high-throughput quantitative assays established here should facilitate the evaluation of the helicase inhibitory activity of compounds.
MeSH term(s)	DEAD-box RNA Helicases/antagonists & inhibitors ; DEAD-box RNA Helicases/metabolism ; Drug Discovery/methods ; Drug Evaluation, Preclinical/methods ; Enzyme Assays/methods ; Eukaryotic Initiation Factor-4A/antagonists & inhibitors ; Eukaryotic Initiation Factor-4A/metabolism ; High-Throughput Screening Assays ; Humans ; Small Molecule Libraries/chemistry ; Small Molecule Libraries/pharmacology
Chemical Substances	Small Molecule Libraries ; Eukaryotic Initiation Factor-4A (EC 2.7.7.-) ; DDX3X protein, human (EC 3.6.1.-) ; EIF4A3 protein, human (EC 3.6.1.-) ; DEAD-box RNA Helicases (EC 3.6.4.13)
Language	English
Publishing date	2020-01-15
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	205723-2
ISSN	1090-2104 ; 0006-291X ; 0006-291X
ISSN (online)	1090-2104 ; 0006-291X
ISSN	0006-291X
DOI	10.1016/j.bbrc.2019.12.094
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Article ; Online: Design, Synthesis, and Optimization of Macrocyclic Peptides as Species-Selective Antimalaria Proteasome Inhibitors.

Journal of medicinal chemistry

2022 Volume 65, Issue 13, Page(s) 9350–9375

Abstract: With over 200 million cases and close to half a million deaths each year, malaria is a threat to global health, particularly in developing countries. ...

Abstract	With over 200 million cases and close to half a million deaths each year, malaria is a threat to global health, particularly in developing countries.
MeSH term(s)	Antimalarials/pharmacology ; Antimalarials/therapeutic use ; Artemisinins/pharmacology ; Drug Resistance ; Humans ; Malaria, Falciparum/drug therapy ; Peptides/therapeutic use ; Plasmodium falciparum ; Proteasome Inhibitors/pharmacology ; Proteasome Inhibitors/therapeutic use ; Protozoan Proteins/genetics
Chemical Substances	Antimalarials ; Artemisinins ; Peptides ; Proteasome Inhibitors ; Protozoan Proteins
Language	English
Publishing date	2022-06-21
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; 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.2c00611
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Article ; Online: Whole Cell Active Inhibitors of Mycobacterial Lipoamide Dehydrogenase Afford Selectivity over the Human Enzyme through Tight Binding Interactions.

ACS infectious diseases

2021 Volume 7, Issue 2, Page(s) 435–444

Abstract: Tuberculosis remains a leading cause of death from a single bacterial infection worldwide. Efforts to develop new treatment options call for expansion into an unexplored target space to expand the drug pipeline and bypass resistance to current ... ...

Abstract	Tuberculosis remains a leading cause of death from a single bacterial infection worldwide. Efforts to develop new treatment options call for expansion into an unexplored target space to expand the drug pipeline and bypass resistance to current antibiotics. Lipoamide dehydrogenase is a metabolic and antioxidant enzyme critical for mycobacterial growth and survival in mice. Sulfonamide analogs were previously identified as potent and selective inhibitors of mycobacterial lipoamide dehydrogenase
MeSH term(s)	Animals ; Anti-Bacterial Agents/therapeutic use ; Dihydrolipoamide Dehydrogenase/metabolism ; Humans ; Kinetics ; Mice ; Mycobacterium tuberculosis/metabolism ; Tuberculosis/drug therapy
Chemical Substances	Anti-Bacterial Agents ; Dihydrolipoamide Dehydrogenase (EC 1.8.1.4)
Language	English
Publishing date	2021-02-02
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ISSN	2373-8227
ISSN (online)	2373-8227
DOI	10.1021/acsinfecdis.0c00788
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Article ; Online: Selective Phenylimidazole-Based Inhibitors of the

Zhan, Wenhu / Hsu, Hao-Chi / Morgan, Trevor / Ouellette, Tierra / Burns-Huang, Kristin / Hara, Ryoma / Wright, Adrian G / Imaeda, Toshihiro / Okamoto, Rei / Sato, Kenjiro / Michino, Mayako / Ramjee, Manoj / Aso, Kazuyoshi / Meinke, Peter T / Foley, Michael / Nathan, Carl F / Li, Huilin / Lin, Gang

Journal of medicinal chemistry

2019 Volume 62, Issue 20, Page(s) 9246–9253

Abstract: Proteasomes of pathogenic microbes have become attractive targets for anti-infectives. Coevolving with its human host, ...

