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Article ; Online: Potential implication of aniline derivatives in the Toxic Oil Syndrome (TOS).

Messeguer, Angel

2011 Volume 192, Issue 1-2, Page(s) 136–141

Abstract: The Toxic Oil Syndrome (TOS) was an epidemic disease appeared in central Spain in 1981, causing over 400 deaths and affecting more than 20,000 people, mainly women and children. The disease was linked to the consumption of rapeseed oil denatured with ... ...

Abstract	The Toxic Oil Syndrome (TOS) was an epidemic disease appeared in central Spain in 1981, causing over 400 deaths and affecting more than 20,000 people, mainly women and children. The disease was linked to the consumption of rapeseed oil denatured with aniline, illegally refined at the ITH oil refinery in Seville, mixed with other oils and sold as edible olive oil. Among the aniline derivatives detected in the oil batches generated by an uncontrolled deodorisation procedure during the refining process, fatty acid anilides were first postulated as the causal agents. Nevertheless, compounds identified as 3-(N-phenylamino)propane-1,2-diol (PAP) and its mono-, di-, and triacyl derivatives (mPAP, dPAP and tPAP, respectively), were subsequently considered better biomarkers of toxic oils and the best candidates for causing the intoxication. In this account, we will discuss the results obtained in recent years by our group concerning: (a) The effect of different variables intervening in the deodorisation process that could influence the formation of PAP derivatives. To this end we decided to take the aniline derivatives linked to oleic acid as compound models since this is the fatty acid present in highest amounts in rapeseed oil. The study was focused on the influence of different parameters on the formation of the diester PAP derivative (OOPAP) the monoester derivative (OPAP) and the corresponding amide (oleanilide, OA), and the interactions between any two of these variables. Of particular interest was the interaction observed between OOPAP and OA, due to its potential relevance to the final composition of the toxic oil model. (b) Xenobiochemical aspects of PAP derivatives, specifically: the stereospecific hydrolysis of OPAP and OOPAP by human pancreatic lipase, the in vitro activation of PAP by human and rat liver microsomes as well as by recombinant 450 enzymes, and the formation and stability of GSH and N-acetylcysteine adducts of a highly reactive iminoquinone intermediate generated in the biotransformation of PAP.
MeSH term(s)	Aniline Compounds/toxicity ; Biotransformation ; Canola Oil ; Fatty Acids, Monounsaturated ; Humans ; Lipase/metabolism ; Plant Oils/pharmacokinetics ; Plant Oils/poisoning
Chemical Substances	Aniline Compounds ; Canola Oil ; Fatty Acids, Monounsaturated ; Plant Oils ; Lipase (EC 3.1.1.3) ; aniline (SIR7XX2F1K)
Language	English
Publishing date	2011-06-30
Publishing country	Ireland
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	218799-1
ISSN	1872-7786 ; 0009-2797
ISSN (online)	1872-7786
ISSN	0009-2797
DOI	10.1016/j.cbi.2010.10.006
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Article ; Online: Discovery of novel 2,3,5-trisubstituted pyridine analogs as potent inhibitors of IL-1β via modulation of the p38 MAPK signaling pathway.

Carrasco, Esther / Gomez-Gutierrez, Patricia / Campos, Pedro M / Vega, Miguel / Messeguer, Angel / Perez, Juan J

European journal of medicinal chemistry

2021 Volume 223, Page(s) 113620

Abstract: Interleukin-1β is a central mediator of innate immune responses and inflammation. It plays a key role in a wide variety of pathologies, ranging from autoinflammatory diseases to metabolic syndrome and malignant tumors. It is well established that its ... ...

