Visible light activation of nucleophilic thiol-x addition via thioether bimane photocleavage for polymer cross-linking

Vinh X. Truong; Fanyi Li; John S. Forsythe

doi:10.1021/acs.biomac.8b01153

Visible light activation of nucleophilic thiol-x addition via thioether bimane photocleavage for polymer cross-linking

Vinh X. Truong, Fanyi Li, John S. Forsythe

Materials Science & Engineering

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

23 Citations (Scopus)

Abstract

On-demand photo-uncaging of reactive thiols have been employed in engineering biomaterial scaffolds for regulation of cellular activities. A drawback of the current photo-uncaging chemistry is the utilization of high energy UV light or 2-photon laser light, which may be harmful to cells and cause undesired side reactions within the biological environment. We introduce an effective approach for the caging of thiol using monobromobimane, which can be removed under irradiation of light at λ = 420 nm and in the presence of electrophiles, such as acrylate, propiolate and maleimide, for trapping of the newly release thiol. This chemical approach can be used in visible light-induced polymer coupling and cross-linking for the preparation of cell-laden hydrogels.

Original language	English
Pages (from-to)	4277-4285
Number of pages	9
Journal	Biomacromolecules
Volume	19
Issue number	11
DOIs	https://doi.org/10.1021/acs.biomac.8b01153
Publication status	Published - 12 Jan 2018

Access to Document

10.1021/acs.biomac.8b01153

253281360-oaAccepted author manuscript, 3.02 MB

Cite this

@article{48d1f1e4fbb74bdb9a3850a78152fc4c,

title = "Visible light activation of nucleophilic thiol-x addition via thioether bimane photocleavage for polymer cross-linking",

abstract = "On-demand photo-uncaging of reactive thiols have been employed in engineering biomaterial scaffolds for regulation of cellular activities. A drawback of the current photo-uncaging chemistry is the utilization of high energy UV light or 2-photon laser light, which may be harmful to cells and cause undesired side reactions within the biological environment. We introduce an effective approach for the caging of thiol using monobromobimane, which can be removed under irradiation of light at λ = 420 nm and in the presence of electrophiles, such as acrylate, propiolate and maleimide, for trapping of the newly release thiol. This chemical approach can be used in visible light-induced polymer coupling and cross-linking for the preparation of cell-laden hydrogels.",

author = "Truong, {Vinh X.} and Fanyi Li and Forsythe, {John S.}",

year = "2018",

month = jan,

day = "12",

doi = "10.1021/acs.biomac.8b01153",

language = "English",

volume = "19",

pages = "4277--4285",

journal = "Biomacromolecules",

issn = "1525-7797",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Visible light activation of nucleophilic thiol-x addition via thioether bimane photocleavage for polymer cross-linking

AU - Truong, Vinh X.

AU - Li, Fanyi

AU - Forsythe, John S.

PY - 2018/1/12

Y1 - 2018/1/12

N2 - On-demand photo-uncaging of reactive thiols have been employed in engineering biomaterial scaffolds for regulation of cellular activities. A drawback of the current photo-uncaging chemistry is the utilization of high energy UV light or 2-photon laser light, which may be harmful to cells and cause undesired side reactions within the biological environment. We introduce an effective approach for the caging of thiol using monobromobimane, which can be removed under irradiation of light at λ = 420 nm and in the presence of electrophiles, such as acrylate, propiolate and maleimide, for trapping of the newly release thiol. This chemical approach can be used in visible light-induced polymer coupling and cross-linking for the preparation of cell-laden hydrogels.

AB - On-demand photo-uncaging of reactive thiols have been employed in engineering biomaterial scaffolds for regulation of cellular activities. A drawback of the current photo-uncaging chemistry is the utilization of high energy UV light or 2-photon laser light, which may be harmful to cells and cause undesired side reactions within the biological environment. We introduce an effective approach for the caging of thiol using monobromobimane, which can be removed under irradiation of light at λ = 420 nm and in the presence of electrophiles, such as acrylate, propiolate and maleimide, for trapping of the newly release thiol. This chemical approach can be used in visible light-induced polymer coupling and cross-linking for the preparation of cell-laden hydrogels.

UR - http://www.scopus.com/inward/record.url?scp=85054410416&partnerID=8YFLogxK

U2 - 10.1021/acs.biomac.8b01153

DO - 10.1021/acs.biomac.8b01153

M3 - Article

C2 - 30226977

AN - SCOPUS:85054410416

SN - 1525-7797

VL - 19

SP - 4277

EP - 4285

JO - Biomacromolecules

JF - Biomacromolecules

IS - 11

ER -

Visible light activation of nucleophilic thiol-x addition via thioether bimane photocleavage for polymer cross-linking

Abstract

Access to Document

Other files and links

Cite this