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Article ; Online: Targeting dihydroceramide desaturase 1 (Des1): Syntheses of ceramide analogues with a rigid scaffold, inhibitory assays, and AlphaFold2-assisted structural insights reveal cyclopropenone PR280 as a potent inhibitor.

Rivero, Pablo / Ivanova, Varbina / Barril, Xavier / Casampere, Mireia / Casas, Josefina / Fabriàs, Gemma / Díaz, Yolanda / Matheu, M Isabel

Bioorganic chemistry

2024 Volume 145, Page(s) 107233

Abstract: Dihydroceramide desaturase 1 (Des1) catalyzes the formation of a CC double bond in dihydroceramide to furnish ceramide. Inhibition of Des1 is related to cell cycle arrest and programmed cell death. The lack of the Des1 crystalline structure, as well as ... ...

Abstract	Dihydroceramide desaturase 1 (Des1) catalyzes the formation of a CC double bond in dihydroceramide to furnish ceramide. Inhibition of Des1 is related to cell cycle arrest and programmed cell death. The lack of the Des1 crystalline structure, as well as that of a close homologue, hampers the detailed understanding of its inhibition mechanism and difficults the design of new inhibitors, thus making Des1 a strategic target. Based on previous structure-activity studies, different ceramides containing rigid scaffolds were designed. The synthesis and evaluation of these compounds as Des1 inhibitors allowed the identification of PR280 as a better Des 1 inhibitor in vitro (IC
MeSH term(s)	Ceramides/pharmacology ; Ceramides/chemistry ; Oxidoreductases/metabolism ; Cyclopropanes/pharmacology
Chemical Substances	dihydroceramide desaturase (EC 1.3.1.-) ; cyclopropenone ; Ceramides ; Oxidoreductases (EC 1.-) ; Cyclopropanes
Language	English
Publishing date	2024-02-23
Publishing country	United States
Document type	Journal Article
ZDB-ID	120080-x
ISSN	1090-2120 ; 0045-2068
ISSN (online)	1090-2120
ISSN	0045-2068
DOI	10.1016/j.bioorg.2024.107233
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Article ; Online: Diets with Higher ω-6/ω-3 Ratios Show Differences in Ceramides and Fatty Acid Levels Accompanied by Increased Amyloid-Beta in the Brains of Male APP/PS1 Transgenic Mice.

Ordóñez-Gutiérrez, Lara / Fábrias, Gemma / Casas, Josefina / Wandosell, Francisco

International journal of molecular sciences

2021 Volume 22, Issue 20

Abstract: Senile plaque formation as a consequence of amyloid-β peptide (Aβ) aggregation constitutes one of the main hallmarks of Alzheimer's disease (AD). This pathology is characterized by synaptic alterations and cognitive impairment. In order to either prevent ...

