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Article ; Online: Discovery of a novel class of inhaled dual pharmacology muscarinic antagonist and β

Rancati, Fabio / Linney, Ian D / Rizzi, Andrea / Delcanale, Maurizio / Knight, Chris K / Schmidt, Wolfgang / Pastore, Fiorella / Riccardi, Benedetta / Mileo, Valentina / Carnini, Chiara / Cesari, Nicola / Blackaby, Wesley P / Patacchini, Riccardo / Carzaniga, Laura

Bioorganic & medicinal chemistry letters

2021 Volume 41, Page(s) 127975

Abstract: The targeting of both the muscarinic and β-adrenergic pathways is a well validated therapeutic approach for the treatment of chronic obstructive pulmonary disease (COPD). In this communication we report our effort to incorporate two pharmacologies into a ...

Abstract	The targeting of both the muscarinic and β-adrenergic pathways is a well validated therapeutic approach for the treatment of chronic obstructive pulmonary disease (COPD). In this communication we report our effort to incorporate two pharmacologies into a single chemical entity, whose characteristic must be suitable for a once daily inhaled administration. Contextually, we aimed at a locally acting therapy with limited systemic absorption to minimize side effects. Our lung-tailored design of bifunctional compounds that combine the muscarinic and β-adrenergic pharmacologies by the elaboration of the muscarinic inhibitor 7, successfully led to the potent, pharmacologically balanced muscarinic antagonist and β
MeSH term(s)	Administration, Inhalation ; Adrenergic beta-2 Receptor Agonists/administration & dosage ; Adrenergic beta-2 Receptor Agonists/pharmacology ; Bronchodilator Agents/administration & dosage ; Bronchodilator Agents/pharmacology ; Dose-Response Relationship, Drug ; Drug Discovery ; Humans ; Molecular Structure ; Muscarinic Antagonists/administration & dosage ; Muscarinic Antagonists/pharmacology ; Pulmonary Disease, Chronic Obstructive/drug therapy ; Pulmonary Disease, Chronic Obstructive/metabolism ; Receptor, Muscarinic M3/antagonists & inhibitors ; Receptor, Muscarinic M3/metabolism ; Receptors, Adrenergic, beta-2/metabolism ; Structure-Activity Relationship
Chemical Substances	Adrenergic beta-2 Receptor Agonists ; Bronchodilator Agents ; Muscarinic Antagonists ; Receptor, Muscarinic M3 ; Receptors, Adrenergic, beta-2
Language	English
Publishing date	2021-03-19
Publishing country	England
Document type	Journal Article
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2021.127975
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Article ; Online: Discovery of Clinical Candidate CHF-6366: A Novel Super-soft Dual Pharmacology Muscarinic Antagonist and β

Carzaniga, Laura / Linney, Ian D / Rizzi, Andrea / Delcanale, Maurizio / Schmidt, Wolfgang / Knight, Christopher K / Pastore, Fiorella / Miglietta, Daniela / Carnini, Chiara / Cesari, Nicola / Riccardi, Benedetta / Mileo, Valentina / Venturi, Luca / Moretti, Elisa / Blackaby, Wesley P / Patacchini, Riccardo / Accetta, Alessandro / Biagetti, Matteo / Bassani, Franco /

Tondelli, Marina / Murgo, Annalisa / Battipaglia, Loredana / Villetti, Gino / Puccini, Paola / Catinella, Silvia / Civelli, Maurizio / Rancati, Fabio

Journal of medicinal chemistry

2022 Volume 65, Issue 15, Page(s) 10233–10250

Abstract: The development of molecules embedding two distinct pharmacophores acting as muscarinic antagonists and ... ...

