Glycosylated PROLI/NO derivatives as nitric oxide prodrugs.
GlcNAc-PROLI/NO prodrugs that are activated by N-acetylglucosaminidase to release nitric oxide (NO) are described. A classical acid-amine coupling is used to bifunctionalize these PROLI/NO prodrugs, which on activation generate up to 4 mol of NO, a peptide residue, and an N-acetylglucosamine residue. Many of the prodrugs synthesized are efficient sources of intracellular NO.
Nandurdikar
Rahul S
RS
Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, Maryland 21702, USA. nandurdikarr@mail.nih.gov
Maciag
Anna E
AE
Hong
Sam Y
SY
Chakrapani
Harinath
H
Citro
Michael L
ML
Keefer
Larry K
LK
Saavedra
Joseph E
JE
D000118:Acetylglucosaminidase / Q000378:metabolism*; D006031:Glycosylation; D015394:Molecular Structure; D009569:Nitric Oxide / Q000737:chemistry / Q000378:metabolism*; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D011355:Prodrugs; C102043:proline-nitric oxide; D009569:Nitric Oxide; D011392:Proline; D000118:Acetylglucosaminidase