Anti-inflammatory activity of 2,5-dihydroxycyclohepta-2,4,6-trienone in rats
详细信息 查看全文
- 作者：Feride Koc (1)
Elif Cadirci (2)
Abdulmecit Albayrak (2)
Zekai Halici (2)
Ahmet Hacimuftuoglu (2)
Halis Suleyman (2) - 关键词：Hyaluronidase ; Tropolone ; Anti ; inflammatory ; Capillary permeability ; Toxicity
- 刊名：Medicinal Chemistry Research
- 出版年：2010
- 出版时间：February 2010
- 年：2010
- 卷：19
- 期：1
- 页码：84-93
- 全文大小：317KB
- 参考文献：1. Arima Y, Nakai Y, Hayakawa R, Nishino T (2003) Antibacterial effect of β-thujaplicin on staphylococci isolated from atopic dermatitis: relationship between changes in the number of viable bacterial cells and clinical improvement in an eczematous lesion of atopic dermatitis. J Antimicrob Chemoth 51:113-22 CrossRef
2. Bagli JF, Bogri T, Palameta B, Martel R, Robinson W, Pugsley T, Lippmann W (1979) Troponoids. 3. Synthesis and antiallergy activity of N-troponyloxamic acid esters. J Med Chem 22:1186-193 CrossRef
3. Budihas SR, Gorshkova I, Gaidamakov S, Wamiru A, Bona MK, Parniak MA, Crouch RJ, McMahon JB, Beutler JA, Le Grice SFJ (2005) Selective inhibition of HIV-1 reverse transcriptase-associated ribonuclease H activity by hydroxylated tropolones. Nucleic Acids Res 33:1249-256 CrossRef
4. Choi Y, Bae E, Kim D, Park S, Kwon S, Na J, Park K (2006) Differential regulation of melanosomal proteins after hinokitiol treatment. J Dermatol Sci 43:181-88 CrossRef
5. Coskun A, Guney M, Dastan A, Balci M (2007) Oxidation of some alkoxy-cycloheptatriene derivatives: unusual formation of furan and furanoids from cycloheptatrienes. Tetrahedron 63:4944-950 CrossRef
6. Dastan A, Balci M (2006) Chemistry of dioxine-annelated cycloheptatriene endoperoxides and their conversion into tropolone derivatives: an unusual non-benzenoid singlet oxygen source. Tetrahedron 62:4003-010 CrossRef
7. Demirezer LO, Kuruuzum-Uz A, Guvenalp Z, Suleyman H (2006) Bioguided fractionation of methanolic extract from / Polygonum alpinum and isolation and structure elucidation of active compounds. Pharm Biol 44:462-66 CrossRef
8. Diouf PN, Delbarre N, Perin D, Gerardin P, Rapin C, Jacquot JP, Gelhaye E (2002) Influence of tropolone on / Poria placenta wood degradation. Appl Environ Microb 68:4377-382 CrossRef
9. Doulias BT, Nousis L, Zhu BZ, Frei B, Galaris D (2004) Protection by tropolones against H2O2-induced DNA damage and apoptosis in cultured Jurkat cells. Free Radical Res 39:125-35 CrossRef
10. Gupta M, Mazumdar UK, Sivakumar T, Vamsi ML, Karki SS, Sambathkumar R, Manikandan L (2003) Evaluation of anti-inflammatory activity of chloroform extract of bryonialaciniosa in experimental animal models. Biol Pharm Bull 26:1342-344 CrossRef
11. Houck JC, Chang CM (1979) Permeability factor contaminating hyaluronidase preparations. Inflammation 3:447-51 CrossRef
12. Inamori Y, Shinohara S, Tsujiho H, Okabe T, Morita Y, Sakagami Y, Kumeda Y, Ishida N (1999) Antimicrobial activity and metalloprotease inhibition of hinokitiol- related compounds, the constituents of Thujopsis dolabrata S. and Z. Hondai MAK. Biol Pharm Bull 22:990-93
