SO Donors and Prodrugs, and Their Possible Applications: A Review

Overview

Journal Front Chem

Specialty Chemistry

Date 2018 Dec 4

PMID 30505833

Citations 14

Authors

Wenyi Wang

Binghe Wang

Affiliations

Soon will be listed here.

Abstract

SO is widely recognized as an air pollutant and is a known cause of acid rain. At a sufficiently high level, it also causes respiratory diseases. A much lesser known side of SO is its endogenous nature and possible physiological roles. There is mounting evidence that SO is produced during normal cellular metabolism and may possibly function as a signaling molecule in normal physiology. The latter aspect is still at the stage of being carefully examined as to the validity of classifying SO as a gasotransmitter with endogenous signaling roles. One difficulty in studying the biological and pharmacological roles of SO is the lack of adequate tools for its controllable and precise delivery. Traditional methods of using SO gas or mixed sulfite salts do not meet research need for several reasons. Therefore, there has been increasing attention on the need of developing SO donors or prodrugs that can be used as tools for the elucidation of SO's physiological roles, pharmacological effects, and possible mechanism(s) of action. In this review, we aim to review basic sulfur chemistry in the context of sulfur signaling and various chemical strategies used for designing SO donors. We will also discuss potential pharmacological applications of SO donors, lay out desirable features for such donors and possibly prodrugs, analyze existing problems, and give our thoughts on research needs.

Citing Articles

Unveiling the Potential of Sulfur-Containing Gas Signaling Molecules in Acute Lung Injury: A Promising Therapeutic Avenue.

Sun X, Mao C, Wang J, Wu S, Qu Y, Xie Y Curr Issues Mol Biol. 2024; 46(7):7147-7168.

PMID: 39057067 PMC: 11275821. DOI: 10.3390/cimb46070426.

Selective anti-tumor activity of glutathione-responsive abasic site trapping agent in anaplastic thyroid carcinoma.

Chai J, Su M, Zhang R, Li N, Jia Y, Zheng W BMC Cancer. 2024; 24(1):816.

PMID: 38977966 PMC: 11229194. DOI: 10.1186/s12885-024-12511-3.

Fluorescent small molecule donors.

Chen G, Yu J, Wu L, Ji X, Xu J, Wang C Chem Soc Rev. 2024; 53(12):6345-6398.

PMID: 38742651 PMC: 11181996. DOI: 10.1039/d3cs00124e.

Advances in the research of sulfur dioxide and pulmonary hypertension.

Liu X, Zhou H, Zhang H, Jin H, He Y Front Pharmacol. 2023; 14:1282403.

PMID: 37900169 PMC: 10602757. DOI: 10.3389/fphar.2023.1282403.

Click chemistry and drug delivery: A bird's-eye view.

Kondengadan S, Bansal S, Yang C, Liu D, Fultz Z, Wang B Acta Pharm Sin B. 2023; 13(5):1990-2016.

PMID: 37250163 PMC: 10213991. DOI: 10.1016/j.apsb.2022.10.015.

References

Yoo J, Chambers E, Mitragotri S . Factors that control the circulation time of nanoparticles in blood: challenges, solutions and future prospects. Curr Pharm Des. 2010; 16(21):2298-307. DOI: 10.2174/138161210791920496. View

Kajiyama H, Nojima Y, Mitsuhashi H, Ueki K, Tamura S, Sekihara T . Elevated levels of serum sulfite in patients with chronic renal failure. J Am Soc Nephrol. 2000; 11(5):923-927. DOI: 10.1681/ASN.V115923. View

Jin H, Wang Y, Wang X, Sun Y, Tang C, Du J . Sulfur dioxide preconditioning increases antioxidative capacity in rat with myocardial ischemia reperfusion (I/R) injury. Nitric Oxide. 2013; 32:56-61. DOI: 10.1016/j.niox.2013.04.008. View

Bora P, Chauhan P, Pardeshi K, Chakrapani H . Small molecule generators of biologically reactive sulfur species. RSC Adv. 2022; 8(48):27359-27374. PMC: 9083908. DOI: 10.1039/c8ra03658f. View

