Synthesis of Sulfur-35-Labeled Trisulfides and GYY-4137 as Donors of Radioactive Hydrogen Sulfide

Eric M. Brown; James P. Grace; Nimesh P. R. Ranasinghe Arachchige; Ned B. Bowden

doi:10.1021/acsomega.3c03258

Back

Synthesis of Sulfur-35-Labeled Trisulfides and GYY-4137 as Donors of Radioactive Hydrogen Sulfide

Journal article

Open access

Peer reviewed

Synthesis of Sulfur-35-Labeled Trisulfides and GYY-4137 as Donors of Radioactive Hydrogen Sulfide

Eric M. Brown, James P. Grace, Nimesh P. R. Ranasinghe Arachchige and Ned B. Bowden

ACS omega, Vol.8(30), pp.27576-27584

08/01/2023

DOI: 10.1021/acsomega.3c03258

Appears in UI Libraries Support Open Access

Files and links (1)

url

https://doi.org/10.1021/acsomega.3c03258View

Published (Version of record) Open Access

Abstract

Hydrogen sulfide has emerged as a key gasotransmitter in humans and in plants, and the addition of exogenous hydrogen sulfide has many beneficial effects in vivo and in vitro. A challenge in investigating the effect of exogenous hydrogen sulfide is tracking the location of exogenous hydrogen sulfide on an organism and cellular level. In this article, we report the synthesis of three key chemicals (cysteine trisulfide, glutathione trisulfide, and GYY-4137) that release radiolabeled 35S as hydrogen sulfide. The synthesis started with the reduction of Na2 35SO4 mixed with Na2SO4 to generate hydrogen sulfide gas that was trapped with aq NaOH to yield radiolabeled Na2S. The Na2S was converted in one step to GYY-4137 at 65% yield. It was also converted to bis(tributyltin) sulfide that readily reacted with N-bromophthalimide to yield a monosulfur transfer reagent. Trisulfides were synthesized by reaction with the monosulfur transfer reagent and the corresponding thiols. The levels of radioactivity of the final products could be varied on a per gram basis to alter the radioactivity for applications that require different loadings of hydrogen sulfide donors.

UIOWA OA Agreement

Details

Title: Subtitle: Synthesis of Sulfur-35-Labeled Trisulfides and GYY-4137 as Donors of Radioactive Hydrogen Sulfide
Creators: Eric M. Brown - University of Iowa
James P. Grace - University of Iowa
Nimesh P. R. Ranasinghe Arachchige
Ned B. Bowden - University of Iowa
Resource Type: Journal article
Publication Details: ACS omega, Vol.8(30), pp.27576-27584
DOI: 10.1021/acsomega.3c03258
ISSN: 2470-1343
eISSN: 2470-1343
Publisher: American Chemical Society
Grant note: DOI: 10.13039/100000070, name: National Institute of Biomedical Imaging and Bioengineering, award: RO3-EB030736; DOI: 10.13039/100008893, name: University of Iowa
Language: English
Date published: 08/01/2023
Academic Unit: Chemistry
Record Identifier: 9984448054702771

Metrics

11 Record Views