Fatty acid conjugates of water-soluble (±)-trans-selenolane-3,4-diol: Effects of alkyl chain length on the antioxidant capacity

ChemBioChem

Volumn 16, Issue 8, 2015, Pages 1226-1234

  Iwaoka, Michio ^a   Sano, Nobukazu ^a   Lin, Ying Yin ^a   Katakura, Arisa ^a   Noguchi, Masato ^a   Takahashi, Kohei ^a   Kumakura, Fumio ^a   Arai, Kenta ^a   Singh, Beena G ^b   Kunwar, Amit ^b   Indira Priyadarsini, K ^b  

^a TOKAI UNIVERSITY   (Japan)

^b BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

enzyme models; liposomes; peroxidases; selenoxides; surfactants

Indexed keywords

ANTIOXIDANT; CHOLESTEROL; FATTY ACID DERIVATIVE; GLUTATHIONE PEROXIDASE; LINOLEIC ACID; LIPID HYDROPEROXIDE; LIPOSOME; MYRISTIC ACID; NORPHENAZONE; PHOSPHATIDYLCHOLINE; SELENIDE; SELENIUM DERIVATIVE; TRANS 4 HYDROXYTETRAHYDROSELENOPHEN 3 YL LAURATE; TRANS 4 HYDROXYTETRAHYDROSELENOPHEN 3 YL MYRISTATE; TRANS 4 HYDROXYTETRAHYDROSELENOPHEN 3 YL PALMITATE; TRANS 4 HYDROXYTETRAHYDROSELENOPHEN 3 YL PROPIONATE; TRANS 4 HYDROXYTETRAHYDROSELENOPHEN 3 YL STEARATE; UNCLASSIFIED DRUG; FATTY ACID; FREE RADICAL; GLYCOL; ORGANOSELENIUM DERIVATIVE; WATER;

ABTS RADICAL SCAVENGING ASSAY; ANTIOXIDANT ACTIVITY; ARTICLE; DRUG STRUCTURE; ELECTRON PROBE MICROANALYSIS; HYDRATION; IC50; LIGHT SCATTERING; LIPID PEROXIDATION; LIPID PEROXIDATION ASSAY; LIPOPHILICITY; LIPOSOME MEMBRANE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; PH; PRIORITY JOURNAL; STEREOSPECIFICITY; TRANSMISSION ELECTRON MICROSCOPY; CHEMICAL PHENOMENA; CHEMISTRY; DRUG EFFECTS; METABOLISM; SOLUBILITY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

ANTIOXIDANTS; CHOLESTEROL; FATTY ACIDS; FREE RADICALS; GLYCOLS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LECITHINS; LIPID PEROXIDATION; LIPOSOMES; ORGANOSELENIUM COMPOUNDS; OXIDATION-REDUCTION; SOLUBILITY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

EID: 84929308440     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201500047     Document Type: Article

References (83)

