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Electrochemistry of Low Molecular Weight Organic Compounds of Biological Interest

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Abstract

The electrochemical behavior of a large number of low molecular weight compounds of biological interest has been studied. Reviews such as those of Brezina and Zuman,(1)Underwood and Burnett,(2)McCreery,(3)and Dryhurst(4)have summarized much of the available information on the electrochemical behavior of biologically significant molecules. However, except in relatively few instances, such reviews have reported the electrochemical results without much attempt to correlate the information with known or suspected biological redox reactions. In this review only a rather small number of low molecular weight biomolecules will be considered. However, they will be discussed in some depth and an attempt will be made to demonstrate that electrochemical studies of biomolecules can provide some unique and valuable insights into their biochemical redox behavior.

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References

  1. M. Brezina and P. Zuman, Polarography in Medicine, Biochemistry and Pharmacy, Wiley ( Interscience ), New York (1958).

    Google Scholar 

  2. L. Underwood and R. W. Burnett, in Electroanalytical Chemistry, Vol. 6, A. J. Bard, ed., Marcel Dekker, New York (1973), pp. 1–85.

    Google Scholar 

  3. R. L. McCreery, CRC Critical Review in Analytical Chemistry, Vol. 7 (1978), pp. 88–119.

    Google Scholar 

  4. G. Dryhurst, Electrochemistry of Biological Molecules, Academic Press, New York (1977).

    Google Scholar 

  5. R. N. Adams, Anal Chem. 48, 1126A (1976).

    Google Scholar 

  6. M. D. Hawley, S. V. Tatawawadi, S. Piekarski, and R. N. Adams, J. Am. Chem. Soc. 89, 447 (1967).

    Article  CAS  Google Scholar 

  7. P. Malachesky, L. Marcoux, and R. N. Adams, J. Phys. Chem. 70, 4068 (1966).

    Article  CAS  Google Scholar 

  8. W. Sternson, R. L. McCreery, B. Feinberg, and R. N. Adams, J. Electroanal. Chem. 46, 313 (1973).

    Article  CAS  Google Scholar 

  9. J. Axelrod, in Adrenergic Mechanisms, J. R. Vane, G. E. W. Wolstenholme, and M. O’Conner, eds., Little, Brown and Co., Boston, Mass. (1960).

    Google Scholar 

  10. J. J. Kapin, in Actions of Hormones on Molecular Processes, G. Litwack and D. Kritchevsky, eds., Wiley, New York (1964).

    Google Scholar 

  11. E. G. Ball and T. T. Chen, J. Biol. Chem. 102, 691 (1933).

    CAS  Google Scholar 

  12. G. Satori and C. Cattaneo, Gazz. Chim. Ital. 72, 525 (1942).

    Google Scholar 

  13. S. Senoh and B. Witkop, Am. Chem. Soc. 81, 6231 (1959).

    Article  CAS  Google Scholar 

  14. S. Kaufman and S. Friedman, Pharmacol. Rev. 17, 71 (1965).

    CAS  Google Scholar 

  15. D. C. S. Tse, R. L. McCreery, and R. N. Adams, J. Med. Chem. 19, 37 (1976).

    Article  CAS  Google Scholar 

  16. R. N. Adams, Bull. Menninger Clin. 38, 57 (1974).

    CAS  Google Scholar 

  17. Saner and H. Thoenen, Mol. Pharmacol. 7, 147 (1970).

    Google Scholar 

  18. J. De Champlain and R. Nadeau, Fed. Proc. 30, 877 (1971).

    Google Scholar 

  19. R. N. Adams, E. Murrill, R. L. McCreery, C. L. Blank, and M. Karolczak, Eur. J. Pharmacol. 17, 287 (1972).

    Article  CAS  Google Scholar 

  20. C. L. Blank, P. T. Kissinger, and R. N. Adams, Eur. J. Pharmacol. 19, 391 (1972).

    Article  CAS  Google Scholar 

  21. Rotman, J. Lundstrom, E. McNeal, J. Daly, and C. Creveling, J. Med. Chem. 18, 138 (1975).

    Article  CAS  Google Scholar 

  22. L. Blank, R. L. McCreery, R. M. Wightman, W. Chey, R. N. Adams, J. R. Reid, and E. E. Smissman, J. Med. Chem. 19 178 (1976).

