Abstract
Many studies have been conducted by using the oil (O)|water (W) interface as a simple model for understanding ion transfer (IT) or electron transfer (ET) across biomembranes. In this review, we revisit the usability of the O|W interface as a biomembrane model. For understanding biomembrane IT, the O|W interface is the simplest and best suited model. For example, the standard Gibbs transfer energy of drug ions at the O|W interface is a useful measure for evaluating their membrane permeability in a conventional in vitro assay, called PAMPA. However, the O|W interface is not necessarily a good model for understanding biomembrane ET. This is because no net current can be observed with the O|W interface, owing to the ET-coupled proton transfer. In such a case, the self-assembled monolayer (SAM) formed on a metal electrode serves as a better model for understanding biomembrane ET.
Similar content being viewed by others
References
J. M. Berg, J. L. Tymoczko, and L. Stryer, “Biochemistry”, 7th ed., 2012, Freeman, New York.
T. Iwata, H. Nagatani, and T. Osakai, Anal. Sci., 2017, 33, 813.
H. T. Tien, R. H. Barish, L.-Q. Gu, and A. L. Ottova, Anal. Sci., 1998, 14, 3.
K. Hichiri, O. Shirai, Y. Kitazumi, and K. Kano, Electrochemistry, 2016, 84, 328.
J. F. Rusling, Acc. Chem. Res., 1998, 31, 363.
L. J. C. Jeuken, S. D. Connell, P. J. F. Henderson, R. B. Gennis, S. D. Evans, and R. J. Bushby, J. Am. Chem. Soc., 2006, 128, 1711.
M. D. Porter, T. B. Bright, D. L. Allara, and C. E. D. Chidsey, J. Am. Chem. Soc., 1987, 109, 3559.
K. Takehara, H. Takemura, Y. Ide, and S. Okayama, J. Electroanal. Chem., 1991, 308, 345.
K. Shiota, M. Ueki, and T. Osakai, J. Electroanal. Chem., 2015, 745, 22.
T. Osakai, T. Yamamoto, and M. Ueki, Electrochemistry, 2019, 87, 59.
M. Senda, T. Kakiuchi, and T. Osakai, Electrochim. Acta, 1991, 36, 253.
H. H. Girault, “Modern Aspects of Electrochemistry”, No. 25, ed. J.O.M. Bockris, B. E. Conway, and R. E. White, 1993, Chap. 1, Plenum Press, New York.
Z. Samec, Pure Appl. Chem., 2004, 76, 2147.
“Liquid Interfaces in Chemical, Biological, and Pharmaceutical Applications”, ed. A. G. Volkov, 2001, Marcel Dekker, New York.
C. Hansch, P. P. Maloney, T. Fujita, and R. M. Muir, Nature, 1962, 194, 178.
C. Hansch and T. Fujita, J. Am. Chem. Soc., 1964, 86, 1616.
T. Fujita, J. Iwasa, and C. Hansch, J. Am. Chem. Soc., 1964, 86, 5175.
A. Leo, C. Hansch, and D. Elkins, Chem. Rev., 1971, 71, 525.
K. Kontturi and L. Murtomäki, J. Pharm. Sci., 1992, 81, 970.
K. Arai, M. Ohsawa, F. Kusu, and K. Takamura, Bioelectrochem. Bioenerg., 1993, 31, 65.
K. Arai, F. Kusu, N. Tsuchiya, S. Fukuyama, and K. Takamura, Denki Kagaku, 1994, 62, 840.
F. Reymond, V. Chopineaux-Courtois, G. Steyaert, G. Bouchard, P. A. Carrupt, B. Testa, and H. H. Girault, J. Electroanal. Chem., 1999, 462, 235.
G. Bouchard, P. A. Carrupt, B. Testa, V. Gobry, and H. H. Girault, Pharm. Res., 2001, 18, 702.
G. Bouchard, P. A. Carrupt, B. Testa, V. Gobry, and H. H. Girault, Chem. Eur. J., 2002, 8, 3478.
J. Ding and T. Osakai, Electroanalysis, 2001, 13, 384.
J. Ding, H. Hotta, and T. Osakai, J. Electroanal. Chem., 2001, 505, 133.
V. Gobry, S. Ulmeanu, F. Reymond, G. Bouchard, P. A. Carrupt, B. Testa, and H. H. Girault, J. Am. Chem. Soc., 2001, 123, 10684.
