title: Diazeniumdiolated carbamates: a novel class of nitric oxide donors.
abstract: We report an indirect method for synthesis of previously inaccessible diazeniumdiolated carbamates. Synthesis involves use of previously reported triisopropylsilyloxymethylated isopropylamine diazeniumdiolate (TOM-ylated IPA/NO). These novel diazeniumdiolated carbamate prodrugs upon activation release nitric oxide (NO) similar to their secondary amine counterparts. They are also efficient sources of intracellular NO. These prodrugs may have potential applications as therapeutic NO-donors.
authors.affiliation: Drug Design Section, Chemical Biology Laboratory, National Cancer Institute at Frederick, Frederick, MD 21702, USA. nandurdikarr@mail.nih.gov
authors.forename: Rahul S
authors.initials: RS
authors.lastname: Nandurdikar
authors.forename: Anna E
authors.initials: AE
authors.lastname: Maciag
authors.forename: Zhao
authors.initials: Z
authors.lastname: Cao
authors.forename: Larry K
authors.initials: LK
authors.lastname: Keefer
authors.forename: Joseph E
authors.initials: JE
authors.lastname: Saavedra
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002219:Carbamates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D005347:Fibroblasts / Q000187:drug effects / Q000378:metabolism; D006801:Humans; D009569:Nitric Oxide / Q000378:metabolism; D020030:Nitric Oxide Donors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011355:Prodrugs / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D001391:Azo Compounds; D002219:Carbamates; D020030:Nitric Oxide Donors; D011355:Prodrugs; C452539:diazeniumdiolate; D009569:Nitric Oxide