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Article ; Online: Development and Characterization of Potent Succinate Receptor Fluorescent Tracers.

Ciba, Marija / Dibnah, Bethany / Hudson, Brian D / Rexen Ulven, Elisabeth

2023 Volume 66, Issue 13, Page(s) 8951–8974

Abstract: The succinate receptor (SUCNR1) has emerged as a potential target for the treatment of various metabolic and inflammatory diseases, including hypertension, inflammatory bowel disease, and rheumatoid arthritis. While several ligands for this receptor have ...

Abstract	The succinate receptor (SUCNR1) has emerged as a potential target for the treatment of various metabolic and inflammatory diseases, including hypertension, inflammatory bowel disease, and rheumatoid arthritis. While several ligands for this receptor have been reported, species differences in pharmacology between human and rodent orthologs have limited the validation of SUCNR1's therapeutic potential. Here, we describe the development of the first potent fluorescent tool compounds for SUCNR1 and use these to define key differences in ligand binding to human and mouse SUCNR1. Starting from known agonist scaffolds, we developed a potent agonist tracer, TUG-2384 (
MeSH term(s)	Mice ; Humans ; Animals ; Succinic Acid/metabolism ; Receptors, G-Protein-Coupled/metabolism ; Coloring Agents
Chemical Substances	Succinic Acid (AB6MNQ6J6L) ; Receptors, G-Protein-Coupled ; Coloring Agents
Language	English
Publishing date	2023-06-15
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.3c00552
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Article ; Online: Structure-Activity Relationship Studies and Optimization of 4-Hydroxypyridones as GPR84 Agonists.

Ieremias, Loukas / Kaspersen, Mads H / Manandhar, Asmita / Schultz-Knudsen, Katrine / Vrettou, Christina Ioanna / Pokhrel, Rina / Heidtmann, Christoffer V / Jenkins, Laura / Kanellou, Christina / Marsango, Sara / Li, Yueming / Bräuner-Osborne, Hans / Rexen Ulven, Elisabeth / Milligan, Graeme / Ulven, Trond

Journal of medicinal chemistry

2024 Volume 67, Issue 5, Page(s) 3542–3570

Abstract: GPR84 is a putative medium-chain fatty acid receptor that is implicated in regulation of inflammation and fibrogenesis. Studies have indicated that GPR84 agonists may have therapeutic potential in diseases such as Alzheimer's disease, atherosclerosis, ... ...

Abstract	GPR84 is a putative medium-chain fatty acid receptor that is implicated in regulation of inflammation and fibrogenesis. Studies have indicated that GPR84 agonists may have therapeutic potential in diseases such as Alzheimer's disease, atherosclerosis, and cancer, but there is a lack of quality tool compounds to explore this potential. The fatty acid analogue LY237 (
MeSH term(s)	Humans ; Receptors, G-Protein-Coupled/metabolism ; Inflammation/metabolism ; Fatty Acids/metabolism ; Structure-Activity Relationship
Chemical Substances	Receptors, G-Protein-Coupled ; Fatty Acids ; GPR84 protein, human
Language	English
Publishing date	2024-02-21
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.3c01923
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Article: Ligand entry pathways control the chemical space recognized by GPR183.

Kjær, Viktoria Madeline Skovgaard / Stępniewski, Tomasz Maciej / Medel-Lacruz, Brian / Reinmuth, Lisa / Ciba, Marija / Rexen Ulven, Elisabeth / Bonomi, Massimiliano / Selent, Jana / Rosenkilde, Mette Marie

Chemical science

2023 Volume 14, Issue 39, Page(s) 10671–10683

Abstract: The G protein-coupled receptor GPR183 is a chemotactic receptor with an important function in the immune system and association with a variety of diseases. It recognizes ligands with diverse physicochemical properties as both the endogenous oxysterol ... ...

