Synthesis and biological evaluation of 2,5-bis(alkylamino)-1,4- benzoquinones

Molecules

Volumn 15, Issue 8, 2010, Pages 5629-5643

  Barbosa, Luiz Cláudio Almeida ^a   Pereira, Ulisses Alves ^a   Maltha, Célia Regina Alvares ^a   Teixeira, Róbson Ricardo ^a   Valente, Vânia Maria Moreira ^a   Ferreira, José Roberto Oliveira ^b   Costa Lotufo, Letícia Veras ^b   Moraes, Manoel Odorico ^b   Pessoa, Cláudia ^b  

^a FEDERAL UNIVERSITY OF VIÇOSA   (Brazil)

^b FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

Author keywords

Cytotoxicity; Herbicide; Quinones

Indexed keywords

ADENOSINE TRIPHOSPHATE; ANTINEOPLASTIC AGENT; BENZOQUINONE DERIVATIVE;

ARTICLE; BIOASSAY; CELL DEATH; CHEMISTRY; DRUG EFFECT; GROWTH, DEVELOPMENT AND AGING; HUMAN; METABOLISM; PLANT ROOT; SYNTHESIS; TUMOR CELL LINE;

ADENOSINE TRIPHOSPHATE; ANTINEOPLASTIC AGENTS; BENZOQUINONES; BIOLOGICAL ASSAY; CELL DEATH; CELL LINE, TUMOR; HUMANS; PLANT ROOTS;

EID: 77956095810     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15085629     Document Type: Article

References (57)

