Vincent Guérineau

Institut de Chimie des Substances Naturelles

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David Touboul

Centre National de la Recherche Scientifique

Mohamed Haouas

Institut Lavoisier de Versailles

Sébastien Floquet

Institut Lavoisier de Versailles

Olivier Laprévôte

Centre National de la Recherche Scientifique

Diana Cebotari

Centre National de la Recherche Scientifique

Aurélian Gulea

Moldova State University

C.M. Thomas

Chimie ParisTech

Habib Nasri

University of Monastir

Jérôme Marrot

Centre National de la Recherche Scientifique

Régis Guillot

Université Paris-Saclay

Cooperative Institutions

Centre National de la Recherche Scientifique

378

Université Paris-Saclay

165

Université Paris-Sud

103

Sorbonne Université

Institut de Chimie des Substances Naturelles

Université Paris Cité

Inserm

Université Paris Sciences et Lettres

Commissariat à l'Énergie Atomique et aux Énergies Alternatives

Chimie ParisTech

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Cover Feature: Tandem Chiral Cu(II) Phosphate‐Catalyzed Deoxygenation of Nitrones/Enantioselective Povarov Reaction with Enecarbamates (Eur. J. Org. Chem. 31‐32/2019)

European Journal of Organic Chemistry (2019)

Coralie Gelis Guillaume Levitre Vincent Guérineau David Touboul Luc Neuville

The Cover Feature shows the tandem deoxygenation–Povarov reaction of nitrones with enecarbamates catalyzed by a chiral copper-diphosphate complex. Under the conditions, the catalyst is able to perform an “enlightening” rapid deoxygenation and subsequently assembles the resulting imine and the enecarbamates to form 4-amino-tetrahydroquinolines with high control of the three stereocenters. This complex is easily formed starting from readily available copper (II) and chiral phosphoric acid. More information can be found in the Communication by G. Masson et al.

Deoxygenation

Stereocenter

Tandem

Phosphoric acid

Imine

10.1002/ejoc.201901089

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Synthesis, Structures, and Solution Studies of a New Class of [Mo₂O₂S₂]-Based Thiosemicarbazone Coordination Complexes

ACS Omega (2022)

Arcadie Fuior Diana Cebotari Mohamed Haouas Jérôme Marrot Guillermo Mı́nguez Espallargas

This paper deals with the synthesis, structural studies, and behavior in solution of unprecedented coordination complexes built by the association of a panel of 14 representative thiosemicarbazone ligands with the cluster [Mo2O2S2]2+. These complexes have been thoroughly characterized both in the solid state and in solution by XRD and by NMR, respectively. In particular, HMBC 1H{15N} and 1H DOSY NMR experiments bring important elements for understanding the complexes' behavior in solution. These studies demonstrate that playing on the nature and the position of various substituents on the ligands strongly influences the coordination modes of the ligands as well as the numbers of isomers in solution, mainly 2 products for the majority of complexes and up to 5 for some of them.

Semicarbazone

Coordination complex

Coordination number

10.1021/acsomega.2c00705

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Citations (11)

Studies on the chemical synthesis of oligodeoxynucleotides containing the s⁵T(6-4)T photoproduct: side reactions derived from the methylsulfenyl thiol protection elucidated by MALDI mass spectrometry

Organic & Biomolecular Chemistry (2004)

Vincent Guérineau Sandra Karina Angulo Matus Guillaume van der Rest Olivier Laprévôte Pascale Clivio

Attempts to incorporate the phosphoramidite of the thymine-thymine (6-4) photoproduct C5 thiol analogue (s(5)T(6-4)T PP), whose sulfur atom was protected with the methylsulfenyl group, into oligodeoxynucleotides (ODNs), are reported. Using matrix-assisted laser desorption-ionisation mass spectrometry (MALDI-MS) coupled to enzymatic digestion, accurate mass measurements and tandem mass spectrometry experiments, we demonstrated that ODNs containing the (2-cyanoethylthio)(5)T(6-4)T PP were obtained. Supported by model reactions, these results were explained 1) by the incorporation, during oligonucleotide synthesis, of the sulfur deprotected phosphoramidite that arose from a Michaelis-Arbusov-type rearrangement, and 2) the Michael addition to the thiol of acrylonitrile released upon the cyanoethyl phosphotriester deprotection. To avoid the formation of the cyanoethyl adduct, the phosphotriester deprotection was carried out in the presence of a thiol in excess. This afforded the ODN containing the h(5)T(6-4)T PP.

