Skip to main content

The structure and reactivity of arsenic compounds: Biological activity and drug design

  • Chapter
  • First Online:
Bioinorganic Chemistry

Part of the book series: Structure and Bonding ((STRUCTURE,volume 78))

Abstract

Arsenic is a potentially essential element for mammals and is abundant in certain marine organisms. Arsenic compounds have been widely used as drugs in the past and were used until recently as growth promoters for some farm animals. Here we review the structures, reactivities and biological and pharmacological activities of arsenic compounds, emphasising both the similarities to and differences from other Group V elements (P, Sb, Bi). There appear to be no crystal structures of As-containing peptides or proteins, and the inhibition of thiol-enzymes by As(III), although widely quoted, is poorly understood. There is much scope for the design of arsenic compounds as drugs, but progress depends on the discovery of new probes for investigating the structural and redox chemistry and biochemistry of arsenic, especially in aqueous media.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Polson CJ, Green MA, Lee MR (1983) Clinical Toxicology, 3rd edn, Pitman, London, chap 23, p 421

    Google Scholar 

  2. Schroeder HA, Balassa JJ (1966) Journal of Chronic Diseases 19: 85 and references cited therein

    CAS  Google Scholar 

  3. Doak GO, Freedman LD in: Medicinal Chemistry (ed A Burger), 2nd edn, Interscience, New York 1960, chap 47, pp 1027–1049 and references cited therein

    Google Scholar 

  4. Vallee BL: AMA Archives of Industrial Health 21, 132 (1960) and references cited therein

    CAS  Google Scholar 

  5. Squibb KS, Fowler BA (1983) In: Fowler BA(ed) Biological and environmental effects of arsenic, Elsevier, Amsterdam, chap 7, p 233 and references cited therein

    Google Scholar 

  6. Albert A: Selective Toxicity, the physicochemical basis of therapy, 7th edn, Chapman and Hall, London 1985, (a) chap 13, pp 551–555 (b) chap 6, pp 206–219

    Google Scholar 

  7. Herrmann W, Hilmer H: Angew Chem 66, 349 (1954)

    CAS  Google Scholar 

  8. Hindmarsh JT, McCurdy RF: CRC Critical Reviews in Clinical Laboratory Sciences 23, 315 (1986) and references cited therein

    CAS  Google Scholar 

  9. Bunclavari S (ed) (1989) The Merck Index 11th edn, Merck, New Jersey

    Google Scholar 

  10. Frost DV in: Inorganic and Nutritional Aspects of Cancer (ed Schrauzer GN), Plenum, New York 1978, chap 18, pp 259–279

    Google Scholar 

  11. Datta DV, Narang APS: Bulletin of the Postgraduate Institute of Med Educ Research, Chandigarh 13, 180 (1979)

    CAS  Google Scholar 

  12. Cullen WR, Reimer KJ: Chem Rev 89, 713 (1989)

    CAS  Google Scholar 

  13. Knowles FC, Benson AA: Trends in Biochemical Science, 178 (1983)

    Google Scholar 

  14. Greenwood NN, Earnshaw A: Chemistry of the Elements, Pergamon, Oxford 1984, chaps 12 (P) and 13 (As, Sb, Bi)

    Google Scholar 

  15. Santhanam KSV, Sundaresan NS: in Standard Potentials in Aqueous Solution (eds Bard AJ, Parsons R, Jordan J), Marcel Dekker, New York 1985, chap 7, part III, pp 162–172

    Google Scholar 

  16. Santhanam KSV in: Standard Potentials in Aqueous Solution (eds Bard AJ, Parsons R, Jordan J), Marcel Dekker, New York 1985, chap 7, part II, pp 139–162; Past V in: ibid, part IV, pp 172–179

    Google Scholar 

  17. Phillips CSG and Williams RJP: Advanced Inorganic Chemistry, Oxford University Press, Oxford 1965, chap 17, p 632

    Google Scholar 

  18. Stanbury DM: Adv Inorg Chem 33, 69 (1989)

    CAS  Google Scholar 

  19. Doak GO, Freedman LD: Organometallic compounds of arsenic, antimony, and bismuth, Wiley, New York 1970 (6) chap 2 and references cited therein (b) chap 3 and references cited therein

