Search results for: Antonio Mouriño

Items from 1 to 20 out of 51 results

article

A vitamin D‐based strategy overcomes chemoresistance in prostate cancer

Kateryna Len‐Tayon, Claire Beraud, Clara Fauveau, Anna Y. Belorusova, more

British Journal of Pharmacology > 181 > 21 > 4279 - 4293

Background and purpose Castration‐resistant prostate cancer (CRPC) is a common male malignancy that requires new therapeutic strategies due to acquired resistance to its first‐line treatment, docetaxel. The benefits of vitamin D on prostate cancer (PCa) progression have been previously reported. This study aimed to investigate the effects of vitamin D on chemoresistance in CRPC. Experimental approach...

article

Pd(0)‐Catalyzed‐Mediated Synthesis of Vitamin D Compounds

Antonio Mouriño

Advanced Synthesis & Catalysis > 366 > 4 > 603 - 616

1α,25‐Dihydroxyvitamin D₃ (1,25D₃), the hormonally active form of vitamin D₃, regulates mineral homeostasis, cell growth, cell differentiation‐proliferation, apoptosis, and immune responses. 1,25D₃ activates more than 229 genes associated with several diseases, including arthritis, diabetes and cancer, suggesting its implications in a broader range of biological functions than originally thought....

article

Efficient Asymmetric Synthesis of an A‐Ring Synthon for Pd‐Catalyzed Preparation of 1α‐Hydroxyvitamin D Metabolites and Analogs

Julian Loureiro, Lars Kattner, Antonio Mouriño

European Journal of Organic Chemistry > 2022 > 33 > n/a - n/a

The secondary parallel hypercalcemic effects associated with the treatment of several hyperproliferative diseases with the natural hormone 1α,25‐dihydroxyvitamin D₃ (calcitriol) and/or known active vitamin D metabolites and analogs, demand the development of efficient and rapid methods for the preparation of vitamin D receptor (VDR) ligands as new selective and non‐calcemic agonists. Here we describe...

article

Design, Synthesis, Evaluation and Structure of Allenic 1α,25‐Dihydroxyvitamin D₃ Analogs with Locked Mobility at C‐17

Ramón Fraga, Kateryna Len, Regis Lutzing, Gilles Laverny, more

Chemistry – A European Journal > 27 > 53 > 13384 - 13389

Vitamin D receptor ligands have potential for the treatment of hyperproliferative diseases and disorders related to the immune system. However, hypercalcemic effects limit their therapeutical uses and call for the development of tissue‐selective new analogs. We have designed and synthesized the first examples of 1α,25‐dihydroxyvitamin D₃ analogs bearing an allenic unit attached to the D ring to restrict...

article

Wikipedia-based hybrid document representation for textual news classification

Marcos Antonio Mouriño-García, Roberto Pérez-Rodríguez, Luis Anido-Rifón, Manuel Vilares-Ferro

Soft Computing > 2018 > 22 > 18 > 6047-6065

The sheer amount of news items that are published every day makes worth the task of automating their classification. The common approach consists in representing news items by the frequency of the words they contain and using supervised learning algorithms to train a classifier. This bag-of-words (BoW) approach is oblivious to three aspects of natural language: synonymy, polysemy, and multiword terms...

article

Stereoselective Palladium‐Catalyzed Approach to Vitamin D₃ Derivatives in Protic Medium

Diego Carballa, Rita Sigüeiro, Zaida Rodríguez‐Docampo, Flavia Zacconi, more

Chemistry – A European Journal > 24 > 13 > 3314 - 3320

We describe an efficient convergent synthesis of vitamin D₃ metabolites and analogues. The synthetic strategy relies on a tandem Pd‐catalyzed A‐ring closure and Suzuki–Miyaura coupling to the CD‐side chain component to set directly the vitamin D triene system under protic conditions. This strategy enables rapid access to vitamin D₃ and 3‐epi‐vitamin D₃ metabolites and analogues modified at the side...

article

A new approach to 19-nor-A-ring phosphine oxide for the convergent synthesis of 19-nor-calcitriol

