共 41 条
Unraveling Tetrazine-Triggered Bioorthogonal Elimination Enables Chemical Tools for Ultrafast Release and Universal Cleavage
被引:135
作者:

Carlson, Jonathan C. T.
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Mikula, Hannes
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
Vienna Univ Technol TU Wien, Inst Appl Synthet Chem, A-1040 Vienna, Austria Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Weissleder, Ralph
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
Harvard Med Sch, Dept Syst Biol, Boston, MA 02115 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
机构:
[1] Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
[2] Vienna Univ Technol TU Wien, Inst Appl Synthet Chem, A-1040 Vienna, Austria
[3] Harvard Med Sch, Dept Syst Biol, Boston, MA 02115 USA
基金:
美国国家卫生研究院;
奥地利科学基金会;
关键词:
DIELS-ALDER REACTION;
FREE CLICK CHEMISTRY;
TRANS-CYCLOOCTENE;
DERIVATIVES;
ACTIVATION;
MECHANISM;
STRATEGY;
DRUG;
D O I:
10.1021/jacs.7b11217
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
Recent developments in bond cleavage reactions have expanded the scope of bioorthogonal chemistry beyond click ligation and enabled new strategies for probe activation and therapeutic delivery. These applications, however, remain in their infancy, with further innovations needed to achieve the efficiency required for versatile and broadly useful tools in vivo. Among these chemistries, the tetrazine/trans-cyclooctene click-to-release reaction has exemplary kinetics and adaptability but achieves only partial release and is incompletely understood, which has limited its application. Investigating the mechanistic features of this reaction's performance, we discovered profound pH sensitivity, exploited it with acid-functionalized tetrazines that both enhance and markedly accelerate release, and ultimately uncovered an unexpected dead-end isomer as the reason for poor release. Implementing facile methods to prevent formation of this dead end, we have achieved exceptional efficiency, with essentially complete release across the full scope of physiologic pH, potentiating drug-delivery strategies and expanding the dynamic range of bioorthogonal on/off control.
引用
收藏
页码:3603 / 3612
页数:10
相关论文
共 41 条
[1]
A fast click-slow release strategy towards the HPLC-free synthesis of RNA
[J].
Agustin, E.
;
Okai, P. N. Asare
;
Khan, I.
;
Miller, M. R.
;
Wang, R.
;
Sheng, J.
;
Royzen, M.
.
CHEMICAL COMMUNICATIONS,
2016, 52 (07)
:1405-1408

Agustin, E.
论文数: 0 引用数: 0
h-index: 0
机构:
SUNY Albany, Dept Chem, Albany, NY 12222 USA SUNY Albany, Dept Chem, Albany, NY 12222 USA

Okai, P. N. Asare
论文数: 0 引用数: 0
h-index: 0
机构:
SUNY Albany, Dept Chem, Albany, NY 12222 USA SUNY Albany, Dept Chem, Albany, NY 12222 USA

Khan, I.
论文数: 0 引用数: 0
h-index: 0
机构:
SUNY Albany, Dept Chem, Albany, NY 12222 USA SUNY Albany, Dept Chem, Albany, NY 12222 USA

Miller, M. R.
论文数: 0 引用数: 0
h-index: 0
机构:
SUNY Albany, Dept Chem, Albany, NY 12222 USA SUNY Albany, Dept Chem, Albany, NY 12222 USA

Wang, R.
论文数: 0 引用数: 0
h-index: 0
机构:
SUNY Albany, Dept Chem, Albany, NY 12222 USA SUNY Albany, Dept Chem, Albany, NY 12222 USA

Sheng, J.
论文数: 0 引用数: 0
h-index: 0
机构:
SUNY Albany, Dept Chem, Albany, NY 12222 USA SUNY Albany, Dept Chem, Albany, NY 12222 USA

Royzen, M.
论文数: 0 引用数: 0
h-index: 0
机构:
SUNY Albany, Dept Chem, Albany, NY 12222 USA SUNY Albany, Dept Chem, Albany, NY 12222 USA
[2]
Copper-free click chemistry for dynamic in vivo imaging
[J].
Baskin, Jeremy M.
;
Prescher, Jennifer A.
;
Laughlin, Scott T.
;
Agard, Nicholas J.
;
Chang, Pamela V.
;
Miller, Isaac A.
;
Lo, Anderson
;
Codelli, Julian A.
;
Bertozzi, Carolyn R.
.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,
2007, 104 (43)
:16793-16797

Baskin, Jeremy M.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

Prescher, Jennifer A.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

Laughlin, Scott T.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

Agard, Nicholas J.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

Chang, Pamela V.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

Miller, Isaac A.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

Lo, Anderson
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

Codelli, Julian A.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

Bertozzi, Carolyn R.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[3]
Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity
[J].
Blackman, Melissa L.
;
Royzen, Maksim
;
Fox, Joseph M.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2008, 130 (41)
:13518-+

