Novel curcumin-based pyrano[2,3-d]pyrimidine anti-oxidant inhibitors for α-amylase and α-glucosidase: Implications for their pleiotropic effects against diabetes complications

International Journal of Biological Macromolecules

Volumn 78, Issue , 2015, Pages 46-55

  Yousefi, Afsoon ^a   Yousefi, Reza ^a   Panahi, Farhad ^a   Sarikhani, Samira ^a   Zolghadr, Amin Reza ^a   Bahaoddini, Aminollah ^a   Khalafi Nezhad, Ali ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Anti diabetic compounds; Curcumin; Multi component reaction; Reactive oxygen species; Glucosidase

Indexed keywords

7 (4 HYDROXY 3 METHOXYSTYRYL) 5 (4 CHLOROPHENYL) 6 [3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLOYL] 1H PYRANO[2,3 D]PYRIMIDINE 2,4(3H,5H)DIONE; 7 (4 HYDROXY 3 METHOXYSTYRYL) 6 [3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLOYL] 5 (1H INDOL 3 YL) 1H PYRANO[2,3 D]PYRIMIDINE 2,4(3H,4H)DIONE; 7 (4 HYDROXY 3 METHOXYSTYRYL) 6 [3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLOYL] 5 (3 NITROPHENYL) 1H PYRANO[2,3 D]PYRIMIDINE 2,4(3H,4H)DIONE; 7 (4 HYDROXY 3 METHOXYSTYRYL) 6 [3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLOYL] 5 PHENYL 1H PYRANO[2,3 D]PYRIMIDINE 2,4(3H,4H)DIONE; ACARBOSE; ALPHA GLUCOSIDASE; AMYLASE; ANTIOXIDANT; CURCUMIN; PYRANO[2,3 D]PYRIMIDINE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; ANTIDIABETIC AGENT; ENZYME INHIBITOR; PYRIMIDINE; REACTIVE OXYGEN METABOLITE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIDIABETIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYSTALLIZATION; DENSITY FUNCTIONAL THEORY; DIABETES MELLITUS; DRUG STRUCTURE; ENZYME ASSAY; ENZYME INHIBITION; INSULIN SYNTHESIS; NONHUMAN; PLEIOTROPY; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ENZYME ACTIVATION; HUMAN; IC50; METABOLISM;

CURCUMA LONGA;

ALPHA-AMYLASES; ALPHA-GLUCOSIDASES; ANIMALS; ANTIOXIDANTS; CURCUMIN; ENZYME ACTIVATION; ENZYME INHIBITORS; HUMANS; HYPOGLYCEMIC AGENTS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIMIDINES; RATS; REACTIVE OXYGEN SPECIES;

EID: 84927609289     PISSN: 01418130     EISSN: 18790003     Source Type: Journal    
DOI: 10.1016/j.ijbiomac.2015.03.060     Document Type: Article

References (66)

