Bimolecular interaction of argpyrimidine (a Maillard reaction product) in in vitro non-enzymatic protein glycation model and its potential role as an antiglycating agent

International Journal of Biological Macromolecules

Volumn 102, Issue , 2017, Pages 1274-1285

  Bhattacherjee, Abhishek ^a,b   Dhara, Kaliprasanna ^a   Chakraborti, Abhay Sankar ^a  

^a UNIVERSITY OF CALCUTTA   (India)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Advanced glycation end products; Antiglycation; Argpyrimidine; Maillard reaction

Indexed keywords

ADVANCED GLYCATION END PRODUCT; ARGPYRIMIDINE; BOVINE SERUM ALBUMIN; GLUCOSE; UNCLASSIFIED DRUG; ORNITHINE; PYRIMIDINE DERIVATIVE;

ARTICLE; CHROMATOGRAPHY; IN VITRO STUDY; MOLECULAR INTERACTION; MOLECULAR MODEL; PROTEIN BINDING; PROTEIN GLYCOSYLATION; PROTEIN PURIFICATION; SPECTROSCOPY; ANALOGS AND DERIVATIVES; CHEMISTRY; DRUG EFFECTS; GLYCATION; GLYCOSYLATION; METABOLISM;

GLUCOSE; GLYCATION END PRODUCTS, ADVANCED; GLYCOSYLATION; MAILLARD REACTION; ORNITHINE; PYRIMIDINES; SERUM ALBUMIN, BOVINE;

EID: 85018890766     PISSN: 01418130     EISSN: 18790003     Source Type: Journal    
DOI: 10.1016/j.ijbiomac.2017.04.108     Document Type: Article

References (39)

