Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs

Zhuzhou Shao; Wei Liu; Huimin Tao; Fang Liu; Ruxin Zeng; Pier Alexandre Champagne; Yang Cao; K. N. Houk; Yong Liang

doi:10.1039/c8cc08533a

Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs

Zhuzhou Shao, Wei Liu, Huimin Tao, Fang Liu, Ruxin Zeng, Pier Alexandre Champagne, Yang Cao, K. N. Houk, Yong Liang

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

42 Scopus citations

Abstract

Sulfonamide derivatives have been used in pharmaceutics for decades. Here we report a new approach to release sulfonamides efficiently using a bioorthogonal reaction of sulfonyl sydnonimines and dibenzoazacyclooctyne (DIBAC). The second-order rate constant of the cycloaddition reaction can be up to 0.62 M^-1 s^-1, and the reactants are highly stable under physiological conditions. Most significantly, we also discovered the mutual orthogonality between the sydnonimine-DIBAC and benzonorbornadiene-tetrazine cycloaddition pairs, which can be used for selective and simultaneous liberation of sulfonamide and primary amine drugs.

Original language	English (US)
Pages (from-to)	14089-14092
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	100
DOIs	https://doi.org/10.1039/c8cc08533a
State	Published - 2018
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs",

abstract = "Sulfonamide derivatives have been used in pharmaceutics for decades. Here we report a new approach to release sulfonamides efficiently using a bioorthogonal reaction of sulfonyl sydnonimines and dibenzoazacyclooctyne (DIBAC). The second-order rate constant of the cycloaddition reaction can be up to 0.62 M-1 s-1, and the reactants are highly stable under physiological conditions. Most significantly, we also discovered the mutual orthogonality between the sydnonimine-DIBAC and benzonorbornadiene-tetrazine cycloaddition pairs, which can be used for selective and simultaneous liberation of sulfonamide and primary amine drugs.",

author = "Zhuzhou Shao and Wei Liu and Huimin Tao and Fang Liu and Ruxin Zeng and Champagne, {Pier Alexandre} and Yang Cao and Houk, {K. N.} and Yong Liang",

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8cc08533a",

language = "English (US)",

volume = "54",

pages = "14089--14092",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs

AU - Shao, Zhuzhou

AU - Liu, Wei

AU - Tao, Huimin

AU - Liu, Fang

AU - Zeng, Ruxin

AU - Champagne, Pier Alexandre

AU - Cao, Yang

AU - Houk, K. N.

AU - Liang, Yong

PY - 2018

Y1 - 2018

N2 - Sulfonamide derivatives have been used in pharmaceutics for decades. Here we report a new approach to release sulfonamides efficiently using a bioorthogonal reaction of sulfonyl sydnonimines and dibenzoazacyclooctyne (DIBAC). The second-order rate constant of the cycloaddition reaction can be up to 0.62 M-1 s-1, and the reactants are highly stable under physiological conditions. Most significantly, we also discovered the mutual orthogonality between the sydnonimine-DIBAC and benzonorbornadiene-tetrazine cycloaddition pairs, which can be used for selective and simultaneous liberation of sulfonamide and primary amine drugs.

AB - Sulfonamide derivatives have been used in pharmaceutics for decades. Here we report a new approach to release sulfonamides efficiently using a bioorthogonal reaction of sulfonyl sydnonimines and dibenzoazacyclooctyne (DIBAC). The second-order rate constant of the cycloaddition reaction can be up to 0.62 M-1 s-1, and the reactants are highly stable under physiological conditions. Most significantly, we also discovered the mutual orthogonality between the sydnonimine-DIBAC and benzonorbornadiene-tetrazine cycloaddition pairs, which can be used for selective and simultaneous liberation of sulfonamide and primary amine drugs.

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JO - Chemical Communications

JF - Chemical Communications

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ER -

Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs

Abstract

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