Coordination of lapachol to bismuth(III) improves its anti-inflammatory and anti-angiogenic activities

BioMetals

Volumn 25, Issue 1, 2012, Pages 55-62

  Parrilha, Gabrieli L ^a   Vieira, Rafael P ^a   Campos, Paula P ^a   Silva, Grácia Divina F ^a   Duarte, Lucienir P ^a   Andrade, Silvia P ^a   Beraldo, Heloisa ^a  

^a FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

Angiogenesis; Bismuth(III) complex; Inflammation; Lapachol; Sponge implants

Indexed keywords

ACETYLGLUCOSAMINIDASE; BISMUTH III COMPLEX; HEMOGLOBIN; LAPACHOL; METAL COMPLEX; POLYETHERURETHAN; UNCLASSIFIED DRUG; ANGIOGENESIS INHIBITOR; ANTIINFLAMMATORY AGENT; BISMUTH; NAPHTHOQUINONE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIANGIOGENIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; DRUG EFFECT; DRUG MIXTURE; DRUG POTENTIATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME DEGRADATION; EXPERIMENTAL MOUSE; HEMOGLOBIN BLOOD LEVEL; HISTOPATHOLOGY; MALE; MOUSE; NONHUMAN; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; IMPLANT; INFLAMMATION;

MURINAE;

ANGIOGENESIS INHIBITORS; ANIMALS; ANTI-INFLAMMATORY AGENTS; BISMUTH; IMPLANTS, EXPERIMENTAL; INFLAMMATION; MALE; MICE; MOLECULAR STRUCTURE; NAPHTHOQUINONES;

EID: 84861212111     PISSN: 09660844     EISSN: 15728773     Source Type: Journal    
DOI: 10.1007/s10534-011-9481-y     Document Type: Article

References (25)

1. Araújo FA, Rocha MA, Mendes JB, Andrade SP (2010) Atorvastatin inhibits inflammatory angiogenesis in mice through down regulation of VEGF, TNF-a and TGF-b1. Biomed Pharmacother 64:29-34
2. Bezerra DP, Alves AP, De Alencar NM, Mesquita RO, Lima MW, Pessoa C, De Moraes MO, Lopes JN, Lopes NP, Costa-Lotufo LV (2008) Antitumor activity of two derivatives from 2-acylamine-1, 4-naphthoquinone in mice bearing S180.tumor. J Exp Ther Oncol. 7:113-121
3. Briand GG, Burford N (1999) Bismuth compounds and preparations with biological or medicinal relevance. Chem Rev 99:2601-2657
4. Caruso F, Mart?́nez MA, Rossi M, Goldberg A, Villalba EC, Aymonino PJ (2009) Crystal and molecular structure of manganese(II) lapacholate, a novel polymeric species undergoing temperature-reversible metal to ligand electron transfer. Inorg Chem 48:3529-3534
5. Da Silva Júnior EN, Cavalcanti BC, Guimarães TT, Pinto MCFR, Cabral IO, Pessoa C, Costa-Lotufo LV, De Moraes MO, De Andrade CKZ, Dos Santos MR, De Simone CA, Goulart MOF, Pinto AV (2011) Synthesis and evaluation of quinonoid compounds against tumor cell lines. Eur J Med Chem 46:399-410
6. De Almeida ER, Da Silva Filho AA, Dos Santos ER, Lopes CAC (1990) Antiinflammatory action of lapachol. J Ethnopharmacol 29: 239-241 (AAPS PharmSciTech 9: 163-168)
7. Eyong KO, Kumar PS, Kuete V, Folefoc GN, Nkengfack EA, Baskaran S (2008) Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol. Bioorg Med Chem Lett 18:5387-5390
8. Ferreira VF (1996) Aprendendo sobre os conceitos de ácido e base. Qu?́mica Nova na Escola 4:35-36
9. Ferreira MA, Barcelos LS, Campos PP, Vasconcelos AC, Teixeira MM, Andrades SP (2004) Sponge-induced angiogenesis and inflammation in PAF receptor-deficient mice (PAFR-KO). Br J Pharmacol 141:1185-1192
10. Gong Y, Koh D-R (2010) Neutrophils promote inflammatory angiogenesis via release of preformed VEGF in an in vivo corneal model. Cell Tissue Res 339:437-448
11. Hall DWR (1989) Review of the modes of action of colloidal bismuth subcitrate. Scand J Gastroenterol 24:3-6
12. Lee SP (1991) The mode of action of colloidal bismuth subcitrate. Scand J Gastroenterol 26:1-6
13. Lin C-Y, Shen Y-H, Wu S-H, Lin C-H, Hwang S-M, Tsai Y-C (2004) Effect of bismuth subgallate on nitric oxide and prostaglandin E2 production by macrophages. Biochem Biophys Res Commun 315:830-835
14. Maeda M, Murakami M, Takegami T, Ota T (2008) Promotion or suppression of experimental metastasis of B16 melanoma cells after oral administration of lapachol. Toxicol Appl Pharm 229:232-238
15. Mart?́nez MA, De Jiménez MCL, Castellano EE, Piro OE, Aymonino PJ (2003) Synthesis, structure and properties of a zinc(II) complex with the lapacholate anion and ethanol as ligands. J Coord Chem 56:803-816
16. Mendes JB, Campos PP, Rocha MA, Andrade SP (2009a) Cilostazol and pentoxifylline decrease angiogenesis, inflammation, and fibrosis in sponge-induced intraperitoneal adhesion in mice. Life Sci 84:537-543
17. Mendes JB, Rocha MA, Araújo FA, Moura SAL, Ferreira MAND, Andrade SP (2009b) Differential effects of rolipram on chronic subcutaneous inflammatory angiogenesis and on peritoneal adhesion in mice. Microvasc Res 78:265-271
18. Nakamoto K (1970) Infrared spectra of inorganic and coordination compounds, 2nd edn. Willey-Interscience, New York
19. Oliveira RAS, Azevedo-Ximenes E, Luzzati R, Garcia RC (2010) The hydroxy-naphthoquinone lapachol arrests mycobacterial growth and immunomodulates host macrophages. Int Immunopharmacol 10:1463-1473
20. Rocha LTS, Costa KA, Oliveira ACP, Nascimento EB, Bertollo CM, Araújo F, Teixeira LR, Andrade SP, Beraldo H, Coelho MM (2006) Antinociceptive, antiedematogenic and antiangiogenic effects of benzaldehyde semicarbazone. Life Sci 79:499-505
21. Sadler PJ, Li H, Sun H (1999) Coordination chemistry of metals in medicine: Target sites for bismuth. Coord Chem Rev 185-186:689-709
22. Severi C, Abdullahi M, Tari R, Vannella L, Marcheggiano A, Capoccia D, Leonetti F, Osborn J, Annibale B (2009) High efficacy of bismuth subcitrate for Helicobacter pylori eradication in pangastritis. Digest Liver Dis. 41:555-558
23. Walsh DA, Pearson CI (2001) Angiogenesis in the pathogenesis of inflammatory joint and lung diseases. Arthritis Res 3:147-153
24. Xavier DO, Amaral LS, Gomes MA, Rocha MA, Campos PR, Cota BDCV, Tafuri LSA, Paiva AMR, Silva JH, Andrade SP, Belo AV (2010) Metformin inhibits inflammatory angiogenesis in a murine sponge model. Biomed Pharmacother 64:220-225
25. Yang N, Sun H (2007) Biocoordination chemistry of bismuth: Recent advances. Coord Chem Rev 251:2354-2366