Abstract	Proteasomes of pathogenic microbes have become attractive targets for anti-infectives. Coevolving with its human host,
MeSH term(s)	Imidazoles/chemistry ; Imidazoles/pharmacology ; Microbial Sensitivity Tests ; Mycobacterium tuberculosis/drug effects ; Mycobacterium tuberculosis/enzymology ; Proteasome Inhibitors/chemistry ; Proteasome Inhibitors/pharmacology ; Reactive Nitrogen Species/metabolism ; Structure-Activity Relationship
Chemical Substances	Imidazoles ; Proteasome Inhibitors ; Reactive Nitrogen Species
Language	English
Publishing date	2019-10-15
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.9b01187
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Article ; Online: Identification of a novel fluoropyrrole derivative as a potassium-competitive acid blocker with long duration of action.

Nishida, Haruyuki / Arikawa, Yasuyoshi / Hirase, Keizo / Imaeda, Toshihiro / Inatomi, Nobuhiro / Hori, Yasunobu / Matsukawa, Jun / Fujioka, Yasushi / Hamada, Teruki / Iida, Motoo / Nishitani, Mitsuyoshi / Imanishi, Akio / Fukui, Hideo / Itoh, Fumio / Kajino, Masahiro

Bioorganic & medicinal chemistry

2017 Volume 25, Issue 13, Page(s) 3298–3314

Abstract: With the aim to find a novel long-lasting potassium-competitive acid blocker (P-CAB) that would perfectly overcome the limitations of proton pump inhibitors (PPIs), we tried various approaches based on pyrrole derivative 1b as a lead compound. As part of ...

Abstract	With the aim to find a novel long-lasting potassium-competitive acid blocker (P-CAB) that would perfectly overcome the limitations of proton pump inhibitors (PPIs), we tried various approaches based on pyrrole derivative 1b as a lead compound. As part of a comprehensive approach to identification of a new drug, we explored excellent compounds that have low lipophilicity by introducing a polar hetero-aromatic group at position 5 of the pyrrole ring. Among the compounds synthesized, fluoropyrrole derivative 37c, which has a 2-F-3-Py group at the fifth position, lower pK
MeSH term(s)	Administration, Oral ; Animals ; Cell Survival/drug effects ; Dogs ; Dose-Response Relationship, Drug ; Ether-A-Go-Go Potassium Channels/antagonists & inhibitors ; Ether-A-Go-Go Potassium Channels/metabolism ; Gastric Acid/metabolism ; H(+)-K(+)-Exchanging ATPase/metabolism ; HEK293 Cells ; Hep G2 Cells ; Humans ; Hydrogen-Ion Concentration ; Molecular Structure ; Proton Pump Inhibitors/administration & dosage ; Proton Pump Inhibitors/chemistry ; Proton Pump Inhibitors/pharmacology ; Pyrroles/administration & dosage ; Pyrroles/chemistry ; Pyrroles/pharmacology ; Rats ; Structure-Activity Relationship
Chemical Substances	Ether-A-Go-Go Potassium Channels ; Proton Pump Inhibitors ; Pyrroles ; H(+)-K(+)-Exchanging ATPase (EC 3.6.3.10)
Language	English
Publishing date	2017-07-01
Publishing country	England
Document type	Journal Article
ZDB-ID	1161284-8
ISSN	1464-3391 ; 0968-0896
ISSN (online)	1464-3391
ISSN	0968-0896
DOI	10.1016/j.bmc.2017.04.014
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Article ; Online: Discovery, synthesis, and structure-activity relations of 3,4-dihydro-1H-spiro(naphthalene-2,2'-piperidin)-1-ones as potassium-competitive acid blockers.

Imaeda, Toshihiro / Ono, Koji / Nakai, Kazuo / Hori, Yasunobu / Matsukawa, Jun / Takagi, Terufumi / Fujioka, Yasushi / Tarui, Naoki / Kondo, Mitsuyo / Imanishi, Akio / Inatomi, Nobuhiro / Kajino, Masahiro / Itoh, Fumio / Nishida, Haruyuki

Bioorganic & medicinal chemistry

2017 Volume 25, Issue 14, Page(s) 3719–3735

Abstract: With the aim to discover a gastric antisecretory agent more potent than the existing proton pump inhibitors, novel 3,4-dihydro-1H-spiro(naphthalene-2,2'-piperidin)-1-one derivatives, which could occupy two important lipophilic pockets (described as LP-1 ... ...

