Development of Thiochroman Dioxide Analogues of Benzothiadiazine Dioxides as New Positive Allosteric Modulators of α-Amino-3- hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptors

Etse, Koffi Senam; Dorosz, Jerzy; Mc Lain Christensen; Thomas, Jean-Yves; Botez Pop, Iuliana; Goffin, Eric; Colson, Thomas; Lestage, Pierre; Danober, Laurence; Pirotte, Bernard; Sandholm Katrup, Jette; Francotte, Pierre

doi:10.1021/acschemneuro.1c00255

Article (Scientific journals)

Development of Thiochroman Dioxide Analogues of Benzothiadiazine Dioxides as New Positive Allosteric Modulators of α-Amino-3- hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptors

Etse, Koffi Senam; Dorosz, Jerzy; Mc Lain Christensen et al.

2021 • In ACS Chemical Neurosciences, 12 (14), p. 2679-2692

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https://hdl.handle.net/2268/261395

DOI
10.1021/acschemneuro.1c00255

PubMed
34242002

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Abstract :

[en] Based on the activity of 1,2,4-benzothiadiazine 1,1-dioxides as AMPAR-PAMs, thiochroman 1,1-dioxides were designed apply- ing the isosteric replacement concept. The new compounds expressed a strong modulatory activity on AMPARs in vitro, although lower than their corresponding benzothiadiazine analogues. The pharmacokinetic profile of three thiochroman 1,1-dioxides (12a, 12b, 12e) was exam- ined in vivo after oral administration, showing that these compounds freely cross the blood-brain barrier. Structural analysis was achieved using X-ray crystallography after cocrystallisation of the racemic compound 12b in complex with GluA2-LBD (L504Y/N775S). Interestingly, both enantiomers of 12b were found to interact with the GluA2-LBD dimer interface, almost identically to its benzothiadiazine analogue, BPAM344 (4). The interactions of the two enantiomers in the cocrystal were further analyzed (mapping Hirshfeld surfaces and 2D finger- print) and compared to those of 4. Taken together, these data explain the lower affinity on AMPARs of thiochroman 1,1-dioxides compared to their corresponding 1,2,4-benzothiadiazine 1,1-dioxides.

Research Center/Unit :

CIRM - Centre Interdisciplinaire de Recherche sur le Médicament - ULiège

Disciplines :

Pharmacy, pharmacology & toxicology

Author, co-author :

Etse, Koffi Senam ; Université de Liège - ULiège > Département de pharmacie > Chimie analytique

Dorosz, Jerzy

Mc Lain Christensen

Thomas, Jean-Yves

Botez Pop, Iuliana

Goffin, Eric

Colson, Thomas ; Université de Liège - ULiège > Master sc. pharma., à fin.

Lestage, Pierre

Danober, Laurence

Pirotte, Bernard ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique

Sandholm Katrup, Jette

Francotte, Pierre ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique

Language :

English

Title :

Development of Thiochroman Dioxide Analogues of Benzothiadiazine Dioxides as New Positive Allosteric Modulators of α-Amino-3- hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptors

Publication date :

09 July 2021

Journal title :

ACS Chemical Neurosciences

ISSN :

1948-7193

Publisher :

American Chemical Society (ACS), United States - District of Columbia

Volume :

Issue :

Pages :

2679-2692

Peer reviewed :

Peer Reviewed verified by ORBi

Funders :

Fonds Léon Fredericq

Available on ORBi :

since 25 June 2021

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