    Article  CAS  Google Scholar 

  23. R. McCreery, R. Dreiling, and R. N. Adams, Brain Res. 73, 15 (1974).

    Article  CAS  Google Scholar 

  24. R. McCreery, R. Dreiling, and R. N. Adams, Brain Res. 73, 22 (1974).

    Google Scholar 

  25. R. L. McCreery, Ph.D. Dissertation, University of Kansas (1974).

    Google Scholar 

  26. Y. O. Liang, R. M. Wightman, P. Plotsky, and R. N. Adams, in Chemical Tools in Catecholamine Research, Vol. I, G. Jonsson, T. Malmfors, and C. Sachs, eds., North-Holland Publishing Co., Amsterdam (1975), p. 15.

    Google Scholar 

  27. Y. O. Liang, P. M. Plotsky, and R. N. Adams, J. Med. Chem. 20, 581 (1977).

    Article  CAS  Google Scholar 

  28. L. Stein and C. D. Wise, Science 171, 1032 (1971).

    Article  CAS  Google Scholar 

  29. S. Senoh, C. R. Creveling, S. Udenfriend, and B. Witkop, J. Am. Chem. Soc. 81, 6236 (1959).

    Article  CAS  Google Scholar 

  30. R. N. Adams, Trends in Neurosciences (Pers. Ed.) 1, 160 (1978).

    Article  Google Scholar 

  31. R. Keller, I. Mefford, A. Oke, E. Strope, J. Conti, R. M. Wightman, P. Plotsky, and R. N. Adams, Modern Pharmacology-Toxicology 10, 761 (1977).

    CAS  Google Scholar 

  32. R. N. Adams, J. Pharm. Sci. 58, 1171 (1969).

    Article  CAS  Google Scholar 

  33. V. Fishman and H. Goldenberg, Proc. Soc. Exp. Biol. Med. 112, 501 (1963).

    CAS  Google Scholar 

  34. J. W Daly and A. A. Manian, Biochem. Pharmacol. 16 2131 (1967).

    Article  CAS  Google Scholar 

  35. Manian, D. H. Efron, and S. R. Harris, Life Sci. 10, (part I), 679 (1971).

    Article  CAS  Google Scholar 

  36. P. Turano, W. J. Turner, and A. A. Manian, J. Chromatogr. 75, 277 (1973).

    Article  CAS  Google Scholar 

  37. R. L. McCreery, J. Pharm. Sci. 66, 357 (1977).

    Article  CAS  Google Scholar 

  38. M. Neptune and R. L. McCreery, J. Org. Chem. 43, 5006 (1978).

    Article  CAS  Google Scholar 

  39. M. Neptune and R. L. McCreery, J. Med. Chem. 21, 362 (1978).

    Article  CAS  Google Scholar 

  40. F. H. Merkle and C. A. Discher, J. Pharm. Sci. 53, 620 (1964).

    Article  CAS  Google Scholar 

  41. H. Y. Cheng, P. H. Sackett, and R. L. McCreery, J. Am. Chem. Soc. 100, 962 (1978).

    Article  CAS  Google Scholar 

  42. H. Y. Cheng, P. H. Sackett, and R L. McCreery, Med. Chem. 21, 948 (1978).

    Article  CAS  Google Scholar 

  43. P. H. Sackett and R. L. McCreery, J. Med. Chem. 22, 1447 (1979).

    Article  CAS  Google Scholar 

  44. T. N. Tozer and D. Tuck, J. Pharm. Sci. 54, 1169 (1965).

    Article  CAS  Google Scholar 

  45. L. Levy, T. N. Tozer, L. D. Tuck, and D. B. Loveland, J. Med. Chem. 15, 898 (1972).

    Article  CAS  Google Scholar 

  46. Creese, D. R. Burt, and S. H. Snyder, Science 192, 481 (1976).

    Google Scholar 

  47. R. Byck, in The Pharmacological Basis of Therapeutics, 5th Ed., L. S. Goodman and A. Oilman, eds., Macmillan, New York (1975).

