Determining the effects of lipophilic drugs on membrane structure by solid-state NMR spectroscopy: The case of the antioxidant curcumin

Journal of the American Chemical Society

Volumn 131, Issue 12, 2009, Pages 4490-4498

  Barry, Jeffrey ^a   Fritz, Michelle ^a   Brender, Jeffrey R ^a   Smith, Pieter E S ^a   Lee, Dong Kuk ^a,b   Ramamoorthy, Ayyalusamy ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b Seoul National University of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE INGREDIENTS; ANTI-INFLAMMATORY; ANTIMUTAGENIC; ATOMIC LEVELS; BI-LAYER; BROAD SPECTRUM; CONCENTRATION DEPENDENCE; CURCUMIN; HEXAGONAL PHASE; HIGHER ORDER; HYDROGEN BONDINGS; LIPOPHILIC DRUGS; LOW CONCENTRATIONS; MEMBRANE FUSION; MEMBRANE PROTEINS; MEMBRANE STRUCTURES; OLIGOMERIC STRUCTURE; ORDER-PARAMETER PROFILE; PHARMACEUTICAL COMPOUNDS; PHARMACOLOGICAL EFFECTS; PHOSPHATE GROUP; SOLID STATE NMR; SOLID-STATE NMR SPECTROSCOPY; TURMERIC POWDER;

CHOLESTEROL; CYTOLOGY; DIFFERENTIAL SCANNING CALORIMETRY; FLEXIBLE STRUCTURES; HYDROGEN; HYDROGEN BONDS; MEMBRANES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEINS; SOLID STATE PHYSICS;

CELL MEMBRANES;

ANTIOXIDANT; CAPSAICIN; CHOLESTEROL; CURCUMIN; HYDROGEN; MEMBRANE PROTEIN; OLIGOMER; PHOSPHATE; PHOSPHOLIPID; ARTIFICIAL MEMBRANE; LIPID; MICELLE; PLANT EXTRACT; TURMERIC EXTRACT;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; ATOMIC PARTICLE; CELL FUSION; CELL MEMBRANE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DEGRADATION; DRUG DESIGN; DRUG EFFECT; EXOCYTOSIS; HYDROGEN BOND; LIPID BILAYER; LIPOPHILICITY; MEMBRANE BINDING; MEMBRANE FUSION; MEMBRANE STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ARTIFICIAL MEMBRANE; CELL STRUCTURE; CHEMICAL STRUCTURE; CHEMISTRY; CURCUMA; DRUG EFFECTS; METABOLISM; MICELLE; PROCEDURES;

ANTIOXIDANTS; CALORIMETRY, DIFFERENTIAL SCANNING; CELL MEMBRANE; CELLULAR STRUCTURES; CHOLESTEROL; CURCUMA; CURCUMIN; LIPIDS; MAGNETIC RESONANCE SPECTROSCOPY; MEMBRANE PROTEINS; MEMBRANES, ARTIFICIAL; MICELLES; MOLECULAR STRUCTURE; PLANT EXTRACTS;

EID: 67749122326     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja809217u     Document Type: Article

References (84)

