Mechanistic studies of the anti-ulcerogenic activity and acute toxicity evaluation of dichlorido-copper(II)-4-(2-5-bromobenzylideneamino)ethyl) piperazin-1-ium phenolate complex against ethanol-induced gastric injury in rats

Molecules

Volumn 16, Issue 10, 2011, Pages 8654-8669

  Salga, Muhammad Saleh ^a   Ali, Hapipah Mohd ^a   Abdullah, Mahmood Ameen ^a   Abdelwahab, Siddig Ibrahim ^a   Hussain, Pouya Davish ^a   Hadi, A Hamid A ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

Acute toxicity; Anti ulcer activity; Cytokines; Mechanism; Schiff bases

Indexed keywords

EID: 80054891338     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16108654     Document Type: Article

References (41)

1. Nehad, A. E.; Fadi, M. A.; Nashwa, A. I.; Mohammed, T. E. Synthesis, anti-inflammatory and ulcerogenicity studies of some substituted pyrimido[1, 6-a]azepine derivatives. Eur. J. Med. Chem. 2010, 45, 3147-3154.
2. Emiliano, R. V. R.; Nayrton, F. M. R.; Edith, T. V.; Brinell, A. M.; Mariana, L. F.; Gilberto, S. C.; Marcos, G. S.; David, J. W.; Francisca, C. F. S.; Luzia Kalyne, A. M. L.; et al. Mechanisms involved in the gastroprotective activity of esculin on acute gastric lesions in mice. Chem. Biol. Interact. 2010, 188, 246-254.
3. Mary, C. B.; Mary, A. F. Pharmacologic management of common gastrointestinal health problems in women. M. Ann. J. Nurse-Midwifery 1997, 42, 145-162.
4. Francesco, B.; Carmen, A.; Savina, F.; Anna, F. R.; Marcello, L.; Nicola, A. C.; Mauro, N.; Roberto, P. Novel 4-(4-aryl) cyclohexyl-1-(2-pyridyl) piperazines as Δ8-Δ7 sterol isomerase (EmopamilBinding Protein) selective ligands with antiproliferative activity. J. Med. Chem. 2008, 51, 7523-7531.
5. Dai, N.; Taketoshi, O.; Takaaki, I.; Kazuaki, T.; Shigeyuki, C.; Shigeru, O.; Atsuro, N. Novel piperazines: Potent melanocortin-4 receptor antagonists with anxiolytic-like activity. Bioorg. Med. Chem. 2007, 15, 2375-2385.
6. Christian, G.; Ivano, T.; Ursula, R. Structural and energetic properties of organometallic ruthenium (II) diamine anticancer compounds and their interaction with nucleobases. J. Chem. Theor. Comput. 2007, 3, 1212-1222.
7. Alka, B.; Komal, S.; Abhishek, B.; Suman, B.; Dinesh, R.; Anant, S.; Anil, K. Synthesis, evaluation and computational studies on a series of acetophenone based 1-(aryloxypropyl)-4-(chloroaryl) piperazines as potential atypical antipsychotics. Eur. J. Med. Chem. 2010, 45, 2656-2662.
8. Shreelekha, A.; Vivek, B.; Di, C.; Fakhara, A.; Ping Dou, Q.; Subhash, P.; Fazlul, H. S. Novel, Schiff base copper complexes of quinoline-2- carboxaldehyde as proteasome inhibitors in human prostate cancer cell. J. Med. Chem. 2006, 49, 7242-7246.
9. Deepa, S.; Anjani, K. T.; Sweta, S.; Gauri, S.; Pushpa, M.; Harish, C.; Anil, K. M. Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde. Eur. J. Med. Chem. 2008, 43, 160-165.
10. Marijana, H.; Kristina, S.; Sandra, K. P.; Pero, L.; Kresimir, P.; Grace, K. Z. Synthesis, spectroscopic characterization and antiproliferative evaluation in vitro of novel Schiff bases related to benzimidazoles. Eur. J. Med. Chem. 2011, 46, 2274-2279.