    Google Scholar 

  20. Watson A, Svehla G: Analyst (London) 100, 489 (1975) and references cited therein

    CAS  Google Scholar 

  21. Brdicka R: Coll Czech Chem Commun 7, 457 (1935)

    CAS  Google Scholar 

  22. Lowry JH, Smart RB, Mancy KH: Anal Chem 50, 1303 (1978) and references cited therein

    CAS  Google Scholar 

  23. DuPont TJ, Mills JL: Inorg Chem 12, 2487 (1973)

    CAS  Google Scholar 

  24. Huttner G, v Seyerl J, Marsili M, Schmid HG: Angew Chem Int Ed Eng 14, 434 (1975)

    Google Scholar 

  25. Huttner G, Muller HD, Frank A, Lorenz H: Angew Chem Int Ed Eng 14, 705 (1975)

    Google Scholar 

  26. v Seyerl H, Moerins H, Wagner A, Frank A, Huttner G: Angew Chem Int Ed Eng 17, 844 (1978)

    Google Scholar 

  27. Kuykendall GL, Mills JL: J Organomet Chem 118, 123 (1976)

    CAS  Google Scholar 

  28. Matsumoto K, Kawaguchi H, Kuroya H, Kawaguchi S: Bull Chem Soc Japan 46, 2424 (1973)

    CAS  Google Scholar 

  29. Kamenar B, Grdenic D, Prout CK: Acta Crystallogr B26, 181 (1970)

    Google Scholar 

  30. Wells AJ: Structural Inorganic Chemistry, 5th edn, Clarendon, Oxford 1984, (a) chap 19, p 844 (b) chap 20, p 866 and references cited therein

    Google Scholar 

  31. Raston CR, White AH: J Chem Soc Dalton Trans, 2425 (1975)

    Google Scholar 

  32. Raston CR, White AH: J Chem Soc Dalton Trans, 791 (1976)

    Google Scholar 

  33. Pertlik P: Monatsheft für Chemie 106, 755 (1975)

    CAS  Google Scholar 

  34. Menary JW: Acta Cryst 11, 742 (1958)

    CAS  Google Scholar 

  35. Corbridge DEC: Acta Cryst 9, 991 (1956)

    CAS  Google Scholar 

  36. Doak GO, Long GG, Freedman LD in: Kirk-Othmer, Encyclopaedia of Chemical Technology (Vol 3), 1982, pp 251–266

    Google Scholar 

  37. Jones DEH, Ledingham KWD: Nature 299, 626 (1982)

    CAS  Google Scholar 

  38. Aylett BJ: Organometallic compounds, The Main Group Elements (Vol 1, Part Two), Groups IV and V, 4th edn, Chapman and Hall, London 1979, chap 7, pp 390–507