1. Hatcher, H.; Planalp, R.; Cho, J.; Tortia, F. M.; Torti, S. V. Cell. Mol. Life Sci. 2008, 65, 1631-1652.
2. Joe, B.; Vijaykumar, M.; Lokesh, B. R. Crit. Rev. Food Sci. Nutr. 2004, 44, 97-111.
3. Hafner-Bratkovic, I.; Gaspersic, J.; Smid, L. M.; Bresjanac, M.; Jerala, R. J. Neurochem. 2008, 104, 1553-1564.
4. Ono, K.; Hasegawa, K.; Naiki, H.; Yamada, M. J. Neurosci. Res. 2004, 75, 742-750.
5. Reinke, A. A.; Gestwicki, J. E. Chem. Biol. Drug Des. 2007, 70, 206-215.
6. De Clercq, E. Med. Res. Rev. 2000, 20, 323-349.
7. Goel, A.; Kunnumakkara, A. B.; Aggarwal, B. B. Biochem. Pharmacol. 2008, 75, 787-809.
8. Strimpakos, A. S.; Sharma, R. A. Antioxid. Redox Signal. 2008, 10, 511-545.
9. Jagetia, G. C.; Aggarwal, B. B. J. Clin. Immunol. 2007, 27, 19-35.
10. Bilmen, J. G.; Khan, S. Z.; Javed, M. U. H.; Michelangeli, F. Eur. J. Biochem. 2001, 268, 6318-6327.
11. Ingolfsson, H. I.; Koeppe, R. E.; Andersen, O. S. Biochemistry 2007, 46, 10384-10391.
12. Oezdirekcan, S.; Nyholm, T. K. M.; Raja, M.; Rijkers, D. T. S.; Liskamp, R. M. J.; Killian, J. A. Biophys. J. 2008, 94, 1315-1325.
13. Adachi, S.; Nagao, T.; Ingolfsson, H. I.; Maxfield, F. R.; Andersen, O. S.; Kopelovich, L.; Weinstein, I. B. Cancer Res. 2007, 67, 6493-6501.
14. Lundbaek, J. A.; Birn, P.; Tape, S. E.; Toombes, G. E. S.; Sogaard, R.; Koeppe, R. E.; Gruner, S. M.; Hansen, A. J.; Andersen, O. S. Mol. Pharmacol. 2005, 68, 680-689.
15. Hwang, T. C.; Koeppe, R. E.; Andersen, O. S. Biochemistry 2003, 42, 13646-13658.
16. Lundbaek, J. A. J. Gen. Physiol. 2008, 131, 421-429.
17. Hung, W. C.; Chen, F. Y.; Lee, C. C.; Sun, Y.; Lee, M. T.; Huang, H. W. Biophys. J. 2008, 94, 4331-4338.
18. Sun, Y.; Lee, C. C.; Hung, W. C.; Chen, F. Y.; Lee, M. T.; Huang, H. W. Biophys. J. 2008, 95, 2318-24.
19. Leung, M. H. A.; Colangelo, H.; Kee, T. W. Langmuir 2008, 24, 5672-5675.
20. Dvinskikh, S. V.; Durr, U. H. N.; Yamamoto, K.; Ramamoorthy, A. J. Am. Chem. Soc. 2007, 129, 794-802.
21. Dvinskikh, S.; Durr, U.; Yamamoto, K.; Ramamoorthy, A. J. Am. Chem. Soc. 2006, 128, 6326-6327.
22. Rand, R. P.; Chapman, D.; Larsson, K. Biophys. J. 1975, 15, 1117-1124.
23. Suurkuusk, J.; Lentz, B. R.; Barenholz, Y.; Biltonen, R. L.; Thompson, T. E. Biochemistry 1976, 15, 1393-1401.
24. Janiak, M. J.; Small, D. M.; Shipley, G. G. Biochemistry 1976, 15, 4575-4580.
25. Gardikis, K.; Hatziantoniou, S.; Viras, K.; Wagner, M.; Demetzos, C. Int. J. Pharm. 2006, 318, 118-123.
26. Israelachvili, J. N.; Marcelja, S.; Horn, R. G. Q. Rev. Biophys. 1980, 13, 121-200.
27. Cullis, P. R.; Dekruijff, B. Biochim. Biophys. Acta 1979, 559, 399-420.
28. Gruner, S. M. J. Phys. Chem. 1989, 93, 7562-7570.
29. Andersen, O. S.; Koeppe, R. E. Annu. Rev. Biophys. Biomol. Struct. 2007, 36, 107-130.