Abstract	Interleukin-1β is a central mediator of innate immune responses and inflammation. It plays a key role in a wide variety of pathologies, ranging from autoinflammatory diseases to metabolic syndrome and malignant tumors. It is well established that its inhibition results in a rapid and sustained reduction in disease severity, underlining the importance of having a repertoire of drugs of this class. At present, there are only three interleukin-1β blockers approved in the clinic. All of them are biologics, requiring parenteral administration and resulting in expensive treatments. In an exercise to identify small molecule allosteric inhibitors of MAP kinases, we discovered a series of compounds that block IL-1β release produced as a consequence of a stimulus involved in triggering an inflammatory response. The present study reports the hit-to-lead optimization process that permitted the identification of the compound 13b (AIK3-305) an orally available, potent and selective inhibitor of IL-1β. Furthermore, the study also reports the results of an in vivo efficacy study of 13b in a LPS endotoxic shock model in male BALB/c mice, where IL-1β inhibition is monitored in different tissues.
MeSH term(s)	Animals ; Female ; Humans ; Interleukin-1beta/antagonists & inhibitors ; MAP Kinase Signaling System/drug effects ; Macrophages/drug effects ; Male ; Mice, Inbred BALB C ; Pyridines/chemical synthesis ; Pyridines/metabolism ; Pyridines/pharmacokinetics ; Pyridines/pharmacology ; Rats, Wistar ; p38 Mitogen-Activated Protein Kinases/metabolism ; Mice ; Rats
Chemical Substances	IL1B protein, mouse ; IL1B protein, rat ; Interleukin-1beta ; Pyridines ; p38 Mitogen-Activated Protein Kinases (EC 2.7.11.24)
Language	English
Publishing date	2021-06-12
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.2021.113620
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Article ; Online: Structure-Activity Studies of Novel Di-substituted [1,2,5]oxadiazolo [3,4-b]pyrazine Analogs Targeting the A-loop Regulatory Site of p38 MAP Kinase.

Carrasco, Esther / Gomez-Gutierrez, Patricia / Campos, Pedro M / Vega, Miguel / Messeguer, Angel / Perez, Juan Jesus

Current medicinal chemistry

2021 Volume 29, Issue 9, Page(s) 1640–1653

Abstract: Introduction: In the quest for novel allosteric inhibitors of the p38 MAP kinase, we recently described the A-loop regulatory site, identified by means of molecular modeling studies together with the disclosure of a small molecule hit with a moderate ... ...

Abstract	Introduction: In the quest for novel allosteric inhibitors of the p38 MAP kinase, we recently described the A-loop regulatory site, identified by means of molecular modeling studies together with the disclosure of a small molecule hit with a moderate inhibitory profile. Starting from this structure, we subsequently identified two additional hits with simpler molecular structures from an in silico screening study, using a substructure search in the SciFinder database. After corroboration of their inhibitory profile, analysis of their structures permitted to conclude about the suitability of the [1,2,5]oxadiazolo[3,4-b]pyrazine (furazano[ 3,4-b]pyrazine) scaffold for the development of potent A-loop regulatory site p38 MAP kinase inhibitors. Accordingly, we report the synthesis and pharmacological evaluation of a series of di-substituted analogs with a potent inhibitory profile of p38 MAP kinase, as shown by in vitro assays of their capability to inhibit IL-1β secretion in human monocyte-derived macrophages. Objective: To find small molecule potent inhibitors of the p38 MAP kinase A-loop regulatory site. Methods: Starting from this structure, we subsequently identified two additional hits with simpler molecular structures from an in silico screening study, using a substructure search in the SciFinder database. After corroboration of their inhibitory profile, we carried out a hit-tolead optimization process guided by molecular modeling using a [1,2,5]oxadiazolo[3,4- b]pyrazine (furazano[3,4-b]pyrazine) scaffold. Results: We report the synthesis and pharmacological evaluation of a series of di-substituted analogs with a potent inhibitory profile of p38 MAP kinase, as shown by in vitro assays of their capability to inhibit IL-1β secretion in human monocyte-derived macrophages. Conclusion: We describe in the present work a series of [1,2,5]oxadiazolo[3,4-b]pyrazine (furazano[3,4-b]pyrazine), which are potent inhibitors of IL-1β secretion in human monocytederived macrophages allosteric modulators of the p38 MAP kinase A-loop regulatory site.
MeSH term(s)	AAA Domain ; Humans ; Macrophages/metabolism ; Molecular Structure ; Pyrazines/pharmacology ; p38 Mitogen-Activated Protein Kinases
Chemical Substances	Pyrazines ; p38 Mitogen-Activated Protein Kinases (EC 2.7.11.24)
Language	English
Publishing date	2021-12-21
Publishing country	United Arab Emirates
Document type	Journal Article
ZDB-ID	1319315-6
ISSN	1875-533X ; 0929-8673
ISSN (online)	1875-533X
ISSN	0929-8673
DOI	10.2174/0929867328666210712165659
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Article: Semaphorin 3A-Glycosaminoglycans Interaction as Therapeutic Target for Axonal Regeneration.