    Google Scholar 

  39. Arif AM, Cowley AH, Pakulski M: J Chem Soc Chem Commun, 165 (1987)

    Google Scholar 

  40. Rheingold AL, DiMaio AJ: Organometallics 5, 393 (1986)

    CAS  Google Scholar 

  41. Camerman N, Trotter J: J Chem Soc, 219 (1964)

    Google Scholar 

  42. Cordes AW, Gwinup PD, Malmstrom MC: Inorg Chem 11, 836 (1972)

    CAS  Google Scholar 

  43. Dräger M: Z Anorg Allg Chem 411, 79 (1975)

    Google Scholar 

  44. Bergerhoff G, Namgung H: Zeitschrift für Kristallographie 150, 209 (1979)

    CAS  Google Scholar 

  45. Cotton FW, Wilkinson G: Advanced Inorganic Chemistry, 4th edn, Wiley-Interscience, Chichester 1980, chap 14

    Google Scholar 

  46. Holmes RR: Acc Chem Res 12, 257 (1979)

    CAS  Google Scholar 

  47. Holmes RR: Prog Inorg Chem 32, 119 (1984)

    CAS  Google Scholar 

  48. Holmes RH, Day RO, Sau AC: Organometallics 4, 714 (1985) and references cited therein

    CAS  Google Scholar 

  49. Worzala H: Acta Cryst B24, 987 (1968)

    Google Scholar 

  50. Mighell AD, Smith JP, Brown WE: Acta Cryst B25, 776 (1969)

    Google Scholar 

  51. Cullen WR: Adv Organomet Chem 4, 145 (1966) and references cited therein

    CAS  Google Scholar 

  52. Kostick A, Secco AS, Billinghurst M, Abrams D, Cantor S: Acta Cryst C45, 1306 (1989)

    CAS  Google Scholar 

  53. Cannon JD, Edmonds JS, Francesconi KA, Raston CL, Saunders JB, Skelton BW, White AH: Aust J Chem 34, 787 (1981)

    CAS  Google Scholar 

  54. Edmonds JS, Francesconi KA, Healy PC, White AH: J Chem Soc Perkin Trans I, 2989 (1982)

    Google Scholar 

  55. Shimada A: Bull Chem Soc Japan 34, 639 (1961)

    CAS  Google Scholar 

  56. Chatterjee A, Gupta SPS: Acta Cryst B33, 3593 (1977)

    CAS  Google Scholar 

  57. Chatterjee A, Gupta SPS: Acta Cryst B33, 164 (1977)

    CAS  Google Scholar 

  58. Stuckey JE, Cordes AW, Handy LB, Perry RW, Fair CK: Inorg Chem 11, 1846 (1972)

    CAS  Google Scholar 

  59. Bohra R, Roesky HW, Noltemeyer M, Sheldrick GM: J Chem Soc Dalton Trans, 2011 (1984)

    Google Scholar 

  60. Dove MFA, Sowerby DB: Coordination Chem Rev 75, 297 (1986)

    CAS  Google Scholar 

  61. Sigwarth B, Zsolnai L, Scheidsteger O, Huttner G: J Organomet Chem 235, 43 (1982)

    CAS  Google Scholar 

  62. Ashe AJ III, Ludwig EG Jr: J Organometallic Chem 303, 197 (1986) and references cited therein

    CAS  Google Scholar 

  63. Hedberg K, Hughes EW, Waser J: Acta Cryst 14, 369 (1961)

    CAS  Google Scholar 

  64. Rheingold AL, Sullivan PJ: Organometallics 2, 327 (1983)

    CAS  Google Scholar 

  65. Smith LR, Mills JL, J Organometal Chem 84, 1 (1975) and references cited therein

    CAS  Google Scholar 

  66. Levinson AS: J Chem Ed 54, 98 (1977)

    CAS  Google Scholar 

  67. Burns JH, Waser J: J Amer Chem Soc 79, 859 (1957)

    CAS  Google Scholar 

  68. Cowley AH, Pinnel RP: Topics in Phosphorus Chemistry 4, 1 (1967)

    CAS  Google Scholar 

  69. Smith LR, Mills JL: J Amer Chem Soc 98, 3852 (1976)

    CAS  Google Scholar 

  70. DuPont TJ, Smith LR, Mills JL: J Chem Soc Chem Commun, 1001 (1974)

    Google Scholar 

  71. Breunig HJ, Häberle K, Dräger M, Severengiz T: Angew Chem Int Ed Eng 24, 72 (1985)

    Google Scholar 

  72. Daly JJ, Sanz, F: Helv Chim Acta 53, 1879 (1970)

    CAS  Google Scholar 

  73. Dimaio AJ, Rheingold AL: Chem Rev 90, 169 (1990)

    CAS  Google Scholar 

  74. Cowley AH, Lasch JG, Norma NC, Pakulski M: J Amer Chem Soc 105, 5506 (1983) and references cited therein

    CAS  Google Scholar 

  75. Cowley AH, Norman NC: Prog Inorg Chem 34, 1 (1986) and references cited therein

    CAS  Google Scholar 

  76. Huttner G: Pure and Appl Chem 58, 585 (1986) and references cited therein

    CAS  Google Scholar 

  77. Carty AJ, Taylor NJ, Coleman AW, Lappert MF: J Chem Soc, Chem Commun, 639 (1979)

    Google Scholar 

  78. Drew MGB, Wolters AP, Tomkins IB: J Chem Soc Dalton Trans, 974 (1977)

    Google Scholar 

  79. Foy RM, Kepert DL, Raston CL, White, AH: J Chem Soc Dalton Trans, 440 (1980)

    Google Scholar 