Abstract	Senile plaque formation as a consequence of amyloid-β peptide (Aβ) aggregation constitutes one of the main hallmarks of Alzheimer's disease (AD). This pathology is characterized by synaptic alterations and cognitive impairment. In order to either prevent or revert it, different therapeutic approaches have been proposed, and some of them are focused on diet modification. Modification of the ω-6/ω-3 fatty acids (FA) ratio in diets has been proven to affect Aβ production and senile plaque formation in the hippocampus and cortex of female transgenic (TG) mice. In these diets, linoleic acid is the main contribution of ω-6 FA, whereas alpha-linoleic acid (ALA), eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA) and docosapentaenoic acid (DPA) are the contributors of ω-3 FA. In the present work, we have explored the effect of ω-6/ω-3 ratio modifications in the diets of male double-transgenic APPswe/PS1ΔE9 (AD model) and wild-type mice (WT). Amyloid burden in the hippocampus increased in parallel with the increase in dietary ω-6/ω-3 ratio in TG male mice. In addition, there was a modification in the brain lipid profile proportional to the ω-6/ω-3 ratio of the diet. In particular, the higher the ω-6/ω-3 ratio, the lower the ceramides and higher the FAs, particularly docosatetraenoic acid. Modifications to the cortex lipid profile was mostly similar between TG and WT mice, except for gangliosides (higher levels in TG mice) and some ceramide species (lower levels in TG mice).
MeSH term(s)	Alzheimer Disease/genetics ; Alzheimer Disease/metabolism ; Amyloid beta-Protein Precursor/genetics ; Amyloid beta-Protein Precursor/metabolism ; Animals ; Ceramides/metabolism ; Disease Models, Animal ; Erucic Acids/metabolism ; Fatty Acids, Omega-3/administration & dosage ; Fatty Acids, Omega-3/adverse effects ; Fatty Acids, Omega-6/administration & dosage ; Fatty Acids, Omega-6/adverse effects ; Gangliosides/metabolism ; Hippocampus/metabolism ; Humans ; Male ; Mice ; Mice, Transgenic
Chemical Substances	APP protein, human ; Amyloid beta-Protein Precursor ; Ceramides ; Erucic Acids ; Fatty Acids, Omega-3 ; Fatty Acids, Omega-6 ; Gangliosides
Language	English
Publishing date	2021-10-09
Publishing country	Switzerland
Document type	Comparative Study ; Journal Article
ZDB-ID	2019364-6
ISSN	1422-0067 ; 1422-0067 ; 1661-6596
ISSN (online)	1422-0067
ISSN	1422-0067 ; 1661-6596
DOI	10.3390/ijms222010907
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Article ; Online: A fluorogenic substrate for the detection of lipid amidases in intact cells.

Casasampere, Mireia / Ung, Johnson / Iñáñez, Alejandro / Dufau, Carine / Tsuboi, Kazuhito / Casas, Josefina / Tan, Su-Fern / Feith, David J / Andrieu-Abadie, Nathalie / Segui, Bruno / Loughran, Thomas P / Abad, José Luis / Fabrias, Gemma

Journal of lipid research

2024 Volume 65, Issue 3, Page(s) 100520

Abstract: Lipid amidases of therapeutic relevance include acid ceramidase (AC), N-acylethanolamine-hydrolyzing acid amidase, and fatty acid amide hydrolase (FAAH). Although fluorogenic substrates have been developed for the three enzymes and high-throughput ... ...

Abstract	Lipid amidases of therapeutic relevance include acid ceramidase (AC), N-acylethanolamine-hydrolyzing acid amidase, and fatty acid amide hydrolase (FAAH). Although fluorogenic substrates have been developed for the three enzymes and high-throughput methods for screening have been reported, a platform for the specific detection of these enzyme activities in intact cells is lacking. In this article, we report on the coumarinic 1-deoxydihydroceramide RBM1-151, a 1-deoxy derivative and vinilog of RBM14-C12, as a novel substrate of amidases. This compound is hydrolyzed by AC (
MeSH term(s)	Fluorescent Dyes ; Amidohydrolases ; Ethanolamines/chemistry ; Lipids
Chemical Substances	N-acylethanolamines ; Fluorescent Dyes ; Amidohydrolases (EC 3.5.-) ; Ethanolamines ; Lipids
Language	English
Publishing date	2024-02-17
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	80154-9
ISSN	1539-7262 ; 0022-2275
ISSN (online)	1539-7262
ISSN	0022-2275
DOI	10.1016/j.jlr.2024.100520
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Article ; Online: S-Adenosyl-l-methionine restores brain mitochondrial membrane fluidity and GSH content improving Niemann-Pick type C disease.

Goicoechea, Leire / Torres, Sandra / Fàbrega, Laura / Barrios, Mónica / Núñez, Susana / Casas, Josefina / Fabrias, Gemma / García-Ruiz, Carmen / Fernández-Checa, José C

Redox biology

2024 Volume 72, Page(s) 103150

Abstract: Niemann-Pick type C (NPC) disease is a lysosomal storage disorder characterized by impaired motor coordination due to neurological defects and cerebellar dysfunction caused by the accumulation of cholesterol in endolysosomes. Besides the increase in ... ...

