Food-related compounds that modulate expression of inducible nitric oxide synthase may act as its inhibitors

Molecules

Volumn 17, Issue 7, 2012, Pages 8118-8135

  Maldonado Rojas, Wilson ^a   Olivero Verbel, Jesus ^a  

^a UNIVERSIDAD DE CARTAGENA   (Colombia)

Author keywords

Gene expression; Inflammation; Molecular docking; Natural compounds

Indexed keywords

AMINO ACID; ENZYME INHIBITOR; INDUCIBLE NITRIC OXIDE SYNTHASE;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; COMPUTER SIMULATION; DRUG ANTAGONISM; FOOD; IC 50; METABOLISM; REPRODUCIBILITY;

ALLOSTERIC SITE; AMINO ACIDS; BINDING SITES; COMPUTER SIMULATION; ENZYME INHIBITORS; FOOD; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; NITRIC OXIDE SYNTHASE TYPE II; REPRODUCIBILITY OF RESULTS;

EID: 84864590114     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17078118     Document Type: Article

References (91)

1. Day, B.J. Antioxidants as potential therapeutics for lung fibrosis. Antioxid. Redox Signal. 2008, 10, 355-370.
2. Song, F.L.; Gan, R.Y.; Zhang, Y.; Xiao, Q.; Kuang, L.; Li, H.B. Total phenolic contents and antioxidant capacities of selected chinese medicinal plants. Int. J. Mol. Sci. 2010, 11, 2362-2372.
3. Lü, J.M.; Lin, P.H.; Yao, Q.; Chen, C. Chemical and molecular mechanisms of antioxidants: Experimental approaches and model systems. J. Cell Mol. Med. 2010, 14, 840-860.
4. Kamat, C.D.; Gadal, S.; Mhatre, M.; Williamson, K.S.; Pye, Q.N.; Hensley, K. Antioxidants in central nervous system diseases: preclinical promise and translational challenges. J. Alzheimers Dis. 2008, 15, 473-493.
5. Kris-Etherton, P.M.; Hecker, K.D.; Bonanome, A.; Coval, S.M.; Binkoski, A.E.; Hilpert, K.F.; Griel, A.E.; Etherton, T.D. Bioactive compounds in foods: Their role in the prevention of cardiovascular disease and cancer. Am. J. Med. 2002, 113, 71-88.
6. Delcourt, C.; Korobelnik, J.F.; Barberger-Gateau, P.; Delyfer, M.N.; Rougier, M.B.; Le Goff, M.; Malet, F.; Colin, J.; Dartigues, J.F. Nutrition and age-related eye diseases: The alienor (antioxydants, lipides essentiels, nutrition et maladies oculaires) Study. J. Nutr. Health Aging 2010, 14, 854-861.
7. Wang, L.S.; Stoner, G.D. Anthocyanins and their role in cancer prevention. Cancer Lett. 2008, 269, 281-290.
8. Xia, E.Q.; Deng, G.F.; Guo, Y.J.; Li, H.B. Biological activities of polyphenols from grapes. Int. J. Mol. Sci. 2010, 11, 622-646.
9. Heima, K.E.; Tagliaferroa, A.R. Flavonoid antioxidants: Chemistry, metabolism and structureactivity relationships. J. Nutr. Biochem. 2002, 13, 572-584.
10. Hammerstone, J.F.; Lazarus, S.A.; Schmitz, H.H. Procyanidin content and variation in some commonly consumed foods. J. Nutr. 2000, 130, 2086-2092.
11. Nichols, J.A.; Katiyar, S.K. Skin photoprotection by natural polyphenols: Anti-inflammatory, anti-oxidant and DNA repair mechanisms. Arch. Dermatol. Res. 2010, 302, 71-83.
12. Rahman, M.A.; Amin, A.R.; Shin, D.M. Chemopreventive potential of natural compounds in head and neck cancer. Nutr. Cancer 2010, 62, 973-987.