  80. Drew MGB, Wolters AP: Acta Cryst B33, 205 (1977)

    CAS  Google Scholar 

  81. Gilli G, Sacerdoti M, Domiano P: Acta Cryst B30, 1485 (1974) and references cited therein

    Google Scholar 

  82. Cullen WR, Dolphin D, Einstein FWB, Mihichuk LM, Willis AC: J Amer Chem Soc. 101, 6898 (1979)

    CAS  Google Scholar 

  83. Busetto C, D'Alfonso A, Maspero F, Perego G, Zazzetta A: J Chem Soc Dalton Trans, 1828 (1977)

    Google Scholar 

  84. Mague JT: Inorg Chem 12, 2649 (1973)

    Google Scholar 

  85. Mague JT: Inorg Chem 9, 1610 (1970)

    CAS  Google Scholar 

  86. Manojlovic-Muir L, Muir KW, Ibers JA: Discussions of the Faraday Society 47, 84 (1969)

    Google Scholar 

  87. Dunn JBR, Jacobs R, Fritchie CJ Jr: J Chem Soc Dalton Trans, 2007 (1972)

    Google Scholar 

  88. Spek AL, van Eijch BP, Jans RJF, van Koten G: Acta Cryst C43, 1878 (1987)

    CAS  Google Scholar 

  89. Pierpoint CG, Eisenberg, R: Inorg Chem 11, 828 (1972)

    Google Scholar 

  90. Holloway RG, Penfold BR, Colton R, McCormick MJ: J Chem Soc, Chem Commun, 485 (1976)

    Google Scholar 

  91. Colton R, McCormick MJ, Pannan CD: Aust J Chem 31, 1425 (1978)

    CAS  Google Scholar 

  92. Cheng PT, Nyburg SC: Can J Chem 50, 912 (1972)

    CAS  Google Scholar 

  93. Russell DR, Tucker PA: J Chem Soc Dalton Trans, 1752 (1975)

    Google Scholar 

  94. Gill JT, Mayerle JJ, Welcker PS, Lewis DF, Ucko DA, Barton DJ, Stowens D, Lippard SJ: Inorg Chem 15, 1155 (1976)

    CAS  Google Scholar 

  95. Puddephatt RJ: The Chemistry of Gold, Elsevier, Amsterdam 1978, pp 261–269 and references cited therein.

    Google Scholar 

  96. Berners-Price SJ, Mazid MA, Sadler PJ: J Chem Soc Dalton Trans, 969 (1984)

    Google Scholar 

  97. Ni Dhubhghaill OM, Sadler PJ, Kuroda R: J Chem Soc Dalton Trans, 2913 (1990)

    Google Scholar 

  98. Critical Stability Constants (eds Smith RM, Martell AE), Plenum, vol 4, pp 55–56 (1976), vol 5, pp 409–410 (1982)

    Google Scholar 

  99. Merijanian A, Zingaro RA: Inorg Chem 5, 187 (1966)

    CAS  Google Scholar 

  100. Cooney RV, Mumma RO, Benson AA: Proc Nat Acad Sci U.S.A 75, 4262 (1978)

    CAS  Google Scholar 

  101. Data for Biochemical Research (eds Dawson RMC, Elliot DC, Elliot WH, Jones KM), 3rd edn, Clarendon Press, Oxford 1986, p 9

    Google Scholar 

  102. Pauling L: The Nature of the Chemical Bond, 3rd edn, Cornell University Press, New York 1960, p 85

    Google Scholar 

  103. Ananthakrishnan R: Proceedings of the Indian Academy of Science 5A, 200 (1937)

    CAS  Google Scholar 

  104. Baudler M: Z Elektrochem 59, 173 (1955); Chem Abs 49, 11418h (1955)

    CAS  Google Scholar 

  105. Van Wazer JR, Callis CF, Shoolery JN, Jones RC: J Amer Chem Soc 78, 5715 (1956)

    Google Scholar 

  106. Furberg S, Landmark P: Acta Chem Scand 11, 1505 (1957)

    CAS  Google Scholar 

  107. Dos Remedios Pinto MAF, Sadler PJ, Neidle S, Sanderson MR, Subbiah A, Kuroda R: J Chem Soc Chem Comm 13 (1980)

    Google Scholar 

  108. Loehr TM, Plane RA: Inorg Chem 7, 1708 (1968)

    CAS  Google Scholar 

  109. Kirschenbaum LJ, Rush JD: Inorg Chem 22, 3304 (1983)

    CAS  Google Scholar 

  110. Baer CD, Edwards JO, Rieger PH, Silva CM: Inorg Chem 22, 1402 (1983)

    CAS  Google Scholar 

  111. Copenhafer WC, Rieger PH: J Amer Chem Soc 100, 3776 (1978)

    CAS  Google Scholar 

  112. Okumura A, Yamamoto N, Okazaki N: Bull Chem Soc Japan 46, 3633 (1973)

    Google Scholar 

  113. Okumura A, Okazaki N: Bull Chem See Japan 46, 2937 (1973)

    CAS  Google Scholar 

  114. Dennard AE, Williams RJP: J Chem Soc A, 812 (1966)

    Google Scholar 

  115. Baer CD, Edwards JO, Kaus MJ, Richmond TG, Rieger PH: J Amer Chem Soc 102, 5793 (1980)

    CAS  Google Scholar 

  116. Baer CD, Edwards JO, Rieger PH: Inorg Chem 20, 905 (1981)

    CAS  Google Scholar 

  117. Lagunas R: Arch Biochem Biophys 205, 67 (1980)

    CAS  Google Scholar 

  118. Mayes PA in: Harper's Review of Biochemistry (20th edn eds Martin DW, Mayes PA, Rodwell VW, Granner DR), Lange, Los Altos 1983, p 170

