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Article ; Online: Tyrosine Conjugation Methods for Protein Labelling.

Alvarez Dorta, Dimitri / Deniaud, David / Mével, Mathieu / Gouin, Sébastien G

Chemistry (Weinheim an der Bergstrasse, Germany)

2020 Volume 26, Issue 63, Page(s) 14257–14269

Abstract: Over the last two decades, the development of chemical biology and the need for more defined protein conjugates have fostered active research on new bioconjugation techniques. In particular, a wide range of biorthogonal labelling strategies have been ... ...

Abstract	Over the last two decades, the development of chemical biology and the need for more defined protein conjugates have fostered active research on new bioconjugation techniques. In particular, a wide range of biorthogonal labelling strategies have been reported to functionalise the phenol side chain of tyrosines (Tyr). Tyr occur at medium frequency and are partially buried at the protein surface, offering interesting opportunities for site-selective labelling of the most reactive residues. Tyr-targeting has proved effective for designing a wide range of important biomolecules including antibody-drug conjugates, fluorescent or radioactive protein probes, glycovaccines, protein aggregates, and PEG conjugates. Innovative methods have also been reported for site-specific labelling with ligand-directed anchors and for the specific affinity capture of proteins. This review will present and discuss these promising alternatives to the conventional labelling of the nucleophilic lysine and cysteine residues.
MeSH term(s)	Cysteine/chemistry ; Immunoconjugates ; Lysine/chemistry ; Proteins/chemistry ; Staining and Labeling/methods ; Tyrosine
Chemical Substances	Immunoconjugates ; Proteins ; Tyrosine (42HK56048U) ; Lysine (K3Z4F929H6) ; Cysteine (K848JZ4886)
Language	English
Publishing date	2020-09-23
Publishing country	Germany
Document type	Journal Article ; Review
ZDB-ID	1478547-X
ISSN	1521-3765 ; 0947-6539
ISSN (online)	1521-3765
ISSN	0947-6539
DOI	10.1002/chem.202001992
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Article ; Online: Regio- and Stereoselectivity of the Norrish-Yang Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State Photochemistry of Two Polymorphs.

Alvarez-Dorta, Dimitri / León, Elisa I / Martín, Ángeles / Kennedy, Alan R / Pérez-Martín, Inés / Shankland, Kenneth / Suárez, Ernesto

The Journal of organic chemistry

2022 Volume 87, Issue 21, Page(s) 14940–14947

Abstract: As shown by X-ray crystallography, crystals of 3β-acetoxy-16,17-seco-17,20-dioxopregn-5-ene-16-nitrile are dimorphic. The regioselectivity of the Norrish-Yang type II photocyclization under visible light of this steroidal 1,2-diketone, which bears ... ...

Abstract	As shown by X-ray crystallography, crystals of 3β-acetoxy-16,17-seco-17,20-dioxopregn-5-ene-16-nitrile are dimorphic. The regioselectivity of the Norrish-Yang type II photocyclization under visible light of this steroidal 1,2-diketone, which bears primary, secondary, and tertiary nonequivalent abstractable γ-hydrogens, dramatically increases in the crystalline state of both polymorphs. X-ray crystallography and molecular mechanics calculations reveal crystal structure-solid state photochemistry relationships.
MeSH term(s)	Cyclization ; Photochemistry ; Ketones/chemistry ; Crystallography, X-Ray ; Light
Chemical Substances	Ketones
Language	English
Publishing date	2022-10-25
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.2c01855
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Article ; Online: Click-electrochemistry for the rapid labeling of virus, bacteria and cell surfaces.

Depienne, Sébastien / Bouzelha, Mohammed / Courtois, Emmanuelle / Pavageau, Karine / Lalys, Pierre-Alban / Marchand, Maia / Alvarez-Dorta, Dimitri / Nedellec, Steven / Marín-Fernández, Laura / Grandjean, Cyrille / Boujtita, Mohammed / Deniaud, David / Mével, Mathieu / Gouin, Sébastien G

Nature communications

2023 Volume 14, Issue 1, Page(s) 5122

Abstract: Methods for direct covalent ligation of microorganism surfaces remain poorly reported, and mostly based on metabolic engineering for bacteria and cells functionalization. While effective, a faster method avoiding the bio-incorporation step would be ... ...