11. Narendra Sharath Chandra, J. N.; Sadashiva, C. T.; Kavitha, C. V.; Rangappa, K. S. Synthesis and in vitro antimicrobial studies of medicinally important novel N-alkyl and N-sulfonyl derivatives of 1-[bis (4-fluorophenyl)-methyl]piperazine. Bioorg. Med. Chem. 2006, 14, 6621-6627. (Pubitemid 44233306)
12. Marijana, H.; Kristina, S.; Sandra, K. P.; Pero, L.; Kresimir, P.; Grace, K. Z. Acute effects of carprofen and meloxicam on canine gastrointestinal permeability and mucosal absorptive capacity. J. Vet. Int. Med. 2007, 21, 917-923.
13. Sadashiva, C. T.; Narendra, S. C. J. N; Ponnappa, K. C; Veerabasappa, G. T.; Rangappa, K. S. Synthesis and efficacy of 1-[bis (4-fluorophenyl)-methyl] piperazine derivatives for acetylcholinesterase inhibition, as a stimulant of central cholinergic neurotransmission in Alzheimer's disease. Bioorg. Med. Chem. Lett. 2006, 16, 3932-3936. (Pubitemid 44425197)
14. Elena, C.; Carmen, A.; Manuel, M.; Marta, G.; Javier, B.; Julian, G. R.; Javier, F. (Pyridylcyanomethy1) piperazines as orally active PAF antagonists. J. Med. Chem. 1992, 35, 4118-4134.
15. Wafa, S.; Nawal, S.; Nathalie, D. B.; Georges, D.; Pascal, C.; Francoise, H. Structure-activity relationships in platelet-activating factor. Part 14: Synthesis and biological evaluation of piperazine derivatives with dual anti-PAF and anti-HIV-1 activity. Bioorg. Med. Chem. 2006, 14, 7999-8013.
16. Guo-Dong, L.; Jian-Pie, L.; Sha-Sheng, H.; Guo-Li, S.; Ru-Qin, Y. Fluorescence spectral study of interaction of water-soluble metal complexes of Schiff-base and DNA. Anal. Sci. 2001, 17, 1031-1036.
17. Neelam, B.; Shailendra, M. T.; Gonzalez, G.; Delia, E. C.; Castro-Garza, J.; Kishwar, S.; Fehmida, N.; Mannar, R. M.; Amir, A. Synthesis, characterization and antiamoebic activity of benzimidazole derivatives and their vanadium and molybdenum complexes. Bioorg. Med. Chem. Lett. 2002, 12, 869-871. (Pubitemid 34214963)
18. Fischer, W. F. F.; L'Abbe, M. R. Copper transport by intestinal brush border membrane vesicles from rats fed high zinc or copper deficient diets. Nutr. Res. 1985, 5, 759-767. (Pubitemid 15048873)
19. Frausto da Silva, J. J. R.; William, R. J. P. The Biological Chemistry of the Elements; Clarendon: Oxford, UK, 1991.
20. Lippard, S. J.; Berg, J. M. Principles of Bioinorganic Chemistry; University Science Books: Mill Valley, CA, USA, 1994.
21. Kraatz, H. B.; Metzler-Nolte, N. Concepts and Models in Bioinorganic Chemistry; Wiley-VCH: Weinheim, Germany, 2006.
22. Darrell, R. V. C.; Priscilla, U. S. Zinc interference with copper absorption in rats. J. Nutr. 1967, 91, 473.
23. L'Abbé, M. R.; Fischer, W. F. F. The effects of high dietary zinc and copper deficiency on the activity of copper-requiring metalloenzymes in the growing rat. J. Nutr. 1984, 114, 813-822. (Pubitemid 14118307)
24. Donna, B.; Micheal, H. Clinical conditions altering copper metabolism in humans. Am. J. Clin. Nutr. 1998, 67, 1017-1021.
25. Yasuhiro, N.; Byung-Eun, K.; Dennis, J. T. Control drives intestinal copper absorption and is essential for growth, iron metabolism, and neonatal cardiac function. Cell Metab. 2006, 4, 235-244.
26. Joseph, R. P. Changes in tissue growth, concentrations of copper, iron, cytochrome oxidase and superoxide dismutase subsequent to dietary or genetic copper deficiency in mice. J. Nutr. 1983, 113, 2148-2158.