Blackman, Melissa L.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Delaware, Dept Chem & Biochem, Brown Labs, Newark, DE 19716 USA Univ Delaware, Dept Chem & Biochem, Brown Labs, Newark, DE 19716 USA

Royzen, Maksim
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Delaware, Dept Chem & Biochem, Brown Labs, Newark, DE 19716 USA Univ Delaware, Dept Chem & Biochem, Brown Labs, Newark, DE 19716 USA

Fox, Joseph M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Delaware, Dept Chem & Biochem, Brown Labs, Newark, DE 19716 USA Univ Delaware, Dept Chem & Biochem, Brown Labs, Newark, DE 19716 USA
[4]
Strain-Promoted Copper-Free "Click" Chemistry for 18F Radiolabeling of Bombesin
[J].
Campbell-Verduyn, Lachlan S.
;
Mirfeizi, Leila
;
Schoonen, Anne K.
;
Dierckx, Rudi A.
;
Elsinga, Philip H.
;
Feringa, Ben L.
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2011, 50 (47)
:11117-11120

Campbell-Verduyn, Lachlan S.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands Univ Groningen, Dept Nucl Med & Mol Imaging, Univ Med Ctr Groningen, NL-9713 GZ Groningen, Netherlands

Mirfeizi, Leila
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Dept Nucl Med & Mol Imaging, Univ Med Ctr Groningen, NL-9713 GZ Groningen, Netherlands Univ Groningen, Dept Nucl Med & Mol Imaging, Univ Med Ctr Groningen, NL-9713 GZ Groningen, Netherlands

Schoonen, Anne K.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands Univ Groningen, Dept Nucl Med & Mol Imaging, Univ Med Ctr Groningen, NL-9713 GZ Groningen, Netherlands

Dierckx, Rudi A.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Dept Nucl Med & Mol Imaging, Univ Med Ctr Groningen, NL-9713 GZ Groningen, Netherlands Univ Groningen, Dept Nucl Med & Mol Imaging, Univ Med Ctr Groningen, NL-9713 GZ Groningen, Netherlands

Elsinga, Philip H.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Dept Nucl Med & Mol Imaging, Univ Med Ctr Groningen, NL-9713 GZ Groningen, Netherlands Univ Groningen, Dept Nucl Med & Mol Imaging, Univ Med Ctr Groningen, NL-9713 GZ Groningen, Netherlands

Feringa, Ben L.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands Univ Groningen, Dept Nucl Med & Mol Imaging, Univ Med Ctr Groningen, NL-9713 GZ Groningen, Netherlands
[5]
BODIPY-Tetrazine Derivatives as Superbright Bioorthogonal Turn-on Probes
[J].
Carlson, Jonathan C. T.
;
Meimetis, Labros G.
;
Hilderbrand, Scott A.
;
Weissleder, Ralph
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2013, 52 (27)
:6917-6920

Carlson, Jonathan C. T.
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Meimetis, Labros G.
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Hilderbrand, Scott A.
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Weissleder, Ralph
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
Harvard Univ, Sch Med, Boston, MA 02115 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
[6]
Monoalkoxy BODIPYs-A Fluorophore Class for Bioimaging
[J].
Courtis, Alexandra M.
;
Santos, Sofia A.
;
Guan, Yinghua
;
Hendricks, J. Adam
;
Ghosh, Balaram
;
Szantai-Kis, D. Miklos
;
Reis, Surya A.
;
Shah, Jagesh V.
;
Mazitschek, Ralph
.
BIOCONJUGATE CHEMISTRY,
2014, 25 (06)
:1043-1051

Courtis, Alexandra M.
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Santos, Sofia A.
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
Massachusetts Gen Hosp, Ctr Human Genet Res, Boston, MA 02114 USA
Univ Lisbon, Fac Farm, Inst Invest Med iMed ULisboa, P-1640003 Lisbon, Portugal Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Guan, Yinghua
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Sch Med, Dept Syst Biol, Boston, MA 02115 USA
Brigham & Womens Hosp, Div Renal, Boston, MA 02115 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Hendricks, J. Adam
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Ghosh, Balaram
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
Massachusetts Gen Hosp, Ctr Human Genet Res, Boston, MA 02114 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Szantai-Kis, D. Miklos
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Reis, Surya A.
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Human Genet Res, Boston, MA 02114 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Shah, Jagesh V.
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Sch Med, Dept Syst Biol, Boston, MA 02115 USA
Brigham & Womens Hosp, Div Renal, Boston, MA 02115 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Mazitschek, Ralph
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
Broad Inst Harvard & MIT, Cambridge, MA 02142 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
[7]
Design, Synthesis, and Evaluation of a Low-Molecular-Weight 11C-Labeled Tetrazine for Pretargeted PET Imaging Applying Bioorthogonal in Vivo Click Chemistry
[J].
Denk, Christoph
;
Svatunek, Dennis
;
Mairinger, Severin
;
Stanek, Johann
;
Filip, Thomas
;
Matscheko, Dominik
;
Kuntner, Claudia
;
Wanek, Thomas
;
Mikula, Hannes
.
BIOCONJUGATE CHEMISTRY,
2016, 27 (07)
:1707-1712