Abstract	Methods for direct covalent ligation of microorganism surfaces remain poorly reported, and mostly based on metabolic engineering for bacteria and cells functionalization. While effective, a faster method avoiding the bio-incorporation step would be highly complementary. Here, we used N-methylluminol (NML), a fully tyrosine-selective protein anchoring group after one-electron oxidation, to label the surface of viruses, living bacteria and cells. The functionalization was performed electrochemically and in situ by applying an electric potential to aqueous buffered solutions of tagged NML containing the viruses, bacteria or cells. The broad applicability of the click-electrochemistry method was explored on recombinant adeno-associated viruses (rAAV2), Escherichia coli (Gram-) and Staphyloccocus epidermidis (Gram + ) bacterial strains, and HEK293 and HeLa eukaryotic cell lines. Surface electro-conjugation was achieved in minutes to yield functionalized rAAV2 that conserved both structural integrity and infectivity properties, and living bacteria and cell lines that were still alive and able to divide.
MeSH term(s)	Humans ; Electrochemistry ; HEK293 Cells ; Cell Membrane ; Bacteria ; Dependovirus/genetics ; Escherichia coli
Language	English
Publishing date	2023-08-23
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2553671-0
ISSN	2041-1723 ; 2041-1723
ISSN (online)	2041-1723
ISSN	2041-1723
DOI	10.1038/s41467-023-40534-0
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Article: Electrochemistry-coupled to liquid chromatography-mass spectrometry-density functional theory as a new tool to mimic the environmental degradation of selected phenylurea herbicides

Tonleu Temgoua, Ranil Clément / Bussy, Ugo / Alvarez-Dorta, Dimitri / Galland, Nicolas / Njanja, Evangeline / Hémez, Julie / Thobie-Gautier, Christine / Tonlé, Ignas Kenfack / Boujtita, Mohammed

Environmental science. 2021 Oct. 20, v. 23, no. 10

2021

Abstract: In vitro and in vivo experimental models, mainly based on cell cultures, animals, healthy humans and clinical trials, are useful approaches for identifying the main metabolic pathways. However, time, cost, and matrix complexity often hinder the success ... ...

Abstract	In vitro and in vivo experimental models, mainly based on cell cultures, animals, healthy humans and clinical trials, are useful approaches for identifying the main metabolic pathways. However, time, cost, and matrix complexity often hinder the success of these methods. In this study, we propose an alternative non-enzymatic method, using electrochemistry (EC) coupled to liquid chromatography (LC) – high resolution mass spectrometry (HRMS) – DFT theoretical calculations (EC/LC-MS/DFT) for the mimicry/simulation of the environmental degradation of phenylurea herbicides, and for the mechanism elucidation of this class of herbicides. Fenuron, monuron, isoproturon, linuron, monolinuron, metoxuron and chlortoluron were selected as relevant model compounds. The intended compounds are oxidized by EC, separated by LC and detected using electrospray ionization HRMS. The main oxidation products were hydroxylated compounds obtained by substitution and addition reactions. Unstable quinone imines/methines, rarely observed by conventional methods, have been identified during the oxidative degradation of phenylurea herbicides for the first time in this study. Some were directly observed and the others were trapped by glutathione GSH. Reactions such as hydrolytic substitutions (−Cl/+OH and −C₃H₇/+OH and −CH₃/+OH and −OCH₃/+OH), aromatic hydroxylation, alkyl carbon hydroxylation, dehydrochlorination/dehydromethylation/dehydromethoxylation and conjugation have been successfully mimicked. The obtained results, supported by theoretical calculations, are useful for simulating/understanding and predicting the oxidative degradation pathways of pesticides in the environment.
Keywords	carbon ; chlorotoluron ; electrochemistry ; electrospray ionization mass spectrometry ; environmental degradation ; fenuron ; glutathione ; hydroxylation ; imines ; isoproturon ; linuron ; liquid chromatography ; metoxuron ; monolinuron ; monuron ; oxidation ; quinones
Language	English
Dates of publication	2021-1020
Size	p. 1600-1611.
Publishing place	The Royal Society of Chemistry
Document type	Article
ZDB-ID	2703814-2
ISSN	2050-7895 ; 2050-7887
ISSN (online)	2050-7895
ISSN	2050-7887
DOI	10.1039/d1em00351h
Database	NAL-Catalogue (AGRICOLA)