    Google Scholar 

  48. S. Forrest and D. E. Green, J.Forensic Sci. 17, 592 (1972).

    CAS  Google Scholar 

  49. L. H. Piette, G. Bulow, and I. Yamazaki, Biochim. Biophys. Acta 88, 120 (1964).

    CAS  Google Scholar 

  50. G. M. Gooley, H. Keyser, and F. Setchell, Nature 223, 80 (1969).

    Article  CAS  Google Scholar 

  51. . S. Forrest, F. M. Forrest, and M. Berger, Biochim. Biophys. Acta 29, 441 (1958).

    Article  CAS  Google Scholar 

  52. Buckley, M. Steenberg, H. Barry, and A. A. Manian, J. Pharm. Sci. 62, 715 (1973).

    Article  CAS  Google Scholar 

  53. Manian, D. H. Efron, and M. Goldberg, Life Sci. 4, 2425 (1965).

    Article  CAS  Google Scholar 

  54. V. P. Mackay, A. F. Healey, and J. Baker, Brit. J. Clin. Pharmacol. 1, 425 (1974).

    Google Scholar 

  55. G. Sakalis, T. L. Chan, S. Gershon, and S. Park, Psychopharmacologia 32, 279 (1973).

    Article  CAS  Google Scholar 

  56. T. L. Perry, C. A. Culling, K. Berry, and S. Hanson, Science 146, 82 (1964).

    Article  Google Scholar 

  57. M. H. Van Woert, Nature 219, 1054 (1968).

    Article  Google Scholar 

  58. H. R. Adams, A. A. Manian, M. L. Steenberg, and J. P. Buckley, in Phenothiazines and Structurally Related Drugs, I. S. Forrest, C. J. Carr, and E. Usdin, eds., Raven Press, New York (1974), p. 281.

    Google Scholar 

  59. T. A. Grover, L. H. Piette and A. A. Manian, in The Phenothiazines and Structurally Related Drugs, I. S. Forrest, C. J. Carr, and E. Usdin, eds., Raven Press, New York (1974), p. 561.