30. Lundbaek, J. A.; Birn, P.; Girshman, J.; Hansen, A. J.; Andersen, O. S. Biochemistry 1996, 35, 3825-3830.
31. Lundbaek, J. A.; Birn, P.; Hansen, A. J.; Sogaard, R.; Nielsen, C.; Girshman, J.; Bruno, M. J.; Tape, S. E.; Egebjerg, J.; Greathouse, D. V.; Mattice, G. L.; Koeppe, R. E.; Andersen, O. S. J. Gen. Physiol. 2004, 123, 599-621.
32. Leeson, P. D.; Springthorpe, B. Nat. Rev. Drug Discovery 2007, 6, 881-890.
33. Ganesan, A. Curr. Opin. Chem. Biol. 2008, 12, 306-317.
34. Jaruga, E.; Salvioli, S.; Dobrucki, J.; Chrul, S.; Bandorowicz-Pikula, J.; Sikora, E.; Franceschi, C.; Cossarizza, A.; Bartosz, G. FEBS Lett. 1998, 433, 287-293.
35. Jaruga, E.; Sokal, A.; Chrul, S.; Bartosz, G. Exp. Cell Res. 1998, 245, 303-312.
36. Tonnesen, H. H.; Karlsen, J. Z. Lebensm.-Unters.-Forsch. 1985, 180, 132-134.
37. Tonnesen, H. H.; Karlsen, J. Z. Lebensm.-Unters.-Forsch. 1985, 180, 402-404.
38. Anand, P.; Kunnumakkara, A. B.; Newman, R. A.; Aggarwal, B. B. Mol. Pharm. 2007, 4, 807-818.
39. Ma, Z. S.; Haddadi, A.; Molavi, O.; Lavasanifar, A.; Lai, R.; Samuel, J. J. Biomed. Mater. Res. A 2008, 86A, 300-310.
40. Tonnesen, H. H. Pharmazie 2002, 57, 820-824.
41. Wang, D.; Veena, M. S.; Stevenson, K.; Tang, C.; Ho, B.; Suh, J. D.; Duarte, V. M.; Faull, K. F.; Mehta, K.; Srivatsan, E. S.; Wang, M. B. Clin. Cancer Res. 2008, 14, 6228-6236.
42. Mishra, V. K.; Mohammad, G.; Mishra, S. K. Dig. J. Nanomater. Biostruct. 2008, 3, 163-169.
43. Thangapazham, R. L.; Puri, A.; Tele, S.; Blumenthal, R.; Maheshwari, R. K. Int. J. Oncol. 2008, 32, 1119-1123.
44. Li, L.; Ahmed, B.; Mehta, K.; Kurzrock, R. Mol. Cancer Ther. 2007, 6, 1276-1282.
45. Li, L.; Braiteh, F. S.; Kurzrock, R. Cancer 2005, 104, 1322-1331.
46. Bruzell, E. M.; Morisbak, E.; Tonnesen, H. H. Photochem. Photobiol. Sci. 2005, 4, 523-530.
47. Tonnesen, H. H.; Kristensen, S.; Grinberg, L. N. Int. J. Pharm. 1994, 110, 161-167.
48. Scherer, P. G.; Seelig, J. Biochemistry 1989, 28, 7720-7728.
49. Porcelli, F.; Buck, B.; Lee, D. K.; Hallock, K. J.; Ramamoorthy, A.; Veglia, G. J. Biol. Chem. 2004, 279, 45815-45823.
50. Giordani, C.; Wakai, C.; Yoshida, K.; Okamura, E.; Matubayasi, N.; Nakahara, M. J. Phys. Chem. B 2008, 112, 2622-2628.
51. Tonnesen, H. H.; Karlsen, J.; Mostad, A. Acta Chem. Scand., Ser. B 1982, 36, 475-479.
52. Parimita, S. P.; Ramshankar, Y. V.; Suresh, S.; Row, T. N. G. Acta Crystallogr., Sect. E 2007, 63, O860-O862.
53. Kucerka, N.; Kiselev, M. A.; Balgavy, P. Eur. Biophys. J. Biophys. Lett. 2004, 33, 328-334.
54. Harroun, T. A.; Heller, W. T.; Weiss, T. M.; Yang, L.; Huang, H. W. Biophys. J. 1999, 76, 3176-3185.
55. McElhaney, R. N. Biochim. Biophys. Acta 1986, 864, 361-421.
56. Henzler-Wildman, K. A.; Martinez, G. V.; Brown, M. F.; Ramamoorthy, A. Biochemistry 2004, 43, 8459-8469.