13. Hooper, L.; Kroon, P.A.; Rimm, E.B.; Cohn, J.S.; Harvey, I.; Le Cornu, K.A.; Ryder, J.J.; Hall, W.L.; Cassidy, A. Flavonoids, flavonoid-rich foods, and cardiovascular risk: A meta-analysis of randomized controlled trials. Am. J. Clin. Nutr. 2008, 88, 38-50. (Pubitemid 351988681)
14. Zaslaver, M.; Offer, S.; Kerem, Z.; Stark, A.H.; Weller, J.I.; Eliraz, A.; Madar, Z. Natural compounds derived from foods modulate nitric oxide production and oxidative status in epithelial lung cells. J. Agric. Food Chem. 2005, 53, 9934-9939. (Pubitemid 43081200)
15. Bian, K.; Murad, F. Nitric oxide (NO)-Biogeneration, regulation, and relevance to human diseases. Front. Biosci. 2003, 8, 264-278.
16. Garcin, E.D.; Arvai, A.S.; Rosenfeld, R.J.; Kroeger, M.D.; Crane, B.R.; Andersson, G.; Andrews, G.; Hamley, P.J.; Mallinder, P.R.; Nicholls, D.J.; et al. Anchored plasticity opens doors for selective inhibitor design in nitric oxide synthase. Nat. Chem. Biol. 2008, 4, 700-707.
17. Rosenfeld, R.J.; Garcin, E.D.; Panda, K.; Andersson, G.; Aberg, A.; Wallace, A.V.; Morris, G.M.; Olson, A.J.; Stuehr, D.J.; Tainer, J.A.; et al. Conformational changes in nitric oxide synthases Induced by chlorzoxazone and nitroindazoles: Crystallographic and computational analyses of Inhibitor potency. Biochemistry 2002, 41, 13915-13925. (Pubitemid 35364865)
18. Li, D.; Stuehr, D.J.; Yeh, S.R.; Rousseau, D.L. Heme distortion modulated by ligand-protein interactions in inducible nitric-oxide synthase. J. Biol. Chem. 2004, 279, 26489-26499. (Pubitemid 38798803)
19. Pan, M.H.; Lai, C.S.; Dushenkov, S.; Ho, C.T. Modulation of inflammatory genes by natural dietary bioactive compounds. J. Agric. Food Chem. 2009, 57, 4467-4477.
20. May, A.; Zacharias, M. Accounting for global protein deformability during protein-protein and protein-ligand docking. Biochim. Biophys. Acta 2005, 1754, 225-231. (Pubitemid 41797702)
21. Maldonado, W.; Olivero, J. Potential interaction of natural dietary bioactive compounds with COX-2. J. Mol. Graph. Model. 2011, 30, 157-166.
22. Trott, O. Olson, A.J. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J. Comput. Chem. 2009, 31, 455-461.
23. Feng, R.; Ni, H.M.; Wang, S.Y.; Tourkova, I.L.; Shurin, M.R.; Harada, H.; Yin, X.M. Cyanidin-3-rutinoside, a natural polyphenol antioxidant, selectively kills leukemic cells by induction of oxidative stress. J. Biol. Chem. 2007, 282, 13468-13476. (Pubitemid 47100551)
24. Sarić, A.; Sobocanec, S.; Balog, T.; Kusić, B.; Sverko, V.; Dragović-Uzelac, V.; Levaj, B.; Cosić, Z.; Macak-Safranko, Z.; Marotti, T. Improved antioxidant and anti-inflammatory potential in mice consuming sour cherry juice (Prunus Cerasus cv. Maraska). Plant Foods Hum. Nutr. 2009, 64, 231-237.
25. Yin, F.; Liu, J.; Ji, X.; Wang, Y.; Zidichouski, J.; Zhang, J. Silibinin: A novel inhibitor of Aβ aggregation. Neurochem. Int. 2011, 58, 399-403.
26. Abenavoli, L.; Capasso, R.; Milic, N.; Capasso, F. Milk thistle in liver diseases: Past, present, future. Phytother. Res. 2010, 24, 1423-1432.