Abstract	The development of molecules embedding two distinct pharmacophores acting as muscarinic antagonists and β
MeSH term(s)	Administration, Inhalation ; Adrenergic beta-2 Receptor Agonists/pharmacology ; Adrenergic beta-2 Receptor Agonists/therapeutic use ; Bronchodilator Agents/therapeutic use ; Drug Discovery ; Humans ; Lung ; Muscarinic Antagonists/pharmacology ; Muscarinic Antagonists/therapeutic use ; Pulmonary Disease, Chronic Obstructive/drug therapy
Chemical Substances	Adrenergic beta-2 Receptor Agonists ; Bronchodilator Agents ; Muscarinic Antagonists
Language	English
Publishing date	2022-07-28
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.2c00609
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Article ; Online: Targeting the m

Burgess, Hannah M / Depledge, Daniel P / Thompson, Letitia / Srinivas, Kalanghad Puthankalam / Grande, Rebecca C / Vink, Elizabeth I / Abebe, Jonathan S / Blackaby, Wesley P / Hendrick, Alan / Albertella, Mark R / Kouzarides, Tony / Stapleford, Kenneth A / Wilson, Angus C / Mohr, Ian

Genes & development

2021 Volume 35, Issue 13-14, Page(s) 1005–1019

Abstract: ... ...

Abstract	N
MeSH term(s)	Adenosine/analogs & derivatives ; Adenosine/genetics ; Adenosine/metabolism ; Cell Line ; Coronavirus Infections/metabolism ; Coronavirus Infections/virology ; Coronavirus OC43, Human/physiology ; Gene Expression Regulation/drug effects ; Host-Pathogen Interactions/drug effects ; Humans ; Methyltransferases/antagonists & inhibitors ; Methyltransferases/metabolism ; Nucleocapsid Proteins ; RNA Processing, Post-Transcriptional/genetics ; RNA, Viral/metabolism ; RNA-Binding Proteins/metabolism ; SARS-CoV-2/physiology ; Virus Replication/drug effects ; Virus Replication/genetics
Chemical Substances	Nucleocapsid Proteins ; RNA, Viral ; RNA-Binding Proteins ; YTHDF1 protein, human ; YTHDF3 protein, human ; N-methyladenosine (CLE6G00625) ; Methyltransferases (EC 2.1.1.-) ; METTL3 protein, human (EC 2.1.1.62) ; Adenosine (K72T3FS567)
Language	English
Publishing date	2021-06-24
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	806684-x
ISSN	1549-5477 ; 0890-9369
ISSN (online)	1549-5477
ISSN	0890-9369
DOI	10.1101/gad.348320.121
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Article ; Online: Discovery of M

Armani, Elisabetta / Rizzi, Andrea / Capaldi, Carmelida / De Fanti, Renato / Delcanale, Maurizio / Villetti, Gino / Marchini, Gessica / Pisano, Anna Rita / Pitozzi, Vanessa / Pittelli, Maria Gloria / Trevisani, Marcello / Salvadori, Michela / Cenacchi, Valentina / Puccini, Paola / Amadei, Francesco / Pappani, Alice / Civelli, Maurizio / Patacchini, Riccardo / Baker-Glenn, Charles A G /

Van de Poël, Hervé / Blackaby, Wesley P / Nash, Kevin / Amari, Gabriele

Journal of medicinal chemistry

2021 Volume 64, Issue 13, Page(s) 9100–9119

Abstract: In this paper, we report the discovery of dual ... ...

Abstract	In this paper, we report the discovery of dual M
MeSH term(s)	Animals ; Cyclic Nucleotide Phosphodiesterases, Type 4/metabolism ; Dose-Response Relationship, Drug ; Drug Discovery ; Guinea Pigs ; Male ; Molecular Structure ; Phosphodiesterase 4 Inhibitors/chemistry ; Phosphodiesterase 4 Inhibitors/pharmacology ; Pulmonary Disease, Chronic Obstructive/drug therapy ; Pulmonary Disease, Chronic Obstructive/metabolism ; Rats ; Rats, Inbred BN ; Rats, Sprague-Dawley ; Receptor, Muscarinic M3/antagonists & inhibitors ; Receptor, Muscarinic M3/metabolism ; Structure-Activity Relationship
Chemical Substances	Phosphodiesterase 4 Inhibitors ; Receptor, Muscarinic M3 ; Cyclic Nucleotide Phosphodiesterases, Type 4 (EC 3.1.4.17)
Language	English
Publishing date	2021-06-18
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.1c00204
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Article ; Online: Optimization of M