1. Y.-Z. Fang, S. Yang, G. Wu, Nutrition 2002, 18, 872-879
2. B. Halliwell, J. M. C. Gutteridge, Free Radicals in Biology and Medicine, 4 th ed., Oxford University Press, New York, 2007
3. H. Yin, L. Xu, N. A. Porter, Chem. Rev. 2011, 111, 5944-5972.
4. R. Dargel, Exp. Toxicol. Pathol. 1992, 44, 169-181
5. A. Negre-Salvayre, N. Auge, V. Ayala, H. Basaga, J. Boada, R. Brenke, S. Chapple, G. Cohen, J. Feher, T. Grune, G. Lengyel, G. E. Mann, R. Pamplona, G. Poli, M. Portero-Otin, Y. Riahi, R. Salvayre, S. Sasson, J. Serrano, O. Shamni, W. Siems, R. C. M. Siow, I. Wiswedel, K. Zarkovic, N. Zarkovic, Free Radical Res. 2010, 44, 1125-1171
6. P. Rajendran, N. Nandakumar, T. Rengarajan, R. Palaniswami, E. N. Gnanadhas, U. Lakshminarasaiah, J. Gopas, I. Nishigaki, Clin. Chim. Acta 2014, 436, 332-347.
7. W. Bors, W. Heller, C. Michel, K. Stettmaier, Flavonoids and Polyphenols: Chemistry and Biology in Handbook of Antioxidants (Eds.:, E. Cadenas, L. Packer,), Marcel Dekker, New York, 1996, pp. 409-466
8. D. DellaPenna, B. J. Pogson, Annu. Rev. Plant Biol. 2006, 57, 711-738.
9. M. G. Traber, J. Atkinson, Free Radical Biol. Med. 2007, 43, 4-15.
10. L. Flohe, W. A. Günzler, H. H. Schock, FEBS Lett. 1973, 32, 132-134
11. N. E. Savaskan, C. Ufer, H. Kühn, A. Borchert, Biol. Chem. 2007, 388, 1007-1017
12. M. Conrad, M. Schneider, A. Seiler, G. W. Bornkamm, Biol. Chem. 2007, 388, 1019-1025
13. S. Toppo, L. Flohé, F. Ursini, S. Vanin, M. Maiorino, Biochim. Biophys. Acta Gen. Subj. 2009, 1790, 1486-1500.
14. B. Hofmann, H.-J. Hecht, L. Flohé, Biol. Chem. 2002, 383, 347-364
15. Z. A. Wood, E. Schröder, J. R. Harris, L. B. Poole, Trends Biochem. Sci. 2003, 28, 32-40
16. J.-G. Park, J.-Y. Yoo, S.-J. Jeong, J.-H. Choi, M.-R. Lee, M.-N. Lee, J. H. Lee, H. C. Kim, H. Jo, D.-Y. Yu, S. W. Kang, S. G. Rhee, M.-H. Lee, G. T. Oh, Circ. Res. 2011, 109, 739-749.
17. W. H. Koppenol, J. Butler, Adv. Free Radical Biol. Med. 1985, 1, 91-131
18. D. M. Miller, G. R. Buettner, S. D. Aust, Free Radical Biol. Med. 1990, 8, 95-108.
19. G. Mugesh, W.-W. du Mont, H. Sies, Chem. Rev. 2001, 101, 2125-2179
20. K. P. Bhabak, G. Mugesh, Acc. Chem. Res. 2010, 43, 1408-1419
21. X. Huang, X. Liu, Q. Luo, J. Liu, J. Shen, Chem. Soc. Rev. 2011, 40, 1171-1184
22. C. Santi, C. Tidei, C. Scalera, M. Piroddi, F. Galli, Curr. Chem. Biol. 2013, 7, 25-36; for recent works, see
23. H. Johansson, O. Svartström, P. Phadnis, L. Engman, M. K. Ott, Bioorg. Med. Chem. 2010, 18, 1783-1788
24. V. Nascimento, E. E. Alberto, D. W. Tondo, D. Dambrowski, M. R. Detty, F. Nome, A. L. Braga, J. Am. Chem. Soc. 2012, 134, 138-141
25. P. Prabhu, P. P. Bag, G. B. Singh, A. Hodge, V. K. Jain, M. Iwaoka, K. I. Priyadarsini, Free Radical Res. 2011, 45, 461-468
26. S. Braverman, M. Cherkinsky, Y. Kalendar, R. Jana, M. Sprecher, I. Goldberg, Synthesis 2014, 46, 119-125
27. Z. Wang, Y. Wang, W. Li, F. Mao, Y. Sun, L. Houng, X. Li, ACS Chem. Neurosci. 2014, 5, 952-962.