27. Cheng, J.C.; Kan, L.S.; Chen, J.T.; Chen, L.G.; Glu, H.C.; Lin, S.M.; Wang, S.H.; Yang, K.H.; Chiou, R.Y. Detection of cyanidin in different-colored peanut testae and identification of peanut cyanidin 3-sambubioside. J. Agric. Food Chem. 2009, 57, 8805-8811.
28. Wang, S.Y.; Chen, C.T.; Sciarappa, W.; Wang, C.Y.; Camp, M.J. Fruit quality, antioxidant capacity, and flavonoid content of organically and conventionally grown blueberries. J. Agric. Food Chem. 2008, 56, 5788-5794.
29. Hosseinian, F.S.; Beta, T. Saskatoon and wild blueberries have higher anthocyanin contents than other Manitoba berries. J. Agric. Food Chem. 2007, 55, 10832-10838.
30. Ichiyanagi, T.; Shida, Y.; Rahman, M.M.; Hatano, Y.; Konishi, T. Bioavailability and tissue distribution of anthocyanins in bilberry (Vaccinium myrtillus L.) extract in rats. J. Agric. Food Chem. 2006, 54, 6578-6587. (Pubitemid 44426931)
31. Kalantari, H.; Das, D.K. Physiological effects of resveratrol. Biofactors 2010, 36, 401-406.
32. Reber, J.D.; Eggett, D.L.; Parker, T.L. Antioxidant capacity interactions and a chemical/structural model of phenolic compounds found in strawberries. Int. J. Food Sci. Nutr. 2011, 62, 445-452.
33. Chen, P.N.; Kuo, W.H.; Chiang, C.L.; Chiou, H.L.; Hsieh, Y.S.; Chu, S.C. Black rice anthocyanins inhibit cancer cells invasion via repressions of MMPs and u-PA expression. Chem. Biol. Interact. 2006, 163, 218-229.
34. Yao, Y.; Sang, W.; Zhou, M.; Ren, G. Phenolic composition and antioxidant activities of 11 celery cultivars. J. Food Sci. 2010, 75, 9-13.
35. Bernardes, W.A.; Lucarini, R.; Tozatti, M.G.; Souza, M.G.; Andrade Silva, M.L.; da Silva Filho, A.A.; Martins, C.H.; Miller Crotti, A.E.; Pauletti, P.M.; Groppo, M.; et al. Antimicrobial activity of Rosmarinus officinalis against oral pathogens: Relevance of carnosica acid and carnosol. Chem. Biodivers. 2010, 7, 1835-1840.
36. Castellarin, S.D.; Di Gaspero, G. Transcriptional control of anthocyanin biosynthetic genes in extreme phenotypes for berry pigmentation of naturally occurring grapevines. BMC Plant Biol. 2007, 30, 7-46.
37. Déziel, B.A.; Patel, K.; Neto, C.; Gottschall-Pass, K.; Hurta, R.A. Proanthocyanidins from the american cranberry (Vaccinium macrocarpon) inhibit matrix metalloproteinase-2 and matrix metalloproteinase-9 activity in human prostate cancer cells via alterations in multiple cellular signaling pathways. J. Cell. Biochem. 2010, 111, 742-754.
38. Wang, P.; Aronson, W.J.; Huang, M.; Zhang, Y.; Lee, R.P.; Heber, D.; Henning, S.M. Green tea polyphenols and metabolites in prostatectomy tissue: Implications for cancer prevention. Cancer Prev. Res. 2010, 3, 985-993.
39. Lehtonen, H.M.; Rantala, M.; Suomela, J.P.; Viitanen, M.; Kallio, H. Urinary excretion of the main anthocyanin in lingonberry (Vaccinium vitis-idaea), Cyanidin 3-O-galactoside, and its metabolites. J. Agric. Food Chem. 2009, 57, 4447-4451.
40. Vasanthi, H.R.; Mukherjee, S.; Das, D.K. Potential health benefits of broccoli- a chemicobiological overview. Mini Rev. Med. Chem. 2009, 9, 749-759.