Pérez, Yolanda / Bonet, Roman / Corredor, Miriam / Domingo, Cecilia / Moure, Alejandra / Messeguer, Àngel / Bujons, Jordi / Alfonso, Ignacio

Pharmaceuticals (Basel, Switzerland)

2021 Volume 14, Issue 9

Abstract: Semaphorin 3A (Sema3A) is a cell-secreted protein that participates in the axonal guidance pathways. Sema3A acts as a canonical repulsive axon guidance molecule, inhibiting CNS regenerative axonal growth and propagation. Therefore, interfering with ... ...

Abstract	Semaphorin 3A (Sema3A) is a cell-secreted protein that participates in the axonal guidance pathways. Sema3A acts as a canonical repulsive axon guidance molecule, inhibiting CNS regenerative axonal growth and propagation. Therefore, interfering with Sema3A signaling is proposed as a therapeutic target for achieving functional recovery after CNS injuries. It has been shown that Sema3A adheres to the proteoglycan component of the extracellular matrix (ECM) and selectively binds to heparin and chondroitin sulfate-E (CS-E) glycosaminoglycans (GAGs). We hypothesize that the biologically relevant interaction between Sema3A and GAGs takes place at Sema3A C-terminal polybasic region (SCT). The aims of this study were to characterize the interaction of the whole Sema3A C-terminal polybasic region (Sema3A 725-771) with GAGs and to investigate the disruption of this interaction by small molecules. Recombinant Sema3A basic domain was produced and we used a combination of biophysical techniques (NMR, SPR, and heparin affinity chromatography) to gain insight into the interaction of the Sema3A C-terminal domain with GAGs. The results demonstrate that SCT is an intrinsically disordered region, which confirms that SCT binds to GAGs and helps to identify the specific residues involved in the interaction. NMR studies, supported by molecular dynamics simulations, show that a new peptoid molecule (CSIC02) may disrupt the interaction between SCT and heparin. Our structural study paves the way toward the design of new molecules targeting these protein-GAG interactions with potential therapeutic applications.
Language	English
Publishing date	2021-09-07
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2193542-7
ISSN	1424-8247
ISSN	1424-8247
DOI	10.3390/ph14090906
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Article: Potential implication of aniline derivatives in the Toxic Oil Syndrome (TOS)

Messeguer, Angel

Chemico-biological interactions. 2011 June 30, v. 192, no. 1-2

2011

Abstract	The Toxic Oil Syndrome (TOS) was an epidemic disease appeared in central Spain in 1981, causing over 400 deaths and affecting more than 20,000 people, mainly women and children. The disease was linked to the consumption of rapeseed oil denatured with aniline, illegally refined at the ITH oil refinery in Seville, mixed with other oils and sold as edible olive oil. Among the aniline derivatives detected in the oil batches generated by an uncontrolled deodorisation procedure during the refining process, fatty acid anilides were first postulated as the causal agents. Nevertheless, compounds identified as 3-(N-phenylamino)propane-1,2-diol (PAP) and its mono-, di-, and triacyl derivatives (mPAP, dPAP and tPAP, respectively), were subsequently considered better biomarkers of toxic oils and the best candidates for causing the intoxication. In this account, we will discuss the results obtained in recent years by our group concerning: (a) The effect of different variables intervening in the deodorisation process that could influence the formation of PAP derivatives. To this end we decided to take the aniline derivatives linked to oleic acid as compound models since this is the fatty acid present in highest amounts in rapeseed oil. The study was focused on the influence of different parameters on the formation of the diester PAP derivative (OOPAP) the monoester derivative (OPAP) and the corresponding amide (oleanilide, OA), and the interactions between any two of these variables. Of particular interest was the interaction observed between OOPAP and OA, due to its potential relevance to the final composition of the toxic oil model. (b) Xenobiochemical aspects of PAP derivatives, specifically: the stereospecific hydrolysis of OPAP and OOPAP by human pancreatic lipase, the in vitro activation of PAP by human and rat liver microsomes as well as by recombinant 450 enzymes, and the formation and stability of GSH and N-acetylcysteine adducts of a highly reactive iminoquinone intermediate generated in the biotransformation of PAP.
Keywords	anilides ; aniline ; biomarkers ; biotransformation ; children ; deodorization ; humans ; hydrolysis ; liver microsomes ; models ; oleic acid ; olive oil ; poisoning ; rapeseed oil ; rats ; refining ; toxic oil syndrome ; toxicity ; triacylglycerol lipase ; women ; Spain
Language	English
Dates of publication	2011-0630
Size	p. 136-141.
Publishing place	Elsevier Ireland Ltd
Document type	Article
ZDB-ID	218799-1
ISSN	1872-7786 ; 0009-2797
ISSN (online)	1872-7786
ISSN	0009-2797
DOI	10.1016/j.cbi.2010.10.006
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Semaphorin 3A—Glycosaminoglycans Interaction as Therapeutic Target for Axonal Regeneration