1. Baynes J.W., Thorpe S.R. Diabetes 1999, 48:1-9.
2. Lee H.B., Ha H., King G.L. J. Am. Soc. Nephrol. 2003, 14:S209-S210.
3. Callaghan M.J., Ceradini D.J., Gurtner G.C. Antioxid. Redox. Signal 2005, 7:1476-1482.
4. Rolo A.P., Palmeira C.M. Toxicol. Appl. Pharmacol. 2006, 212:167-178.
5. Sesti F., Tsitsilonis O.E., Kotsinas A., Trougakos I.P. In Vivo 2012, 26:395-402.
6. Basta G., Schmidt A.M., De Caterina R. Cardiovasc. Res. 2004, 63:582-592.
7. Maritim A., Sanders R., Watkins r.J. J. Biochem. Mol. Toxicol. 2003, 17:24-38.
8. Kajaria D., Ranjana J.T., Tripathi Y.B., Tiwari S. J. Adv. Pharm. Technol. Res. 2013, 4:206.
9. Kuppusamy A., Muthusamy U., Andichetiar Thirumalaisamy S., Varadharajan S., Ramasamy K., Ramanathan S. J. Complement Integr. Med. 2011, 8.
10. Senger M.R., Gomes L.d.C.A., Ferreira S.B., Kaiser C.R., Ferreira V.F., Silva F.P. ChemBioChem 2012, 13:1584-1593.
11. Bachhawat J.A., Shihabudeen M.S., Thirumurugan K. Int. J. Pharm. Pharm. Sci. 2011, 3.
12. Standl E., Schnell O. Diab. Vasc. Dis. Res. 2012, 9:163-169.
13. Zhang L., Hogan S., Li J., Sun S., Canning C., Zheng S.J., Zhou K. Food Chem. 2011, 126:466-471.
14. Konya H., Miuchi M., Konishi K., Nagai E., Ueyama T., Kusunoki Y., Kimura Y., Nakamura Y., Ishikawa T., Inokuchi C. J. Int. Med. Res. 2009, 37:1904-1912.
15. Yagi S., Drouart N., Bourgaud F., Henry M., Chapleur Y., Laurain-Mattar D. S. Afr. J. Bot. 2013, 84:124-127.
16. Kowluru R.A., Kanwar M. Nutr. Metab. (Lond) 2007, 4:8.
17. Gupta S.C., Patchva S., Aggarwal B.B. AAPS J. 2013, 15:195-218.
18. Du Z.Y., Liu R.R., Shao W.Y., Mao X.P., Ma L., Gu L.Q., Huang Z.S., Chan A.S.C. Eur. J. Med. Chem. 2006, 41:213-218.
19. Li M., Liu Z., Zhang Z., Ma L. Front. Chem. China 2006, 1:227-231.
20. Lin J., Tang Y., Kang Q., Feng Y., Chen A. Br. J. Pharmacol. 2012, 166:2212-2227.
21. Muthenna P., Suryanarayana P., Gunda S.K., Petrash J.M., Reddy G.B. FEBS Lett. 2009, 583:3637-3642.
22. Mahmoud A.A., Nor El-Din A.K.A. J. Biomarkers 2013, 2013:7.
23. Menon V.P., Sudheer A.R. Antioxidant and anti-inflammatory properties of curcumin. The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease 2007, 105-125. Springer.
24. Aziz M.T.A., El-Asmar M.F., Rezq A.M., Wassef M.A.A., Fouad H., Roshdy N.K., Ahmed H.H., Rashed L.A., Sabry D., Taha F.M. Chin. Med. 2014, 9:3.
25. Yousefi R., Alavian-Mehr M.M., Mokhtari F., Panahi F., Mehraban M.H., Khalafi-Nezhad A. J. Enzyme Inhib. Med. Chem. 2013, 28:1228-1235.
26. Aggarwal B.B., Surh Y.J., Shishodia S. The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease 2007, Springer.
27. Panahi F., Yousefi R., Mehraban M.H., Khalafi-Nezhad A. Carbohydr. Res. 2013, 380:81-91.
28. Cortes A., Cascante M., Cardenas M., Cornish-Bowden A. Biochem. J. 2001, 357:263-268.
29. Re R., Pellegrini N., Proteggente A., Pannala A., Yang M., Rice-Evans C. Free Radic. Biol. Med. 1999, 26:1231-1237.
30. Gupta S.C., Prasad S., Kim J.H., Patchva S., Webb L.J., Priyadarsini I.K., Aggarwal B.B. Nat. Prod. Rep. 2011, 28:1937-1955.
31. Qiu X., Du Y., Lou B., Zuo Y., Shao W., Huo Y., Huang J., Yu Y., Zhou B., Du J. J. Med. Chem. 2010, 53:8260-8273.
32. Lenhart J.A., Ling X., Gandhi R., Guo T.L., Gerk P.M., Brunzell D.H., Zhang S. J. Med. Chem. 2010, 53:6198-6209.
33. Li W., Wu W., Yu F., Huang H., Liang X., Ye J. Org. Biomol. Chem. 2011, 9:2505-2511.