41. Mullen, W.; Edwards, C.A.; Serafini, M.; Crozier, A.; Bioavailability of pelargonidin-3-Oglucoside and its metabolites in humans following the ingestion of strawberries with and without cream. J. Agric. Food Chem. 2008, 56, 713-719. (Pubitemid 351300235)
42. Rasyid, A.; Rahman, A.R.; Jaalam, K.; Lelo, A. Effect of different curcumin dosages on human gall bladder. Asia Pac. J. Clin. Nutr. 2002, 11, 314-318. (Pubitemid 35464067)
43. Lai, C.S.; Li, S.; Chai, C.Y.; Lo, C.Y.; Ho, C.T.; Wang, Y.J.; Pan, M.H. Inhibitory effect of citrus 5-hydroxy-3,6,7,8,3′,4′- hexamethoxyflavone on 12-O-tetradecanoylphorbol 13-acetate-induced skin inflammation and tumor promotion in mice. Carcinogenesis 2007, 28, 2581-2588. (Pubitemid 350238961)
44. Theodosiou, M.; Laudet, V.; Schubert, M. From carrot to clinic: An overview of the retinoic acid signaling pathway. Cell. Mol. Life Sci. 2010, 67, 1423-1445.
45. Lien, L.T.; Yeh, H.S.; Su, W.T. Effect of adding extracted hesperetin, naringenin and pectin on egg cholesterol, serum traits and antioxidant activity in laying hens. Arch. Anim. Nutr. 2008, 62, 33-43.
46. Alosi, J.A.; McDonald, D.E.; Schneider, J.S.; Privette, A.R.; McFadden, D.W. Pterostilbene inhibits breast cancer in vitro through mitochondrial depolarization and induction of caspasedependent apoptosis. J. Surg. Res. 2010, 161, 195-201.
47. Stuetz, W.; Prapamontol, T.; Hongsibsong, S.; Biesalski, H.K. Polymethoxylated flavones, flavanone glycosides, carotenoids, and antioxidants in different cultivation types of tangerines (Citrus reticulata Blanco cv. Sainampueng) from Northern Thailand. J. Agric. Food Chem. 2010, 58, 6069-6074.
48. Basini, G.; Bussolati, S.; Santini, S.E.; Grasselli, F. The impact of the phyto-oestrogen genistein on swine granulosa cell function. J. Anim. Physiol. Anim. Nutr. (Berl.) 2010, 94, 374-382.
49. Mann, N.J.; O'Connell, S.L.; Baldwin, K.M.; Singh, I.; Meyer, B.J. Effects of seal oil and tuna-fish oil on platelet parameters and plasma lipid levels in healthy subjects. Lipids 2010, 45, 669-681.
50. Weng, C.J.; Wu, C.F.; Huang, H.W.; Ho, C.T.; Yen, G.C. Anti-invasion effects of 6-shogaol and 6-gingerol, two active components in ginger, on human hepatocarcinoma cells. Mol. Nutr. Food Res. 2010, 54, 1618-1627.
51. Visanji, J.M.; Duthie, S.J.; Pirie, L.; Thompson, D.G.; Padfield, P.J. Dietary isothiocyanates inhibit Caco-2 cell proliferation and induce G2/M phase cell cycle arrest, DNA damage, and G2/M checkpoint activation. J. Nutr. 2004, 134, 3121-3126. (Pubitemid 39470094)
52. Vogel, J.T.; Tieman, D.M.; Sims, C.A.; Odabasi, A.Z.; Clark, D.G.; Klee, H.J. Carotenoid content impacts flavor acceptability in tomato (Solanum lycopersicum). J. Sci. Food Agric. 2010, 90, 2233-2340.
53. Muhammad, S.A.; Muhammad, S.; Waqar, A.; Masood, P.; Raghav, Y. Chlorinated monoterpene ketone, acylated β-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae). Phytochemistry 2002, 59, 889-895.
