Triggered and Tunable Hydrogen Sulfide Release from Photogenerated Thiobenzaldehydes

Zeyun Xiao, Thomas Bonnard, Aida Shakouri-Motlagh, Ross A.L. Wylie, Joe Collins, Jonathan White, Daniel E. Heath, Christoph E. Hagemeyer, Luke A. Connal

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Hydrogen sulfide (H2S) has been identified as an important cell-signaling mediator and has a number of biological functions, such as vascular smooth muscle relaxation, neurotransmission, and regulation of inflammation. A facile and versatile approach for H2S production initiated by light irradiation and controlled by reaction with an amine or an amino acid was developed. The donor was synthesized in a one-pot reaction, and simple crystallization led to a yield of approximately 90 %. The synthetic strategy is scalable and versatile, and the H2S donors can be expressed ina number of different molecular and macromolecular forms, including crystalline small-molecule compounds, water-soluble polymers, polystyrene films, and hydrogels. The H2S donors based on polystyrene film and hydrogel were used as cell-culture scaffolds. The H2S donor based on water-soluble polymer was applied in photocontrolled inhibition of P-selectin expression on human platelets and subsequent regulation of platelet aggregation. This study provides the simplest controllable H2S source to study its biological functions. The developed materials are also new therapeutic platforms to deliver H2S, as there is no accumulation of toxic byproducts, and the donor materials from polystyrene films and hydrogels can be readily removed after releasing H2S.

Original languageEnglish
Pages (from-to)11294-11300
Number of pages7
JournalChemistry - A European Journal
Volume23
Issue number47
DOIs
Publication statusPublished - 22 Aug 2017

Keywords

  • gels
  • hydrogen sulfide
  • photochemistry
  • polymers
  • thioaldehydes

Cite this

Xiao, Z., Bonnard, T., Shakouri-Motlagh, A., Wylie, R. A. L., Collins, J., White, J., ... Connal, L. A. (2017). Triggered and Tunable Hydrogen Sulfide Release from Photogenerated Thiobenzaldehydes. Chemistry - A European Journal, 23(47), 11294-11300. https://doi.org/10.1002/chem.201701206
Xiao, Zeyun ; Bonnard, Thomas ; Shakouri-Motlagh, Aida ; Wylie, Ross A.L. ; Collins, Joe ; White, Jonathan ; Heath, Daniel E. ; Hagemeyer, Christoph E. ; Connal, Luke A. / Triggered and Tunable Hydrogen Sulfide Release from Photogenerated Thiobenzaldehydes. In: Chemistry - A European Journal. 2017 ; Vol. 23, No. 47. pp. 11294-11300.
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Xiao, Z, Bonnard, T, Shakouri-Motlagh, A, Wylie, RAL, Collins, J, White, J, Heath, DE, Hagemeyer, CE & Connal, LA 2017, 'Triggered and Tunable Hydrogen Sulfide Release from Photogenerated Thiobenzaldehydes', Chemistry - A European Journal, vol. 23, no. 47, pp. 11294-11300. https://doi.org/10.1002/chem.201701206

Triggered and Tunable Hydrogen Sulfide Release from Photogenerated Thiobenzaldehydes. / Xiao, Zeyun; Bonnard, Thomas; Shakouri-Motlagh, Aida; Wylie, Ross A.L.; Collins, Joe; White, Jonathan; Heath, Daniel E.; Hagemeyer, Christoph E.; Connal, Luke A.

In: Chemistry - A European Journal, Vol. 23, No. 47, 22.08.2017, p. 11294-11300.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Triggered and Tunable Hydrogen Sulfide Release from Photogenerated Thiobenzaldehydes

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AU - Bonnard, Thomas

AU - Shakouri-Motlagh, Aida

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AU - Collins, Joe

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AU - Hagemeyer, Christoph E.

AU - Connal, Luke A.

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AB - Hydrogen sulfide (H2S) has been identified as an important cell-signaling mediator and has a number of biological functions, such as vascular smooth muscle relaxation, neurotransmission, and regulation of inflammation. A facile and versatile approach for H2S production initiated by light irradiation and controlled by reaction with an amine or an amino acid was developed. The donor was synthesized in a one-pot reaction, and simple crystallization led to a yield of approximately 90 %. The synthetic strategy is scalable and versatile, and the H2S donors can be expressed ina number of different molecular and macromolecular forms, including crystalline small-molecule compounds, water-soluble polymers, polystyrene films, and hydrogels. The H2S donors based on polystyrene film and hydrogel were used as cell-culture scaffolds. The H2S donor based on water-soluble polymer was applied in photocontrolled inhibition of P-selectin expression on human platelets and subsequent regulation of platelet aggregation. This study provides the simplest controllable H2S source to study its biological functions. The developed materials are also new therapeutic platforms to deliver H2S, as there is no accumulation of toxic byproducts, and the donor materials from polystyrene films and hydrogels can be readily removed after releasing H2S.

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JF - Chemistry - A European Journal

SN - 1521-3765

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Xiao Z, Bonnard T, Shakouri-Motlagh A, Wylie RAL, Collins J, White J et al. Triggered and Tunable Hydrogen Sulfide Release from Photogenerated Thiobenzaldehydes. Chemistry - A European Journal. 2017 Aug 22;23(47):11294-11300. https://doi.org/10.1002/chem.201701206