Abstract	The G protein-coupled receptor GPR183 is a chemotactic receptor with an important function in the immune system and association with a variety of diseases. It recognizes ligands with diverse physicochemical properties as both the endogenous oxysterol ligand 7α,25-OHC and synthetic molecules can activate the G protein pathway of the receptor. To better understand the ligand promiscuity of GPR183, we utilized both molecular dynamics simulations and cell-based validation experiments. Our work reveals that the receptor possesses two ligand entry channels: one lateral between transmembrane helices 4 and 5 facing the membrane, and one facing the extracellular environment. Using enhanced sampling, we provide a detailed structural model of 7α,25-OHC entry through the lateral membrane channel. Importantly, the first ligand recognition point at the receptor surface has been captured in diverse experimentally solved structures of different GPCRs. The proposed ligand binding pathway is supported by
Language	English
Publishing date	2023-09-25
Publishing country	England
Document type	Journal Article
ZDB-ID	2559110-1
ISSN	2041-6539 ; 2041-6520
ISSN (online)	2041-6539
ISSN	2041-6520
DOI	10.1039/d2sc05962b
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Article ; Online: Discovery of Potent Tetrazole Free Fatty Acid Receptor 2 Antagonists.

Valentini, Alice / Schultz-Knudsen, Katrine / Højgaard Hansen, Anders / Tsakoumagkou, Argyro / Jenkins, Laura / Christensen, Henriette B / Manandhar, Asmita / Milligan, Graeme / Ulven, Trond / Rexen Ulven, Elisabeth

Journal of medicinal chemistry

2023 Volume 66, Issue 9, Page(s) 6105–6121

Abstract: The free fatty acid receptor 2 (FFA2), also known as GPR43, mediates effects of short-chain fatty acids and has attracted interest as a potential target for treatment of various metabolic and inflammatory diseases. Herein, we report the results from ... ...

Abstract	The free fatty acid receptor 2 (FFA2), also known as GPR43, mediates effects of short-chain fatty acids and has attracted interest as a potential target for treatment of various metabolic and inflammatory diseases. Herein, we report the results from bioisosteric replacement of the carboxylic acid group of the established FFA2 antagonist CATPB and SAR investigations around these compounds, leading to the discovery of the first high-potency FFA2 antagonists, with the preferred compound TUG-2304 (
MeSH term(s)	Fatty Acids, Nonesterified ; Propionates ; Receptors, Cell Surface/antagonists & inhibitors ; Receptors, Cell Surface/chemistry ; Receptors, G-Protein-Coupled/metabolism
Chemical Substances	Fatty Acids, Nonesterified ; Propionates ; Receptors, Cell Surface ; Receptors, G-Protein-Coupled ; FFA2R protein, human
Language	English
Publishing date	2023-05-02
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.2c01935
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Article ; Online: Glucose-stimulated insulin secretion depends on FFA1 and Gq in neonatal mouse islets.

Lorza-Gil, Estela / Kaiser, Gabriele / Carlein, Christopher / Hoffmann, Markus D A / König, Gabriele M / Haug, Sieglinde / Prates Roma, Leticia / Rexen Ulven, Elisabeth / Ulven, Trond / Kostenis, Evi / Birkenfeld, Andreas L / Häring, Hans-Ulrich / Ullrich, Susanne / Gerst, Felicia

Diabetologia

2023 Volume 66, Issue 8, Page(s) 1501–1515

Abstract: Aims/hypothesis: After birth, the neonatal islets gradually acquire glucose-responsive insulin secretion, a process that is subjected to maternal imprinting. Although NEFA are major components of breastmilk and insulin secretagogues, their role for ... ...

Abstract	Aims/hypothesis: After birth, the neonatal islets gradually acquire glucose-responsive insulin secretion, a process that is subjected to maternal imprinting. Although NEFA are major components of breastmilk and insulin secretagogues, their role for functional maturation of neonatal beta cells is still unclear. NEFA are the endogenous ligands of fatty acid receptor 1 (FFA1, encoded by Ffar1 in mice), a Gq-coupled receptor with stimulatory effect on insulin secretion. This study investigates the role of FFA1 in neonatal beta cell function and in the adaptation of offspring beta cells to parental high-fat feeding. Methods: Wild-type (WT) and Ffar1 Results: Blood glucose levels were higher in CD-fed Ffar1 Conclusions/interpretation: FFA1 promotes glucose-responsive insulin secretion and functional maturation of newborn islets and is required for adaptive offspring insulin secretion in the face of metabolic challenge, such as parental HFD.
MeSH term(s)	Female ; Mice ; Animals ; Glucose/pharmacology ; Glucose/metabolism ; Insulin Secretion ; Blood Glucose/metabolism ; Animals, Newborn ; Islets of Langerhans/metabolism ; Fatty Acids, Nonesterified/metabolism ; Insulin/metabolism ; Insulin-Secreting Cells/metabolism ; Palmitates/metabolism
Chemical Substances	Glucose (IY9XDZ35W2) ; Blood Glucose ; Fatty Acids, Nonesterified ; Insulin ; Palmitates
Language	English
Publishing date	2023-05-23
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1694-9
ISSN	1432-0428 ; 0012-186X
ISSN (online)	1432-0428
ISSN	0012-186X
DOI	10.1007/s00125-023-05932-5
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Article ; Online: Structure-Activity Relationship Explorations and Discovery of a Potent Antagonist for the Free Fatty Acid Receptor 2.