Rita Sigüeiro, Rocio Otero, Patricia González-Berdullas, Julian Loureiro, more

The Journal of Steroid Biochemistry and Molecular Biology > 2017 > 173 > C > 86-88

A new approach to 19-nor-A-ring phosphine oxide 5 together with a convergent synthesis of the vitamin D₃ analogue 1α,25-dihydroxy-19-norvitamin D₃ (3) have been developed. The 19-nor-A-ring is constructed from (S)-carvone. The triene system is assembled by a Wittig-Horner coupling.

article

Wikipedia-based cross-language text classification

Marcos Antonio Mouriño García, Roberto Pérez Rodríguez, Luis Anido Rifón

Information Sciences > 2017 > 406-407 > C > 12-28

This paper presents the application of a Wikipedia-based bag of concepts (WikiBoC) document representation to cross-language text classification (CLTC). Its main objective is to alleviate the major drawbacks of the state-of-the-art CLTC approaches – typically based on the machine translation (MT) of documents, which are represented as bags of words (BoW). We propose a technique called cross-language...

chapter

Wikipedia-Based Hybrid Document Representation for Textual News Classification

Marcos Antonio Mourino Garcia, Roberto Perez Rodriguez, Manuel Vilares Ferro, Luis Anido Rifon

2016 3rd International Conference on Soft Computing & Machine Intelligence (ISCMI) > 148 - 153

2016 3rd International Conference on Soft Computing & Machine Intelligence (ISCMI)

Automatic classification of news articles is a relevant problem due to the large amount of news generated every day, so it is crucial that these news are classified to allow for users to access to information of interest quickly and effectively. On the one hand, traditional classification systems represent documents as bag-of-words (BoW), which are oblivious to two problems of language: synonymy and...

article

Stereoselective synthesis of 1β,25-Dihydroxyvitamin D3 and its 26,27-hexadeuterated derivative

Julian Loureiro, Miguel A. Maestro, Antonio Mouriño, Rita Sigüeiro

The Journal of Steroid Biochemistry and Molecular Biology > 2016 > 164 > C > 56-58

A mild convergent synthesis of 1β,25-dihydroxyvitamin D₃ (3a), a metabolite of vitamin D₃, and its C26,27-hexadeuterated derivative (3b) are described. The A-ring and the CD-fragments are constructed from (R)-carvone and Inhoffen–Lythgoe diol, respectively. The triene system is assembled by a Pd(0)-catalyzed process, which involves an enol-triflate (A-ring fragment) and an alkenyl boronate (CD-side...

chapter

Influence of the S-Au Bond Strength on the Magnetic Behavior of S-Capped Au Nanoparticles

María J. Rodríguez Vázquez, José Rivas, M. Arturo López-Quintela, Antonio Mouriño Mosquera, more

NATO Science for Peace and Security Series B: Physics and Biophysics > Nanomaterials for Application in Medicine and Biology > 113-125

Recently, large permanent atomic magnetic moments have been found in Au nanoparticles capped with thiols. It is assumed that the formation of localized Au-S bonds at the particle surface induces the damping of the surface plasmon resonance and the appearance of a ferromagnetic-like behavior. In this work we will show for the first time that thioethers can also induce both phenomena, i.e., the damping...

article

An efficient convergent synthesis of 1α,25-dihydroxy-3-epi-vitamin D2

Rita Sigüeiro, Rocio Otero, Patricia González-Berdullas, Miguel Maestro, more

Journal of Steroid Biochemistry and Molecular Biology > 2015 > 148 > Complete > 31-33

The first synthesis of 1α,25-dihydroxy-3-epi-vitamin D ₂ is described. Key steps of the synthesis entail the construction of the triene unit by a Pd-catalyzed ring closure of an enol-triflate (A-ring fragment) followed by a Suzuki–Miyaura coupling with a boronate (upper fragment), and the installation of the methyl group at C-24 by an S _N 2′-syn displacement of an allylic carbamate...