34. Safavy A., Raisch K.P., Mantena S., Sanford L.L., Sham S.W., Krishna N.R., Bonner J.A. J. Med. Chem. 2007, 50:6284-6288.
35. Lin L., Shi Q., Nyarko A.K., Bastow K.F., Wu C.C., Su C.Y., Shih C.C.Y., Lee K.H. J. Med. Chem. 2006, 49:3963-3972.
36. Valentini A., Conforti F., Crispini A., De Martino A., Condello R., Stellitano C., Rotilio G., Ghedini M., Federici G., Bernardini S. J. Med. Chem. 2008, 52:484-491.
37. Caruso F., Rossi M., Benson A., Opazo C., Freedman D., Monti E., Gariboldi M.B., Shaulky J., Marchetti F., Pettinari R. J. Med. Chem. 2012, 55:1072-1081.
38. Sagnou M., Benaki D., Triantis C., Tsotakos T., Psycharis V., Raptopoulou C.P., Pirmettis I., Papadopoulos M., Pelecanou M. Inorg. Chem. 2011, 50:1295-1303.
39. Sahu P.K., Sahu P.K., Gupta S.K., Agarwal D.D. Catal. Sci. Technol. 2013, 3:1520-1530.
40. Lal J., Gupta S., Thavaselvam D., Agarwal D. Bioorg. Med. Chem. Lett. 2012, 22:2872-2876.
41. Organic Chemistry-Breakthroughs and Perspectives 2012, 413-476. Wiley-VCH, Weinheim, Germany. K. Ding, L.-X. Dai (Eds.).
42. Toure B.B., Hall D.G. Chem. Rev. 2009, 109:4439-4486.
43. Dömling A. Chem. Rev. 2006, 106:17-89.
44. Khalafi-Nezhad A., Sarikhani S., Shahidzadeh E.S., Panahi F. Green Chem. 2012, 14:2876-2884.
45. Khalafi-Nezhad A., Shahidzadeh E.S., Sarikhani S., Panahi F. J. Mol. Catal. A: Chem. 2013, 379:1-8.
46. Panoutsopoulos G.I., Beedham C. Cell Physiol. Biochem. 2005, 15:89-98.
47. Reuter S., Charlet J., Juncker T., Teiten M.H., Dicato M., Diederich M. Ann. NY Acad Sci 2009, 1171:436-447.
48. López-Lázaro M. Mol. Nutr. Food Res. 2008, 52:S103-S127.
49. Xie L., Li X.-K., Takahara S. Int. Immunopharmacol. 2011, 11:323-330.
50. Funk J.L., Oyarzo J.N., Frye J.B., Chen G., Lantz R.C., Jolad S.D., Sólyom A.M., Timmermann B.N. J. Nat. Prod. 2006, 69:351-355.
51. Sui Z., Salto R., Li J., Craik C., Ortiz de Montellano P.R. Bioorg. Med. Chem. 1993, 1:415-422.
52. Rivera-Espinoza Y., Muriel P. Liver Int. 2009, 29:1457-1466.
53. Mishra S., Palanivelu K. Ann. Indian Acad. Neurol. 2008, 11:13.
54. Punithavathi D., Venkatesan N., Babu M. Br. J. Pharmacol. 2000, 131:169-172.
55. Saleheen D., Ali S.A., Ashfaq K., Siddiqui A.A., Agha A., Yasinzai M.M. Biol. Pharm. Bull. 2002, 25:386-389.
56. Wang N.P., Wang Z.F., Tootle S., Philip T., Zhao Z.Q. Br. J. Pharmacol. 2012, 167:1550-1562.
57. Suryanarayana P., Saraswat M., Mrudula T., Krishna T.P., Krishnaswamy K., Reddy G.B. Invest. Ophthalmol. Vis. Sci. 2005, 46:2092-2099.
58. Chuengsamarn S., Rattanamongkolgul S., Luechapudiporn R., Phisalaphong C., Jirawatnotai S. Diab. Care 2012, 35:2121-2127.
59. Cheppudira B., Fowler M., McGhee L., Greer A., Mares A., Petz L., Devore D., Loyd D.R., Clifford J.L. Expert Opin. Invest. Drugs 2013, 22:1295-1303.
60. Mahmmoud Y.A. Br. J. Pharmacol. 2007, 150:200-208.
61. Aldebasi Y.H., Aly S.M., Rahmani A.H. Int. J. Physiol. Pathophysiol. Pharmacol. 2013, 5:194.
62. Singh U., Barik A., Singh B.G., Priyadarsini K.I. Free Radic. Res. 2011, 45:317-325.
63. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian, Inc., Wallingford, CT, 2004.
64. Butterworth P.J., Warren F.J., Ellis P.R. Starch-Stärke 2011, 63:395-405.
65. Sales P.M., Souza P.M., Simeoni L.A., Magalhães P.O., Silveira D. J. Pharm. Pharm. Sci. 2012, 15:141-183.
66. Hong J., Bose M., Ju J., Ryu J.-H., Chen X., Sang S., Lee M.-J., Yang C.S. Carcinogenesis 2004, 25:1671-1679.