Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells

Jan Dommerholt; Samuel Schmidt; Rinske Temming; L.J.A. Hendriks; F.P.J.T. Rutjes; J.C.M. Hest, van; D.J. Lefeber; Peter Friedl; F.L. van Delft

doi:10.1002/anie.201003761

Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells

Jan Dommerholt, Samuel Schmidt, Rinske Temming, L.J.A. Hendriks, F.P.J.T. Rutjes, J.C.M. Hest, van, D.J. Lefeber, Peter Friedl, F.L. van Delft

Research output: Contribution to journal › Article › Academic › peer-review

508 Citations (Scopus)

Abstract

I can see clearly now: Bicyclo[6.1.0]non-4-yne, an easily prepared, symmetrical cycloalkyne, displays excellent reaction kinetics in strain-promoted cycloaddition reactions with azides and nitrones (see scheme). Highly specific protein modifications are demonstrated in vitro and subcellular-resolved imaging of glycan expression was achieved in metastatic melanoma cells during invasive migration into three-dimensional collagen lattices.

Original language	English
Pages (from-to)	9422-9425
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	49
DOIs	https://doi.org/10.1002/anie.201003761
Publication status	Published - 3 Dec 2010
Externally published	Yes

Keywords

cycloadditions
cycloalkynes
imaging
kinetics
protein modification

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10.1002/anie.201003761

Cite this

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title = "Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells",

abstract = "I can see clearly now: Bicyclo[6.1.0]non-4-yne, an easily prepared, symmetrical cycloalkyne, displays excellent reaction kinetics in strain-promoted cycloaddition reactions with azides and nitrones (see scheme). Highly specific protein modifications are demonstrated in vitro and subcellular-resolved imaging of glycan expression was achieved in metastatic melanoma cells during invasive migration into three-dimensional collagen lattices.",

keywords = "cycloadditions, cycloalkynes, imaging, kinetics, protein modification",

author = "Jan Dommerholt and Samuel Schmidt and Rinske Temming and L.J.A. Hendriks and F.P.J.T. Rutjes and {Hest, van}, J.C.M. and D.J. Lefeber and Peter Friedl and {van Delft}, F.L.",

year = "2010",

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Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells. / Dommerholt, Jan; Schmidt, Samuel; Temming, Rinske; Hendriks, L.J.A.; Rutjes, F.P.J.T.; Hest, van, J.C.M.; Lefeber, D.J.; Friedl, Peter; van Delft, F.L.

In: Angewandte Chemie - International Edition, Vol. 49, No. 49, 03.12.2010, p. 9422-9425.

Research output: Contribution to journal › Article › Academic › peer-review

TY - JOUR

T1 - Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells

AU - Dommerholt, Jan

AU - Schmidt, Samuel

AU - Temming, Rinske

AU - Hendriks, L.J.A.

AU - Rutjes, F.P.J.T.

AU - Hest, van, J.C.M.

AU - Lefeber, D.J.

AU - Friedl, Peter

AU - van Delft, F.L.

PY - 2010/12/3

Y1 - 2010/12/3

N2 - I can see clearly now: Bicyclo[6.1.0]non-4-yne, an easily prepared, symmetrical cycloalkyne, displays excellent reaction kinetics in strain-promoted cycloaddition reactions with azides and nitrones (see scheme). Highly specific protein modifications are demonstrated in vitro and subcellular-resolved imaging of glycan expression was achieved in metastatic melanoma cells during invasive migration into three-dimensional collagen lattices.

AB - I can see clearly now: Bicyclo[6.1.0]non-4-yne, an easily prepared, symmetrical cycloalkyne, displays excellent reaction kinetics in strain-promoted cycloaddition reactions with azides and nitrones (see scheme). Highly specific protein modifications are demonstrated in vitro and subcellular-resolved imaging of glycan expression was achieved in metastatic melanoma cells during invasive migration into three-dimensional collagen lattices.

KW - cycloadditions

KW - cycloalkynes

KW - imaging

KW - kinetics

KW - protein modification

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DO - 10.1002/anie.201003761

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 0570-0833

IS - 49

ER -

Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells

Abstract

Keywords

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