1. Oliveros-Bastidas, A.J.; Macías, F.A.; Fernández, C.C.; Marín, D.; Molinillo, J.M.G. Exudados dela raiz y su relevancia actual en las interacciones alelopaticas. Quim. Nova. 2009, 32, 198-213.
2. Bais, H.P.; Weir, T.L.; Perry, L.G.; Gilroy, S.; Vivanco, J.M. The role of root exudates in rhizosphere interactions with plants and other organisms. Annu. Rev. Plant Biol. 2006, 57, 233-266.
3. Walker, T.S.; Bais, H.P.; Grotewold, E.; Vivanco, J.M. Root exudation and rhizosphere biology. Plant Physiol. 2003, 132, 44-51.
4. Bertin C.; Yang, X.; Weston L.A. The role of root exudates and allelochemicals in the rhizosphere. Plant Soil. 2003, 256, 67-83.
5. Macías, F.A.; Molinillo, J.M.G.; Varela, R.M.; Galindo, J.C.G. Allelopathy - A natural alternative for weed Control. Pest Manag. Sci. 2007, 63, 327-348.
6. Macías, F.A.; Galindo, J.C.G.; Molinillo, J.M.G.; Cutler, H.G. Allelopathy - Chemistry and Mode of Action of Allelochemicals; CRC Press: Boca Raton, FL, USA, 2004.
7. Copping, L.G.; Duke, S.O. Natural products that have been used commercially as crop protection agents - A review. Pest Manag. Sci. 2007, 63, 524-554.
8. Barbosa, L.C.A.; Teixeira, R.R.; Montanari, R.M. Phytotoxic Natural Products as Models for the development of crop protection agents. In Current Trends in Phytochemistry; Epifano, F., Ed.; Research Signpost: Kerala, India, 2008; pp. 21-59.
9. Chang, M.; Netzly, D.H.; Butler, L.G.; Lynn, D.G. Chemical regulation of distance. Characterization of the first natural host germination stimulant for Striga asiatica. J. Am. Chem. Soc. 1986, 108, 7858-7860.
10. Einhellig, F.A.; Souza, I.F. Phytotoxicity of sorgoleone found in grain Sorghum root exudates. J. Chem. Ecol. 1992, 18, 1-11.
11. Gonzales, V.M.; Kazimir, J.; Nimbal, C.; Weston, L.A.; Cheniae, G.M. Inhibition of a photosystem II electron transfer reaction by the natural product sorgoleone. J. Agric. Food Chem. 1997, 45, 1415-1421.
12. Rasmussen, J.A.; Hejl, A.M.; Einhellig, F.A.; Thomas, J.A. Sorgoleone from root exudate inhibits mitochondrial functions. J. Chem. Ecol. 1992, 18, 197-207.
13. Czarnota, M.A.; Paul, R.N., Dayan, F.E.; Nimbal, C.I.; Weston, L.A. Mode of action, localization, of production, chemical nature, and activity of sorgolene: A potent PSII inhibitor in Sorghum spp. root exudates. Weed Technol. 2001, 15, 813-825.
14. Streibig, J.C.; Dayan, F.E.; Rimando, A.M.; Duke, S.O. Joint action of natural and synthetic photosystem II inhibitors. Pest. Sci. 1999, 55, 137-146.
15. Hejl, A.M.; Koster, K.L. The allelochemical sorgoleone inhibits root H+-ATPase and water uptake. J. Chem. Ecol. 2004, 30, 2181-2191.
16. Kubo, I.; Chaudhuri, S.K. Structure of maesaquinone. Bioorg. Med. Chem. Lett. 1994, 4, 1131-1134.
17. Silva, M.N. da; Ferreira, V.F.; de Souza, M.C.B.V. Um panorama atual da química e da farmacologia de naftoquinonas, com ênfase na β-lapachona e derivados. Quim. Nova 2003, 26, 407-416.
18. Pan, S.S.; Andrews, P.A.; Glover, C.J. Reductive activation of mitomycin C and mitomycin C metabolites catalyzed by NADPH-cytochrome P-450 reductase and xanthine oxidase. J. Biol. Chem. 1984, 259, 959-966.
19. Tomasz, M.; Palom, Y. The mitomycin bioreductive antitumor agents: cross-linking and alkylation of DNA as the molecular basis of their activity. Pharmacol. Ther. 1997, 76, 73-87.
20. Dettrakul, S.; Surerum, S.; Rajviroongit, S.; Kittakoop, P. Biomimetic transformation and biological activities of globiferin, a terpenoid benzoquinone from Cordia globifera. J. Nat. Prod. 2009, 72, 861-865.
21. Marinho-Filho, J.D.; Bezerra, D.P.; Araújo, A.J.; Montenegro, R.C.; Pessoa, C.; Diniz, J.C.; Viana, F.A.; Pessoa, O.D.; Silveira, E.R.; de Moraes, M.O.; Costa-Lotufo, L.V. Oxidative stress induction by (+)-cordiaquinone J triggers both mitochondria-dependent apoptosis and necrosis in leukemia cells. Chem. Biol. Interact. 2010, 183, 369-379.
22. Barbosa, L.C.A.; Costa, A.V.; Veloso, D.P.; Lopes, J.L.C.; Hernandez-Terrones, M.G.; King- Diaz, B.; Lotina-Hennsen, B. Phytogrowth-inhibitory lactones derivatives of glaucolide B. Z Naturforsch. 2004, 59c, 803-810.
23. Chaves, F.C.; Barbosa, L.C.A.; Demuner, A.J.; Silva, A.A. New helminthosporal analogues with plant-growth regulatory properties synthesized via oxyallyl cation. Z. Naturforsch. 2006, 61b, 1287-1294.
24. Barbosa, L.C.A.; Demuner, A.J.; Maltha, C.R.A.; da Silva, P.S.; Silva, A.A. Sintese e avaliação da ativadade fitotóxica de novos análogos oxigenados do ácido helmintospórico. Quim. Nova 2003, 26, 655-660.
25. Demuner, A.J.; Barbosa, L.C.A.; Veloso, D.P.; Howarth, O.W. Synthesis and plant growth regulatory activity of 6α,7β-dihydroxyvouacapan- 17β-oic acid derivatives. Aust. J. Chem. 1998, 51, 61-66.
26. Barbosa, L.C.A.; Demuner, A.J.; Alvarenga, E.S.; Oliveira, A.; King-Diaz, B.; Lotina-Hennsen, B. Phytogrowth- and photosynthesis-inhibiting properties of nostoclide analogues. Pest Manag. Sci. 2006, 62, 214-222.
27. Barbosa, L.C.A.; Demuner, A.J.; Maltha, C.R.A.; Teixeira, R.R.; Souza, K.A.P.; Bicalho, K.U. Phytogrowth activity of 3-(3-chlorobenzyl)-5- arylidenefuran-2(5H)-ones. Z. Naturforsch. 2009, 64b, 245-251.