Højgaard Hansen, Anders / Christensen, Henriette B / Pandey, Sunil K / Sergeev, Eugenia / Valentini, Alice / Dunlop, Julia / Dedeo, Domonkos / Fratta, Simone / Hudson, Brian D / Milligan, Graeme / Ulven, Trond / Rexen Ulven, Elisabeth

ChemMedChem

2021 Volume 16, Issue 21, Page(s) 3326–3341

Abstract: Free fatty acid receptor 2 (FFA2) is a sensor for short-chain fatty acids that has been identified as an interesting potential drug target for treatment of metabolic and inflammatory diseases. Although several ligand series are known for the receptor, ... ...

Abstract	Free fatty acid receptor 2 (FFA2) is a sensor for short-chain fatty acids that has been identified as an interesting potential drug target for treatment of metabolic and inflammatory diseases. Although several ligand series are known for the receptor, there is still a need for improved compounds. One of the most potent and frequently used antagonists is the amide-substituted phenylbutanoic acid known as CATPB (1). We here report the structure-activity relationship exploration of this compound, leading to the identification of homologues with increased potency. The preferred compound 37 (TUG-1958) was found, besides improved potency, to have high solubility and favorable pharmacokinetic properties.
MeSH term(s)	Amides/chemical synthesis ; Amides/chemistry ; Amides/pharmacology ; Animals ; Dose-Response Relationship, Drug ; Drug Discovery ; Humans ; Mice ; Molecular Structure ; Phenylbutyrates/chemical synthesis ; Phenylbutyrates/chemistry ; Phenylbutyrates/pharmacology ; Receptors, Cell Surface/antagonists & inhibitors ; Receptors, Cell Surface/metabolism ; Structure-Activity Relationship
Chemical Substances	Amides ; FFA2R protein, human ; Phenylbutyrates ; Receptors, Cell Surface ; free fatty acid 2 receptor, mouse
Language	English
Publishing date	2021-09-12
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2218496-X
ISSN	1860-7187 ; 1860-7179
ISSN (online)	1860-7187
ISSN	1860-7179
DOI	10.1002/cmdc.202100356
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Article ; Online: Hypothalamic free fatty acid receptor-1 regulates whole-body energy balance.

Dragano, Nathalia R V / Milbank, Edward / Haddad-Tóvolli, Roberta / Garrido-Gil, Pablo / Nóvoa, Eva / Fondevilla, Marcos F / Capelli, Valentina / Zanesco, Ariane Maria / Solon, Carina / Morari, Joseane / Pires, Leticia / Estevez-Salguero, Ánxela / Beiroa, Daniel / González-García, Ismael / Barca-Mayo, Olga / Diéguez, Carlos / Nogueiras, Ruben / Labandeira-García, José L / Rexen Ulven, Elisabeth /

Ulven, Trond / Claret, Marc / Velloso, Licio A / López, Miguel

Molecular metabolism

2023 Volume 79, Page(s) 101840

Abstract: Objective: Free fatty acid receptor-1 (FFAR1) is a medium- and long-chain fatty acid sensing G protein-coupled receptor that is highly expressed in the hypothalamus. Here, we investigated the central role of FFAR1 on energy balance.: Methods: Central ...