Rizzi, Andrea / Amari, Gabriele / Pivetti, Fausto / Delcanale, Maurizio / Amadei, Francesco / Pappani, Alice / Fornasari, Luca / Villetti, Gino / Marchini, Gessica / Pisano, Anna Rita / Pitozzi, Vanessa / Pittelli, Maria Gloria / Trevisani, Marcello / Salvadori, Michela / Cenacchi, Valentina / Fioni, Alessandro / Puccini, Paola / Civelli, Maurizio / Patacchini, Riccardo /

Baker-Glenn, Charles / Van de Poël, Hervé / Blackaby, Wesley / Nash, Kevin / Armani, Elisabetta

Journal of medicinal chemistry

2023 Volume 66, Issue 16, Page(s) 11476–11497

Abstract: Aiming at the inhaled treatment of pulmonary diseases, the optimization process of the previously reported MAPI ... ...

Abstract	Aiming at the inhaled treatment of pulmonary diseases, the optimization process of the previously reported MAPI compound
MeSH term(s)	Rats ; Animals ; Phosphodiesterase 4 Inhibitors/pharmacology ; Phosphodiesterase 4 Inhibitors/therapeutic use ; Bronchodilator Agents/pharmacology ; Bronchodilator Agents/therapeutic use ; Anti-Inflammatory Agents/pharmacology ; Pulmonary Disease, Chronic Obstructive/drug therapy
Chemical Substances	Phosphodiesterase 4 Inhibitors ; microbial alkaline proteinase inhibitor ; Bronchodilator Agents ; Anti-Inflammatory Agents
Language	English
Publishing date	2023-08-10
Publishing country	United States
Document type	Journal Article ; 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.3c01012
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Article ; Online: European Medicinal Chemistry Leaders in Industry (EMCL) - On the Status and Future of Medicinal Chemistry Research in Europe.

Ali, Amjad / Bauser, Marcus / Bertrand, Sophie / Blackaby, Wesley / Boss, Christoph / Bossart, Martin / Hall, Adrian / Binch, Hayley / Czechtizky, Werngard / Gijsen, Harrie / Haning, Helmut / Hartung, Ingo V / Kilburn, Paul / Lassalle, Gilbert / Lücking, Ulrich / Mack, Jürgen / Missbach, Martin / Otsomaa, Leena / Torrens, Antoni /

Wagner, Michael / Walter, Magnus / Weinstabl, Harald / van Hijfte, Luc / von Nussbaum, Franz

ChemMedChem

2023 Volume 18, Issue 13, Page(s) e202300127

Abstract: The status of industrial Medicinal Chemistry was discussed with European Medicinal Chemistry Leaders from large to mid-sized pharma and CRO companies as well as biotechs. The chemical modality space has expanded recently from small molecules to address ... ...

Abstract	The status of industrial Medicinal Chemistry was discussed with European Medicinal Chemistry Leaders from large to mid-sized pharma and CRO companies as well as biotechs. The chemical modality space has expanded recently from small molecules to address new challenging targets. Besides the classical SAR/SPR optimization of drug molecules also their 'greenness' has increasing importance. The entire pharma discovery ecosystem has developed significantly. Beyond pharma and academia new key players such as Biotech and integrated CROs as well as Digital companies have appeared and are now to a large extend fueled by VC money. Digitalization is happening everywhere but surprisingly did not change speed and success rates of projects so far. Future Medicinal Chemists will still have to be excellent synthetic chemists but in addition they must be knowledgeable in new computational areas such as data sciences. Their ability to collaborate and to work in teams is key.
MeSH term(s)	Chemistry, Pharmaceutical ; Drug Industry ; Ecosystem ; Europe
Language	English
Publishing date	2023-06-05
Publishing country	Germany
Document type	Journal Article ; Review
ZDB-ID	2218496-X
ISSN	1860-7187 ; 1860-7179
ISSN (online)	1860-7187
ISSN	1860-7179
DOI	10.1002/cmdc.202300127
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Article ; Online: Developing HDAC4-Selective Protein Degraders To Investigate the Role of HDAC4 in Huntington's Disease Pathology.