Abstract	With the aim to discover a gastric antisecretory agent more potent than the existing proton pump inhibitors, novel 3,4-dihydro-1H-spiro(naphthalene-2,2'-piperidin)-1-one derivatives, which could occupy two important lipophilic pockets (described as LP-1 and LP-2) of H
MeSH term(s)	Administration, Intravenous ; Animals ; Area Under Curve ; Binding Sites ; Drug Evaluation, Preclinical ; Gastric Acid/metabolism ; Gastric Acid/secretion ; Gastric Mucosa/drug effects ; Gastric Mucosa/metabolism ; Gastric Mucosa/secretion ; H(+)-K(+)-Exchanging ATPase/chemistry ; H(+)-K(+)-Exchanging ATPase/metabolism ; Half-Life ; Histamine/toxicity ; Inhibitory Concentration 50 ; Molecular Docking Simulation ; Naphthalenes/chemistry ; Piperidines/chemical synthesis ; Piperidines/chemistry ; Piperidines/pharmacokinetics ; Potassium/chemistry ; Potassium/metabolism ; Proton Pump Inhibitors/chemical synthesis ; Proton Pump Inhibitors/chemistry ; Proton Pump Inhibitors/pharmacokinetics ; ROC Curve ; Rats ; Spiro Compounds/chemical synthesis ; Spiro Compounds/chemistry ; Spiro Compounds/pharmacokinetics ; Structure-Activity Relationship
Chemical Substances	N-(1'-(2-(2-methylphenyl)ethyl)-1-oxo-3,4-dihydro-1H-spiro(naphthalene-2,2'-piperidin)-6-yl)acetamide ; Naphthalenes ; Piperidines ; Proton Pump Inhibitors ; Spiro Compounds ; naphthalene (2166IN72UN) ; piperidine (67I85E138Y) ; Histamine (820484N8I3) ; H(+)-K(+)-Exchanging ATPase (EC 3.6.3.10) ; Potassium (RWP5GA015D)
Language	English
Publishing date	2017-07-15
Publishing country	England
Document type	Journal Article
ZDB-ID	1161284-8
ISSN	1464-3391 ; 0968-0896
ISSN (online)	1464-3391
ISSN	0968-0896
DOI	10.1016/j.bmc.2017.05.012
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Article ; Online: Macrocyclic Peptides that Selectively Inhibit the

Zhang, Hao / Hsu, Hao-Chi / Kahne, Shoshanna C / Hara, Ryoma / Zhan, Wenhu / Jiang, Xiuju / Burns-Huang, Kristin / Ouellette, Tierra / Imaeda, Toshihiro / Okamoto, Rei / Kawasaki, Masanori / Michino, Mayako / Wong, Tzu-Tshin / Toita, Akinori / Yukawa, Takafumi / Moraca, Francesca / Vendome, Jeremie / Saha, Priya / Sato, Kenjiro /

Aso, Kazuyoshi / Ginn, John / Meinke, Peter T / Foley, Michael / Nathan, Carl F / Darwin, K Heran / Li, Huilin / Lin, Gang

Journal of medicinal chemistry

2021 Volume 64, Issue 9, Page(s) 6262–6272

Abstract: Treatment of tuberculosis (TB) currently takes at least 6 months. ... ...

Abstract	Treatment of tuberculosis (TB) currently takes at least 6 months. Latent
MeSH term(s)	Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Drug Design ; Humans ; Mycobacterium tuberculosis/drug effects ; Mycobacterium tuberculosis/enzymology ; Peptides, Cyclic/chemistry ; Peptides, Cyclic/pharmacology ; Proteasome Endopeptidase Complex/metabolism ; Proteasome Inhibitors/chemistry ; Proteasome Inhibitors/pharmacology ; Structure-Activity Relationship
Chemical Substances	Anti-Bacterial Agents ; Peptides, Cyclic ; Proteasome Inhibitors ; Proteasome Endopeptidase Complex (EC 3.4.25.1)
Language	English
Publishing date	2021-05-05
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.1c00296
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