    Google Scholar 

  119. Brill TR, Campbell NC: Inorg Chem 12, 1884 (1973)

    CAS  Google Scholar 

  120. Kolling OW, Mawdsley EA: Inorg Chem 9, 408 (1970)

    CAS  Google Scholar 

  121. Huheey JE: Inorganic Chemistry, 2nd edn., Harper and Row, New York 1978, Chap 4, 162

    Google Scholar 

  122. Gamayurova VS: Uspekhi Khimii 50, 1601 (1981) [Engl trans: Russian Chem Rev 50, 836 (1981)]

    CAS  Google Scholar 

  123. Laskorin AN, Yakshin VV, Lyubosvetova, NA: Uspekhi Khimii 50, 860 (1981) [Engl trans: Russian Chem Rev 50, 454 (1981)]

    CAS  Google Scholar 

  124. Ahrland S, Chatt J, Davies NR: Quart Rev Chem Soc 12, 265 (1958)

    CAS  Google Scholar 

  125. Ahrland S, Berg T, Trinderup P: Acta Chem Scand A31, 775 (1977)

    CAS  Google Scholar 

  126. Ahrland S, Hultén F, Persson I: Acta Chem Scand A40, 595 (1986)

    CAS  Google Scholar 

  127. Ahrland S, Berg T, Bläuenstein P: Acta Chem Scand A32, 933 (1978)

    CAS  Google Scholar 

  128. Hancock RD, Marsicano F: J Chem Soc Dalton Trans., 1832 (1976)

    Google Scholar 

  129. Roulet R, Lan NQ, Mason WR, Fenske Jr GP: Helv Chim Acta 56, 2405 (1973)

    CAS  Google Scholar 

  130. Kidd RG in: Multinuclear Approach to NMR spectroscopy, NATO ASI Series, Series C, vol 103 (eds Lambert JB, Riddell FG), D Reidel, Dordrecht 1983, Chap 18, pp 379–387

    Google Scholar 

  131. Harris RK in: NMR and the Periodic Table (eds Harris RK, Mann B), Academic Press, London 1978, Chap 11, pp 379–382 and references cited therein

    Google Scholar 

  132. Balimann G, Pregosin PS: J Magn Res 26, 283 (1977)

    CAS  Google Scholar 

  133. Brevard C, Granger P in: Handbook of High Resolution Multinuclear NMR, Wiley, N.Y. 1981, p 90(N), p 102(P), p 136(As), p 170(Sb), p 210(Bi)