54. Skupinska, K.; Misiewicz-Krzeminska, I.; Lubelska, K.; Kasprzycka-Guttman, T. The effect of isothiocyanates on CYP1A1 and CYP1A2 activities induced by polycyclic aromatic hydrocarbons in Mcf7 cells. Toxicol. In Vitro 2009, 23, 763-771.
55. Thürmann, P.A.; Steffen, J.; Zwernemann, C.; Aebischer, C.P.; Cohn, W.; Wendt, G.; Schalch, W. Plasma concentration response to drinks containing beta-carotene as carrot juice or formulated as a water dispersible powder. Eur. J. Nutr. 2002, 41, 228-235. (Pubitemid 36056321)
56. Burns-Whitmore, B.L.; Haddad, E.H.; Sabaté, J.; Jaceldo-Siegl, K.; Tanzman, J.; Rajaram, S. Effect of n-3 fatty acid enriched eggs and organic eggs on serum lutein in free-living lacto-ovo vegetarians. Eur. J. Clin. Nutr. 2010, 64, 1332-1337.
57. Salado, C.; Olaso, E.; Gallot, N.; Valcarcel, M.; Egilegor, E.; Mendoza, L.; Vidal-Vanaclocha, F. Resveratrol prevents inflammation-dependent hepatic melanoma metastasis by inhibiting the secretion and effects of interleukin-18. J. Transl. Med. 2011, 9, 59.
58. Au, A.Y.; Hasenwinkel, J.M.; Frondoza, C.G. Silybin inhibits interleukin-1β-induced production of pro-inflammatory mediators in canine hepatocyte cultures. J. Vet. Pharmacol. Ther. 2011, 34, 120-129.
59. Mauray, A.; Felgines, C.; Morand, C.; Mazur, A.; Scalbert, A.; Milenkovic, D. Bilberry anthocyanin-rich extract alters expression of genes related to atherosclerosis development in aorta of apo E-deficient mice. Nutr. Metab. Cardiovasc. Dis. 2012, 22, 72-80.
60. Seymour, E.M.; Lewis, S.K.; Urcuyo-Llanes, D.E.; Tanone, I.I.; Kirakosyan, A.; Kaufman, P.B.; Bolling, S.F. Regular tart cherry intake alters abdominal adiposity, adipose gene transcription, and inflammation in obesity-prone rats fed a high fat diet. J. Med. Food. 2009, 5, 935-942.
61. Karlsen, A.; Retterstøl, L.; Laake, P.; Paur, I.; Kjølsrud-Bøhn, S.; Sandvik, L.; Blomhoff, R. Anthocyanins inhibit nuclear factor-kB activation in monocytes and reduce plasma concentrations of pro-Inflammatory mediators in healthy adults. J. Nutr. 2007, 137, 1951-1954. (Pubitemid 47292744)
62. Terashima, M.; Ehara, S.; Yang, E.; Kosuge, H.; Tsao, P.S.; Quertermous, T.; Contag, C.H.; McConnell, M.V. In vivo bioluminescence imaging of inducible nitric oxide synthase gene expression in vascular Inflammation. Mol. Imaging Biol. 2010, 13, 1061-1066.
63. Krieglstein, C.F.; Anthoni, C.; Cerwinka, W.H.; Stokes, K.Y.; Russell, J.; Grisham, M.B.; Granger, D.N. Role of blood- and tissue-associated inducible nitric-oxide synthase in colonic inflammation. Am. J. Pathol. 2007, 170, 490-496. (Pubitemid 47339386)
64. Ramasamy, K.; Dwyer-Nield, L.D.; Serkova, N.J.; Hasebroock, K.M.; Tyagi, A.; Raina, K.; Singh, R.P.; Malkinson, A.M.; Agarwal, R. Silibinin prevents lung tumorigenesis in wild-type but not in iNOS-/- mice: Potential of real-time micro-CT in lung cancer chemoprevention studies. Clin. Cancer Res. 2011, 17, 753-761.