13. Kayaalp SO (1998) Medical Pharmacology, in terms of rational treatment [Rasyonel tedavi y?nünden t?bbi farmakoloji]. Hacettepe-Ta?, Ltd., Sti, Ankara
14. Kitamura S, Iida T, Shirahata K, Kase H (1986) Studies on lipoxygenase inhibitors I. MY3-69 (3-methoxytropolone), a potent and selective inhibitor of 12-lipoxygenase, produced by Streptoverticillium hadanonense KY11449. J Antibiot 39:589-93
15. Korth H, Brüsewithz G, Pulverer G (1982) Isolation of antibacterial active tropolone from a / Pseudomonas cepacia strain. Zentralbl Bakteriol Mikrobiol Hjy (A) 252:83-6
16. Lee CP, Hegarty MP, Christie GS (1979) Antithyroid and antiperoxidase activity of tropolone and 3-hydroxy-4-pyrone. Chem Biol Interact 27:17-6 CrossRef
17. Marzocco S, Di Paola R, Serraino I, Sorrentino R, Meli R, Mattaceraso G, Cuzzocrea S, Pinto A, Autore G (2004) Effect of methylguanidine in carrageenan-induced acute inflammation in the rats. Eur J Pharmacol 484:341-50 CrossRef
18. Maslinska D, Gajewski M (1998) Some aspects of the inflammatory process. Folia Neuropathol 36:199-04
19. Miyamato D, Kusagaya Y, Endo N, Sometani A, Takeo S, Suzuki T, Arima Y, Nakajima K, Suzuki Y (1998) Thujaplicin–copper chelates inhibit replication of human influenza viruses. Antivir Res 39:89-00 CrossRef
20. Mori A, Kubo K, Takeshita H (1993) Synthesis of 5-(dicyanomethylene)-2,3-dihydrocyclohepta-1,4-dithiins, and 7-(dicyanomethylene)-2,3-dihydrocyclohepta-1,4-dithiins, “push-pull-heptafulvene derivatives - 8,8-dicyanoheptafulvenes from alpha-bromomalononitrile and cycloheptatrienylium salt. Bull Chem Soc Jpn 66:3742-746 CrossRef
21. Morita Y, Matsumura E, Tsujibo H, Yasuda M, Okabe T, Sakagami Y, Kumeda Y, Ishida N, Inamori Y (2002) Biological activity of 4-acetyltropolone, the minor component of / Thujopsis dolabrata SIEB. et ZUCC. Hondai MAKINO. Biol Pharm Bull 25:981-85 CrossRef
22. Morita Y, Matsumura E, Okabe T, Fukui T, Ohe T, Ishida N, Inamori Y (2004a) Biological activity of β-dolabrin, γ-thujaplicin, and 4-acetyltropolone, hinokitiol-related compounds. Biol Pharm Bull 27:1666-669 CrossRef
23. Morita Y, Matsumura E, Okabe T, Fukui T, Shibata M, Sugiura M, Ohe T, Tsujibo H, Ishida N, Inamori Y (2004b) Biological activity of α-thujaplicin, the isomer of hinokitiol. Biol Pharm Bull 27:899-02 CrossRef
24. Nacife VP, Soeiro Mde N, Gomes RN, D’Avila H, Castro-Faria Neto HC, Meirelles Mde N (2004) Morphological and biochemical characterization of macrophages activated by carrageenan and lipopolysaccharide in vivo. Cell Struct Funct 29:27-4 CrossRef
25. Nakano Y, Wada M, Tani H, Sasai K, Baba E (2005) Effects of β-thujaplicin on anti-malassezia pachydermatis remedy for canin otitis externe. J Vet Med Sci 67:1243-247 CrossRef
26. Ogata A, Ando H, Kubo Y, Nagasawa H, Ogawa H, Yasuda K, Aoki N (1999) Teratogenicity of thujaplicin in ICR mice. Food Chem Toxicol 37:1097-104 CrossRef