1. Vhangani, L.N., Wyk, J.V., Antioxidant activity of Maillard reaction products (MRPs) derived from fructose–lysine and ribose–lysine model systems. Food Chem. 137 (2013), 92–98.
2. Bhattacherjee, A., Hrynets, Y., Betti, M., Fructosazine, a polyhydroxyalkylpyrazine with antimicrobial activity: mechanism of inhibition against extremely heat resistant Escherichia coli. J. Agric. Food Chem. 64 (2016), 8530–8539.
3. 2+)-catalyzed glucosamine browning at 50 °C: identification and quantification of major flavor compounds for antibacterial activity. J. Agric. Food Chem. 4 (2016), 3266–3275.
4. Coca, M., Garcia, M.T., Gonzales, G., Pena, M., Garcia, J., A study of coloured components formed in sugar beet processing. Food Chem. 86 (2004), 421–433.
5. Padival, A.K., Crabb, J.W., Nagaraj, R.H., Methylglyoxal modifies heat shock protein 27 in glomerular mesangial cells. FEBS Lett. 551 (2003), 113–118.
6. Nemet, I., Defterdarovic, L.V., Turk, Z., Methylglyoxal in food and living organisms. Mol. Nutr. Food Res. 50 (2006), 1105–1117.
7. Henle, T., AGEs in foods: do they play a role in uremia?. Kidney Int. 63 (2003), S145–S147.
8. Wilker, S.C., Chellan, P., Arnold, B.M., Nataraj, R.H., Chromatographic quantification of argpyrimidine, a methylglyoxal derived product in tissue protein: comparisons with pentosidine. Anal. Biochem. 290 (2001), 353–358.
9. Uribarri, J., Cai, W., Sandu, O., Peppa, M., Goldberg, T., Vlassara, H., Diet-derived advanced glycation end products are major contributors to the body's AGE po,l and induce inflammation in healthy subjects. Ann. N. Y. Acad. Sci. 1043 (2005), 461–466.
10. Gomes, R., Silva, M.S., Quintas, A., Cordeiro, C., Freire, A., Pereira, P., Martins, A., Monteiro, E., Barroso, E., Freire, A.P., Argpyrimidine, a methylglyoxal-derived advanced glycation end-product in familial amyloidotic polyneuropathy. Biochem. J. 385 (2005), 339–345.
11. Sreejayan, N., Yang, X., Palanichamy, K., Dolence, K., Ren, J., Antioxidant properties of argpyrimidine. Eur. J. Pharmacol. 593 (2008), 30–35.
12. Benjakul, S., Lertittikul, W., Bauer, F., Antioxidant activity of Maillard reaction products from a porcine plasma protein–sugar model system. Food Chem. 93 (2005), 189–196.
13. 2+) form. Int. J. Biol. Macromol. 48 (2011), 202–209.
14. Ruhs, S., Nass, N., Bartling, B., Bromme, H.J., Leuner, B., Somoza, V., Friess, U., Silber, R.E., Simm, A., Preconditioning with Maillard reaction products improves antioxidant defense leading to increased stress tolerance in cardiac cells. Exp. Gerontology 45 (2010), 752–762.
15. Bhattacherjee, A., Dhara, K., Chakraborti, A.S., Argpyrimidine-tagged rutin-encapsulated biocompatible (ethylene glycol dimers) nanoparticles: synthesis, characterization and evaluation for targeted drug delivery. Int. J. Pharm. 509 (2016), 507–517.
16. Wu, J.W., Hsieh, C.L., Wang, H.Y., Chen, H.Y., Inhibitory effects of guava (Psidium guajava L.) leaf extracts and its active compounds on the glycation process of protein. Food Chem. 113 (2009), 78–84.
17. Trinder, P., Determination of blood glucose using 4-amino phenazone as oxygen acceptor. J. Clin. Patho., 22, 1969, 246.
18. Geraci, G., Parkhurst, L.J., Circular dichroism spectra of hemoglobins. Methods Enzymol. 76 (1981), 262–275.
19. Benjakul, S., Kittiphattanabawon, P., Shahidi, F., Maqsood, S., Antioxidant activity and inhibitory effects of lead (Leucaena leucocephala) seed extracts against lipid oxidation in model systems. Food Sci. Technol. Int. 19 (2013), 365–376.
20. Morris, G.M., Goodsell, D.S., Halliday, R.S., Huey, R., Hart, W.E., Belew, R.K., Olson, A.J., Automatic docking using a Lamarckian genetic alogarithm and an empirical binding free energy function. J. Comput. Chem. 19 (1998), 1639–1662.
21. Laskowski, R.A., MacArthur, M.W., Moss, D.S., Thornton, J.M., PROCHEK: a program to check the stereochemical quality of protein structures. J. Appl. Cryst. 26 (1993), 283–291.
22. Bose, T., Bhattacherjee, A., Banerjee, S., Chakraborti, A.S., Methylglyoxal-induced modifications of hemoglobin: structural and functional characteristics. Arch. Biochem. Biophys. 529 (2013), 99–104.
23. Banfi, D., Patiny, L., Resurrecting and processing NMR spectra on-line. Chimia 62 (2008), 280–281.
24. Bhattacherjee, A., Chakraborti, A.S., Inhibitory effect of piper betle Linn. leaf extract on protein glycation −quantification and characterization of the antiglycation components. Ind. J. Biochem. Biophys. 50 (2013), 529–536.
25. Wu, C.H., Yen, G.C., Inhibitory effect of naturally occurring flavonoids on the formation of advantage glycation endproducts. J. Agric. Food Chem. 53 (2005), 3167–3173.
26. Wang, J., Sung, B.G., Cao, Y.P., Tian, Y., Protein glycation inhibitory activity of wheat bran feruloyl oligosaccharides. Food Chem. 112 (2009), 350–353.
27. Roy, A., Sil, R., Chakraborti, A.S., Non-enzymatic glycation induced structural modifications of myoglobin. Mol. Cell. Biochem. 338 (2010), 105–114.
28. Banerjee, S., Chakraborti, A.S., In vitro study on structural alteration of myoglobin by methylglyoxal. Protein J. 32 (2003), 216–222.
29. Bose, T., Chakraborti, A.S., Fructose-induced structural and functional modifications of hemoglobin: implication for oxidative stress in diabetes mellitus. Biochim. Biophys. Acta 1780 (2008), 800–808.
30. Nacharaju, P., Acharya, S., Amadori rearrangement potential of hemoglobin at its glycation sites is dependent on the three-dimensional structure of protein. Biochemistry 31 (1992), 12673–12679.
31. Peng, X., Cheng, K.W., Ma, J., Chen, B., Ho, C.T., Lo, C., Chen, F., Wang, M., Cinnamon bark proanthocyanidins as reactive carbonyl scavengers to prevent the formation of advanced glycation endproducts. J. Agric. Food Chem. 56 (2008), 1907–1911.
32. Hu, T.Y., Liu, C.L., Chyau, C.C., Hu, M.L., Trapping of methylglyoxal by curcumin in cell-free systems and in human umbilical vein endothelial cells. J. Agric. Food Chem. 60 (2012), 8190–8196.
33. Osuna, A.I.L., Clamont, G.R., Moreno, L.V., Characterization of bovine serum albumin glycated with glucose, galactose and lactose. Acta. Biochem. Polonica 55 (2008), 491–497.
34. Zieman, S., Kass, D., Advanced glycation end product crosslinking pathophysiologic role and therapeutic target in cardiovascular disease. Congest. Heart Fail. 10 (2004), 144–149.
35. Ahmed, N., Babaei-Jadidi, R., Howell, S.K., Beisswenger, P.J., Thornalley, P.J., Degradation products of proteins damaged by glycation, oxidation and nitration in clinical type 1 diabetes. Diabetologia 48 (2005), 1590–1603.
36. Vlassara, H., Striker, G., Glycotoxins in the diet promote diabetes and diabetic complications. Curr. Diab. Rep. 7 (2007), 235–241.
37. Cho, S.J., Roman, G., Yeboah, F., Konishi, Y., The road to advanced glycation end products: a mechanistic perspective. Curr. Med. Chem. 14 (2007), 1653–1671.
38. Valgimigli, L., Banks, J.T., Lusztyk, J., Ingold, K.U., Solvent effects on the antioxidant activity of vitamin E. J. Org. Chem. 64 (1999), 3381–3383.
39. Pratt, D.A., DiLabio, G.A., Brigati, G., Pedulli, G., Valgimigli, L., 5-Pyrimidinols: novel chain-breaking antioxidants more effective than phenols. J. Am. Chem. Soc. 123 (2001), 4625–4626.