Macabuag, Natsuko / Esmieu, William / Breccia, Perla / Jarvis, Rebecca / Blackaby, Wesley / Lazari, Ovadia / Urbonas, Liudvikas / Eznarriaga, Maria / Williams, Rachel / Strijbosch, Annelieke / Van de Bospoort, Rhea / Matthews, Kim / Clissold, Cole / Ladduwahetty, Tammy / Vater, Huw / Heaphy, Patrick / Stafford, Douglas G / Wang, Hong-Jun / Mangette, John E /

McAllister, George / Beaumont, Vahri / Vogt, Thomas F / Wilkinson, Hilary A / Doherty, Elizabeth M / Dominguez, Celia

Journal of medicinal chemistry

2022 Volume 65, Issue 18, Page(s) 12445–12459

Abstract: Huntington's disease (HD) is a lethal autosomal dominant neurodegenerative disorder resulting from a CAG repeat expansion in the huntingtin ( ...

Abstract	Huntington's disease (HD) is a lethal autosomal dominant neurodegenerative disorder resulting from a CAG repeat expansion in the huntingtin (
MeSH term(s)	Animals ; Disease Models, Animal ; Drug Development ; Histone Deacetylases/metabolism ; Huntingtin Protein/genetics ; Huntingtin Protein/metabolism ; Huntington Disease/genetics ; Mice ; Neurons/metabolism ; Proteolysis ; Ubiquitins
Chemical Substances	Huntingtin Protein ; Ubiquitins ; Hdac5 protein, mouse (EC 3.5.1.98) ; Histone Deacetylases (EC 3.5.1.98)
Language	English
Publishing date	2022-09-13
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.2c01149
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Article: Probing Mechanisms of CYP3A Time-Dependent Inhibition Using a Truncated Model System.

Wang, Xiaojing / Sun, Minghua / New, Connie / Nam, Spencer / Blackaby, Wesley P / Hodges, Alastair J / Nash, David / Matteucci, Mizio / Lyssikatos, Joseph P / Fan, Peter W / Tay, Suzanne / Chang, Jae H

ACS medicinal chemistry letters

2015 Volume 6, Issue 8, Page(s) 925–929

Abstract: Time-dependent inhibition (TDI) of cytochrome P450 (CYP) enzymes may incur serious undesirable drug-drug interactions and in rare cases drug-induced idiosyncratic toxicity. The reactive metabolites are often generated through multiple sequential ... ...

Abstract	Time-dependent inhibition (TDI) of cytochrome P450 (CYP) enzymes may incur serious undesirable drug-drug interactions and in rare cases drug-induced idiosyncratic toxicity. The reactive metabolites are often generated through multiple sequential biotransformations and form adducts with CYP enzymes to inactivate their function. The complexity of these processes makes addressing TDI liability very challenging. Strategies to mitigate TDI are therefore highly valuable in discovering safe therapies to benefit patients. In this Letter, we disclose our simplified approach toward addressing CYP3A TDI liabilities, guided by metabolic mechanism hypotheses. By adding a methyl group onto the α carbon of a basic amine, TDI activities of both the truncated and full molecules (7a and 11) were completely eliminated. We propose that truncated molecules, albeit with caveats, may be used as surrogates for full molecules to investigate TDI.
Language	English
Publishing date	2015-07-12
Publishing country	United States
Document type	Journal Article
ISSN	1948-5875
ISSN	1948-5875
DOI	10.1021/acsmedchemlett.5b00191
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Article ; Online: Optimization of Potent and Selective Ataxia Telangiectasia-Mutated Inhibitors Suitable for a Proof-of-Concept Study in Huntington's Disease Models.