Abstract	Objective: Free fatty acid receptor-1 (FFAR1) is a medium- and long-chain fatty acid sensing G protein-coupled receptor that is highly expressed in the hypothalamus. Here, we investigated the central role of FFAR1 on energy balance. Methods: Central FFAR1 agonism and virogenic knockdown were performed in mice. Energy balance studies, infrared thermographic analysis of brown adipose tissue (BAT) and molecular analysis of the hypothalamus, BAT, white adipose tissue (WAT) and liver were carried out. Results: Pharmacological stimulation of FFAR1, using central administration of its agonist TUG-905 in diet-induced obese mice, decreases body weight and is associated with increased energy expenditure, BAT thermogenesis and browning of subcutaneous WAT (sWAT), as well as reduced AMP-activated protein kinase (AMPK) levels, reduced inflammation, and decreased endoplasmic reticulum (ER) stress in the hypothalamus. As FFAR1 is expressed in distinct hypothalamic neuronal subpopulations, we used an AAV vector expressing a shRNA to specifically knockdown Ffar1 in proopiomelanocortin (POMC) neurons of the arcuate nucleus of the hypothalamus (ARC) of obese mice. Our data showed that knockdown of Ffar1 in POMC neurons promoted hyperphagia and body weight gain. In parallel, these mice developed hepatic insulin resistance and steatosis. Conclusions: FFAR1 emerges as a new hypothalamic nutrient sensor regulating whole body energy balance. Moreover, pharmacological activation of FFAR1 could provide a therapeutic advance in the management of obesity and its associated metabolic disorders.
MeSH term(s)	Mice ; Animals ; Fatty Acids, Nonesterified/metabolism ; Pro-Opiomelanocortin/genetics ; Pro-Opiomelanocortin/metabolism ; Mice, Obese ; Body Weight ; Hypothalamus/metabolism ; Receptors, G-Protein-Coupled/genetics ; Receptors, G-Protein-Coupled/metabolism ; Energy Metabolism/physiology
Chemical Substances	Fatty Acids, Nonesterified ; Pro-Opiomelanocortin (66796-54-1) ; Receptors, G-Protein-Coupled
Language	English
Publishing date	2023-11-29
Publishing country	Germany
Document type	Journal Article
ZDB-ID	2708735-9
ISSN	2212-8778 ; 2212-8778
ISSN (online)	2212-8778
ISSN	2212-8778
DOI	10.1016/j.molmet.2023.101840
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Article: Dihydropyridine Fluorophores Allow for Specific Detection of Human Antibodies in Serum.

Domljanovic, Ivana / Rexen Ulven, Elisabeth / Ulven, Trond / Thomsen, Rasmus P / Okholm, Anders H / Kjems, Jørgen / Voss, Anne / Taskova, Maria / Astakhova, Kira

ACS omega

2018 Volume 3, Issue 7, Page(s) 7580–7586

Abstract: Antigen recognition by antibodies plays an important role in human biology and in the development of diseases. This interaction provides a basis for multiple diagnostic assays and is a guide for treatments. We have developed dihydropyridine-based ... ...

Abstract	Antigen recognition by antibodies plays an important role in human biology and in the development of diseases. This interaction provides a basis for multiple diagnostic assays and is a guide for treatments. We have developed dihydropyridine-based fluorophores that form stable complexes with double-stranded DNA and upon recognition of the antibodies to DNA (anti-DNA) provide an optical response. The fluorophores described herein have advantageous optical properties compared to those of the currently available dyes making them valuable for research and clinical diagnostics. By studying a series of novel fluorophores, crucial parameters for the design were established, providing the required sensitivity and specificity in the detection of antibodies. Using these DNA-fluorophore complexes in a direct immunofluorescence assay, antibodies to DNA are specifically detected in 80 patients diagnosed with an autoimmune disease, systemic lupus erythematosus. Positivity indicated by emission change of α-(4'-
Language	English
Publishing date	2018-07-10
Publishing country	United States
Document type	Journal Article
ISSN	2470-1343
ISSN	2470-1343
DOI	10.1021/acsomega.8b00424
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Article ; Online: Structure-Activity Investigations and Optimisations of Non-metabolite Agonists for the Succinate Receptor 1.

Rexen Ulven, Elisabeth / Trauelsen, Mette / Brvar, Matjaz / Lückmann, Michael / Bielefeldt, Line Ø / Jensen, Lisa K I / Schwartz, Thue W / Frimurer, Thomas M

Scientific reports

2018 Volume 8, Issue 1, Page(s) 10010

Abstract: The succinate receptor 1 (SUCNR1) is a receptor for the metabolite succinate, which functions as a metabolic stress signal in the liver, kidney, adipose tissue and the retina. However, potent non-metabolite tool compounds are needed to reveal the ... ...