    Google Scholar 

  134. Minkwitz R, Prenzel H, Schardey A, Oberhammer H: Inorg Chem 26, 2730 (1987)

    CAS  Google Scholar 

  135. Irgolic KJ (personal communication)

    Google Scholar 

  136. Knoll F, Marsmann HC, Van Wazer JR: J Amer Chem Soc 91, 4986 (1969)

    CAS  Google Scholar 

  137. Elmes PS, Middleton S, West BO: Aust J Chem 23, 1559 (1970)

    CAS  Google Scholar 

  138. Marsmann HC, Van Wazer JR: J Amer Chem Soc 92, 3969 (1970)

    CAS  Google Scholar 

  139. Durand M, Laurent JP: J Organomet Chem 77, 225 (1974)

    CAS  Google Scholar 

  140. Baudler M, Carlsohn B, Böhm W, Reuschenbach G: Z Naturforsch 31b, 558 (1976)

    CAS  Google Scholar 

  141. Pouchert CJ: Aldrich Library of NMR spectra, 2nd edn, vol 2, Milwaukee, Aldrich Chemical Co 1983

    Google Scholar 

  142. Schiemenz GP: J Organomet Chem 52, 349 (1973)

    CAS  Google Scholar 

  143. Hendrickson JB, Maddox ML, Sims JJ, Kaesz HD: Tetrahedron 20, 449 (1964)

    CAS  Google Scholar 

  144. Verstuyft AW, Cary LW, Nelson JH: Inorg Chem 14, 1495 (1975)

    CAS  Google Scholar 

  145. Randall EW, Shaw D: Spectrochim Acta A23, 1235 (1967)

    Google Scholar 

  146. Shiomi K, Kakehashi Y, Yamanaka H, Kikuchi T: Appl Organomet Chem 1, 177 (1987)

    CAS  Google Scholar 

  147. Massey AG, Randall EW, Shaw D: Spectrochim Acta A21, 263 (1965)

    Google Scholar 

  148. Brown JCC: Ph.D Thesis, University of London (1987)

    Google Scholar 

  149. Edwards RG, Hands AR: Biochim Biophys Acta 431, 303 (1976)

    CAS  Google Scholar 

  150. Irgolic KJ, Junk T, Kos C, McShane WS, Pappalardo GC: Appl Organomet Chem 1, 403 (1987)

    CAS  Google Scholar 

  151. Cushley RJ, Mautner HG: Tetrahedron 26, 2151 (1970)

    CAS  Google Scholar 

  152. Schmidbaur H, Nusstein P: Organometallics 4, 344 (1985)

    CAS  Google Scholar 

  153. Buslaev YA, Kravcenko EA, Kolditz L: Coord Chem Rev 82, 7 (1987) and references cited therein.

    Google Scholar 

  154. Zakirov DU, Safin IA: Khim Tekhnol Elementoorg Soedin Polim, 36 (1981); Chem Abs 96, 191811c (1981)

    Google Scholar 

  155. Bastow TJ, Elmes PS: Aust J Chem 27, 413 (1974)

    CAS  Google Scholar 

  156. Brill TB, Parris GE, Long GG, Bowen LH: Inorg Chem 12, 1888 (1973)

    CAS  Google Scholar 

  157. Crow JP, Cullen WR, Herring FG, Sams JR, Tapping RL: Inorg Chem 10, 1616 (1971)

    Google Scholar 

  158. Mosbæk, H: Acta Chem Scand A29, 957 (1975)

    Google Scholar 

  159. Bowen LH, Garrou PE, Long GG: Inorg Chem 11, 182 (1972)

    CAS  Google Scholar 

  160. Brown SSD, Salter ID, Dyson DB, Parish RV, Bates PA, Hursthouse MB: J Chem Soc Dalton Trans., 1795 (1988) and references cited therein

    Google Scholar 

  161. Nakamoto K: Infrared Spectra of Inorganic and Coordination Compounds, 2nd edn., Wiley-Interscience, New York 1970, Section II, pp 78–148

    Google Scholar 

  162. Bardos TJ, Datta-Gupta N, Hebborn P: J Med Chem 9, 221 (1966)

    CAS  Google Scholar 

  163. Pouchert CJ: Aldrich Library of Infrared spectra, 3rd edn., Milwaukee Aldrich Chemical Co 1981, 1557G

    Google Scholar 

  164. Brooks RR, Ryan DR, Zhang H: Anal Chim Acta 131, 1 (1981)

    CAS  Google Scholar 

  165. Cullen WR, Dodd M: Appl Organomet Chem 2, 1 (1988)

    Google Scholar 

  166. Cappon CJ: LC-GC 5, 400 (1987)

    CAS  Google Scholar 

  167. Irgolic KJ, Stockton RA, Chakraborti D in: Arsenic, Industrial, Biomedical, and Environmental Perspectives (eds Lederer WH, Fensterheim RJ), Van Nostrand Reinhold, New York 1983, Chap 22, pp 282–308

    Google Scholar 

  168. Irgolic KJ, Stockton RA: Marine Chemistry 22, 265 (1987)

    CAS  Google Scholar 

  169. Braman RS in: Biological and Environmental Effects of Arsenic (ed Fowler BA), Elsevier, Amsterdam 1983, Chap 3

    Google Scholar 

  170. Kirchgessner M, Grassmann E, Roth HP, Spoerl R, Schnegg A in: Nuclear Techniques in Animal Production and Health, International Atomic Energy Agency, Vienna 1976, p 61

    Google Scholar 

  171. Anke M, Groppel B, Kronemann H: in Trace element— Analytical Chemistry in Medicine and Biology (ed Braetter P), Vol 3, de Gruyter, Berlin 1984, pp 430–451 and references cited therein

    Google Scholar 

  172. Anke M: in Trace Elements in Human and Animal Nutrition (ed W Mertz), Vol 2, Academic Press, New York 1986, pp 347–372 and references cited therein

    Google Scholar 

  173. Uthus EO, Cornatzer WE, Nielsen FH: in Arsenic: Industrial, Biomedical and Environmental Perspectives (eds Lederer WH, Fensterheim RJ), Van Nostrand Rheinhold, New York 1983, Part III, pp 173–189