Zhang D, Devarie-Baez N, Li Q, Lancaster Jr J, Xian M . Methylsulfonyl benzothiazole (MSBT): a selective protein thiol blocking reagent. Org Lett. 2012; 14(13):3396-9. PMC: 3391333. DOI: 10.1021/ol301370s. View

Goldberg R, Parker V . Thermodynamics of Solution of SO(g) in Water and of Aqueous Sulfur Dioxide Solutions. J Res Natl Bur Stand (1977). 2021; 90(5):341-358. PMC: 6658418. DOI: 10.6028/jres.090.024. View

Brown S, Piantadosi C . In vivo binding of carbon monoxide to cytochrome c oxidase in rat brain. J Appl Physiol (1985). 1990; 68(2):604-10. DOI: 10.1152/jappl.1990.68.2.604. View

Knauert M, Vangala S, Haslip M, Lee P . Therapeutic applications of carbon monoxide. Oxid Med Cell Longev. 2014; 2013:360815. PMC: 3932177. DOI: 10.1155/2013/360815. View

Mathew N, Schlipalius D, Ebert P . Sulfurous gases as biological messengers and toxins: comparative genetics of their metabolism in model organisms. J Toxicol. 2011; 2011:394970. PMC: 3216388. DOI: 10.1155/2011/394970. View

10.

Sang N, Yun Y, Li H, Hou L, Han M, Li G . SO2 inhalation contributes to the development and progression of ischemic stroke in the brain. Toxicol Sci. 2010; 114(2):226-36. DOI: 10.1093/toxsci/kfq010. View

11.

Liu Y, Li K, Xie K, Li L, Yu K, Wang X . A water-soluble and fast-response mitochondria-targeted fluorescent probe for colorimetric and ratiometric sensing of endogenously generated SO2 derivatives in living cells. Chem Commun (Camb). 2016; 52(16):3430-3. DOI: 10.1039/c5cc10505f. View

12.

Naldini L . Gene therapy returns to centre stage. Nature. 2015; 526(7573):351-60. DOI: 10.1038/nature15818. View

13.

Xu J, Pan J, Jiang X, Qin C, Zeng L, Zhang H . A mitochondria-targeted ratiometric fluorescent probe for rapid, sensitive and specific detection of biological SO2 derivatives in living cells. Biosens Bioelectron. 2015; 77:725-32. DOI: 10.1016/j.bios.2015.10.049. View

14.

Wang X, Du J, Cui H . Signal pathways involved in the biological effects of sulfur dioxide. Eur J Pharmacol. 2015; 764:94-99. DOI: 10.1016/j.ejphar.2015.06.044. View

15.

Yu B, Zheng Y, Yuan Z, Li S, Zhu H, De La Cruz L . Toward Direct Protein S-Persulfidation: A Prodrug Approach That Directly Delivers Hydrogen Persulfide. J Am Chem Soc. 2017; 140(1):30-33. DOI: 10.1021/jacs.7b09795. View

16.

Wang W, Ji X, Du Z, Wang B . Sulfur dioxide prodrugs: triggered release of SOvia a click reaction. Chem Commun (Camb). 2017; 53(8):1370-1373. PMC: 5292044. DOI: 10.1039/c6cc08844a. View

17.

Meng Z . Oxidative damage of sulfur dioxide on various organs of mice: sulfur dioxide is a systemic oxidative damage agent. Inhal Toxicol. 2003; 15(2):181-95. DOI: 10.1080/08958370304476. View

18.

Malwal S, Sriram D, Yogeeswari P, Konkimalla V, Chakrapani H . Design, synthesis, and evaluation of thiol-activated sources of sulfur dioxide (SO₂) as antimycobacterial agents. J Med Chem. 2011; 55(1):553-7. DOI: 10.1021/jm201023g. View

19.

Kaelin Jr W, Ratcliffe P . Oxygen sensing by metazoans: the central role of the HIF hydroxylase pathway. Mol Cell. 2008; 30(4):393-402. DOI: 10.1016/j.molcel.2008.04.009. View

20.

Wang X, Du J, Cui H . Sulfur dioxide, a double-faced molecule in mammals. Life Sci. 2014; 98(2):63-7. DOI: 10.1016/j.lfs.2013.12.027. View