Synthesis of [18F]4-(4-fluorophenyl)-1,2,4-triazole-3,5-dione: an agent for specific radiolabelling of tyrosine

Flagothier, Jessica; Warnier, Corentin; Dammicco, Sylvestre; Christian, Lemaire; Luxen, André

doi:10.1039/c3ra44666b

Cited by 19 publications

(16 citation statements)

References 28 publications

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“…Similarly, a three component Mannich reaction between tyrosine and imines formed from aldehydes and electron rich anilines has also been described (entry 7) (Joshi et al, 2004), although it is relatively slow and requires a large excess of regents (McFarland et al, 2008; Romanini and Francis, 2007). The aqueous ene-type reaction of tyrosine with cyclic diazodicarboxamides seems more generally promising (Ban et al, 2010; Ban et al, 2013; Jessica et al, 2013), which reacts selectively at the o-position of the phenol side chain, and was shown to be thermally and hydrolytically stable (entry 8).…”

Section: B Bioorthogonal Conjugation Strategies and Applicationsmentioning

confidence: 99%

Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation

McKay

Finn

2014

Chemistry & Biology

670

555

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The selective chemical modification of biological molecules drives a good portion of modern drug development and fundamental biological research. While a few early examples of reactions that engage amine and thiol groups on proteins helped establish the value of such processes, the development of reactions that avoid most biological molecules so as to achieve selectivity in desired bond-forming events has revolutionized the field. We provide an update on recent developments in bioorthogonal chemistry that highlights key advances in reaction rates, biocompatibility, and applications. While not exhaustive, we hope this summary allows the reader to appreciate the rich continuing development of good chemistry that operates in the biological setting.

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Section: B Bioorthogonal Conjugation Strategies and Applicationsmentioning

confidence: 99%

Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation

McKay

Finn

2014

Chemistry & Biology

670

555

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“…The synthetic strategy involved the alkynylation of tyrosine units of the nontoxic mutant diphtheria toxin CRM197, a protein carrier in many licensed vaccines, via 1,2,4‐triazoline‐3,5‐dione (TAD) chemistry followed by the attachment of glucan chains via azide‐alkyne click chemistry. TAD functionalization was also recently used to radiolabel tyrosine of natural proteins using [18F]4‐(4‐fluorophenyl)‐1,2,4‐triazole‐3,5‐dione . In another example, Bauer et al prepared bifunctional TAD linkers and showed protein–DNA conjugation …”

Section: Introductionmentioning

confidence: 99%

“…TAD functionalization was also recently used to radiolabel tyrosine of natural proteins using [18F]4-(4-fluorophenyl)-1,2,4-triazole-3,5-dione. [25] In another example, Bauer et al prepared bifunctional TAD linkers and showed protein-DNA conjugation. [26] While TAD-mediated conjugation of tyrosine in natural proteins is feasible, the applicability of this chemistry in synthetic polymers was explored by Stadler and Kuhrau [27] and more recently by DuPrez and co-workers.…”

Section: Introductionmentioning

confidence: 99%

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Hanay

Ritzen

Brougham

et al. 2017

Macromolecular Bioscience

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Highly efficient functionalization and cross-linking of polypeptides is achieved via tyrosine-triazolinedione (TAD) conjugation chemistry. The feasibility of the reaction is demonstrated by the reaction of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) with tyrosine containing block copolymer poly(ethylene glycol)-Tyr as well as a statistical copolymer of tyrosine and lysine (poly(Lys -st-Tyr )) prepared form N-carboxyanhydride polymerization. Selective reaction of PTAD with the tyrosine units is obtained and verified by size exclusion chromatography and NMR spectroscopy. Moreover, two monofunctional and two difunctional TAD molecules are synthesized. It is found that their stability in the aqueous reaction media significantly varied. Under optimized reaction conditions selective functionalization and cross-linking, yielding polypeptide hydrogels, can be achieved. TAD-mediated conjugation can offer an interesting addition in the toolbox of selective (click-like) polypeptide conjugation methodologies as it does not require functional non-natural amino acids.

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“…Recently, first attempts have been undertaken to introduce PTAD derivatives onto radiochemistry using either aliphatic tosylate precursor which gave poor results or by multi-step synthesis, starting with nucliophilic aromatic substitution of nitrobenzene compound with leaving group on para-position (Jessica et al, 2013). Here, we describe an innovative simple procedure by avoiding time consuming azeotropic drying to obtain a radiofluorinated PTAD using sulfonyl chloride precursor.…”

Section: Resultsmentioning

confidence: 98%