article

Metabolic stability of 3‐Epi‐1α,25‐dihydroxyvitamin D₃ over 1α, 25‐dihydroxyvitamin D₃: Metabolism and molecular docking studies using rat CYP24A1

Steve Y. Rhieu, Andrew J. Annalora, Guochun Wang, Caroline C. Flarakos, more

Journal of Cellular Biochemistry > 114 > 10 > 2293 - 2305

3‐epi‐1α,25‐dihydroxyvitamin D₃ (3‐epi‐1α,25(OH)₂D₃), a natural metabolite of 1α,25‐dihydroxyvitamin D₃ (1α,25(OH)₂D₃), exhibits potent vitamin D receptor (VDR)‐mediated actions such as inhibition of keratinocyte growth or suppression of parathyroid hormone secretion. These VDR‐mediated actions of 3‐epi‐1α,25(OH)₂D₃ needed an explanation as 3‐epi‐1α,25(OH)₂D₃, unlike 1α,25(OH)₂D₃, exhibits low affinity...

article

Synthesis of 1α,25-dihydroxyvitamin D3 analogues with α-hydroxyalkyl substituents at C12

Diego M. Carballa, Flavia Zacconi, Urszula Kulesza, Antonio Mouriño, more

Journal of Steroid Biochemistry and Molecular Biology > 2013 > 136 > Complete > 34-38

Convergent syntheses of three new analogues of 1α,25-dihydroxyvitamin D ₃ with α-hydroxyalkyl substituents at C12 (4a–c) are described. The A-ring and triene system of each analogue were assembled by a tandem Pd-catalysed intramolecular cyclization and Suzuki–Miyaura coupling process. The stereoselective introduction of substituents at C12 was achieved by Johnson–Claisen rearrangement on allylic...

article

Synthesis and biological evaluation of novel 6-substituted analogs of 1α,25-dihydroxy-19-norvitamin D3

Katarzyna Sokolowska, Rafal R. Sicinski, Antonio Mouriño, Lori A. Plum, more

Journal of Steroid Biochemistry and Molecular Biology > 2013 > 136 > Complete > 30-33

We have recently described the synthesis and biological evaluation of 1α,25-dihydroxy-6-methylvitamin D ₃ which binds the vitamin D receptor (VDR) very effectively. Unfortunately, this compound has a strong tendency to rearrange to its previtamin form. Taking this into consideration, we decided to synthesize a series of 6-substituted analogs of 1α,25-dihydroxy-19-norvitamin D ₃ which...

article

Synthesis of novel 19-norvitamin D3 analogs with unnatural triene system

Urszula Kulesza, Antonio Mouriño, Lori A. Plum, Hector F. DeLuca, more

Journal of Steroid Biochemistry and Molecular Biology > 2013 > 136 > Complete > 23-26

9-Alkylidene analogs of 19-nor-1α,25-(OH) ₂ D ₃ were synthesized, possessing a ‘reversed’ triene system compared to the natural hormone. The conjugated triene moiety of the novel analogs was constructed by coupling an enyne anion, representing an A-ring synthon, with a 9α-substituted Grundmann ketone derivative. Regioselective dehydration followed by semihydrogenation under Lindlar...

article

Synthesis of (1α)‐1,25‐Dihydroxyvitamin D₃ with a β‐Positioned Seven‐Carbon Side Chain at C(12)

Diego M. Carballa, Antonio Rumbo, Mercedes Torneiro, Miguel Maestro, more

Helvetica Chimica Acta > 95 > 10 > 1842 - 1850

A convergent synthesis of an analogue of (1α)‐1,25‐dihydroxyvitamin D₃ (1b) with a C₇ side chain at C(12), i.e., of 5 (Fig.), is described. A key step of the synthesis is the assembly of the triene system by a Pd^II‐catalyzed ring closure of an enol triflate (‘bottom’ fragment) followed by coupling of the resulting Pd^II intermediate with an alkenylboronate (‘upper’ fragment) (Scheme 2). The synthetic...

article

Design, Synthesis, Evaluation, and Structure of Vitamin D Analogues with Furan Side Chains