    Google Scholar 

  174. Nielsen FH, Uthus EO, Cornatzer WE: Biological Trace Element Research 5, 389 (1983)

    CAS  Google Scholar 

  175. Nielsen FH, Uthus EO: Biochemistry of the Elements 3 (Biochemistry of the Essential Ultratrace Elements), 319 (1984) and references cited therein

    CAS  Google Scholar 

  176. Zingaro RA in: Arsenic: Industrial, Biomedical, and Environmental Perspectives (eds. Lederer WH, Fensterheim RJ), Van Nostrand Rheinhold, New York 1983, Part V, pp. 327–347

    Google Scholar 

  177. Most K.-H: Ph.D thesis (1939) Graz University, Austria

    Google Scholar 

  178. Lenihan J: The Crumbs of Creation, IOP, Bristol 1988, pp 116–123

    Google Scholar 

  179. Moncada S, Palmer RM, Higgs EA: Biochem Pharmacol 38, 1709 (1989)

    CAS  Google Scholar 

  180. Schmidt LH, Anke M, Groppel B: Zentralbl Pharm Pharmakother Laboratoriumdiagn. 127, 197 (1988)

    CAS  Google Scholar 

  181. Frost DV: Sci Total Environ 28, 455 (1983)

    CAS  Google Scholar 

  182. Kaemmerer K: Der praktische Tierarzt 4, 380 (1982)

    Google Scholar 

  183. Vahter M, Marafante E in: The biological alkylation of heavy elements (eds Craig PJ, Glocking F), Royal Society of Chemistry, London 1988, pp 105–119

    Google Scholar 

  184. Thayer JS, Brinckman FE: Adv Organomet Chem 20, 313 (1982)

    CAS  Google Scholar 

  185. Irgolic KJ in: Frontiers in Bioinorganic Chemistry (ed Xavier AV), VCH, Weinheim 1986, pp 399–408 and references cited therein

    Google Scholar 

  186. Aposhian HV in: Reviews in Biochemical Toxicology (eds Hodgson E, Bend J R, Philpot RM), Vol 10, Elsevier, Amsterdam 1989, pp 265–299

    Google Scholar 

  187. Challenger F: Chem Rev 36, 315 (1945)

    CAS  Google Scholar 

  188. Cullen WR, McBride BC, Manji H, Pickett AW, Reglinski J: Appl Organomet Chem 3, 71 (1989)

    CAS  Google Scholar 

  189. Pickett AW, McBride BC, Cullen WC: Appl Organomet Chem 2, 479 (1988)

    CAS  Google Scholar 

  190. Irgolic KJ, Banks CH, Bottino NR, Chakraborti D, Gennity JM, Hillman DC, O'Brien DH, Pyles RA, Stockton RA, Wheeler AE, Zingaro RA: NBS Special Publications (U.S.) 618, 244 (1981)

    CAS  Google Scholar 

  191. Lewin PK, Hancock RGV, Voynovich P: Nature 299, 627 (1982)

    CAS  Google Scholar 

  192. Buchet JP, Lauwerys R: Toxicology and Applied Pharmacology 91, 65 (1987)

    CAS  Google Scholar 

  193. Buchet JP, Lauwerys R: Biochem Pharmacol 37, 3149 (1988)

    CAS  Google Scholar 

  194. Cullen WR, McBride BC, Reglinski J: J Inorg Biochem 21, 179 (1984)

    CAS  Google Scholar 

  195. Cullen WR, McBride BC, Reglinski J: J Inorg Biochem 21, 45 (1984)

    CAS  Google Scholar 

  196. Reglinski J, Smith WE, Sturrock RD: Magnetic Resonance in Medicine 6, 217 (1988)

    CAS  Google Scholar 

  197. Wilson IB in: Molecular Basis of Nerve Activity; Proceedings of the International Symposium in Memory of David Nachmansohn (ed Changeux JP), de Gruyter, Berlin 1985, pp 667–78 and references cited therein

    Google Scholar 

  198. Webb JL: Enzymes and Metabolic Inhibitors, Vol 3, Academic Press, London 1966, Chap 6, pp 595–793 and references cited therein

    Google Scholar 

  199. Oehme FW in: Toxicity of Heavy Metals in the Environment (ed Oehme FW), Marcel Dekker, New York 1979, Part 2, Chap 31, pp 945–952