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Article: Using electrochemistry coupled to high resolution mass spectrometry for the simulation of the environmental degradation of the recalcitrant fungicide carbendazim

Temgoua, Ranil C.T / Bussy, Ugo / Alvarez-Dorta, Dimitri / Galland, Nicolas / Hémez, Julie / Thobie-Gautier, Christine / Tonlé, Ignas Kenfack / Boujtita, Mohammed

Talanta. 2021 Jan. 01, v. 221

2021

Abstract: Currently, there is a growing interest in the study of environmental degradation pathways of organic contaminants such as pesticides, with the objective to better understand their potential risk for environmental systems and living organisms. In this ... ...

Abstract	Currently, there is a growing interest in the study of environmental degradation pathways of organic contaminants such as pesticides, with the objective to better understand their potential risk for environmental systems and living organisms. In this context, DFT (conceptual density functional theory) and predictive methods may systematically be used to simplify and accelerate the elucidation of environmental degradation. We report herein the electrochemical behavior/degradation of the carbendazim (CBZ) fungicide widely used to treat cereal and fruit crops. Oxidative degradation of CBZ was studied using an electrochemical flow-through cell directly coupled to a mass spectrometer for rapid identification of CBZ degradation products. The structural elucidation of CBZ oxidation products was based on retention time, accurate mass, isotopic distribution and fragmentation pattern by using LC-HRMS an LC-HRMS². The most important chemical reactions found to occur in the transformation of CBZ were hydrolysis and hydroxylation. EC-LC-MS and EC-MS analysis has made it possible to highlight the identification of degradation products of CBZ. In addition to previously known transformation products common to those observed during environmental degradation (monocarbomethoxyguanidine, benzimidazole-isocyanate, 2-aminobenzimidazole, hydroxy-2-aminobenzimidazole, hydroxycarbendazim, CBZ-CBZ dimer), two new degradation products were identified in this work: a quinone imine and a nitrenium ion. Electrochemistry mass spectrometry hyphenated techniques represent an accessible, rapid and reliable tool to elucidate the oxidative degradation of CBZ, including reactive degradation products and conjugates.
Keywords	carbendazim ; density functional theory ; electrochemistry ; environmental degradation ; fruit crops ; fungicides ; hydrolysis ; hydroxylation ; imines ; mass spectrometry ; oxidation ; quinones ; spectrometers
Language	English
Dates of publication	2021-0101
Publishing place	Elsevier B.V.
Document type	Article
ZDB-ID	1500969-5
ISSN	1873-3573 ; 0039-9140
ISSN (online)	1873-3573
ISSN	0039-9140
DOI	10.1016/j.talanta.2020.121448
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Article: Mannose-coupled AAV2: A second-generation AAV vector for increased retinal gene therapy efficiency.

Mével, Mathieu / Pichard, Virginie / Bouzelha, Mohammed / Alvarez-Dorta, Dimitri / Lalys, Pierre-Alban / Provost, Nathalie / Allais, Marine / Mendes, Alexandra / Landagaray, Elodie / Ducloyer, Jean-Baptiste / Toublanc, Estelle / Galy, Anne / Brument, Nicole / Lefevre, Gaëlle M / Gouin, Sébastien G / Isiegas, Carolina / Le Meur, Guylène / Cronin, Thérèse / Le Guiner, Caroline /

Weber, Michel / Moullier, Philippe / Ayuso, Eduard / Deniaud, David / Adjali, Oumeya

Molecular therapy. Methods & clinical development

2024 Volume 32, Issue 1, Page(s) 101187

Abstract: Inherited retinal diseases are a leading and untreatable cause of blindness and are therefore candidate diseases for gene therapy. Recombinant vectors derived from adeno-associated virus (rAAV) are currently the most promising vehicles ... ...