27. Piettre SR, Ganzhorn A, Hoflack J, Islam K, Hornsperger J (1997) α- hydroxytropolones: a new class of potent inhibitors of inositol monophosphatase and other bimetallic enzymes. J Am Chem Soc 119:3201-204 CrossRef
28. Procide C, Montovani V, Bianchi P (1971) Aktivita antihyalurodasica dialcuniderivati pirazolici. Biol Soc Ital Biol Sper 47:159-63
29. Rekka E, Chrysselis M, Siskou I, Kourounakis A (2002) Synthesis of new azulen derivatives and study of their effect on lipid peroxidation and lipoxygenase activity. Chem Pharm Bull 50:904-07 CrossRef
30. Suleyman H, Demirezer LO, Kuruuzum A, Banoglu ZN, Gocer F, Ozbakir G, Gepdiremen A (1999) Anti-inflammatory effect of the aqueous extract from Rumex patientia L. Roots. J Ethnopharmacol 65:141-48 CrossRef
31. Suleyman H, Demirezer LO, Kuruuzum A, Buyukokuroglu ME, Gocer F, Banoglu ZN, Gepdiremen A (2001) Effect of the aqueous extract of / Rumex patientia on xylol and hyaluronidase induced capillary permeability compared to indomethacin. Pharmazie 56:92-3
32. Suleyman H, Gul HI, Asoglu M (2003) Anti-inflammatory activity of 3-benzoyl-1-methyl-4-phenyl-4-piperidinol hydrochloride. Pharmacol Res 47:471-75 CrossRef
33. Suleyman H, Demircan B, Karagoz Y, Oztasan N, Suleyman B (2004) Anti-inflammatory effects of selective COX-2 inhibitors. Pol J Pharmacol 56:775-80
34. Suleyman H, Gul HI, Gul M, Alkan M, Gocer F (2007a) Anti-inflammatory activity of Bis (3-aryl-3-oxo-propyl) methylamine hidrochloride in rat. Biol Pharm Bull 30:63-7 CrossRef
35. Suleyman H, Demircan B, Karagoz Y (2007b) Anti-inflammatory and side effects of cyclooxygenase inhibitors. Pharmacol Rep 59:247-58
36. Suzuki H, Ueda T, Juranek I, Yamamoto S, Katoh T, Node M, Suzuki T (2000) Hinokitiol, a selective inhibitor of the platelet-type isosyme of arachidonate 12-lipoxygenase. Biochem Bioph Res Commun 275:885-89 CrossRef - 作者单位：Feride Koc (1)
Elif Cadirci (2)
Abdulmecit Albayrak (2)
Zekai Halici (2)
Ahmet Hacimuftuoglu (2)
Halis Suleyman (2)
1. Department of Pharmacology and Toxicology, Faculty of Veterinary Medicine, Atatürk University, Erzurum, Turkey
2. Department of Pharmacology, Faculty of Medicine, Atatürk University, Erzurum, 25240, Turkey
文摘
In this study, the anti-inflammatory effects of a tropolone derivative, 2,5-dihydroxycyclohepta-2,4,6-trienone (AD-4), were investigated. The anti-inflammatory potency of AD-4 was compared with that of indomethacin in carrageenan-induced inflammation models in rats. The effect on vascular permeability was also determined by hyaluronidase-induced capillary permeability. AD-4 decreased carrageenan-induced paw edema at doses of 3.62?×?102, 7.24?×?102, and 14.48?×?102?μmol/kg by 45% (p?<?0.001), 79% (p?<?0.001), and 83% (p?<?0.001), respectively, compared with the value of 49% (p?<?0.001) for indomethacin (69.8?μmol/kg). Additionally, AD-4 decreased hyaluronidase-induced capillary permeability significantly. In conclusion, AD-4 was determined to have anti-inflammatory effects with lower toxicity than indomethacin. Anti-inflammatory effect of AD-4 may be related to its effects on vascular permeability.