Abstract	Niemann-Pick type C (NPC) disease is a lysosomal storage disorder characterized by impaired motor coordination due to neurological defects and cerebellar dysfunction caused by the accumulation of cholesterol in endolysosomes. Besides the increase in lysosomal cholesterol, mitochondria are also enriched in cholesterol, which leads to decreased membrane fluidity, impaired mitochondrial function and loss of GSH, and has been shown to contribute to the progression of NPC disease. S-Adenosyl-l-methionine (SAM) regulates membrane physical properties through the generation of phosphatidylcholine (PC) from phosphatidylethanolamine (PE) methylation and functions as a GSH precursor by providing cysteine in the transsulfuration pathway. However, the role of SAM in NPC disease has not been investigated. Here we report that Npc1
MeSH term(s)	Animals ; Mice ; Membrane Fluidity ; S-Adenosylmethionine/metabolism ; Mitochondrial Membranes/metabolism ; Niemann-Pick Disease, Type C/metabolism ; Niemann-Pick Disease, Type C/drug therapy ; Niemann-Pick Disease, Type C/genetics ; Glutathione/metabolism ; Brain/metabolism ; Mitochondria/metabolism ; Niemann-Pick C1 Protein ; Disease Models, Animal ; Mice, Knockout ; Phosphatidylcholines/metabolism
Chemical Substances	S-Adenosylmethionine (7LP2MPO46S) ; Glutathione (GAN16C9B8O) ; Niemann-Pick C1 Protein ; Npc1 protein, mouse ; Phosphatidylcholines
Language	English
Publishing date	2024-04-03
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, N.I.H., Extramural
ZDB-ID	2701011-9
ISSN	2213-2317 ; 2213-2317
ISSN (online)	2213-2317
ISSN	2213-2317
DOI	10.1016/j.redox.2024.103150
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Article ; Online: Introduction to the special issue: Inhibitors of enzymes involved in lipid metabolism.

Fabrias, Gemma / Epand, Richard M

Chemistry and physics of lipids

2016 Volume 197, Page(s) 1–2

MeSH term(s)	Enzyme Inhibitors/pharmacology ; Enzymes/metabolism ; Lipid Metabolism
Chemical Substances	Enzyme Inhibitors ; Enzymes
Language	English
Publishing date	2016-05
Publishing country	Ireland
Document type	Editorial ; Introductory Journal Article
ZDB-ID	213869-4
ISSN	1873-2941 ; 0009-3084
ISSN (online)	1873-2941
ISSN	0009-3084
DOI	10.1016/j.chemphyslip.2015.08.006
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Article ; Online: Synthesis and characterization of bichromophoric 1-deoxyceramides as FRET probes.

Izquierdo, Eduardo / Casasampere, Mireia / Fabriàs, Gemma / Abad, José Luís / Casas, Josefina / Delgado, Antonio

Organic & biomolecular chemistry

2021 Volume 19, Issue 11, Page(s) 2456–2467

Abstract: The suitability as FRET probes of two bichromophoric 1-deoxydihydroceramides containing a labelled spisulosine derivative as a sphingoid base and two differently ω-labelled fluorescent palmitic acids has been evaluated. The ceramide synthase (CerS) ... ...

Abstract	The suitability as FRET probes of two bichromophoric 1-deoxydihydroceramides containing a labelled spisulosine derivative as a sphingoid base and two differently ω-labelled fluorescent palmitic acids has been evaluated. The ceramide synthase (CerS) catalyzed metabolic incorporation of ω-azido palmitic acid into the above labeled spisulosine to render the corresponding ω-azido 1-deoxyceramide has been studied in several cell lines. In addition, the strain-promoted click reaction between this ω-azido 1-deoxyceramide and suitable fluorophores has been optimized to render the target bichromophoric 1-deoxydihydroceramides. These results pave the way for the development of FRET-based assays as a new tool to study sphingolipid metabolism.
MeSH term(s)	Animals ; Cell Line ; Ceramides/metabolism ; Click Chemistry ; Fluorescence Resonance Energy Transfer ; Fluorescent Dyes/chemical synthesis ; Humans ; Lipids/chemical synthesis ; Mice ; Oxidoreductases/metabolism ; Palmitic Acids/chemistry ; Spectrometry, Fluorescence ; Tandem Mass Spectrometry
Chemical Substances	Ceramides ; Fluorescent Dyes ; Lipids ; Palmitic Acids ; Oxidoreductases (EC 1.-) ; dihydroceramide desaturase (EC 1.3.1.-) ; spisulosine (ZX5D253CYY)
Language	English
Publishing date	2021-03-02
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2097583-1
ISSN	1477-0539 ; 1477-0520
ISSN (online)	1477-0539
ISSN	1477-0520
DOI	10.1039/d1ob00113b
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Article ; Online: Methuosis Contributes to Jaspine-B-Induced Cell Death.