Abstract	Inherited retinal diseases are a leading and untreatable cause of blindness and are therefore candidate diseases for gene therapy. Recombinant vectors derived from adeno-associated virus (rAAV) are currently the most promising vehicles for
Language	English
Publishing date	2024-01-17
Publishing country	United States
Document type	Journal Article
ZDB-ID	2872938-9
ISSN	2329-0501 ; 2329-0501
ISSN (online)	2329-0501
ISSN	2329-0501
DOI	10.1016/j.omtm.2024.101187
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Article ; Online: Novel chemical tyrosine functionalization of adeno-associated virus improves gene transfer efficiency in liver and retina.

Leray, Aurélien / Lalys, Pierre-Alban / Varin, Juliette / Bouzelha, Mohammed / Bourdon, Audrey / Alvarez-Dorta, Dimitri / Pavageau, Karine / Depienne, Sébastien / Marchand, Maia / Mellet, Anthony / Demilly, Joanna / Ducloyer, Jean-Baptiste / Girard, Tiphaine / Fraysse, Bodvaël / Ledevin, Mireille / Guilbaud, Mickaël / Gouin, Sébastien G / Ayuso, Eduard / Adjali, Oumeya /

Larcher, Thibaut / Cronin, Thérèse / Le Guiner, Caroline / Deniaud, David / Mével, Mathieu

Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie

2024 Volume 171, Page(s) 116148

Abstract: Decades of biological and clinical research have led to important advances in recombinant adeno-associated viruses rAAV-based gene therapy gene therapy. However, several challenges must be overcome to fully exploit the potential of rAAV vectors. ... ...

Abstract	Decades of biological and clinical research have led to important advances in recombinant adeno-associated viruses rAAV-based gene therapy gene therapy. However, several challenges must be overcome to fully exploit the potential of rAAV vectors. Innovative approaches to modify viral genome and capsid elements have been used to overcome issues such as unwanted immune responses and off-targeting. While often successful, genetic modification of capsids can drastically reduce vector yield and often fails to produce vectors with properties that translate across different animal species, such as rodents, non-human primates, and humans. Here, we describe a chemical bioconjugation strategy to modify tyrosine residues on AAV capsids using specific ligands, thereby circumventing the need to genetically engineer the capsid sequence. Aromatic electrophilic substitution of the phenol ring of tyrosine residues on AAV capsids improved the in vivo transduction efficiency of rAAV2 vectors in both liver and retinal targets. This tyrosine bioconjugation strategy represents an innovative technology for the engineering of rAAV vectors for human gene therapy.
MeSH term(s)	Animals ; Dependovirus ; Genetic Therapy ; Transduction, Genetic ; Tyrosine/genetics ; Liver ; Retina ; Capsid Proteins/genetics ; Genetic Vectors ; Gene Transfer Techniques
Chemical Substances	Tyrosine (42HK56048U) ; Capsid Proteins
Language	English
Publishing date	2024-01-16
Publishing country	France
Document type	Journal Article
ZDB-ID	392415-4
ISSN	1950-6007 ; 0753-3322 ; 0300-0893
ISSN (online)	1950-6007
ISSN	0753-3322 ; 0300-0893
DOI	10.1016/j.biopha.2024.116148
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Article: Intravitreal air tamponade after AAV2 subretinal injection modifies retinal EGFP distribution.

Ducloyer, Jean-Baptiste / Pichard, Virginie / Mevel, Mathieu / Galy, Anne / Lefevre, Gaelle M / Brument, Nicole / Alvarez-Dorta, Dimitri / Deniaud, David / Mendes-Madeira, Alexandra / Libeau, Lyse / Le Guiner, Caroline / Cronin, Therese / Adjali, Oumeya / Weber, Michel / Le Meur, Guylène

Molecular therapy. Methods & clinical development

2023 Volume 28, Page(s) 387–393

Abstract: The subretinal injection protocol for the only approved retinal gene therapy (voretigene neparvovec-rzyl) includes air tamponade at the end of the procedure, but its effects on the subretinal bleb have not been described. In the present study, we ... ...