Toledo-Sherman, Leticia / Breccia, Perla / Cachope, Roger / Bate, Jennifer R / Angulo-Herrera, Ivan / Wishart, Grant / Matthews, Kim L / Martin, Sarah L / Cox, Helen C / McAllister, George / Penrose, Stephen D / Vater, Huw / Esmieu, William / Van de Poël, Amanda / Van de Bospoort, Rhea / Strijbosch, Annelieke / Lamers, Marieke / Leonard, Philip / Jarvis, Rebecca E /

Blackaby, Wesley / Barnes, Karen / Eznarriaga, Maria / Dowler, Simon / Smith, Graham D / Fischer, David F / Lazari, Ovadia / Yates, Dawn / Rose, Mark / Jang, Sung-Wook / Muñoz-Sanjuan, Ignacio / Dominguez, Celia

Journal of medicinal chemistry

2019 Volume 62, Issue 6, Page(s) 2988–3008

Abstract: ... we aimed with few modifications to increase brain exposure by decreasing P-glycoprotein liability ...

Abstract	Genetic and pharmacological evidence indicates that the reduction of ataxia telangiectasia-mutated (ATM) kinase activity can ameliorate mutant huntingtin (mHTT) toxicity in cellular and animal models of Huntington's disease (HD), suggesting that selective inhibition of ATM could provide a novel clinical intervention to treat HD. Here, we describe the development and characterization of ATM inhibitor molecules to enable in vivo proof-of-concept studies in HD animal models. Starting from previously reported ATM inhibitors, we aimed with few modifications to increase brain exposure by decreasing P-glycoprotein liability while maintaining potency and selectivity. Here, we report brain-penetrant ATM inhibitors that have robust pharmacodynamic (PD) effects consistent with ATM kinase inhibition in the mouse brain and an understandable pharmacokinetic/PD (PK/PD) relationship. Compound 17 engages ATM kinase and shows robust dose-dependent inhibition of X-ray irradiation-induced KAP1 phosphorylation in the mouse brain. Furthermore, compound 17 protects against mHTT (Q73)-induced cytotoxicity in a cortical-striatal cell model of HD.
MeSH term(s)	ATP Binding Cassette Transporter, Subfamily B, Member 1/metabolism ; Animals ; Ataxia Telangiectasia Mutated Proteins/antagonists & inhibitors ; Disease Models, Animal ; Dogs ; Humans ; Huntington Disease/drug therapy ; Madin Darby Canine Kidney Cells ; Mice ; Neuroprotective Agents/metabolism ; Neuroprotective Agents/pharmacokinetics ; Neuroprotective Agents/therapeutic use ; Proof of Concept Study
Chemical Substances	ATP Binding Cassette Transporter, Subfamily B, Member 1 ; Neuroprotective Agents ; ATM protein, human (EC 2.7.11.1) ; Ataxia Telangiectasia Mutated Proteins (EC 2.7.11.1)
Language	English
Publishing date	2019-03-19
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.8b01819
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Article: Evaluation of 5-(Trifluoromethyl)-1,2,4-oxadiazole-Based Class IIa HDAC Inhibitors for Huntington's Disease.

Stott, Andrew J / Maillard, Michel C / Beaumont, Vahri / Allcock, David / Aziz, Omar / Borchers, Alexander H / Blackaby, Wesley / Breccia, Perla / Creighton-Gutteridge, Gillian / Haughan, Alan F / Jarvis, Rebecca E / Luckhurst, Christopher A / Matthews, Kim L / McAllister, George / Pollack, Scott / Saville-Stones, Elizabeth / Van de Poël, Amanda J / Vater, Huw D / Vann, Julie /

Williams, Rachel / Yates, Dawn / Muñoz-Sanjuán, Ignacio / Dominguez, Celia

ACS medicinal chemistry letters

2021 Volume 12, Issue 3, Page(s) 380–388

Abstract: Using an iterative structure-activity relationship driven approach, we identified a CNS-penetrant 5-(trifluoromethyl)-1,2,4-oxadiazole (TFMO, ...

Abstract	Using an iterative structure-activity relationship driven approach, we identified a CNS-penetrant 5-(trifluoromethyl)-1,2,4-oxadiazole (TFMO,
Language	English
Publishing date	2021-02-11
Publishing country	United States
Document type	Journal Article
ISSN	1948-5875
ISSN	1948-5875
DOI	10.1021/acsmedchemlett.0c00532
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