Bielsa, Núria / Casasampere, Mireia / Abad, Jose Luis / Enrich, Carlos / Delgado, Antonio / Fabriàs, Gemma / Lizcano, Jose M / Casas, Josefina

International journal of molecular sciences

2022 Volume 23, Issue 13

Abstract: Methuosis is a type of programmed cell death in which the cytoplasm is occupied by fluid-filled vacuoles that originate from macropinosomes (cytoplasmic vacuolation). A few molecules have been reported to behave as methuosis inducers in cancer cell lines. ...

Abstract	Methuosis is a type of programmed cell death in which the cytoplasm is occupied by fluid-filled vacuoles that originate from macropinosomes (cytoplasmic vacuolation). A few molecules have been reported to behave as methuosis inducers in cancer cell lines. Jaspine B (JB) is a natural anhydrous sphingolipid (SL) derivative reported to induce cytoplasmic vacuolation and cytotoxicity in several cancer cell lines. Here, we have investigated the mechanism and signalling pathways involved in the cytotoxicity induced by the natural sphingolipid Jaspine B (JB) in lung adenocarcinoma A549 cells, which harbor the G12S K-Ras mutant. The effect of JB on inducing cytoplasmic vacuolation and modifying cell viability was determined in A549 cells, as well as in mouse embryonic fibroblasts (MEF) lacking either the autophagy-related gene
MeSH term(s)	Animals ; Apoptosis ; Autophagy ; Cell Death ; Cell Line, Tumor ; Cell Survival ; Endosomes ; Fibroblasts ; Mechanistic Target of Rapamycin Complex 1 ; Mice ; Neoplasms ; Phosphatidylinositol 3-Kinases ; Sphingolipids/pharmacology ; Sphingosine/analogs & derivatives
Chemical Substances	Sphingolipids ; pachastrissamine ; Mechanistic Target of Rapamycin Complex 1 (EC 2.7.11.1) ; Sphingosine (NGZ37HRE42)
Language	English
Publishing date	2022-06-29
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2019364-6
ISSN	1422-0067 ; 1422-0067 ; 1661-6596
ISSN (online)	1422-0067
ISSN	1422-0067 ; 1661-6596
DOI	10.3390/ijms23137257
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Article ; Online: Fluorescently Labeled Ceramides and 1-Deoxyceramides: Synthesis, Characterization, and Cellular Distribution Studies.

Izquierdo, Eduardo / López-Corrales, Marta / Abad-Montero, Diego / Rovira, Anna / Fabriàs, Gemma / Bosch, Manel / Abad, José Luís / Marchán, Vicente

The Journal of organic chemistry

2022

Abstract: Ceramides (Cer) are bioactive sphingolipids that have been proposed as potential disease biomarkers since they are involved in several cellular stress responses, including apoptosis and senescence. 1-Deoxyceramides (1-deoxyCer), a particular subtype of ... ...