Abstract	The subretinal injection protocol for the only approved retinal gene therapy (voretigene neparvovec-rzyl) includes air tamponade at the end of the procedure, but its effects on the subretinal bleb have not been described. In the present study, we evaluated the distribution of enhanced green fluorescent protein (EGFP) after subretinal injection of AAV2 in non-human primates (NHP) without (group A = 3 eyes) or with (group B = 3 eyes) air tamponade. The retinal expression of EGFP was assessed 1 month after subretinal injection with
Language	English
Publishing date	2023-02-15
Publishing country	United States
Document type	Journal Article
ZDB-ID	2872938-9
ISSN	2329-0501 ; 2329-0501
ISSN (online)	2329-0501
ISSN	2329-0501
DOI	10.1016/j.omtm.2023.02.006
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Article ; Online: Using electrochemistry coupled to high resolution mass spectrometry for the simulation of the environmental degradation of the recalcitrant fungicide carbendazim.

Temgoua, Ranil C T / Bussy, Ugo / Alvarez-Dorta, Dimitri / Galland, Nicolas / Hémez, Julie / Thobie-Gautier, Christine / Tonlé, Ignas Kenfack / Boujtita, Mohammed

Talanta

2020 Volume 221, Page(s) 121448

Abstract	Currently, there is a growing interest in the study of environmental degradation pathways of organic contaminants such as pesticides, with the objective to better understand their potential risk for environmental systems and living organisms. In this context, DFT (conceptual density functional theory) and predictive methods may systematically be used to simplify and accelerate the elucidation of environmental degradation. We report herein the electrochemical behavior/degradation of the carbendazim (CBZ) fungicide widely used to treat cereal and fruit crops. Oxidative degradation of CBZ was studied using an electrochemical flow-through cell directly coupled to a mass spectrometer for rapid identification of CBZ degradation products. The structural elucidation of CBZ oxidation products was based on retention time, accurate mass, isotopic distribution and fragmentation pattern by using LC-HRMS an LC-HRMS
MeSH term(s)	Benzimidazoles ; Carbamates ; Electrochemistry ; Fungicides, Industrial ; Mass Spectrometry ; Oxidation-Reduction
Chemical Substances	Benzimidazoles ; Carbamates ; Fungicides, Industrial ; carbendazim (H75J14AA89)
Language	English
Publishing date	2020-07-31
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1500969-5
ISSN	1873-3573 ; 0039-9140
ISSN (online)	1873-3573
ISSN	0039-9140
DOI	10.1016/j.talanta.2020.121448
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Article: Luminol anchors improve the electrochemical-tyrosine-click labelling of proteins.

Depienne, Sébastien / Alvarez-Dorta, Dimitri / Croyal, Mikael / Temgoua, Ranil C T / Charlier, Cathy / Deniaud, David / Mével, Mathieu / Boujtita, Mohammed / Gouin, Sébastien G

Chemical science

2021 Volume 12, Issue 46, Page(s) 15374–15381

Abstract: New methods for chemo-selective modifications of peptides and native proteins are important in chemical biology and for the development of therapeutic conjugates. Less abundant and uncharged amino-acid residues are interesting targets to form less ... ...

Abstract	New methods for chemo-selective modifications of peptides and native proteins are important in chemical biology and for the development of therapeutic conjugates. Less abundant and uncharged amino-acid residues are interesting targets to form less heterogeneous conjugates and preserve biological functions. Phenylurazole (PhUr),
Language	English
Publishing date	2021-11-10
Publishing country	England
Document type	Journal Article
ZDB-ID	2559110-1
ISSN	2041-6539 ; 2041-6520
ISSN (online)	2041-6539
ISSN	2041-6520
DOI	10.1039/d1sc04809k
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