Phosphoramidite

Thymine

Thiol

Fast atom bombardment

Reactive intermediate

10.1039/b314831a

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Citations (3)

A Novel Near‐IR Absorbing Ruthenium(II) Complex as Photosensitizer for Photodynamic Therapy and its Cetuximab Bioconjugates

ChemBioChem (2023)

Marta Martínez‐Alonso Albert Gandioso Chloé Thibaudeau Xue Qin Philippe Arnoux

Abstract A novel Ru(II) cyclometalated photosensitizer (PS), Ru‐NH 2 , for photodynamic therapy (PDT) of formula [Ru(appy)(bphen) 2 ]PF 6 (where appy=4‐amino‐2‐phenylpyridine and bphen=bathophenanthroline) and its cetuximab (CTX) bioconjugates, Ru‐Mal‐CTX and Ru‐BAA‐CTX (where Mal=maleimide and BAA=benzoylacrylic acid) were synthesised and characterised. The photophysical properties of Ru‐NH 2 revealed absorption maxima around 580 nm with an absorption up to 725 nm. The generation of singlet oxygen ( 1 O 2 ) upon light irradiation was confirmed with a 1 O 2 quantum yield of 0.19 in acetonitrile. Preliminary in vitro experiments revealed the Ru‐NH 2 was nontoxic in the dark in CT‐26 and SQ20B cell lines but showed outstanding phototoxicity when irradiated, reaching interesting phototoxicity indexes (PI) >370 at 670 nm, and >150 at 740 nm for CT‐26 cells and >50 with NIR light in SQ20B cells. The antibody CTX was successfully attached to the complexes in view of the selective delivery of the PS to cancer cells. Up to four ruthenium fragments were anchored to the antibody (Ab), as confirmed by MALDI‐TOF mass spectrometry. Nonetheless, the bioconjugates were not as photoactive as the Ru‐NH 2 complex.

Phototoxicity

Bioconjugation

10.1002/cbic.202300203

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Citations (11)

Enzyme Activation with a Synthetic Catalytic Co‐enzyme Intermediate: Nucleotide Methylation by Flavoenzymes

Angewandte Chemie International Edition (2017)

Charles Bou‐Nader David Cornu Vincent Guérineau Thibault Fogeron Marc Fontecave

Abstract To facilitate production of functional enzymes and to study their mechanisms, especially in the complex cases of coenzyme‐dependent systems, activation of an inactive apoenzyme preparation with a catalytically competent coenzyme intermediate is an attractive strategy. This is illustrated with the simple chemical synthesis of a flavin‐methylene iminium compound previously proposed as a key intermediate in the catalytic cycle of several important flavoenzymes involved in nucleic acid metabolism. Reconstitution of both flavin‐dependent RNA methyltransferase and thymidylate synthase apoproteins with this synthetic compound led to active enzymes for the C5‐uracil methylation within their respective transfer RNA and dUMP substrate. This strategy is expected to be of general application in enzymology.

10.1002/anie.201706219

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Citations (12)

tRNA 2’-O-methylation modulates small RNA silencing and life span in Drosophila

bioRxiv (Cold Spring Harbor Laboratory) (2019)

Margarita T. Angelova Dilyana G. Dimitrova Bruno da Silva Virginie Marchand Catherine Goyenvalle

Abstract 2’-O-methylation (Nm) represents one of the most common RNA modifications. Nm affects RNA structure and function with crucial roles in various RNA-mediated processes ranging from RNA silencing, translation, self versus non-self recognition to viral defense mechanisms. Here, we identify two novel Nm methyltransferases (Nm-MTases) in Drosophila melanogaster (CG7009 and CG5220) as functional orthologs of yeast TRM7 and human FTSJ1, respectively. Genetic knockout studies together with MALDI-TOF mass spectrometry and RiboMethSeq mapping revealed that CG7009 is responsible for methylating the wobble position in tRNA Phe , tRNA Trp and tRNA Leu , while subsequently, CG5220 methylates position C32 in the same tRNAs and targets also additional tRNAs. CG7009 or CG5220 mutant animals were viable and fertile but exhibited various phenotypes such as life span reduction, small RNA pathways dysfunction and increased sensitivity to RNA virus infections. Our results provide the first detailed characterization of two TRM7 family members in Drosophila and uncover a molecular link between enzymes catalysing Nm at specific tRNAs and small RNA-induced gene silencing pathways.