65. Chittezhath, M.; Deep, G.; Singh, R.P.; Agarwal, C.; Agarwal, R. Silibinin inhibits cytokineinduced signaling cascades and down-regulates inducible nitric oxide synthase in human lung carcinoma A549 cells. Mol. Cancer Ther. 2008, 7, 1817-1826.
66. Zikri, N.N.; Riedl, K.M.; Wang, L.S.; Lechner, J.; Schwartz, S.J.; Stoner, G.D. Black raspberry components inhibit proliferation, induce apoptosis, and modulate gene expression in rat esophageal epithelial cells. Nutr. Cancer 2009, 61, 816-826.
67. Jin, X.H.; Ohgami, K.; Shiratori, K.; Suzuki, Y.; Koyama, Y.; Yoshida, K.; Ilieva, I.; Tanaka, T.; Onoe, K.; Ohno, S. Effects of blue honeysuckle (Lonicera caerulea L.) extract on lipopolysaccharide-induced inflammation in vitro and in vivo. Exp. Eye Res. 2006, 82, 860-867. (Pubitemid 43170886)
68. Khan, N., Afaq, F.; Kweon, M.H.; Kim, K.M.; Mukhtar, H. Oral consumption of pomegranate fruit extract inhibits growth and progression of primary lung tumors in mice. Cancer Res. 2007, 67, 3475-3482. (Pubitemid 46724889)
69. Laua, F.C.; Joseph, J.A.; Mcdonald, J.E.; Kalt, W. Attenuation of iNOS and COX-2 by blueberry polyphenols. J. Funct. Foods 2009, 1, 274-283.
70. Pergola, C.; Rossi, A.; Dugo, P.; Cuzzocrea, S.; Sautebin, L. Inhibition of nitric oxide biosynthesis by anthocyanin fraction of blackberry extract. Nitric Oxide 2006, 15, 30-39. (Pubitemid 43963421)
71. Leiroa, J.M.; lvarezb, E.A.; Arranza, J.A.; González Sisoc, I.; Orallob, F. In vitro effects of mangiferin on superoxide concentrations and expression of the inducible nitric oxide synthase, tumour necrosis factor-a and transforming growth factor-b genes. Biochem. Pharmacol. 2003, 65, 1361-1371.
72. Chin, Y.W.; Park, E.Y.; Seo, S.Y.; Yoon, K.D.; Ahn, M.J.; Suh, Y.G.; Kim, S.G.; Kim, J. A novel iNOS and COX-2 inhibitor from the aerial parts of Rodgersia Podophylla. Biol. Med. Chem. Lett. 2006, 16, 4600-4602. (Pubitemid 44094064)
73. Oh, J.H.; Lee, T.J.; Park, J.W.; Kwon, T.K. Withaferin A inhibits iNOS expression and nitric oxide production by Akt inactivation and down-regulating LPS-induced activity of NF-?b in RAW 264.7 cells. Eur. J. Pharmacol. 2008, 599, 11-17.
74. PubChem. Available online: http://pubchem.ncbi.nlm.nih.gov (accessed on 10 January 2011).
75. Cheshire, D.R.; Berg, A.; Andersson, G.M.K.; Andrews, G.; Beaton, H.G.; Birkinshaw, T.N.; Boughton-Smith, N.; Connolly, S.; Cook, T.R.; Cooper, A.; et al. The discovery of novel, potent and highly selective inhibitors of inducible nitric oxide synthase (iNOS). Bioorg. Med. Chem. Lett. 2011, 21, 2468-2471.
76. Bourdonnec, B.L.; Leister, L.K.; Ajello, C.A.; Cassel, J.A.; Seida, P.R.; O'Hare, H.; Gu, M.; Chu, G.-H.; Tuthill, P.A.; DeHaven, R.N.; et al. Discovery of a series of aminopiperidines as novel iNOS inhibitors. Bioog. Med. Chem. Lett. 2008, 18, 336-343.
