Chemical modification of ascorbic acid and evaluation of its lipophilic derivatives as inhibitors of secretory phospholipase A2 with anti-inflammatory activity

Molecular and Cellular Biochemistry

Volumn 345, Issue 1-2, 2010, Pages 69-76

  Mohamed, Riyaz ^a   Dharmappa, K K ^a   Tarannum, Shaista ^a   Jameel, N M ^b   Kannum, S A ^c   Ashrafulla, H S ^d   Rai, Lokanath ^a   Souza, Cletus Jmd' ^a   Shekhar, M A ^b,e   Vishwanath, Bannikuppe S ^a  

^a UNIVERSITY OF MYSORE   (India)

^b Apoorva Diabetes Foundation Centre for Diabetes Care and Research   (India)

^c UNIVERSITY OF MYSORE   (India)

^d Volvox Technologies   (India)

^e MYSORE MEDICAL COLLEGE AND RESEARCH INSTITUTE   (India)

Author keywords

6 fatty acid esters of l ascorbic acid; Anti inflammatory activity; Anti oxidant; Docking; SPLA2

Indexed keywords

ALPHA TOCOPHEROL; ASCORBIC ACID; ASCORBIC ACID DERIVATIVE; PHOSPHOLIPASE A2; THIOCTIC ACID;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO SELECTION; LIPID PEROXIDATION; MOUSE; NONHUMAN; PAW EDEMA;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTIOXIDANTS; ASCORBIC ACID; DRUG EVALUATION, PRECLINICAL; EDEMA; FATTY ACIDS; HEMOLYSIS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIPID PEROXIDATION; MICE; PHOSPHOLIPASES A2, SECRETORY; PROTEIN BINDING; SNAKE VENOMS; STRUCTURE-ACTIVITY RELATIONSHIP;

DABOIA RUSSELLII; NAJA NAJA;

EID: 78449302830     PISSN: 03008177     EISSN: 15734919     Source Type: Journal    
DOI: 10.1007/s11010-010-0561-z     Document Type: Article

References (38)