Yolanda Pérez / Roman Bonet / Miriam Corredor / Cecilia Domingo / Alejandra Moure / Àngel Messeguer / Jordi Bujons / Ignacio Alfonso

Pharmaceuticals, Vol 14, Iss 906, p

2021 Volume 906

Abstract	Semaphorin 3A (Sema3A) is a cell-secreted protein that participates in the axonal guidance pathways. Sema3A acts as a canonical repulsive axon guidance molecule, inhibiting CNS regenerative axonal growth and propagation. Therefore, interfering with Sema3A signaling is proposed as a therapeutic target for achieving functional recovery after CNS injuries. It has been shown that Sema3A adheres to the proteoglycan component of the extracellular matrix (ECM) and selectively binds to heparin and chondroitin sulfate-E (CS-E) glycosaminoglycans (GAGs). We hypothesize that the biologically relevant interaction between Sema3A and GAGs takes place at Sema3A C-terminal polybasic region (SCT). The aims of this study were to characterize the interaction of the whole Sema3A C-terminal polybasic region (Sema3A 725–771) with GAGs and to investigate the disruption of this interaction by small molecules. Recombinant Sema3A basic domain was produced and we used a combination of biophysical techniques (NMR, SPR, and heparin affinity chromatography) to gain insight into the interaction of the Sema3A C-terminal domain with GAGs. The results demonstrate that SCT is an intrinsically disordered region, which confirms that SCT binds to GAGs and helps to identify the specific residues involved in the interaction. NMR studies, supported by molecular dynamics simulations, show that a new peptoid molecule (CSIC02) may disrupt the interaction between SCT and heparin. Our structural study paves the way toward the design of new molecules targeting these protein–GAG interactions with potential therapeutic applications.
Keywords	semaphorin 3A ; NMR ; glycosaminoglycan–protein interaction ; peptoids ; Medicine ; R ; Pharmacy and materia medica ; RS1-441
Subject code	572
Language	English
Publishing date	2021-09-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Dynamic Covalent Identification of an Efficient Heparin Ligand.

Corredor, Miriam / Carbajo, Daniel / Domingo, Cecilia / Pérez, Yolanda / Bujons, Jordi / Messeguer, Angel / Alfonso, Ignacio

Angewandte Chemie (International ed. in English)

2018 Volume 57, Issue 37, Page(s) 11973–11977

Abstract: Despite heparin being the most widely used macromolecular drug, the design of small-molecule ligands to modulate its effects has been hampered by the structural properties of this polyanionic polysaccharide. Now a dynamic covalent selection approach is ... ...

Abstract	Despite heparin being the most widely used macromolecular drug, the design of small-molecule ligands to modulate its effects has been hampered by the structural properties of this polyanionic polysaccharide. Now a dynamic covalent selection approach is used to identify a new ligand for heparin, assembled from extremely simple building blocks. The amplified molecule strongly binds to heparin (K
MeSH term(s)	Blood Coagulation/drug effects ; Heparin/chemistry ; Heparin/metabolism ; Heparin/pharmacology ; Humans ; Hydrogen Bonding ; Hydrolysis ; Ligands ; Magnetic Resonance Spectroscopy ; Models, Molecular ; Spectrometry, Fluorescence ; Static Electricity
Chemical Substances	Ligands ; Heparin (9005-49-6)
Language	English
Publishing date	2018-08-10
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.201806770
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Article: Regioselective Synthesis of a Family of β-Lactams Bearing a Triazole Moiety as Potential Apoptosis Inhibitors.

Garrido, Maria / Corredor, Miriam / Orzáez, Mar / Alfonso, Ignacio / Messeguer, Angel

ChemistryOpen

2016 Volume 5, Issue 5, Page(s) 485–494

Abstract: Apoptosis is a biological process important to several human diseases; it is strongly regulated through protein-protein interactions and complex formation. We previously reported the synthesis of apoptosis inhibitors bearing an exocyclic triazole amide ... ...

