2-Hydroxy-5-nitrobenzyl as a diazeniumdiolate protecting group: application in NO-releasing polymers with enhanced biocompatibility.
The 2-hydroxy-5-nitrobenzyl group is shown to be an effective protecting group for diazeniumdiolates. O(2)-(2-hydroxy-5-nitrobenzyl)-substituted diazeniumdiolates display enhanced thermal stability, but efficiently release nitric oxide (NO) in pH 7.4 aqueous solutions. A lipophilic analogue incorporated into hydrophobic polymers shows NO surface flux rates comparable to that of the natural endothelium. Importantly, these polymer formulations also show significantly enhanced biocompatibility in vivo with use of a porcine implant model.
Xu
Hua
H
Department of Chemistry, Johns Hopkins University, Baltimore, Maryland 21218, USA.
Reynolds
Melissa M
MM
Cook
Keith E
KE
Evans
Anthony S
AS
Toscano
John P
JP
D001391:Azo Compounds / Q000737:chemistry*; D001672:Biocompatible Materials / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D006900:Hydroxylation; D015394:Molecular Structure; D009569:Nitric Oxide / Q000737:chemistry*; D009578:Nitrobenzenes / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D011355:Prodrugs / Q000737:chemistry; D013499:Surface Properties
D001391:Azo Compounds; D001672:Biocompatible Materials; D009578:Nitrobenzenes; D011108:Polymers; D011355:Prodrugs; C452539:diazeniumdiolate; D009569:Nitric Oxide; C036077:nitrobenzene