S. M. Ulmeanu, H. Jensen, G. Bouchard, P. A. Carrupt, and H. H. Girault, Pharm. Res., 2003, 20, 1317.
A. Mälkiä, L. Murtomäki, A. Urtti, and K. Kontturi, Eur. J. Pharm. Sci., 2004, 23, 13.
M. Nakamura and T. Osakai, J. Electroanal. Chem., 2016, 779, 55.
Y. Fujii, E. Yoshida, and T. Osakai, Bull. Chem. Soc. Jpn., 2018, 91, 1618.
K. Maeda, S. Nagami, Y. Yoshida, H. Ohde, and S. Kihara, J. Electroanal. Chem., 2001, 496, 124.
Y. Tatsuno, T. Kozuru, Y. Yoshida, and K. Maeda, Anal. Sci., 2012, 28, 1145.
T. Kozuru, Y. Tatsuno, Y. Yamaguchi, Y. Choda, Y. Yoshida, and K. Maeda, Rev. Polarogr., 2016, 62, 101.
Y. Kushida, O. Shirai, Y. Takano, Y. Kitazumi, and K. Kano, Anal. Sci., 2015, 31, 677.
O. Shirai and K. Kano, Rev. Polarogr., 2015, 61, 93.
O. Shirai, Anal. Sci., 2018, 34, 753.
M. Suzuki, S. Umetani, M. Matsui, and S. Kihara, J. Electroanal. Chem., 1997, 420, 119.
T. Osakai, N. Akagi, H. Hotta, J. Ding, and S. Sawada, J. Electroanal. Chem., 2000, 490, 85.
T. Osakai, H. Jensen, H. Nagatani, D. J. Fermín, and H. H. Girault, J. Electroanal. Chem., 2001, 510, 43.
M. Suzuki, M. Matsui, and S. Kihara, J. Electroanal. Chem., 1997, 438, 147.
H. Ohde, K. Maeda, Y. Yoshida, and S. Kihara, Electrochim. Acta, 1998, 44, 23.
Y. Imai, T. Sugihara, and T. Osakai, J. Phys. Chem. B, 2012, 116, 585.
D. G. Georganopoulou, D. J. Caruana, J. Strutwolf, and D. E. Williams, Faraday Discuss., 2000, 116, 109.
T. Sugihara, H. Hotta, and T. Osakai, Phys. Chem. Chem. Phys., 2004, 6, 3563.
Y. Sasaki, T. Sugihara, and T. Osakai, Anal. Biochem., 2011, 417, 129.
H. Hotta, S. Ichikawa, T. Sugihara, and T. Osakai, J. Phys. Chem. B, 2003, 107, 9717.
A. R. Hilgers, R. A. Conradi, and P. S. Burton, Pharm. Res., 1990, 7, 902.
P. Artursson, J. Pharm. Sci., 1990, 79, 476.
M. J. Cho, D. P. Thompson, C. T. Cramer, T. J. Vidmar, and J. F. Scieszka, Pharm. Res., 1989, 6, 71.
J. D. Irvine, L. Takahashi, K. Lockhart, J. Cheong, J. W. Tolan, H. E. Selick, and J. R. Grove, J. Pharm. Sci., 1999, 88, 28.
M. Kansy, F. Senner, and K. Gubernator, J. Med. Chem., 1998, 41, 1007.
E. H. Kerns, J. Pharm. Sci., 2001, 90, 1838.
K. Sugano, H. Hamada, M. Machida, and H. Ushio, J. Biomol. Screen., 2001, 6, 189.
M. Fujikawa, R. Ano, K. Nakao, R. Shimizu, and M. Akamatsu, Bioorg. Med. Chem., 2005, 13, 4721.
M. Fujikawa, R. Ano, K. Nakao, R. Shimizu, and M. Akamatsu, Bioorg. Med. Chem., 2007, 15, 3756.
A. Avdeef, S. Bendels, L. Di, B. Faller, M. Kansy, K. Sugano, and Y. Yamauchi, J. Pharm. Sci., 2007, 96, 2893.
M. Nakamura and T. Osakai, Eur. J. Pharm. Sci., 2016, 91, 154.
T. Osakai, Y. Naito, K. Eda, and M. Yamamoto, J. Phys. Chem. B, 2015, 119, 13167.
A. Yamada, E. Yoshida, K. Eda, and T. Osakai, Anal. Sci., 2018, 34, 919.
Y. Naito, W. Murakami, K. Eda, M. Yamamoto, and T. Osakai, J. Phys. Chem. B, 2015, 119, 6010.
O. Shirai, Y. Yoshida, and S. Kihara, Anal. Bioanal. Chem., 2006, 386, 494.
Z. Samec, V. Marecek, and J. Weber, J. Electroanal. Chem., 1979, 103, 11.
H. Hotta, S. Ichikawa, T. Sugihara, and T. Osakai, J. Phys. Chem. B, 2003, 107, 9717.
T. Osakai, S. Ichikawa, H. Hotta, and H. Nagatani, Anal. Sci., 2004, 20, 1567.
It was assumed that UQ and Cyt c coexist in a reaction layer on the base gold electrode and that UQ undergoes a two-step one-electron transfer at the electrode. See Fig. 4 in Ref. 10.
G. J. Gordillo and D. J. Shiffrin, J. Chem. Soc., Faraday Trans., 1994, 90, 1913.
T. Yamamoto, “Directional Electron Transfer from Ubiquinone-10 to Cytochrome c at the Self-Assembled Monolayer Modified Electrode” (Master’s thesis; in Japanese), 2018, Kobe University, Nada, Kobe, Japan.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Osakai, T. Water Interface the Simplest and Best Suited Model for Understanding Biomembranes?. ANAL. SCI. 35, 361–366 (2019). https://doi.org/10.2116/analsci.18R005
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2116/analsci.18R005