Author(s): Cassano R, Trombino S, Cilea A, Ferrarelli T, Muzzalupo R, et al.
In the present work, we report the synthesis of a new 5-amino salicylic acid (5-ASA) pro-prodrug, useful in Crohn disease treatment, and the evaluation of its antioxidant activity. Using as pharmacological carrier L-lysine amino acid and taking advantage of its intrinsic chemical reactivity, due to the presence of two amino groups, placed on the chiral center and in epsilon-position, we inserted trans-ferulic acid in epsilon-position, through amidation reaction, esterified with methanol the carboxylic group and, finally, submitted the free amino group to diazotation with 5-ASA, principal drug for inflammatory bowel diseases (IBD) care. All intermediates of synthesis and the final product (derivative A) were characterized with usual spectroscopic techniques, as FT-IR, GC/MS and (1)H-MNR. Finally, the derivative A antioxidant activity in inhibiting the lipid peroxidation, in rat-liver microsomal membranes, induced in vitro by two different sources of free radicals, 2,2'-azobis (2-amidinopropane) (AAPH) and tert-butyl hydroperoxide (tert-BOOH), was evaluated. Our pro-prodrug could be successfully applied in pharmaceutical field both as prodrug of 5-ASA than as carrier of trans-ferulic acid.
Referred From: https://www.ncbi.nlm.nih.gov/pubmed/20045975
Author(s): McLeod AD, Fedorak RN, Friend DR, Tozer TN, Cui N
Author(s): McLeod AD, Friend DR, Tozer TN
Author(s): Fedorak RN, Haeberlin B, Empey LR, Cui N, Nolen H 3rd, et al.
Author(s): Fedorak RN, Cui N, Friend DR, Madsen KL, Empey LR
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Author(s): Chourasia MK, Jain SK
Author(s): Kong L, Cooperwood JS, Oh CH, Chu CK, Boudinot FD
Author(s): Teng XW, Wang SW, Davies NM
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Author(s): Duan Y, Yu J, Liu S, Ji M
Author(s): Tanaka S, Matsui H, Kasai M, Kunishiro K, Kakeya N, et al.
Author(s): Reiner A
Author(s): Friedrich RB, Ravanello A, Cichota LC, Rolim CMB, Beck RCR