77. Davey, D.D.; Adler, M.; Arnaiz, D.; Eagen, K.; Erickson, S.; Guilford, W.; Kenrick, M.; Morrissey, M.M.; Ohlmeyer, M.; Pan, G.; et al. Design, synthesis, and activity of 2-imidazol-1-ylpyrimidine derived inducible nitric oxide synthase dimerization inhibitors. J. Med. Chem. 2007, 50, 1146-1157. (Pubitemid 46496315)
78. Nakane, M.; Klinghofer, V.; Kuk, J.E.; Donnelly, J.L.; Budzik, G.P.; Pollock, J.S.; Basha, F.; Carter, G.W. Novel potent and selective inhibitors of inducible nitric oxide synthase. Mol. Pharmacol. 1995, 47, 831-834.
79. Hare, A.A.; Leng, L.; Gandavadi, S.; Du, X.; Cournia, Z.; Bucala, R.; Jorgensen, W.L. Optimization of N-benzyl-benzoxazol-2-ones as receptor antagonists of macrophage migration inhibitory factor (MIF). Bioorg. Med. Chem. Lett. 2010, 20, 5811-5814.
80. RCSB PDB Protein Data Bank. Available online: http://www.pdb.org/pdb/ home/home.do (accessed on 14 February 2011).
81. SYBYL molecular modeling software, Version 8.1. Tripos: St. Louis, MO, USA, 2007.
82. Hwang, Y.P.; Choi, J.H.; Yun, H.J.; Han, E.H.; Kim, H.G.; Kim, J.Y.; Park, B.H.; Khanal, T.; Choi, J.M.; Chung, Y.C.; et al. Anthocyanins from purple sweet potato attenuate dimethylnitrosamine-induced liver injury in rats by inducing Nrf2-mediated antioxidant enzymes and reducing COX-2 and iNOS expression. Food Chem. Toxicol. 2011, 49, 93-99.
83. Li, J.; Shi, R.; Yang, C.; Zhu, X. Exploration of the binding of benzimidazole-biphenyl derivatives to hemoglobin using docking and molecular dynamics simulation. Int. J. Biol. Macromol. 2011, 48, 20-26.
84. Frisch, M.J.; Trucks, G.W.; Schlegel, H.R.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, J.A., Jr.; Vreven, T.; Kudin, K.N.; Burant, J.C.; et al. Gaussian03; Gaussian, Inc.: Pittsburgh, PA, USA, 2003.
85. Guha, R.; Howard, M.T.; Hutchison, G.R.; Murray-Rust, P.; Rzepa, H.; Steinbeck, C.; Wegner, J.K.; Willighagen, E. The blue obelisk-Interoperability in chemical informatics. J. Chem. Inf. Model. 2006, 46, 991-998.
86. Sanner, M.F. Python: A programming language for software integration and development. J. Mol. Graph. Model. 1999, 17, 57-61. (Pubitemid 30029318)
87. Wolber, G.; Langer, T. LigandScout: 3-D pharmacophores derived from protein-bound ligands and their use as virtual screening filters. J. Chem. Inf. Model. 2005, 45, 160-169. (Pubitemid 40736968)
88. DeLano, W.L. The PyMOL Molecular Graphics System; DeLano Scientific LLC: San Carlos, CA, USA, 1998-2003.
89. Connolly, S.; Aberg, A.; Arvai, A.; Beaton, H.G.; Cheshire, D.R.; Cook, A.R.; Cooper, S.; Cox, D.; Hamley, P.; Mallinder, P.; et al. 2-aminopyridines as highly selective inducible nitric oxide synthase inhibitors. Differential binding modes dependent on nitrogen substitution. J. Med. Chem. 2004, 47, 3320-3323. (Pubitemid 38702724)
90. Zhou, Z.; Wang, Y.; Bryant, S.H. Computational analysis of the cathepsin B inhibitors activities through LR-MMPBSA binding affinity calculation based on docked complex. J. Comput. Chem. 2009, 30, 2165-2175.
91. GraphPad Software, Inc. Version 3.06 for Windows. GraphPad Software, Inc.: San Diego, CA, USA, 2003.