1. 2 structure/function, mechanism, and signaling. J Lipid Res 50 Suppl: S237-S242
2. 2 Prostaglandins Leukot Essent Fatty Acids 69 87 97 1:CAS:528:DC%2BD3sXlvVKjsLY%3D 10.1016/S0952- 3278(03)00069-3 12895591
3. 2-IIA and ROS generation in peripheral mitochondria are critical for neuronal death Brain Res 1153 43 51 1:CAS:528:DC%2BD2sXlvVyisLo%3D 10.1016/j.brainres.2007.03. 067 17462609
4. 2, lipoxygenase metabolites, and reactive oxygen species BMB Rep 41 555 559 1:CAS:528:DC%2BD1cXhtFSnur%2FJ 18755069
5. K Imai T Aimoto T Shima T Nakashima M Sato R Kimura 2000 Alteration in membrane fluidity of rat liver microsomes and of liposomes by protoporphyrin and its anti-lipid peroxidative effect Biol Pharm Bull 23 415 419 1:CAS:528:DC%2BD3cXisVagsL4%3D 10784419
6. 2, reactive oxygen species, and lipid peroxidation in cerebral ischemia Free Radic Biol Med 40 376 387 1:CAS:528:DC%2BD28XovVShsQ%3D%3D 10.1016/j.freeradbiomed. 2005.08.044 16443152
7. 2 Blood 110 3407 3416 1:CAS:528:DC%2BD2sXht1yqurvN 10.1182/blood-2007-04-085845 17666570
8. 2-induced oxidative stress on antioxidant enzyme activities Free Radic Res 43 340 347 1:CAS:528:DC%2BD1MXjvFOnt7w%3D 10.1080/10715760902751894 19212855
9. JN Keller MP Mattson 1998 Roles of lipid peroxidation in modulation of cellular signaling pathways, cell dysfunction, and death in the nervous system Rev Neurosci 9 105 116 1:STN:280:DyaK1cznsFOhsg%3D%3D 9711902
10. K Uchida M Shiraishi Y Naito Y Torii Y Nakamura T Osawa 1999 Activation of stress signaling pathways by the end product of lipid peroxidation. 4-hydroxy-2-nonenal is a potential inducer of intracellular peroxide production J Biol Chem 274 2234 2242 1:CAS:528:DyaK1MXovVGlsg%3D%3D 10.1074/jbc.274.4.2234 9890986
11. 2, reactive oxygen species, and lipid peroxidation in CNS pathologies BMB Rep 41 560 567 1:CAS:528:DC%2BD1cXhtFSnur%2FK 18755070
12. 2 and a designed peptide Leu-Ala-Ile-Tyr-Ser (LAIYS) Acta Crystallogr D Biol Crystallogr 58 Pt 10 Pt 2 1813 1819 10.1107/S0907444902013720 12351825
13. 2 enzyme by bilirubin: a new role as endogenous anti-inflammatory molecule Mol Cell Biochem 276 219 225 1:CAS:528:DC%2BD2MXnsl2htrc%3D 10.1007/s11010-005-4441-x 16132704
14. 2 by retinoids and flavonoids. Mechanism of action Agents Actions 25 394 400 1:CAS:528:DyaL1MXitVekug%3D%3D 10.1007/BF01965048 3218613
15. NM Jameel MA Shekhar BS Vishwanath 2006 Alpha-lipoic acid: an inhibitor of secretory phospholipase A2 with anti-inflammatory activity Life Sci 80 146 153 1:CAS:528:DC%2BD28Xht12ktbzN 10.1016/j.lfs.2006.08.032 17011589
16. J Mandl A Szarka G Bánhegyi 2009 Vitamin C: update on physiology and pharmacology Br J Pharmacol 157 1097 1110 1:CAS:528:DC%2BD1MXhtVelt7nO 10.1111/j.1476-5381.2009.00282.x 19508394
17. QX Song DZ Wei WY Zhou WQ Xu SL Yang 2004 Enzymatic synthesis and antioxidant properties of l-ascorbyl oleate and l-ascorbyl linoleate Biotechnol Lett 26 1777 1780 1:CAS:528:DC%2BD2MXntF2qsw%3D%3D 10.1007/s10529-004-4607-8 15672213
18. 2 inhibition and neutralization of free radicals by anti-oxidants-a new role as anti-inflammatory molecule Curr Top Med Chem 7 765 777 1:CAS:528: DC%2BD2sXlvVGqurc%3D 10.2174/156802607780487623 17456040
19. J Takebayashi A Tai E Gohda I Yamamoto 2006 Characterization of the radical-scavenging reaction of 2-O-substituted ascorbic acid derivatives, AA-2G, AA-2P, and AA-2S: a kinetic and stoichiometric study Biol Pharm Bull 29 766 771 1:CAS:528:DC%2BD28XkslOit7g%3D 10.1248/bpb.29.766 16595915
20. Q Fang KA Naidu KA Naidu H Zhao M Sun HC Dan A Nasir HE Kaiser JQ Cheng SV Nicosia D Coppola 2006 Ascorbyl stearate inhibits cell proliferation and tumor growth in human ovarian carcinoma cells by targeting the PI3K/AKT pathway Anticancer Res 26 203 209 1:CAS:528:DC%2BD28Xhs1aht7w%3D 16475700
21. CC Raymond AS Paul R Carl hoseney WD Charles YL Yun WL Donold 1977 Synthesis of 6-fatty acid esters of l-ascorbic acid J Am Oil Chem Soc 54 308 312 10.1007/BF02672431
22. MS Blois 1957 Antioxidant determination by the use of a stable free radical Nature 181 1199 1200 10.1038/1811199a0
23. Halliwell B, Gutteridge JMC (1989) Free radicals in Biology and Medicine, 2nd edn. Clarendon Press, Oxford
24. 2 from synovial fluid in rheumatoid arthritis J Biochem 100 1297 1303 1:CAS:528:DyaL2sXks1WksA%3D%3D 2434471
25. 2 from Russell's viper (Vipera russelli) venom Toxicon 27 229 237 1:CAS:528:DyaL1MXhsV2mt7k%3D 10.1016/0041-0101(89)90136-0 2718191
26. 2 from Indian cobra (Naja naja) venom Toxicon 36 921 932 10.1016/S0041-0101(97)00097-4
27. P Patriarca S Beckerdite P Elsbach 1972 Phospholipases and phospholipid turnover in Escherichia coli spheroplasts Biochim Biophys Acta 260 593 600 1:CAS:528:DyaE38XhsFSrsrw%3D 4623878
28. 2 activity in rats J Clin Invest 92 1974 1980 1:CAS:528:DyaK2cXivVKjsQ%3D%3D 10.1172/JCI116791 8408650
29. HG Boman U Kaletta 1957 Chromatography of rattlesnake venom; a separation of three phosphodiesterases Biochim Biophys Acta 24 619 631 1:CAS:528:DyaG2sXnslaqsA%3D%3D 10.1016/0006-3002(57)90256-1 13436488
30. Yamakawa MM, Hokama NZ (1976) In: A. Ohsaka, K. Hayashi, Y Sawai (eds) Animal, Plant and microbial toxins, vol 1. Plenum press, New York, p 97
31. 2 purified from human synovial fluid and inhibition by aristolochic acid Inflammation 12 549 561 1:CAS:528:DyaL1MXlsFeksA%3D%3D 10.1007/BF00914317 3220517
32. D Mustard DW Ritchie 2005 Docking essential dynamics eigenstructures Proteins 60 269 274 1:CAS:528:DC%2BD2MXlvFCmtbg%3D 10.1002/prot.20569 15981272
33. AT Laurie RM Jackson 2005 Q-SiteFinder: an energy-based method for the prediction of protein-ligand binding sites Bioinformatics 21 1908 1916 1:CAS:528:DC%2BD2MXjsl2ntL0%3D 10.1093/bioinformatics/bti315 15701681
34. 2 in oxidative and inflammatory responses in neurodegenerative diseases J Neurochem 103 1 16 1:CAS:528:DC%2BD2sXhtF2qu7jF 10.1111/j.1471-4159.2007.05003.x 17561938
35. V Weber P Coudert C Rubat E Duroux F Leal J Couquelet 2000 Antioxidant properties of novel lipophilic ascorbic acid analogues J Pharm Pharmacol 52 523 530 1:CAS:528:DC%2BD3cXktVGjtr4%3D 10.1211/0022357001774318 10864140
36. 2 enzymes from habu (Trimeresurus flavoviridis) venom and their interaction with the alkaloid aristolochic acid Toxicon 25 501 515 1:CAS:528:DyaL2sXlsV2qt78%3D 10.1016/0041-0101(87)90286-8 3617087
37. 2: a new insight in down regulation of inflammation Inflammopharmacol 18 25 31 1:CAS:528: DC%2BC3cXpslWhsQ%3D%3D 10.1007/s10787-009-0018-8
38. Virupakshaiah DBM, Chandrakanth K, Rachanagouda P, Prasad H (2007) Computer Aided Docking Studies on Antiviral Drugs for SARS. Proceedings of world academy of science, engineering and technology 24: 307-6884