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

Although sulfur dioxide (SO ) finds widespread use in the food industry as its hydrated sulfite form, a number of aspects of SO biology remain to be completely understood. Of the tools available for intracellular enhancement of SO levels, most suffer from poor cell permeability and a lack of control over SO release. We report 1,2-cyclic sulfite diesters as a new class of reliable SO donors that dissociate in buffer through nucleophilic displacement to produce SO with tunable release profiles.

Targeted Antibacterial Activity Guided by Bacteria-Specific Nitroreductase Catalytic Activation to Produce Ciprofloxacin.

Fluoroquinolones (FQs) are among the front-line antibiotics used to treat severe infections caused by Gram-negative bacteria. However, recently, due to toxicity concerns, their use has been severely restricted. Hence, efforts to direct delivery of this antibiotic specifically to bacteria/site of infection are underway.

Small molecule generators of biologically reactive sulfur species.

Sulfur metabolism is integral to cellular growth and survival. The presence of a wide range of oxidation states of sulfur in biology coupled with its unique reactivity are some key features of the biology of this element. In particular, nearly all oxidation states of sulfur not only occur but are also inter-convertible.

Esterase Sensitive Self-Immolative Sulfur Dioxide Donors.

A series of cell-permeable esterase-sensitive sulfonates that undergo self-immolation to produce sulfur dioxide (SO), a gaseous pollutant with new and emerging biological roles, is reported. These compounds should facilitate the study SO biology and will lay the platform for newer stimuli-responsive donors of this gas.

Thiol activated prodrugs of sulfur dioxide (SO2) as MRSA inhibitors.

Drug resistant infections are becoming common worldwide and new strategies for drug development are necessary. Here, we report the synthesis and evaluation of 2,4-dinitrophenylsulfonamides, which are donors of sulfur dioxide (SO2), a reactive sulfur species, as methicillin-resistant Staphylococcus aureus (MRSA) inhibitors. N-(3-Methoxyphenyl)-2,4-dinitro-N-(prop-2-yn-1-yl)benzenesulfonamide (5e) was found to have excellent in vitro MRSA inhibitory potency.