28. Barbosa, L.C.A.; Rocha, M.E.; Teixeira, R.R.; Maltha, C.R.A.; Forlani, G. Synthesis of 3-(4-bromobenzyl)-5-(aryl methylene)-5H-furan-2-ones and their activity as inhibitors of the photosynthetic electron transport chain. J. Agric. Food Chem. 2007, 55, 8562-8569.
29. Teixeira, R.R.; Barbosa, L.C.A.; Forlani, G.; Piló-Veloso, D.; Carneiro, J.W.M. Synthesis of photosynthesis-inhibiting nostoclide analogues. J. Agric. Food Chem. 2008, 56, 2321-2329.
30. Lima, L.S.; Barbosa, L.C.A.; Alvarenga, E.S.; Demuner, A.J.; Silva, A.A. Synthesis and phytotoxicity evaluation of substituted para-benzoquinones. Aust. J. Chem. 2003, 56, 625-630.
31. Barbosa, L.C.A.; Alvarenga, E.S.; Demuner, A.J.; Virtuoso, L.S.; Silva, A.A. Synthesis of new phytogrowth-inhibitory substituted aryl-p-benzoquinones. Chem. Biod. 2006, 3, 553-567.
32. Bayen, S.; Barooah, N.; Sarma, R.J.; Sen, T.K.; Karmakar, A.; Baruah, J.B. Synthesis, structure and electrochemical properties of 2,5-bis(alkyl/ arylamino)1,4-benzoquinones and 2-arylamino- 1,4-naphthoquinones. Dye Pigment. 2007, 75, 770-775.
33. Hassan, S.S.M.; Iskander, M.L.; Nashed, N.E. Spectrophotometric determination of aliphatic primary and secondary amines by reaction with p-benzoquinone. Talanta 1985, 32, 301-305.
34. Tindale, C.R. Reactions of biogenic amines with quinones. Aust. J. Chem. 1984, 37, 611-617.
35. Nithianandam, V.S.; Erhan, S. Quinone-amine polymers: 18. A novel method for the synthesis of poly(alkyl aminoquinone)s. Polymer 1998, 39, 4095-4098.
36. Einhellig, F.A.; Schon, M.K.; Rasmussen, J.A. Synergistic effects of four cinnamic acid compounds on grain sorghum. J. Plant Growth Regul. 1982, 1, 251-258.
37. Hennsen, B.L.; Achine, L.; Ruvalcaba, N.M.; Ortiz, A.; Hernández, J.; Farbán, N.; Martínez, M. A. 2,5-Diamino-p-benzoquinone derivatives as photosystem I electron acceptors: Synthesis and electrochemical and physicochemical properties. J. Agric. Food Chem. 1998, 46, 724-730.
38. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Method. 1983, 16, 55-63.
39. Ahmed, S.A.; Gogal, R.M.J.; Walsh, J.E. A new rapid and simple non-radioactive assay to monitor and determine the proliferation of lymphocytes: An alternative to 3H-thymidine incorporation assay. J. Immunol. Method. 1994, 170, 211-224.
40. Zhi-Jun, Y.; Sriranganathan, N.; Vaught, T.; Arastu, S.K.; Ahmed, S.A. A dye-based lymphocyte proliferation assay that permits multiple immunological analyses: mRNA, cytogenetic, apoptosis, and immunophenotyping studies. J. Immunol. Method. 1997, 210, 25-39.
41. Chari, R.V.J. Targeted cancer therapy: conferring specificity to cytotoxic drugs. Acc. Chem. Res. 2008, 41, 98-107.
42. O'Brien, P.J. Molecular mechanisms of quinone cytotoxicity. Chem.-Biol. Interact. 1991, 80, 1-41.
43. Perrin, D.D.; Armarego, W.L.F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, UK, 1988.
44. Brondani, D.J.; Bieber, L.W. Regioselective lithiation and alkylation of 2-methoxy-hydroquinone. Quim. Nova 1995, 18, 144-146.
45. Zhou, Q.; Swager, T.M. Probing delocalization across alkyne-containing linkages: Synthesis and cyclic voltammetry of bridged phenylenediamines. J. Org. Chem. 1995, 60, 7096-7100.
46. Wellington, K.W.; Steenkamp, P.; Brady, D. Diamination by N-coupling using a commercial laccase. Bioorg. Med. Chem. 2010, 18, 1406-1414.
47. Garreau, Y. Oxidation products of gentisic acid in the presene of primary amines. Bull. Soc. Chim. Fr. 1950, 501-502.
48. Garreau, Y. [Interaction of] phenols and sulfites. Ann. Chim. Applicata 1938, 10, 485-558.
49. Torigoe, M. Cancerocidal substances. XIII. Effect of some quinones and related compounds upon the Yoshida sarcoma. Pharm. Bull. 1955, 3, 337-342.
50. Makarova, A.N.; Berlin, A.Y. Reaction of ethylenimino-1,4-benzoquinones with amines. I. Reaction between ethylenimino-1,4-benzoquinones and secondary amines. Zh. Org. Khim. 1959, 29, 666-672.
51. Cavalitto, C.J.; Soria, A.E.; Hoppe, J.O. Amino- and ammonium- alkylaminobenzoquinones as curarimimetic agents. J. Am. Chem. Soc. 1950, 72, 2661-2665.
52. Barbosa, L.C.A.; Pereira, U.A.; Teixeira, R.R.; Maltha, C.R.A.; Fernandes, S.A.; Forlani, G. Synthesis and phytotoxic activity of ozonides. J. Agric. Food Chem. 2008, 56, 9434-9440.
53. Barbosa, L.C.A.; Maltha, C.R.A.; Cusati, R.C.; Teixeira, R.R.; Rodrigues, F.F.; Silva, A.A.; Drew, M.G.B.; Ismail, F.M.D. Synthesis and biological evaluation of new ozonides with improved plant growth regulatory activity. J. Agric. Food Chem. 2009, 57, 10107-10115.
54. Gomes, F.P. Curso de Estatística Experimental, 13th ed.; Nobel: Piracicaba, Brasil, 1990.
55. Macías, M.L.; Rojas, I.S.; Matar, R.; Lotina-Hennsen, B. Effect of selected coumarins on spinach chloroplast photosynthesis. J. Agric. Food Chem. 1999, 47, 2137-2140.
56. Strain, H.H.; Coppe, B.T.; Svec, W.A. Analytical procedures for the isolation, identification, estimation and investigation of the chlorophylls. In Methods of Enzymology; San Pietro, A., Ed.; Academic Press: New York, NY, USA, 1971, p. 452.
57. Demuner, A.J.; Barbosa, L.C.A.; Veiga, T.A.M.; Barreto, R.W.; King-Diaz , B.; Lotina-Hennsen, B. Phytotoxic constituents from Nimbya alternantherae. Bioch. Syst. Ecol. 2006, 34, 790-795.