Synthesis of Cyclic Sulfite Diesters and their Evaluation as Sulfur Dioxide (SO2 ) Donors

Satish R Malwal; Kundansingh A Pardeshi; Harinath Chakrapani

doi:10.1002/cbic.201900614

Synthesis of Cyclic Sulfite Diesters and their Evaluation as Sulfur Dioxide (SO₂ ) Donors

Chembiochem. 2020 Apr 17;21(8):1201-1205. doi: 10.1002/cbic.201900614. Epub 2020 Jan 20.

Authors

Satish R Malwal^{1

2}, Kundansingh A Pardeshi¹, Harinath Chakrapani¹

Affiliations

¹ Indian Institute of Science Education and Research Pune, Dr. Homi Bhabha Road, Pashan Pune, 411 008, Maharashtra, India.
² Present address: Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA.

PMID: 31709695
DOI: 10.1002/cbic.201900614

Abstract

Although sulfur dioxide (SO₂ ) finds widespread use in the food industry as its hydrated sulfite form, a number of aspects of SO₂ biology remain to be completely understood. Of the tools available for intracellular enhancement of SO₂ levels, most suffer from poor cell permeability and a lack of control over SO₂ release. We report 1,2-cyclic sulfite diesters as a new class of reliable SO₂ donors that dissociate in buffer through nucleophilic displacement to produce SO₂ with tunable release profiles. We provide data in support of the suitability of these SO₂ donors to enhance intracellular SO₂ levels more efficiently than sodium bisulfite, the most commonly used SO₂ donor for cellular studies.

Keywords: cyclic sulfite esters; nucleophilic substitution; substituent effects; sulfites; sulfur dioxide.

Publication types

Evaluation Study
Research Support, Non-U.S. Gov't

MeSH terms

Colonic Neoplasms / metabolism*
Colonic Neoplasms / pathology
Esters / chemical synthesis*
Humans
Sulfites / chemical synthesis*
Sulfur Dioxide / metabolism*
Tumor Cells, Cultured

Substances

Esters
Sulfites
Sulfur Dioxide