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. 2012 Jul 23;51(30):7476-9.
doi: 10.1002/anie.201202122. Epub 2012 Jun 13.

Live-cell imaging of cyclopropene tags with fluorogenic tetrazine cycloadditions

Jun Yang  1 , Jolita Šečkutė, Christian M Cole, Neal K Devaraj
Affiliations

Live-cell imaging of cyclopropene tags with fluorogenic tetrazine cycloadditions

Jun Yang et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Figure 1
Figure 1
a) Inverse Diels–Alder reaction of cyclopropene with tetrazine results in loss of nitrogen gas and formation of a diazanorcaradiene. b) Examples of substituted cyclopropene handles that may be suitable dienophiles for tetrazine cycloaddition.
Figure 2
Figure 2
a) Synthesis of 2-methylcycloprop-2-enecarboxamide (2). DMF =dimethylformamide. b) Reaction of 2 with monoaryl tetrazine 3 leads to formation of diazanorcaradiene isomers (only one regioisomer is depicted). d) Synthesis of 2-methylcyclopropene carbamate (5). DIBAL-H =diisobutylaluminum hydride; CDI =carbonyldiimidazole; THF =tetrahydrofuran; TBAF =tetra-n-butylammonium fluoride. e) Reaction of 5 with monoaryl tetrazine 3 leads to formation of diazanorcaradiene isomers (only one regioisomer is depicted). c, f) Plots of tetrazine absorbance versus time during the reaction between 0.6 mM tetrazine 3 and 6 (blue), 8 (green), or 10 mM (red) of cyclopropene 2 (c) or cyclopropene 5 (f). Data was fit to a first-order exponential decay. Inset: kobs plotted against concentration with the slope taken as the second-order rate constant.
Figure 3
Figure 3
Reaction of fluorogenic tetrazine-BODIPY FL (6) with 5. a) Reaction scheme. b) Emission spectra of tetrazine-BODIPY FL before reaction with 5 (black) and after reaction (green).
Figure 4
Figure 4
a) Synthesis of cyclopropene phospholipid 7. b) Reaction of fluorogenic tetrazine-BODIPY FL with membrane-bound 7. The BODIPY chromophore is initially quenched by tetrazine with the fluorescence recovered after cycloaddition and formation of the coupling adduct. DOPE =1,2-dioleoyl-sn-glycero-3-phosphoethanol-amine. c) Live-cell confocal imaging of 7 distribution in SKBR3 cells with the fluorogenic probe tetrazine-BODIPY FL. Left: cells incubated (t =1 h) with 50 μM 7 followed by 10 μM tetrazine-BODIPY FL probe (t =1 h; green). Right: control in which SKBR3 cells were treated with 10 μM tetrazine-BODIPY FL (t =1 h; green). Cells were treated with 300 nM DAPI to visualize the nuclei (blue). Scale bar =20 μm.
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