    Google Scholar 

  60. W. H. Sebrell and R. S. Harris, eds., The Vitamins, Vol. V, Academic Press, New York (1972), Chap. 16.

    Google Scholar 

  61. H. M. Evans, Vitamins and Hormones 20, 379 (1962).

    Article  CAS  Google Scholar 

  62. F. L. Crane, in Biological Oxidations, T. P. Singer, ed., Interscience, New York (1968), p. 533.

    Google Scholar 

  63. Smith, I. M. Kolthoff, S. Wawzonek, and P. M. Ruoff, J. Am.Chem. Soc. 63, 1018 (1941).

    Article  CAS  Google Scholar 

  64. Smith, L. J. Spillane, and I. M. Kolthoff, J. Am. Chem. Soc. 64, 447 (1942).

    Article  CAS  Google Scholar 

  65. P. D. Boyer, J. Am. Chem. Soc. 73, 733 (1951).

    Article  CAS  Google Scholar 

  66. W. Dürckheimer and L. A. Cohen, Biochem. Biophys. Res. Commun. 9, 262 (1962).

    Article  Google Scholar 

  67. W. Dürckheimer and L. A. Cohen, J. Am. Chem. Soc. 86, 4388 (1964).

    Article  Google Scholar 

  68. Green and D. McHale, in Biochemistry of Quin

    Google Scholar 

  69. F. Marcus and M. D. Hawley, Biochim. Biophys. Acta 201, 1 (1970).

    CAS  Google Scholar 

  70. W. H. Harrison, J. E. Gander, E. R. Blakley, and P. D. Boyer, Biochim. Biophys. Acta 21, 150 (1956).

    Article  CAS  Google Scholar 

  71. F. Marcus and M. D. Hawley, J. Org. Chem. 35, 2185 (1970).

    Article  CAS  Google Scholar 

  72. S. Wawzonek, R. Berkey, E. W. Blaha, and M. E. Runner, J. Electrochem. Soc. 103, 456 (1956).

    Article  CAS  Google Scholar 

  73. S. Wawzonek, R. Berkey, E. W. Blaha, and M. E. Runner, J. Electrochem. Soc. 103, 456 (1956).

    Article  CAS  Google Scholar 

  74. G. J. Hoijtink, J. van Schooten, E. de Bdfer, and W. Y. Aalbersberg, Recl. Trav. Chim. Pays-Bas 73, 355 (1954).

    Article  CAS  Google Scholar 

  75. G. Dryhurst, K. Kadish, and F. Scheller, Biological Electrochemistry, Vol. I, Academic Press, New York (1982), pp. 67–85.

    Google Scholar 

  76. F. L. Crane, Ann. Rev. Biochem. 46, 439 (1977).

    Article  CAS  Google Scholar 

  77. D. D. Tyler, J. Gonze, R. W. Estabrook, and R. A. Butow, in Non-Heme Iron Proteins, A. San Pietro, ed., Antioch Press, Yellow Springs, Ohio (1965), pp. 447–60.

    Google Scholar 

  78. D. Backstrom, B. Norling, A. Ehrenberg, and L. Ernster, Biochim. Biophys. Acta 197,108 (1970).

    Article  CAS  Google Scholar 

  79. S. Odashima and H. Abe, Saibo Siebutsugaku Shimpojiumu 22, 217 (1972).

    CAS  Google Scholar 

  80. P. Kayushin and O. N. Brzhevskaya, Biofizika 23,1024 (1978); Chem. Abstr. 90,67919h.

    CAS  Google Scholar 

  81. N. Brzhevskaya, O. S. Nedelina, E. M. Sheksheev, and L. P. Kayushin, Dokl. Akad. Nauk. SSSR 232, 221 (1977): Chem. Abstr. 86, 84865x.

    CAS  Google Scholar 

  82. . L. Lehninger, The Mitochondrion, Benjamin, New York (1964).

    Google Scholar 

  83. Klingenberg and A. Kroger, in Current Topics in Bioenergetics, Vol. 2, D. R. Sanadi, ed., Academic Press, New York (1967), p. 186.

    Google Scholar 

  84. R. C. Bohinski, Modern Concepts in Biochemistry, Third Edition, Allyn and Bacon, Boston, Mass. (1979), p. 446.

    Google Scholar 

  85. R. C. Bohinski, Modern Concepts in Biochemistry, Third Edition, Allyn and Bacon, Boston, Mass. (1979), p. 446.

    Google Scholar 

  86. S. Goodman and A. Gilman, eds., The Pharmacological Basis of Therapeutics, 3rd Ed., Macmillan, New York (1967), p. 355.

    Google Scholar 

  87. G. Dryhurst, Electrochemistry of Biological Molecules, Academic Press, New York (1977), Chap. 3.

    Google Scholar 

  88. D. Benedict, P. H. Forsham, and D. Stetten, J. Biol. Chem. 181, 183 (1949).

    CAS  Google Scholar 

  89. Buzard, C. Bishop, and J. H. Talbott, J. Biol. Chem. 196, 179 (1952).

    CAS  Google Scholar 

  90. J. B. Wyngaarden and D. Stetten, J. Biol. Chem. 203, 9 (1953).

    CAS  Google Scholar 

  91. B. Sorensen, Metabolism 8, 687 (1959).

    CAS  Google Scholar 

  92. E. S. Canellakis, A. L. Tuttle, and P. P. Cohen, J. Biol. Chem. 213, 397 (1955).

    CAS  Google Scholar 

  93. K. Agner, J. Exp. Med. 92, 337 (1950).

    Article  CAS  Google Scholar 

  94. K. G. Paul and Y. Avi-Dor, Acta Chem. Scand. 8, 637 (1954).

    Article  CAS  Google Scholar 

  95. J. B. Wyngaarden, J.Biol. Chem. 235, 3544 (1960).

    Google Scholar 

  96. . D. Polis and H. W. Shmukler, in Methods of Enzymology, Vol. II, S. P. Colowick and N. O. Kaplan, eds., Academic Press, New York (1955), p. 813.

