M.A.A. Baheej, H.M. Haniffa, H. Siddiqui, A. Jabeen
{"title":"没食子酸酯作为吞噬细胞氧化爆发抑制剂的合成及生物学评价","authors":"M.A.A. Baheej, H.M. Haniffa, H. Siddiqui, A. Jabeen","doi":"10.4038/jnsfsr.v51i3.11199","DOIUrl":null,"url":null,"abstract":"Several degenerative diseases, including cancer, are caused by oxidative stress, which is caused by the overproduction and accumulation of free radicals. The purpose of the study was to synthesize gallic acid (GA or 3,4,5-trihydroxybenzoic acid) esters and evaluate their anti-inflammatory potential through the inhibition of reactive oxygen species (ROS). The compounds methyl gallate (2), sec-butyl gallate (3), ethyl gallate (4), isopropyl gallate (5), 2-methoxyethyl gallate (6), 4-methoxybutyl gallate (7), 2-methylbutyl gallate (8) and pentan-3-yl gallate (9) were synthesized. 1H NMR, MS and IR data are reported for compounds 2-9, and 13C NMR data for compounds 2, 3, 5, and 6. The molecular formulae of compounds 3 and 7-9 were established by HREI-MS spectroscopic data. All the synthesized compounds were tested for their anti-inflammatory and cytotoxic activities by chemiluminescence and MTT cytotoxicity assay respectively. The results revealed the anti-inflammatory potential of compounds 2-8 with an IC50 range between (13.3 – 54.3 µM) as compared to the standard anti-inflammatory drug, Ibuprofen (IC50 = 54.3 ± 9.2 μM). The most potent inhibitors were found to be compound 3 (ROS IC50 = 15.0 ± 6.6 µM) and compound 7 (ROS IC50 = 13.3 ± 0.8 µM). All compounds were found to be non-cytotoxic in the NIH-3T3 fibroblast cell line. Compounds 3, 7- 9 were identified as new compounds.","PeriodicalId":17429,"journal":{"name":"Journal of the National Science Foundation of Sri Lanka","volume":"68 1","pages":"0"},"PeriodicalIF":0.4000,"publicationDate":"2023-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and biological evaluation of gallic acid esters as phagocyte oxidative burst inhibitors\",\"authors\":\"M.A.A. Baheej, H.M. Haniffa, H. Siddiqui, A. Jabeen\",\"doi\":\"10.4038/jnsfsr.v51i3.11199\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Several degenerative diseases, including cancer, are caused by oxidative stress, which is caused by the overproduction and accumulation of free radicals. The purpose of the study was to synthesize gallic acid (GA or 3,4,5-trihydroxybenzoic acid) esters and evaluate their anti-inflammatory potential through the inhibition of reactive oxygen species (ROS). The compounds methyl gallate (2), sec-butyl gallate (3), ethyl gallate (4), isopropyl gallate (5), 2-methoxyethyl gallate (6), 4-methoxybutyl gallate (7), 2-methylbutyl gallate (8) and pentan-3-yl gallate (9) were synthesized. 1H NMR, MS and IR data are reported for compounds 2-9, and 13C NMR data for compounds 2, 3, 5, and 6. The molecular formulae of compounds 3 and 7-9 were established by HREI-MS spectroscopic data. All the synthesized compounds were tested for their anti-inflammatory and cytotoxic activities by chemiluminescence and MTT cytotoxicity assay respectively. The results revealed the anti-inflammatory potential of compounds 2-8 with an IC50 range between (13.3 – 54.3 µM) as compared to the standard anti-inflammatory drug, Ibuprofen (IC50 = 54.3 ± 9.2 μM). The most potent inhibitors were found to be compound 3 (ROS IC50 = 15.0 ± 6.6 µM) and compound 7 (ROS IC50 = 13.3 ± 0.8 µM). All compounds were found to be non-cytotoxic in the NIH-3T3 fibroblast cell line. Compounds 3, 7- 9 were identified as new compounds.\",\"PeriodicalId\":17429,\"journal\":{\"name\":\"Journal of the National Science Foundation of Sri Lanka\",\"volume\":\"68 1\",\"pages\":\"0\"},\"PeriodicalIF\":0.4000,\"publicationDate\":\"2023-10-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of the National Science Foundation of Sri Lanka\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.4038/jnsfsr.v51i3.11199\",\"RegionNum\":4,\"RegionCategory\":\"综合性期刊\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"MULTIDISCIPLINARY SCIENCES\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the National Science Foundation of Sri Lanka","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.4038/jnsfsr.v51i3.11199","RegionNum":4,"RegionCategory":"综合性期刊","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"MULTIDISCIPLINARY SCIENCES","Score":null,"Total":0}
Synthesis and biological evaluation of gallic acid esters as phagocyte oxidative burst inhibitors
Several degenerative diseases, including cancer, are caused by oxidative stress, which is caused by the overproduction and accumulation of free radicals. The purpose of the study was to synthesize gallic acid (GA or 3,4,5-trihydroxybenzoic acid) esters and evaluate their anti-inflammatory potential through the inhibition of reactive oxygen species (ROS). The compounds methyl gallate (2), sec-butyl gallate (3), ethyl gallate (4), isopropyl gallate (5), 2-methoxyethyl gallate (6), 4-methoxybutyl gallate (7), 2-methylbutyl gallate (8) and pentan-3-yl gallate (9) were synthesized. 1H NMR, MS and IR data are reported for compounds 2-9, and 13C NMR data for compounds 2, 3, 5, and 6. The molecular formulae of compounds 3 and 7-9 were established by HREI-MS spectroscopic data. All the synthesized compounds were tested for their anti-inflammatory and cytotoxic activities by chemiluminescence and MTT cytotoxicity assay respectively. The results revealed the anti-inflammatory potential of compounds 2-8 with an IC50 range between (13.3 – 54.3 µM) as compared to the standard anti-inflammatory drug, Ibuprofen (IC50 = 54.3 ± 9.2 μM). The most potent inhibitors were found to be compound 3 (ROS IC50 = 15.0 ± 6.6 µM) and compound 7 (ROS IC50 = 13.3 ± 0.8 µM). All compounds were found to be non-cytotoxic in the NIH-3T3 fibroblast cell line. Compounds 3, 7- 9 were identified as new compounds.
期刊介绍:
The Journal of National Science Foundation of Sri Lanka (JNSF) publishes the results of research in Science and Technology. The journal is released four times a year, in March, June, September and December. This journal contains Research Articles, Reviews, Research Communications and Correspondences.
Manuscripts submitted to the journal are accepted on the understanding that they will be reviewed prior to acceptance and that they have not been submitted for publication elsewhere.