57. Harris, J. S.; Epps, D. E.; Davio, S. R.; Kezdy, F. J. Biochemistry 1995, 34, 3851-3857.
58. Wang, Y. J.; Pan, M. H.; Cheng, A. L.; Lin, L. I.; Ho, Y. S.; Hsieh, C. Y.; Lin, J. K. J. Pharm. Biomed. Anal. 1997, 15, 1867-1876.
59. Chignell, C. F.; Bilski, P.; Reszka, K. J.; Motten, A. G.; Sik, R. H.; Dahl, T. A. Photochem. Photobiol. 1994, 59, 295-302.
60. Began, G.; Sudharshan, E.; Sankar, K. U.; Rao, A. G. A. J. Agric. Food Chem. 1999, 47, 4992-4997.
61. Armen, R. S.; Uitto, O. D.; Feller, S. E. Biophys. J. 1998, 75, 734-744.
62. Jovanovic, S. V.; Boone, C. W.; Steenken, S.; Trinoga, M.; Kaskey, R. B. J. Am. Chem. Soc. 2001, 123, 3064-3068.
63. Ohara, K.; Mizukami, W.; Tokunaga, A.; Nagaoka, S.; Uno, H.; Mukai, K. Bull. Chem. Soc. Jpn. 2005, 78, 615-621.
64. Dix, T. A.; Aikens, J. Chem. Res. Toxicol. 1993, 6, 2-18.
65. Schnitzer, E.; Pinchuk, I.; Lichtenberg, D. Eur. Biophys. J. Biophys. Lett. 2007, 36, 499-515.
66. Cubillos, M.; Lissi, E.; Abuin, E. J. Chil. Chem. Soc. 2006, 51, 825-828.
67. Atkinson, J.; Epand, R. F.; Epand, R. M. Free Radical Biol. Med. 2008, 44, 739-764.
68. Wang, X. Y.; Quinn, P. J. Mol. Membr. Biol. 2000, 17, 143-156.
69. Tonnesen, H. H.; Arrieta, A. F.; Lerner, D. Pharmazie 1995, 50, 689-693.
70. Rukmini, R.; Rawat, S. S.; Biswas, S. C.; Chattopadhyay, A. Biophys. J. 2001, 81, 2122-2134.
71. Mukherjee, S.; Chattopadhyay, A. Biochemistry 1996, 35, 1311-1322.
72. Gardikis, K.; Hatziantoniou, S.; Viras, K.; Demetzos, C. Thermochim. Acta 2006, 447, 1-4.
73. Epand, R. M. Biochim. Biophys. Acta-Rev. Biomembr. 1998, 1376, 353-368.
74. Epand, R. M.; Epand, R. F. Biophys. J. 1994, 66, 1450-1456.
75. Lundbaek, J. A. J. Phys.: Condens. Matter 2006, 18, S1305-S1344.
76. Aranda, F. J.; Villalain, J.; Gomezfernandez, J. C. Biochim. Biophys. Acta-Biomembr. 1995, 1234, 225-234.
77. Boland, L. M.; Drzewiecki, M. M. Cell Biochem. Biophys. 2008, 52, 59-84.
78. Bruno, M. J.; Koeppe, R. E.; Andersen, O. S. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 9638-9643.
79. Sogaard, R.; Werge, T. M.; Bertelsen, C.; Lundbye, C.; Madsen, K. L.; Nielsen, C. H.; Lundbaek, J. A. Biochemistry 2006, 45, 13118-13129.
80. Lemmich, J.; Mortensen, K.; Ipsen, J. H.; Honger, T.; Bauer, R.; Mouritsen, O. G. Eur. Biophys. J. 1997, 25, 293-304.
81. Bezrukov, S. M. Curr. Opin. Colloid Interface Sci. 2000, 5, 237-243.
82. Cevc, G.; Richardsen, H. Adv. Drug Delivery Rev. 1999, 38, 207-232.
83. Epand, R. F.; Martinou, J. C.; Fornallaz-Mulhauser, M.; Hughes, D. W.; Epand, R. M. J. Biol. Chem. 2002, 277, 32632-32639.
84. Priyadarsini, K. I.; Maity, D. K.; Naik, G. H.; Kumar, M. S.; Unnikrishnan, M. K.; Satav, J. G.; Mohan, H. Free Radical Biol. Med. 2003, 35, 475-484.