title: Synthesis and in vitro Bioactivity Evaluation of New Galactose and Fructose Ester Derivatives of 5-Aminosalicylic Acid.
abstract: Inflammatory bowel disease (IBD) is the main risk factor for developing colorectal cancer which is common in patients of all ages. 5-Aminosalicylic acid (5-ASA), structurally related to the salicylates, is highly active in the treatment of IBD with minor side effects. In this study, the synthesis of galactose and fructose esters of 5-ASA was planned to evaluate the role of glycoconjugation on the bioactivity of the parent drug. The antibacterial activity of the new compounds were evaluated against two Gram-negative and two Gram-positive species of bacteria, with a notable effect observed against Staphylococcus aureus and Escherichia coli in comparisons with the 5-ASA. Cytotoxicity testing over HT-29 and 3T3 cell lines indicated that the toxicity of the new products against normal cells was significantly reduced compared with the original drug, whereas their activity against cancerous cells was slightly decreased. The anti-inflammatory activity test in RAW264.7 macrophage cells indicated that the inhibition of nitric oxide by both of the monosaccharide conjugated derivatives was slightly improved in comparison with the non-conjugated drug.
authors.affiliation: Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400, UPM Serdang, Selangor, Malaysia.
authors.forename: Samira
authors.initials: S
authors.lastname: Yousefi
authors.affiliation: Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400, UPM Serdang, Selangor, Malaysia.
authors.forename: Saadi
authors.initials: S
authors.lastname: Bayat
authors.affiliation: Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400, UPM Serdang, Selangor, Malaysia.|Enzyme and Microbial Technology Centre, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia.|Structural and Synthetic Biology Research Center, Malaysia Genome Institute, 43600, Bangi, Selangor, Malaysia.
authors.forename: Mohd Basyaruddin Abdul
authors.initials: MB
authors.lastname: Rahman
authors.affiliation: Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400, UPM Serdang, Selangor, Malaysia.
authors.forename: Zalikha
authors.initials: Z
authors.lastname: Ibrahim
authors.affiliation: Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400, UPM Serdang, Selangor, Malaysia.|Enzyme and Microbial Technology Centre, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia.
authors.forename: Emilia
authors.initials: E
authors.lastname: Abdulmalek
mesh_terms: D016475:3T3 Cells; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D004952:Esters / Q000138:chemical synthesis; D005632:Fructose / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry*; D019073:HT29 Cells; D006801:Humans; D015212:Inflammatory Bowel Diseases / Q000188:drug therapy*; D008264:Macrophages / Q000378:metabolism; D019804:Mesalamine / Q000737:chemistry*; D051379:Mice; D009569:Nitric Oxide / Q000037:antagonists & inhibitors; D000067996:RAW 264.7 Cells
chemical_list: D000900:Anti-Bacterial Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D004952:Esters; D005632:Fructose; D009569:Nitric Oxide; D019804:Mesalamine; D005690:Galactose
keywords: 5-ASA; Biological evaluation; Fructose; Galactose