Small nuclear RNA

RNA methylation

Wobble base pair

RNA-induced transcriptional silencing

10.1101/699934

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Citations (1)

CCDC 2023648: Experimental Crystal Structure Determination

The Cambridge Structural Database (2021)

Mouhieddinne Guergueb Soumaya Nasri Jihed Brahmi Youssef O. Al‐Ghamdi Frédérique Loiseau

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.cc25xrzv

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Gas-Phase Reactivity of Acylphenols in Electrospray and Matrix-Assisted Laser Desorption Ionization Mass Spectrometry

European Journal of Mass Spectrometry (2009)

Isabelle Schmitz‐Afonso Vincent Guérineau Alessandra Maia‐Grondard Khalijah Awang Marc Litaudon

Acylphenols from Myristica crassa were identified based on liquid chromatography high-resolution mass spectrometry and liquid chromatography tandem mass spectrometry (MS/MS) experiments. Two types of compound were found in the extract of the plant: monomeric (malabaricone B and C) and dimeric compounds (C-C bonded biphenyl and C-C bonded phenyl-linear carbon chain). Evidence of formation of covalent dimeric ions during the electrospray ionization and matrix-assisted laser desorption ionization (MALDI) processes was established. [2M-3H](-) dimeric ions were detected on the mass spectra of each monomeric compound during high-performance liquid chromatography separation. The MS/MS spectra of those species were compared to the MS/MS spectra obtained for the dimeric compounds synthesized by the plant. Fragmentation pathways were studied for the two classes of dimer. The dimeric ions formed in the ion source were C-C bonded biphenyl compounds. Further evidence was obtained from MALDI experiments: increase in the extraction delay time leads to an increase of the dimeric ions relative abundance. Their formation is based on the high reactivity of phenols or phenolate ions which are easily oxidized yielding phenoxy radicals.

Fragmentation

Biphenyl

10.1255/ejms.969

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Citations (3)

Analysis of ancient Greco–Roman cosmetic materials using laser desorption ionization and electrospray ionization mass spectrometry

Analytical and Bioanalytical Chemistry (2008)

Elsa Van Elslande Vincent Guérineau Vincent Thirioux Ghislaine Richard Pascale Richardin

Desorption electrospray ionization

Ambient ionization

10.1007/s00216-008-1924-0

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Citations (40)

An extended dsRBD is required for post-transcriptional modification in human tRNAs

Nucleic Acids Research (2015)

Charles Bou‐Nader Ludovic Pecqueur Damien Brégeon Amina Kamah Vincent Guérineau

In tRNA, dihydrouridine is a conserved modified base generated by the post-transcriptional reduction of uridine. Formation of dihydrouridine 20, located in the D-loop, is catalyzed by dihydrouridine synthase 2 (Dus2). Human Dus2 (HsDus2) expression is upregulated in lung cancers, offering a growth advantage throughout its ability to interact with components of the translation apparatus and inhibit apoptosis. Here, we report the crystal structure of the individual domains of HsDus2 and their functional characterization. HsDus2 is organized into three major modules. The N-terminal catalytic domain contains the flavin cofactor involved in the reduction of uridine. The second module is the conserved α-helical domain known as the tRNA binding domain in HsDus2 homologues. It is connected via a flexible linker to an unusual extended version of a dsRNA binding domain (dsRBD). Enzymatic assays and yeast complementation showed that the catalytic domain binds selectively NADPH but cannot reduce uridine in the absence of the dsRBD. While in Dus enzymes from bacteria, plants and fungi, tRNA binding is essentially achieved by the α-helical domain, we showed that in HsDus2 this function is carried out by the dsRBD. This is the first reported case of a tRNA-modifying enzyme carrying a dsRBD used to bind tRNAs.

10.1093/nar/gkv989

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Citations (23)