Irene Ortín

Universidad San Pablo CEU

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Darren J. Dixon

University of Oxford

Elena de la Cuesta

Universidad Complutense de Madrid

Juan F. González

Universidad Politécnica de Cartagena

Carmen Avendaño

Universidad Complutense de Madrid

Beatriz de Pascual‐Teresa

Universidad San Pablo CEU

Ana Ramos

Universidad San Pablo CEU

Raquel de la Campa

Universidad de Oviedo

Claire Coderch

Universidad San Pablo CEU

Loganathan Rangasamy

Vellore Institute of Technology University

José María Zapico

Universidad San Pablo CEU

Cooperative Institutions

Universidad San Pablo CEU

University of Oxford

Science Oxford

Universidad Complutense de Madrid

Consejo Superior de Investigaciones Científicas

Universidad San Pablo

AstraZeneca (United Kingdom)

Oxford Research Group

Universidad de Salamanca

Universidad de Alcalá

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New Advances in the Exploration of Esterases wit PET and Fluorescent Probes

Alba Gil-Rivas Beatriz de Pascual‐Teresa Irene Ortín Ana Ramos

Esterases are hydrolases that catalyze the hydrolysis of esters into the corresponding acids and alcohols. The development of fluorescent probes for detecting esterases is of great importance due to their wide spectrum of biological and industrial applications. These probes can provide a rapid and sensitive method for detecting the presence and activity of esterases in various samples, including biological fluids, food products, and environmental samples. Fluorescent probes can also be used for monitoring the effects of drugs and environmental toxins on esterase activity, as well as to study the functions and mechanisms of these enzymes in several biological systems. Additionally, fluorescent probes can be designed to selectively target specific types of esterases, such as those found in pathogenic bacteria or cancer cells. In this review, we summarize the recent fluorescent probes described for the visualization of cell viability and some applications for in vivo imaging. On the other hand, Positron Emission Tomography (PET) is a nuclear-based molecular imaging modality of great value to study the activity of enzymes in vivo. We provide some examples of PET probes for imaging acetylcholinesterases and butyrylcholinesterases in brain, which are valuable tools for diagnosing dementia and monitoring the effects of anticholinergic drugs on the central nervous system.

Esterase

Molecular Imaging

10.20944/preprints202308.0118.v1

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Citations (1)

Mechanistic Investigations into the Enantioselective Conia‐Ene Reaction Catalyzed by Cinchona‐Derived Amino Urea Pre‐Catalysts and Cu^I

Chemistry - A European Journal (2013)

Filippo Sladojevich Ángel L. Fuentes de Arriba Irene Ortín Ting Yang Alessandro Ferrali

Abstract The enantioselective Conia‐ene cyclization of alkyne‐tethered β‐ketoesters is efficiently catalyzed by the combination of cinchona‐derived amino‐urea pre‐catalysts and copper(I) salts. The reaction scope is broad and a series of substrates can be efficiently cyclized with high yields and enantioselectivities. Herein, we present a detailed mechanistic study based on experimental considerations and quantum mechanical calculations. Several variables, such as the nature of the organic pre‐catalyst and the metal‐ion source, have been thoroughly investigated. Kinetic studies, as well as kinetic isotope effects and deuterium labeling experiments have been used to gain further insights into the mechanism and prove the cooperative nature of the catalytic system. Our studies suggest that the rate‐limiting step for the reaction involves the β‐ketoester deprotonation and that the active species responsible for the enantiodeterming step is monomeric in amino‐urea pre‐catalyst. Computational studies provide a quantitative understanding of the observed stereoinduction and identify hydrogen bonding from the urea group as a crucial factor in determining the observed enantioselectivity.

Kinetic isotope effect

Cinchona Alkaloids

Ene reaction

10.1002/chem.201200832

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Citations (33)

ChemInform Abstract: Direct Catalytic Enantio‐ and Diastereoselective Ketone Aldol Reactions of Isocyanoacetates.

ChemInform (2015)

Raquel de la Campa Irene Ortín Darren J. Dixon

Abstract A diastereo‐ and enantioselective aldol/cyclization reaction of isocyanate esters with unactivated ketones to yield functionalized oxazolines is developed.

Aldol reaction

Isocyanate

10.1002/chin.201534170

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Direct Catalytic Enantio- and Diastereoselective Ketone Aldol Reactions of Isocyanoacetates

Angewandte Chemie (2015)

Raquel de la Campa Irene Ortín Darren J. Dixon

Abstract A catalytic asymmetric aldol addition/cyclization reaction of unactivated ketones with isocyanoacetate pronucleophiles has been developed. A quinine‐derived aminophosphine precatalyst and silver oxide were found to be an effective binary catalyst system and promoted the reaction to afford chiral oxazolines possessing a fully substituted stereocenter with good diastereoselectivities and excellent enantioselectivities.

Aldol reaction

Stereocenter

10.1002/ange.201411852

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Citations (25)

ChemInform Abstract: Direct Catalytic Enantio‐ and Diastereoselective Mannich Reaction of Isocyanoacetates and Ketimines.

ChemInform (2014)

Irene Ortín Darren J. Dixon

10.1002/chin.201436137

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Privileged scaffolds in synthesis: 2,5-piperazinediones as templates for the preparation of structurally diverse heterocycles

Chemical Society Reviews (2012)

Juan F. González Irene Ortín Elena de la Cuesta J. Carlos Menéndez

2,5-Piperazinediones (2,5-diketopiperazines, DKPs) can be viewed as privileged building blocks for the synthesis of heterocyclic systems. This tutorial review aims at underscoring the large number and structural variety of nitrogen heterocycles that are available by suitable manipulation of DKP starting materials, including many bioactive compounds and natural products.

Template

Diketopiperazines

10.1039/c2cs35158g

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Citations (61)

Direct Catalytic Enantio‐ and Diastereoselective Mannich Reaction of Isocyanoacetates and Ketimines

Angewandte Chemie International Edition (2014)

Irene Ortín Darren J. Dixon

Abstract A catalytic asymmetric synthesis of imidazolines with a fully substituted β‐carbon atom by a Mannich‐type addition/cyclization reaction of isocyanoacetate pronucleophiles and N ‐diphenylphosphinoyl ketimines has been developed. When a combination of a cinchona‐derived aminophosphine precatalyst and silver oxide was employed as a binary catalyst system, good reactivity, high diastereoselectivities (up to 99:1 d.r.), and excellent enantioselectivities (up to 99 % ee ) were obtained for a range of substrates.

Reactivity

Cinchona

Carbon atom

Mannich reaction

10.1002/anie.201309719

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Citations (116)

ChemInform Abstract: Synthesis of a Novel Tetrahydroisoquinoline Pentacyclic Framework

ChemInform (2009)

Irene Ortín Juan F. González Elena de la Cuesta Carmen Avendaño

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Tetrahydroisoquinoline

10.1002/chin.200930168

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Cytotoxicity of new pyrazino[1,2-b]isoquinoline and 6,15-iminoisoquino[3,2-b]3-benzazocine compounds

Bioorganic & Medicinal Chemistry (2010)

Irene Ortín Juan F. González Elena de la Cuesta Carmen Avendaño

Isoquinoline

Structure–activity relationship

Carcinoma Cell

10.1016/j.bmc.2010.07.049

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Citations (8)

CCDC 1493438: Experimental Crystal Structure Determination

The Cambridge Structural Database (2016)

Raquel de la Campa Adam D. Gammack Yamagata Irene Ortín Allegra Franchino Amber L. Thompson

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc1m41f7

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Citations (0)