27. Danks, D. M. Copper deficiency in humans. Annu. Rev. Nutr. 1988, 8, 235-257. (Pubitemid 19136326)
28. Loren, L.; Koji, T.; Andrzej, T. Reviews in basic and clinical gastroenterology Gastric mucosal defense and cytoprotection: Bench to bedside. Gastroenterology 2008, 135, 41-60.
29. Jong-il, C.; Hanumatha, R. B. R.; Nak-Yun, S.; Jae-Hun, K.; Byeong, S. C.; Dong, H. A.; Hong-Seok, C.; Keon-Wook, K; Ju-Woon, L. Effect of fucoidan on aspirin-induced stomach ulceration in rats. Chem. Biol. Interact. 2010, 183, 249-254.
30. Kryger, G.; Harel, M.; Giles, K.; Toker, L.; Velan, B.; Lazar, A.; Kronman, C.; Barak, D.; Ariel, N.; Shafferman, A.; et al. Structures of recombinant native and E202Q mutant human acetylcholinesterase complexed with the snake-venom toxin fasciculin-II. Acta Crystallogr. D Biol. Crystallogr. 2000, 56, 1385-1394.
31. Sandor, S. Mechanisms of mucosal injury in the stomach and duodenum: time-sequence analysis of morphologic, functional, biochemical and histochemical studies. Scand. J. Gastroenterol. 1987, 22, 21-28.
32. Bo-Sheng, Q.; Qi-Bing, M.; Li, L.; Kam-Meng, T. W. Effects of nitric oxide on gastric ulceration induced by nicotine and cold-restraint stress. World J. Gastroenterol. 2004, 10, 594-597.
33. Mahmoud, M. K.; Mohamed, Z. G.; Dalaal, A. Protective role of nitric oxide in indomethacininduced gastric ulceration by a mechanism independent of gastric acid secretion. Pharmacol. Res. 2001, 43, 463-467.
34. Dixon W. J. Design and Analysis of Quantal Dose-Response Experiments (with Emphasis on Staircase Designs); Dixon Statistical Associates: Los Angeles, CA, USA, 1991.
35. Mansoor, S. A.; Ageel, A. M.; Parmar, N. S. Tariq, M. Evaluation of mastic, a crude drug obtained from Pistacia lentiscus for gastric and duodenal anti-ulcer activity. J. Ethnopharmacol. 1986, 15, 271-278. (Pubitemid 16082456)
36. Jenna, G. W.; Anthony, B. S.; Blikslager, T.; Kathleen, A.; Ryan, B. S.; Steve, L. M.; Mac, L.; Duncan, B.; Lascelles, X. Cyclooxygenase expression and prostanoid production in pyloric and duodenal mucosae in dogs after administration of nonsteroidal anti-inflammatory drugs. Am. J. Vet. Res. 2008, 69, 457-464.
37. Njar, V. C. O.; Adesanwo, J. K.; Raji, Y. Methyl Angolenate: The Antiulcer Agent from the Stem Bark of Entandrophragmaangolense. Planta Med. 1995, 61, 91-91.
38. Ota, H.; Katsuyama, T.; Ishii, K.; Nakayama, J.; Shiozawa, T.; Tsukahara, Y. A dual staining method for identifying mucins of different gastric epithelial mucous cells. J. Histochem. 1991, 23, 22-28.
39. Sripanidkulchai, K.; Teepsawang, S.; Sripanidkulchai, B. Protective effect of cratoxylumformosum extract against acid/alcohol-induced gastric mucosal damage in rats. J. Med. Food 2010, 13, 1097-1103.
40. Anderson, L. F.; Maira, C. M.; Victor, B.; Clelia, A. H. L.; Wagner, V.; Alba, R. M. S. B. Should Anacardiumhumile St. Hil be used as an antiulcer agent? A scientific approach to the traditional knowledge. Fitoterapia 2008, 79, 207-209.
41. Adami, H. O.; Bergstrom, R.; Mohner, M.; Zatooski, W.; Storm, H.; Ekbom, A.; Rahu, M. Testicular cancer in nine northern European countries. Int. J. Cancer 1994, 59 33-38.