Denk, Christoph
论文数: 0 引用数: 0
h-index: 0
机构:
Vienna Univ Technol, Inst Appl Synthet Chem, A-1040 Vienna, Austria Vienna Univ Technol, Inst Appl Synthet Chem, A-1040 Vienna, Austria

Svatunek, Dennis
论文数: 0 引用数: 0
h-index: 0
机构:
Vienna Univ Technol, Inst Appl Synthet Chem, A-1040 Vienna, Austria Vienna Univ Technol, Inst Appl Synthet Chem, A-1040 Vienna, Austria

论文数: 引用数:
h-index:
机构:

Stanek, Johann
论文数: 0 引用数: 0
h-index: 0
机构:
Austrian Inst Technol, Hlth & Environm Dept, Biomed Syst, A-2411 Seibersdorf, Austria Vienna Univ Technol, Inst Appl Synthet Chem, A-1040 Vienna, Austria

Filip, Thomas
论文数: 0 引用数: 0
h-index: 0
机构:
Austrian Inst Technol, Hlth & Environm Dept, Biomed Syst, A-2411 Seibersdorf, Austria Vienna Univ Technol, Inst Appl Synthet Chem, A-1040 Vienna, Austria

Matscheko, Dominik
论文数: 0 引用数: 0
h-index: 0
机构:
Vienna Univ Technol, Inst Appl Synthet Chem, A-1040 Vienna, Austria Vienna Univ Technol, Inst Appl Synthet Chem, A-1040 Vienna, Austria

Kuntner, Claudia
论文数: 0 引用数: 0
h-index: 0
机构:
Austrian Inst Technol, Hlth & Environm Dept, Biomed Syst, A-2411 Seibersdorf, Austria Vienna Univ Technol, Inst Appl Synthet Chem, A-1040 Vienna, Austria

论文数: 引用数:
h-index:
机构:

Mikula, Hannes
论文数: 0 引用数: 0
h-index: 0
机构:
Vienna Univ Technol, Inst Appl Synthet Chem, A-1040 Vienna, Austria Vienna Univ Technol, Inst Appl Synthet Chem, A-1040 Vienna, Austria
[8]
Biomedical Applications of Tetrazine Cycloadditions
[J].
Devaraj, Neal K.
;
Weissleder, Ralph
.
ACCOUNTS OF CHEMICAL RESEARCH,
2011, 44 (09)
:816-827

Devaraj, Neal K.
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Weissleder, Ralph
论文数: 0 引用数: 0
h-index: 0
机构:
Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
Harvard Univ, Sch Med, Dept Syst Biol, Boston, MA 02115 USA Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
[9]
Tetrazine-Based Cycloadditions: Application to Pretargeted Live Cell Imaging
[J].
Devaraj, Neal K.
;
Weissleder, Ralph
;
Hilderbrand, Scott A.
.
BIOCONJUGATE CHEMISTRY,
2008, 19 (12)
:2297-2299

Devaraj, Neal K.
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Sch Med, Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA Harvard Univ, Sch Med, Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Weissleder, Ralph
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Sch Med, Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
Harvard Univ, Sch Med, Massachusetts Gen Hosp, Ctr Mol Imaging Res, Boston, MA 02129 USA Harvard Univ, Sch Med, Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA

Hilderbrand, Scott A.
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Sch Med, Massachusetts Gen Hosp, Ctr Mol Imaging Res, Boston, MA 02129 USA Harvard Univ, Sch Med, Massachusetts Gen Hosp, Ctr Syst Biol, Boston, MA 02114 USA
[10]
Room temperature phosphorescence of the 1-bromonaphthalene/β-cyclodextrin inclusion complex: comparison between right-angle and front-face illumination geometry
[J].
Emilia Pacheco, Maria
;
Bruzzone, Liliana
.
ANALYTICAL METHODS,
2013, 5 (24)
:6908-6910

Emilia Pacheco, Maria
论文数: 0 引用数: 0
h-index: 0
机构:
UNLP, Fac Ciencias Exactas, Dept Quim, Div Quim Analit, RA-1900 La Plata, Buenos Aires, Argentina UNLP, Fac Ciencias Exactas, Dept Quim, Div Quim Analit, RA-1900 La Plata, Buenos Aires, Argentina

Bruzzone, Liliana
论文数: 0 引用数: 0
h-index: 0
机构:
UNLP, Fac Ciencias Exactas, Dept Quim, Div Quim Analit, RA-1900 La Plata, Buenos Aires, Argentina UNLP, Fac Ciencias Exactas, Dept Quim, Div Quim Analit, RA-1900 La Plata, Buenos Aires, Argentina