28. A. Kunwar, B. Mishra, A. Barik, L. B. Kumbhare, R. Panday, V. K. Jain, K. I. Priyadarsini, Chem. Res. Toxicol. 2007, 20, 1482-1487
29. W. Hassan, S. Pinton, J. T. da Rocha, A. M. Deobald, A. L. Braga, C. W. Nogueira, A. S. Latini, J. B. T. Rocha, Chem.-Biol. Interact. 2011, 190, 35-44
30. C. Luchese, R. Brandão, C. I. Acker, C. W. Nogueira, Mol. Cell. Biochem. 2012, 367, 153-163
31. M. Ibrahim, W. Hassan, A. M. Deobald, A. L. Braga, J. B. T. Rocha, Biol. Trace Elem. Res. 2012, 149, 399-404.
32. T. G. Back, Z. Moussa, M. Parvez, Angew. Chem. Int. Ed. 2004, 43, 1268-1270
33. Angew. Chem. 2004, 116, 1288-1290
34. H. Tsukagoshi, M. Kotatsu, M. Kato, M. Kurabayashi, A. Nishina, H. Kimura, FEBS J. 2007, 274, 6046-6054
35. Z. Selamoglu Talas, I. Ozdemir, I. Yilmaz, Y. Gok, I. Orun, Exp. Biol. Med. 2008, 233, 575-579
36. C. Storkey, M. J. Davies, J. M. White, C. H. Scheisser, Chem. Commun. 2011, 47, 9693-9695
37. P. Merino-Montiel, O. Lõpez, E. Álvarez, J. G. Fernández-Bolaños, Tetrahedron 2012, 68, 4888-4898
38. N. M. R. McNeil, M. C. Matz, T. G. Back, J. Org. Chem. 2013, 78, 10369-10382.
39. F. C. Meotti, E. C. Stangherlin, G. Zeni, C. W. Nogueira, J. B. T. Rocha, Environ. Res. 2004, 94, 276-282
40. F. W. Santos, G. Zeni, J. B. T. Rocha, S. N. Weis, J. M. Fachinetto, A. M. Favero, C. W. Nogueira, Chem.-Biol. Interact. 2005, 151, 159-165
41. A. Sausen de Freitas, A. de Souza Prestes, C. Wagner, J. Haigert Sudati, D. Alves, L. Oliveira Porciúncula, I. J. Kade, J. B. Teixeira Rocha, Molecules 2010, 15, 7699-7714
42. J. T. da Rocha, S. Pinton, A. Mazzanti, C. M. Mazzanti, D. V. Beckemann, C. W. Nogueira, G. Zeni, J. Pharm. Pharmacol. 2011, 63, 663-669.
43. A. Müller, H. Gabriel, H. Sies, Biochem. Pharmacol. 1985, 34, 1185-1189
44. H. Imai, D. I. Graham, H. Masayasu, I. M. Macrae, Free Radical Biol. Med. 2003, 34, 56-63
45. K. P. Bhabak, G. Mugesh, Chem. Eur. J. 2007, 13, 4594-4601
46. A. P. Ardais, F. W. Santos, C. W. Nogueira, J. Appl. Toxicol. 2008, 28, 322-328
47. G. Mugesh, Curr. Chem. Biol. 2013, 7, 47-56.
48. L. H. Duntas, Horm. Metab. Res. 2009, 41, 443-447
49. M. P. Rayman, Lancet 2012, 379, 1256-1268.
50. S. Kumari, S. L. Mehta, P. A. Li, PLoS ONE 2012, 7, e 39382
51. N. E. Savaskan, A. U. Bräuer, M. Kühbacher, I. Y. Eyüpoglu, A. Kyriakopoulos, O. Ninnemann, D. Behne, R. Nitsch, FASEB J. 2003, 17, 112-114.
52. T. Sakurai, M. Kanayama, T. Shibata, K. I, A. Kobayashi, M. Yamamoto, K. Uchida, Chem. Res. Toxicol. 2006, 19, 1196-1204
53. W. Hassan, M. Ibrahim, J. B. T. Rocha, Chem.-Biol. Interact. 2009, 182, 52-58
54. E. E. Battin, M. T. Zimmerman, R. R. Ramoutar, C. E. Quarles, J. L. Brumaghim, Metallomics 2011, 3, 503-512.
55. V. Raneva, H. Shimasaki, Y. Furukawa, N. Ueta, N. Yanishlieva, J. E. Aaseng, V. Partali, H.-R. Sliwka, Y. Yoshida, E. Niki, Lipids 2002, 37, 633-640.
56. D. Shanks, R. Amorati, M. G. Fumo, G. F. Pedulli, L. Valgimigli, L. Engman, J. Org. Chem. 2006, 71, 1033-1038.