Abstract	The succinate receptor 1 (SUCNR1) is a receptor for the metabolite succinate, which functions as a metabolic stress signal in the liver, kidney, adipose tissue and the retina. However, potent non-metabolite tool compounds are needed to reveal the physiological role and pharmacological potential of SUCNR1. Recently, we published the discovery of a computationally receptor-structure derived non-metabolite SUCNR1 agonist series with high target selectivity. We here report our structure-activity exploration and optimisation that has resulted in the development of agonists with nanomolar potency and excellent solubility and stability properties in a number of in vitro assays. Ligand-guided receptor models with high discriminative power between binding of active and inactive compounds were developed for design of novel chemotypes.
MeSH term(s)	Animals ; Crystallography, X-Ray ; Humans ; Mice ; Receptors, G-Protein-Coupled/agonists ; Receptors, G-Protein-Coupled/metabolism ; Receptors, Purinergic P2Y1/metabolism ; Receptors, Purinergic P2Y1/ultrastructure ; Structure-Activity Relationship ; Succinic Acid/metabolism
Chemical Substances	GPR91 protein, mouse ; Receptors, G-Protein-Coupled ; Receptors, Purinergic P2Y1 ; SUCNR1 protein, human ; Succinic Acid (AB6MNQ6J6L)
Language	English
Publishing date	2018-07-03
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2615211-3
ISSN	2045-2322 ; 2045-2322
ISSN (online)	2045-2322
ISSN	2045-2322
DOI	10.1038/s41598-018-28263-7
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Article ; Online: FFA2-, but not FFA3-agonists inhibit GSIS of human pseudoislets: a comparative study with mouse islets and rat INS-1E cells.

Lorza-Gil, Estela / Kaiser, Gabriele / Rexen Ulven, Elisabeth / König, Gabriele M / Gerst, Felicia / Oquendo, Morgana Barroso / Birkenfeld, Andreas L / Häring, Hans-Ulrich / Kostenis, Evi / Ulven, Trond / Ullrich, Susanne

Scientific reports

2020 Volume 10, Issue 1, Page(s) 16497

Abstract: The expression of short chain fatty acid receptors FFA2 and FFA3 in pancreatic islets raised interest in using them as drug targets for treating hyperglycemia in humans. This study aims to examine the efficacy of synthetic FFA2- and FFA3-ligands to ... ...

Abstract	The expression of short chain fatty acid receptors FFA2 and FFA3 in pancreatic islets raised interest in using them as drug targets for treating hyperglycemia in humans. This study aims to examine the efficacy of synthetic FFA2- and FFA3-ligands to modulate glucose-stimulated insulin secretion (GSIS) in human pseudoislets which display intact glucose responsiveness. The FFA2-agonists 4-CMTB and TUG-1375 inhibited GSIS, an effect reversed by the FFA2-antagonist CATPB. GSIS itself was not augmented by CATPB. The FFA3-agonists FHQC and 1-MCPC did not affect GSIS in human pseudoislets. For further drug evaluation we used mouse islets. The CATPB-sensitive inhibitory effect of 100 µM 4-CMTB on GSIS was recapitulated. The inhibition was partially sensitive to the G
MeSH term(s)	Adult ; Animals ; Blood Glucose/drug effects ; Cells, Cultured ; Depsipeptides/pharmacology ; Fatty Acids, Volatile/agonists ; Female ; GTP-Binding Protein alpha Subunits, Gq-G11/metabolism ; Glucose/metabolism ; Humans ; Insulin ; Insulin Secretion/drug effects ; Insulin-Secreting Cells/drug effects ; Insulin-Secreting Cells/metabolism ; Ligands ; Male ; Mice ; Mice, Inbred C3H ; Mice, Inbred C57BL ; Mice, Transgenic ; Middle Aged ; Rats ; Receptors, Cell Surface/agonists ; Receptors, G-Protein-Coupled/agonists ; Signal Transduction
Chemical Substances	Blood Glucose ; Depsipeptides ; FFA2R protein, human ; FFAR3 protein, human ; FR900359 ; Fatty Acids, Volatile ; Insulin ; Ligands ; Receptors, Cell Surface ; Receptors, G-Protein-Coupled ; GTP-Binding Protein alpha Subunits, Gq-G11 (EC 3.6.5.1) ; Glucose (IY9XDZ35W2)
Language	English
Publishing date	2020-10-05
Publishing country	England
Document type	Comparative Study ; Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2615211-3
ISSN	2045-2322 ; 2045-2322
ISSN (online)	2045-2322
ISSN	2045-2322
DOI	10.1038/s41598-020-73467-5
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