    Google Scholar 

  97. J. Hunter, in Methods in Enzymology, Vol. II, S. P. Colowick and N. O. Kaplan, eds., Academic Press, New York (1955), p. 791.

    Chapter  Google Scholar 

  98. G. C. Mills, J. Biol. Chem. 234, 502 (1959).

    CAS  Google Scholar 

  99. S. Huszak, cited by R. Lemberg and J. W. Legge, in Hematin Compounds and Bile Pigments, Wiley ( Interscience ), New York (1947), p. 430.

    Google Scholar 

  100. G. Soberon and P. P. Cohen, Rev. Soc. Chim. Mexico 6, 45 (1962).

    CAS  Google Scholar 

  101. G. Soberon and P. P. Cohen, Arch. Biochem. Biophys. 103, 331 (1963).

    Article  CAS  Google Scholar 

  102. L. Tuttle, Ph.D. Thesis, University of Wisconsin (1953), cited in reference (101).

    Google Scholar 

  103. J. S. Dunn, H. K. Shelhan, and M. C. B. MacLetchie, Lancet 1, 484 (1943).

    Google Scholar 

  104. Griffiths, J. Biol. Chem. 172, 853 (1948).

    CAS  Google Scholar 

  105. G. Dryhurst, J. Electrochem. Soc. 119, 1559 (1972).

    Article  Google Scholar 

  106. J. L. Owens, H. A. Marsh, and G. Dryshurst, J. Electroanal. Chem. 91, 231 (1978).

    CAS  Google Scholar 

  107. Z. Wrona, J. L. Owens, and G. Dryhurst, J. Electroanal. Chem. 105, 295 (1979).

    Article  CAS  Google Scholar 

  108. V. E. Norvell and G. Mamantov, Anal. Chem. 49, 1470 (1977).

    Article  CAS  Google Scholar 

  109. Brajter-Toth and G. Dryhurst, J. Electroanal. Chem. 122, 205 (1981).

    CAS  Google Scholar 

  110. M. Z. Wrona and G. Dryhurst, Biochim. Biophys. Acta 570, 371 (1979).

    CAS  Google Scholar 

  111. H. R. Howell and J. B. Wyngaarden, J. Biol. Chem. 235, 3544 (1960).

    CAS  Google Scholar 

  112. M. Z. Wrona, R. N. Goyal, and G. Dryhurst, Bioelectrochem. Bioenerg. 7, 433 (1980).

    Article  CAS  Google Scholar 

  113. R. Bentley and A. Neuberger, Biochem. J. 52, 694 (1952).

    CAS  Google Scholar 

  114. E. S. Cancellakis and P. P. Cohen, J. Biol. Chem. 213, 385 (1955).

    Google Scholar 

  115. H. R. Mahler, H. M. Baum, and G. Hübscher, Science 124, 705 (1956).

    Article  CAS  Google Scholar 

  116. O.M. Pitts and D. G. Priest, Biochemistry 12 1358 (1973).

    Article  CAS  Google Scholar 

  117. G. P. A. Bongaerts and G. D. Vogels, Biochim. Biophys. Acta 567, 295 (1979).

    CAS  Google Scholar 

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Dryhurst, G. (1985). Electrochemistry of Low Molecular Weight Organic Compounds of Biological Interest. In: Srinivasan, S., Chizmadzhev, Y.A., Bockris, J.O., Conway, B.E., Yeager, E. (eds) Comprehensive Treatise of Electrochemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2359-4_2

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