Polymers with Dithiobenzoate End Groups Constitutively Release Hydrogen Sulfide upon Exposure to Cysteine and Homocysteine

Matthew C. Urquhart; Nam V. Dao; Francesca Ercole; Ben J. Boyd; Thomas P. Davis; Michael R. Whittaker; John F. Quinn

doi:10.1021/acsmacrolett.0c00066

Polymers with Dithiobenzoate End Groups Constitutively Release Hydrogen Sulfide upon Exposure to Cysteine and Homocysteine

Matthew C. Urquhart, Nam V. Dao, Francesca Ercole, Ben J. Boyd, Thomas P. Davis, Michael R. Whittaker, John F. Quinn

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

14 Citations (Scopus)

Abstract

Dithioesters are well-established as efficient reversible addition-fragmentation chain transfer (RAFT) agents. More recently, certain small molecule dithioesters have been reported to release the biological signaling molecule hydrogen sulfide (H₂S) upon exposure to cysteine. Herein, we examine the propensity of polymers synthesized using RAFT with a dithioester chain transfer agent to release H₂S via reaction of cysteine with constitutive dithioester end-groups. Homocysteine-triggered release of H₂S from these materials is also observed, with evidence suggesting that the mechanism is analogous to the reaction with cysteine.

Original language	English
Pages (from-to)	553-557
Number of pages	5
Journal	ACS Macro Letters
Volume	9
Issue number	4
DOIs	https://doi.org/10.1021/acsmacrolett.0c00066
Publication status	Published - 21 Apr 2020

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10.1021/acsmacrolett.0c00066

301912625-oaAccepted author manuscript, 586 KBLicence: CC BY

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title = "Polymers with Dithiobenzoate End Groups Constitutively Release Hydrogen Sulfide upon Exposure to Cysteine and Homocysteine",

abstract = "Dithioesters are well-established as efficient reversible addition-fragmentation chain transfer (RAFT) agents. More recently, certain small molecule dithioesters have been reported to release the biological signaling molecule hydrogen sulfide (H2S) upon exposure to cysteine. Herein, we examine the propensity of polymers synthesized using RAFT with a dithioester chain transfer agent to release H2S via reaction of cysteine with constitutive dithioester end-groups. Homocysteine-triggered release of H2S from these materials is also observed, with evidence suggesting that the mechanism is analogous to the reaction with cysteine.",

author = "Urquhart, \{Matthew C.\} and Dao, \{Nam V.\} and Francesca Ercole and Boyd, \{Ben J.\} and Davis, \{Thomas P.\} and Whittaker, \{Michael R.\} and Quinn, \{John F.\}",

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doi = "10.1021/acsmacrolett.0c00066",

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T1 - Polymers with Dithiobenzoate End Groups Constitutively Release Hydrogen Sulfide upon Exposure to Cysteine and Homocysteine

AU - Urquhart, Matthew C.

AU - Dao, Nam V.

AU - Ercole, Francesca

AU - Boyd, Ben J.

AU - Davis, Thomas P.

AU - Whittaker, Michael R.

AU - Quinn, John F.

PY - 2020/4/21

Y1 - 2020/4/21

N2 - Dithioesters are well-established as efficient reversible addition-fragmentation chain transfer (RAFT) agents. More recently, certain small molecule dithioesters have been reported to release the biological signaling molecule hydrogen sulfide (H2S) upon exposure to cysteine. Herein, we examine the propensity of polymers synthesized using RAFT with a dithioester chain transfer agent to release H2S via reaction of cysteine with constitutive dithioester end-groups. Homocysteine-triggered release of H2S from these materials is also observed, with evidence suggesting that the mechanism is analogous to the reaction with cysteine.

AB - Dithioesters are well-established as efficient reversible addition-fragmentation chain transfer (RAFT) agents. More recently, certain small molecule dithioesters have been reported to release the biological signaling molecule hydrogen sulfide (H2S) upon exposure to cysteine. Herein, we examine the propensity of polymers synthesized using RAFT with a dithioester chain transfer agent to release H2S via reaction of cysteine with constitutive dithioester end-groups. Homocysteine-triggered release of H2S from these materials is also observed, with evidence suggesting that the mechanism is analogous to the reaction with cysteine.

UR - https://www.scopus.com/pages/publications/85082536054

U2 - 10.1021/acsmacrolett.0c00066

DO - 10.1021/acsmacrolett.0c00066

M3 - Article

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VL - 9

SP - 553

EP - 557

JO - ACS Macro Letters

JF - ACS Macro Letters

IS - 4

ER -

Polymers with Dithiobenzoate End Groups Constitutively Release Hydrogen Sulfide upon Exposure to Cysteine and Homocysteine

Abstract

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New materials for manipulating intracellular communication

Designing Nanoparticles to Combat Cellular Dysfunction

Macromolecular design for bio-imaging and targeted delivery

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Polymers with Dithiobenzoate End Groups Constitutively Release Hydrogen Sulfide upon Exposure to Cysteine and Homocysteine

Abstract

Access to Document

Other files and links

Projects

New materials for manipulating intracellular communication

Designing Nanoparticles to Combat Cellular Dysfunction

Macromolecular design for bio-imaging and targeted delivery

Cite this