Abstract	Apoptosis is a biological process important to several human diseases; it is strongly regulated through protein-protein interactions and complex formation. We previously reported the synthesis of apoptosis inhibitors bearing an exocyclic triazole amide isoster by using an Ugi four-component coupling reaction (Ugi-4CC), followed by a base-promoted intramolecular cyclization. Depending on the substitution patterns and the reaction conditions, this cyclization forms the six- or four-membered ring. Two compounds bearing the β-lactam scaffold turned out to be the most potent inhibitors. This encouraged us to optimize the modulation of the cyclization, and prepare a library of 15 β-lactams with total regioselectivity. Moreover, we aimed to improve the bioavailability of these compounds through the introduction of diversity at different substitution positions. The activity of these compounds as apoptosis inhibitors in cellular extracts has been evaluated, showing an increase in their potency.
Language	English
Publishing date	2016-08-02
Publishing country	Germany
Document type	Journal Article
ZDB-ID	2655605-4
ISSN	2191-1363
ISSN	2191-1363
DOI	10.1002/open.201600052
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Article ; Online: 15N NMR spectroscopic and theoretical GIAO-DFT studies for the unambiguous characterization of disubstituted 1,2,3-triazoles.

Corredor, Miriam / Bujons, Jordi / Messeguer, Àngel / Alfonso, Ignacio

Organic & biomolecular chemistry

2013 Volume 11, Issue 42, Page(s) 7318–7325

Abstract: The 1,2,3-triazole ring has recently attracted a renewed interest as a structural scaffold with many applications in different fields. However, very often, the unambiguous assignment of the correct structure is not an easy task, and the development of ... ...

Abstract	The 1,2,3-triazole ring has recently attracted a renewed interest as a structural scaffold with many applications in different fields. However, very often, the unambiguous assignment of the correct structure is not an easy task, and the development of robust characterization methodologies is needed. Herein, the three possible isomeric forms of disubstituted 1,2,3-triazole (1,4- or 1,5- or 2,4-disubstituted derivatives) have been characterized and distinguished by routine (1)H/(15)N gHMBC experiments at (15)N natural abundance. The calculated (GIAO-B3LYP/6-311++G**) (15)N NMR chemical shifts showed good agreement with the experimental values, further supporting their unambiguous structural characterization.
MeSH term(s)	Magnetic Resonance Spectroscopy ; Quantum Theory ; Triazoles/chemistry
Chemical Substances	Triazoles
Language	English
Publishing date	2013-11-14
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/c3ob41587b
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Article ; Online: Synthesis of enantiomerically pure perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives exhibiting potent activity as apoptosis inhibitors.

Moure, Alejandra / Orzáez, Mar / Sancho, Mónica / Messeguer, Angel

Bioorganic & medicinal chemistry letters

2012 Volume 22, Issue 23, Page(s) 7097–7099

Abstract: Apoptosis is the process of programmed cell death and plays a fundamental role in several human diseases. We have previously reported the synthesis of the perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives as racemic mixtures. ... ...

Abstract	Apoptosis is the process of programmed cell death and plays a fundamental role in several human diseases. We have previously reported the synthesis of the perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives as racemic mixtures. Compounds 1 and 2 showed a potent in vitro and in cellular extracts antiapoptotic activity. In view that the chiral discrimination has been an issue in the development and use of pharmaceutical drugs, the present contribution reports the synthesis of enantiopure peptidomimetics 1 and 2. The biological evaluation of these enantiomers as apoptosis inhibitors is also reported.
MeSH term(s)	Apoptosis/drug effects ; Apoptosomes/antagonists & inhibitors ; Apoptosomes/metabolism ; Apoptotic Protease-Activating Factor 1/antagonists & inhibitors ; Apoptotic Protease-Activating Factor 1/genetics ; Apoptotic Protease-Activating Factor 1/metabolism ; Azepines/chemical synthesis ; Azepines/chemistry ; Azepines/pharmacology ; HEK293 Cells ; Humans ; Peptidomimetics ; Piperazines/chemical synthesis ; Piperazines/chemistry ; Piperazines/pharmacology ; Protein Binding ; Recombinant Proteins/antagonists & inhibitors ; Recombinant Proteins/genetics ; Recombinant Proteins/metabolism ; Stereoisomerism
Chemical Substances	Apoptosomes ; Apoptotic Protease-Activating Factor 1 ; Azepines ; Peptidomimetics ; Piperazines ; Recombinant Proteins ; piperazine (1RTM4PAL0V)
Language	English
Publishing date	2012-12-01
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2012.09.078
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