Abstract	Ceramides (Cer) are bioactive sphingolipids that have been proposed as potential disease biomarkers since they are involved in several cellular stress responses, including apoptosis and senescence. 1-Deoxyceramides (1-deoxyCer), a particular subtype of noncanonical sphingolipids, have been linked to the pathogenesis of type II diabetes. To investigate the metabolism of these bioactive lipids, as well as to have a better understanding of the signaling processes where they participate, it is essential to expand the toolbox of fluorescent sphingolipid probes exhibiting complementary subcellular localization. Herein, we describe a series of new sphingolipid probes tagged with two different organic fluorophores, a far-red/NIR-emitting coumarin derivative (COUPY) and a green-emitting BODIPY. The assembly of the probes involved a combination of olefin cross metathesis and click chemistry reactions as key steps, and these fluorescent ceramide analogues exhibited excellent emission quantum yields, being the Stokes' shifts of the COUPY derivatives much higher than those of the BODIPY counterparts. Confocal microscopy studies in HeLa cells confirmed an excellent cellular permeability for these sphingolipid probes and revealed that most of the vesicles stained by COUPY probes were either lysosomes or endosomes, whereas BODIPY probes accumulated either in Golgi apparatus or in nonlysosomal intracellular vesicles. The fact that the two sets of fluorescent Cer probes have such different staining patterns indicates that their subcellular distribution is not entirely defined by the sphingolipid moiety but rather influenced by the fluorophore.
Language	English
Publishing date	2022-11-28
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.2c02019
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Article ; Online: Discovery of deoxyceramide analogs as highly selective ACER3 inhibitors in live cells.

Bielsa, Núria / Casasampere, Mireia / Aseeri, Mazen / Casas, Josefina / Delgado, Antonio / Abad, José Luis / Fabriàs, Gemma

European journal of medicinal chemistry

2021 Volume 216, Page(s) 113296

Abstract: Acid (AC), neutral (NC) and alkaline ceramidase 3 (ACER3) are the most ubiquitous ceramidases and their therapeutic interest as targets in cancer diseases has been well sustained. This supports the importance of discovering potent and specific inhibitors ...

Abstract	Acid (AC), neutral (NC) and alkaline ceramidase 3 (ACER3) are the most ubiquitous ceramidases and their therapeutic interest as targets in cancer diseases has been well sustained. This supports the importance of discovering potent and specific inhibitors for further use in combination therapies. Although several ceramidase inhibitors have been reported, most of them target AC and a few focus on NC. In contrast, well characterized ACER3 inhibitors are lacking. Here we report on the synthesis and screening of two series of 1-deoxy(dihydro)ceramide analogs on the three enzymes. Activity was determined using fluorogenic substrates in recombinant human NC (rhNC) and both lysates and intact cells enriched in each enzyme. None of the molecules elicited a remarkable AC inhibitory activity in either experimental setup, while using rhNC, several compounds of both series were active as non-competitive inhibitors with K
MeSH term(s)	Alkaline Ceramidase/antagonists & inhibitors ; Alkaline Ceramidase/genetics ; Alkaline Ceramidase/metabolism ; Cell Line ; Cell Survival/drug effects ; Ceramides/chemistry ; Ceramides/metabolism ; Ceramides/pharmacology ; Chromatography, High Pressure Liquid ; Drug Evaluation, Preclinical ; Humans ; Kinetics ; Mass Spectrometry ; Recombinant Proteins/biosynthesis ; Recombinant Proteins/chemistry ; Recombinant Proteins/isolation & purification ; Sphingolipids/analysis ; Substrate Specificity
Chemical Substances	Ceramides ; Recombinant Proteins ; Sphingolipids ; ACER3 protein, human (EC 3.5.1.23) ; Alkaline Ceramidase (EC 3.5.1.23)
Language	English
Publishing date	2021-02-24
Publishing country	France
Document type	Journal Article
ZDB-ID	188597-2
ISSN	1768-3254 ; 0009-4374 ; 0223-5234
ISSN (online)	1768-3254
ISSN	0009-4374 ; 0223-5234
DOI	10.1016/j.ejmech.2021.113296
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Article ; Online: Introduction to the Robert Bittman Memorial Issue.

Fabrias, Gemma / Greer, Alexander / Lankalapalli, Ravi S / Engel, Robert

Chemistry and physics of lipids

2016 Volume 194, Page(s) 1

MeSH term(s)	Lipids ; Periodicals as Topic
Chemical Substances	Lipids
Language	English
Publishing date	2016-01
Publishing country	Ireland
Document type	Editorial ; Introductory Journal Article
ZDB-ID	213869-4
ISSN	1873-2941 ; 0009-3084
ISSN (online)	1873-2941
ISSN	0009-3084
DOI	10.1016/j.chemphyslip.2015.12.004
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