Ramón Fraga, Flavia Zacconi, Fredy Sussman, Paloma Ordóñez‐Morán, more

Chemistry – A European Journal > 18 > 2 > 603 - 612

Based on the crystal structures of human vitamin D receptor (hVDR) bound to 1α,25‐dihydroxy‐vitamin D₃ (1,25 D) and superagonist ligands, we previously designed new superagonist ligands with a tetrahydrofuran ring at the side chain that optimize the aliphatic side‐chain conformation through an entropy benefit. Following a similar strategy, four novel vitamin D analogues with aromatic furan side chains...

article

Design and synthesis of active vitamin D analogs

Silvina Eduardo-Canosa, Ramón Fraga, Rita Sigüeiro, Maria Marco, more

Journal of Steroid Biochemistry and Molecular Biology > 2010 > 121 > 1-2 > 7-12

A review of the design and synthesis of structural analogs of the vitamin D hormone recently investigated in our laboratories, and the first report on a new class of vitamin D analogs characterized by an aromatic D-ring, is described.

article

Stereoselective synthesis of C24-hydroxylated vitamin D3 analogs: A practical and expeditius route to calcipotriol

Antonio Rumbo, Xenxo Pérez-García, Antonio Mouriño

Journal of Steroid Biochemistry and Molecular Biology > 2010 > 121 > 1-2 > 68-70

The synthesis of the clinically important drug calcipotriol (2, MC903) is described as an example of a new and efficient approach to C24-hydroxylated analogs and metabolites of vitamin D ₃ (1). The key step of the process is the generation of the C24 stereocenter by DAIB [(−)-3-exo-(dimethylamino)isoborneol]-catalyzed addition of the alkenylzinc derivative of alkyne 3 to cyclopropylcarboxaldehyde.

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INFONA - science communication portal

Search results for: Antonio Mouriño

A vitamin D‐based strategy overcomes chemoresistance in prostate cancer

Pd(0)‐Catalyzed‐Mediated Synthesis of Vitamin D Compounds

Efficient Asymmetric Synthesis of an A‐Ring Synthon for Pd‐Catalyzed Preparation of 1α‐Hydroxyvitamin D Metabolites and Analogs

Design, Synthesis, Evaluation and Structure of Allenic 1α,25‐Dihydroxyvitamin D₃ Analogs with Locked Mobility at C‐17

Wikipedia-based hybrid document representation for textual news classification

Stereoselective Palladium‐Catalyzed Approach to Vitamin D₃ Derivatives in Protic Medium

A new approach to 19-nor-A-ring phosphine oxide for the convergent synthesis of 19-nor-calcitriol

Wikipedia-based cross-language text classification

Wikipedia-Based Hybrid Document Representation for Textual News Classification

Stereoselective synthesis of 1β,25-Dihydroxyvitamin D3 and its 26,27-hexadeuterated derivative

Influence of the S-Au Bond Strength on the Magnetic Behavior of S-Capped Au Nanoparticles

An efficient convergent synthesis of 1α,25-dihydroxy-3-epi-vitamin D2

Metabolic stability of 3‐Epi‐1α,25‐dihydroxyvitamin D₃ over 1α, 25‐dihydroxyvitamin D₃: Metabolism and molecular docking studies using rat CYP24A1

Synthesis of 1α,25-dihydroxyvitamin D3 analogues with α-hydroxyalkyl substituents at C12

Synthesis and biological evaluation of novel 6-substituted analogs of 1α,25-dihydroxy-19-norvitamin D3

Synthesis of novel 19-norvitamin D3 analogs with unnatural triene system

Synthesis of (1α)‐1,25‐Dihydroxyvitamin D₃ with a β‐Positioned Seven‐Carbon Side Chain at C(12)

Design, Synthesis, Evaluation, and Structure of Vitamin D Analogues with Furan Side Chains

Design and synthesis of active vitamin D analogs

Stereoselective synthesis of C24-hydroxylated vitamin D3 analogs: A practical and expeditius route to calcipotriol

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