2016
DOI: 10.1002/anie.201609607
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Vinyl Ether/Tetrazine Pair for the Traceless Release of Alcohols in Cells

Abstract: The cleavage of aprotecting group from aprotein or drug under bioorthogonal conditions enables accurate spatiotemporal control over protein or drug activity.Disclosed herein is that vinyl ethers serve as protecting groups for alcoholcontaining molecules and as reagents for bioorthogonal bondcleavage reactions.Avinyl ether moiety was installed in arange of molecules,including amino acids,amonosaccharide,afluorophore,a nd an analogue of the cytotoxic drug duocarmycin. Tetrazine-mediated decaging proceeded under … Show more

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Cited by 113 publications
(106 citation statements)
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“…The broad applicability of this reaction on other chemotypes, including the protected amino acids serine and tyrosine, an 1,6-anhydro sugar, and a fluorophore, expand the scope and potential of this reaction for applications on proteins and glycans. 352 Furthermore, based on the vinyl ether decaging chemistry, a tetrazine responsive self-immolative cleavable linker was developed by Bradley et al to achieve molecular triggered drug delivery (Fig. 56a).…”
Section: Vinyl-ether For Function Reactivation By Iedda Ligationmentioning
confidence: 99%
“…The broad applicability of this reaction on other chemotypes, including the protected amino acids serine and tyrosine, an 1,6-anhydro sugar, and a fluorophore, expand the scope and potential of this reaction for applications on proteins and glycans. 352 Furthermore, based on the vinyl ether decaging chemistry, a tetrazine responsive self-immolative cleavable linker was developed by Bradley et al to achieve molecular triggered drug delivery (Fig. 56a).…”
Section: Vinyl-ether For Function Reactivation By Iedda Ligationmentioning
confidence: 99%
“…5,6 Dissociative bioorthogonal chemistry has been applied to the on-demand dissolution of polymers and micelles, 7-9 site-specic actuation of prodrugs, [10][11][12] and control of enzyme activity in vivo. [13][14][15] Although a growing number of "click-to-release" reactions [16][17][18][19][20][21][22][23] has provided a solid foundation for applications in the life sciences, extending the reaction scope will be necessary to access the full range of capabilities. Moreover, there is a need for chemistry to allow for the controlled and simultaneous release of more than one molecule.…”
Section: Introductionmentioning
confidence: 99%
“…[20] After Devaraj reported vinyl ether as as uitable bioorthogonal dienophile for DA INV , [21] our group and that of Bernardes independently reported tetrazine-responsive prodrug systems that use vinyl ether masking of phenols( Scheme 1B). [22,23] Vinyl ethers are rapidly incorporated onto phenols by readily scalable methods and are bench stable andb iocompatible, thus overcoming someo ft he disadvantages of the previouslyr eported TCO moiety.H owever,t heir rates in the DA INV reaction are several orders of magnitude lower than those of TCO (k 2 = 7.2 10 À4 m À1 s À1 ), [21] although in vitro resultsh aved emonstrated their high stabilities and biocompatibility.A ll this leads to an efficient prodrug system,w hile the water acceleration effect remains substantial. [5] Thus, linking doxorubucin through a vinyl ether-based, self-immolative( safety-catch) linker to a polymer backbone allowed generation of an amphiphilic block-copolymer (DOX-b-PEG) and formation of tetrazine-responsivep olymericn anoparticles (Scheme 2).…”
Section: Tetrazines As Activators For Prodrugsmentioning
confidence: 99%
“…Bernardes modified ad uorcamycin-like drug by masking a phenol with av inyl ether;t his resulted in an increased IC 50 ,a s demonstrated in A549 cells (from 5t o3 6mm). [23] In cytotoxicity assays,i tw as shown that cotreatmento ft he vinyl ether-based prodrug and tetrazine switched on cytotoxicity by regenerating the parent drug throughaW insteins pirocyclisation once the phenol had been decaged. In addition, Bernardes showed that tetrazines could not only tracelessly removet he vinyl ether from phenols, but also from ar ange of hydroxy moieties including those of serine.…”
Section: Tetrazines As Activators For Prodrugsmentioning
confidence: 99%