57. I. J. Kade, M. W. Paixão, O. E. D. Rodrigues, N. B. V. Barbosa, A. L. Braga, D. S. Ávila, C. W. Nogueira, J. B. T. Rocha, Neurochem. Res. 2008, 33, 167-178
58. P. Merino-Montiel, S. Maza, S. Martos, Ó. Lõpez, I. Maya, J. G. Fernández-Bolaños, Eur. J. Pharm. Sci. 2013, 48, 582-592
59. F. N. Victoria, R. Anversa, F. Penteado, M. Castro, E. J. Lenardão, L. Savegnago, Eur. J. Pharmacol. 2014, 742, 131-138.
60. F. Kumakura, B. Mishra, K. I. Priyadarsini, M. Iwaoka, Eur. J. Org. Chem. 2010, 440-445.
61. M. Iwaoka, K. Arai, Curr. Chem. Biol. 2013, 7, 2-24.
62. M. Iwaoka, F. Kumakura, Phosphorus Sulfur Silicon Relat. Elem. 2008, 183, 1009-1017.
63. B. G. Singh, E. Thomas, F. Kumakura, K. Dedachi, M. Iwaoka, K. I. Priyadarsini, J. Phys. Chem. A 2010, 114, 8271-8277.
64. S. Chakraborty, S. Yadav, M. Subramanian, K. I. Priyadarsini, M. Iwaoka, S. Chattopadhyay, Free Radical Res. 2012, 46, 13780-13786
65. S. Chakraborty, S. Yadav, M. Subramanian, M. Iwaoka, S. Chattopadhyay, Biochim. Biophys. Acta Gen. Subj. 2014, 1840, 3385-3392.
66. H. Shichinohe, S. Kuroda, H. Yasuda, T. Ishikawa, M. Iwai, M. Horiuchi, Y. Iwasaki, Brain Res. 2004, 1029, 200-206
67. J. I. Noor, Y. Ueda, T. Ikeda, T. Ikenoue, Neurosci. Lett. 2007, 414, 5-9.
68. S. L. Law, H. Y. Hung, Int. J. Pharm. 1998, 161, 253-259
69. E. Moghimipour, S. Handali, Adv. Pharm. Bull. 2012, 2, 93-98.
70. H. Ohkawa, N. Ohishi, K. Yagi, Anal. Biochem. 1979, 95, 351-358
71. Y.-J. Cai, J.-G. Fang, L.-P. Ma, L. Yang, Z.-L. Liu, Biochim. Biophys. Acta Mol. Basis Dis. 2003, 1637, 31-38.
72. P. Chetanachan, P. Akarachalanon, D. Worawirunwong, P. Dararutana, A. Bangtrakulnonth, M. Bunjop, S. Kongmuang, Adv. Mater. Res. 2008, 55-57, 709-711
73. B. Ruozi, D. Belletti, A. Tombesi, G. Tosi, L. Bondioli, F. Forni, M. A. Vandelli, Int. J. Nanomed. 2011, 6, 557-563.
74. N. Noguchi, H. Yamashita, N. Gotoh, Y. Yamamoto, R. Numano, E. Niki, Free Radical Biol. Med. 1998, 24, 259-268.
75. R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, C. Rice-Evans, Free Radical Biol. Med. 1999, 26, 1231-1237.
76. J. Malmström, M. Jonsson, I. A. Cotgreave, L. Hammarström, M. Sjödin, L. Engman, J. Am. Chem. Soc. 2001, 123, 3434-3440
77. S. Kumar, H. Johansson, L. Engman, L. Valgimigli, R. Amorati, M. G. Fumo, G. F. Pedulli, J. Org. Chem. 2007, 72, 2583-2595.
78. R. Yamauchi, J. Clin. Biochem. Nutr. 2003, 34, 111-120.
79. P. V. Kumar, B. G. Singh, N. Maiti, M. Iwaoka, K. I. Priyadarsini, J. Colloid Interface Sci. 2014, 436, 179-185.
80. G. R. Buettner, Arch. Biochem. Biophys. 1993, 300, 535-543.
81. A. de Souza Prestes, S. T. Stefanello, S. M. Salman, A. M. Pazini, R. S. Schwab, A. L. Braga, N. B. de Vargas Barbosa, J. B. Rocha, Mol. Cell. Biochem. 2012, 365, 85-92.
82. M. Iwaoka, T. Takahashi, S. Tomoda, Heteroat. Chem. 2001, 12, 293-299.
83. M. Piętka-Ottlik, H. Wõjtowicz-Młochowska, K. Kołodziejczyk, E. Piasecki, J. Młochowski, Chem. Pharm. Bull. 2008, 56, 1423-1427.