One- and two-photon responsive sulfur dioxide (SO₂) donors: a combinatorial drug delivery for improved antibiotic therapy

Abstract

Light-activated sulfur dioxide donors have been developed and explored their applicability for combinatorial antibiotic therapy with self-monitoring ability.

Photolysis of dimethoxynitrobenzyl-“caged” acids yields fluorescent products

“…The fluorescence of DMNB-“caged” compounds residuals after photolysis was observed in previous studies 20,21 , but it was attributed to the release of fluorescent target compound and used as a measure of “uncaging” degree. Our study shows that this approach could be a source of systematical errors.…”

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

“…reported sodium benzothiazole sulfonate as a water‐soluble SO 2 donor but with the limitation of a prolonged half‐life ( t 1/2 =13 d) at physiological pH 7.4 . Recently, SO 2 donors based on esterases, nitroreductases, thiols, and light as triggers, as well as on click chemistry as a mode of SO 2 donation, have been reported by our group and by the Singh and Wang groups (Scheme ). These strategies rely on the use of a cellular enzyme or a bio‐orthogonal reaction, and so can result in variable generation of sulfur dioxide depending on the availability of the stimulus.…”

“…The chemical biology of SO 2 thus remains largely uncharacterized . Our laboratory has developed several strategies involving different triggers for generating SO 2 under physiological conditions by using small organic molecules .…”

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

“…The chemical biology of SO 2 thus remains largely uncharacterized. [15] Our laboratory has developed severals trategies involvingd ifferent triggers for generating SO 2 under physiological conditions by using smallo rganic molecules. [8] Firstly,( 2,4dinitrophenyl)sulfonamidesw ith tunable rates of generation of SO 2 when triggered by biological thiols were reported (Scheme 1).…”

“…[10] Xian et al reporteds odium benzothiazole sulfonate as aw ater-soluble SO 2 donor but with the limitation of ap rolongedh alf-life (t 1/2 = 13 d) at physiological pH 7.4. [11] Recently, SO 2 donors based on esterases, [8f, 12] nitroreductases, [13] thiols, [14] and light [15] as triggers, as well as on click chemistry as am ode of SO 2 donation, have been reported by our group and by the Singh and Wang groups (Scheme 1). These strategies rely on the use of ac ellular enzyme or ab io-orthogonal reaction, and so can result in variableg eneration of sulfur dioxide depending on the availability of the stimulus.T herefore, new self-immolative SO 2 donors that are stable at room temperature and permeate cellst oe nhance intracellular SO 2 levels could help better understanding of cellular responses to this important gaseous compound.…”