    Google Scholar 

  200. Dill K, Adams ER, O'Connor RJ, Chong S, McGown EL: Arch Biochem Biophys 257, 293 (1987)

    CAS  Google Scholar 

  201. Kobayashi JH, Yuyama A, Ishihara M, Matsusaka N: Neuropharmacology 26, 1707 (1987)

    CAS  Google Scholar 

  202. Bernier M, Laird DM, Lane MD: J Biol Chem 263, 13626 (1988)

    CAS  Google Scholar 

  203. Steinhelper ME, Olson MS: Biochem Pharmacology 37, 1167 (1988)

    CAS  Google Scholar 

  204. Pressman D, Sternberger LA: J Immunology 66, 609 (1951)

    CAS  Google Scholar 

  205. Grossberg AL, Pressman D: Biochemistry 7, 272 (1968)

    CAS  Google Scholar 

  206. Freedman MH, Grossberg AL, Pressman D: J Biol Chem 243, 6186 (1968)

    CAS  Google Scholar 

  207. Freedman MH, Grossberg AL, Pressman D: Biochemistry 7, 1941 (1968)

    CAS  Google Scholar 

  208. Milner ECB, Capra JD: J Immunology 129, 193 (1982)

    CAS  Google Scholar 

  209. Rathbun G, Sanz I, Meek K, Tucker P, Capra JD: Adv Immunology 42, 95 (1988)

    CAS  Google Scholar 

  210. Goodman JW: Annales de L'Institut Pasteur 137D, 303 (1986) and references cited therein

    CAS  Google Scholar 

  211. Bullock WW: Immunological Rev 39, 3 (1978)

    CAS  Google Scholar 

  212. Alkan SS in: The Immune System (eds Steinberg CM, Lefkovits I), Vol. II, Karger, Basel 1981, pp 329–335

    Google Scholar 

  213. Goodman JW, Fong S, Lewis GK, Kamin R, Nitecki DE, Der Balian G: Immunological Rev 39, 36 (1978)

    CAS  Google Scholar 

  214. Barber HJ: J Chem Soc., 1020 (1929); (b) Cohen A, King H, Strangeways WI: J Chem Soc, 2505 (1932)

    Google Scholar 

  215. Blakley BR, Sisoda CS, Mukkur TK: Toxicol Appl Pharmacol 52, 245 (1980)

    CAS  Google Scholar 

  216. Bauer H: Annals New York Acad Sci 59, 150 (1954)

    CAS  Google Scholar 

  217. Schwyzer R: Angew Chem 66, 345 (1954)

    Google Scholar 

  218. Holmstedt B, Liljestrand G: Readings in Pharmacology, Pergamon, Oxford 1963, pp 281–293

    Google Scholar 

  219. Cullen WR in: Dictionary of Organometallic Compounds (ed Buckingham J), Chapman and Hall, London 1984, pp 123–187, (As-00152, As-00093, As-00106, 00107)

    Google Scholar 

  220. Abernathy JR in: Arsenic, Industrial, Biomedical, and Environmental Perspectives (eds. Lederer WH, Fensterheim RJ), Van Nostrand Reinhold, New York 1983, Chap 5, pp 57–62

    Google Scholar 

  221. Alden JC in: Arsenic, Industrial, Biomedical, and Environmental Perspectives (eds. Lederer WH, Fensterheim RJ), Van Nostrand Reinhold, New York 1983, Chap 6, pp 63–71

    Google Scholar 

  222. Woolson EA in: Biological and Environmental Effects of Arsenic (ed Fowler BA), Elsevier, Amsterdam 1983, Chap 2, pp 51–139

    Google Scholar 

  223. Dictionary of Organometallic Compounds (ed Macintyre JE), 1st Supplement, Chapman and Hall, London 1985, pp 19–24, (As-10002)

    Google Scholar 

  224. Nagasawa M: Chem Abs 56, 10637 (1962)

    Google Scholar 

  225. Yeager CC: Chem Abs 66, 86431 (1967)

    Google Scholar 

  226. Wang CS, McGee TW: Chem Abs 74, 64308 (1971); Wang C. S, McGee TW: Chem Abs 76, 127155 (1972)

    Google Scholar 

  227. Knowles FC, Benson AA: Plant Physiol 71, 235 (1983)

    CAS  Google Scholar 

  228. Anderson CE in: Arsenic, Industrial, Biomedical, and Environmental Perspectives (eds Lederer WH, Fensterheim RJ), Van Nostrand Reinhold, New York 1983, Chap 8, pp 89–97 and references cited therein

    Google Scholar 

  229. Ledet AE, Buck WB in: Toxicity of Heavy Metals in the Environment (ed Oehme FW), Marcel Dekker, New York 1979, Part One, Chap 17, pp 375–391

    Google Scholar 

  230. Hedlund B, Norin H, Christakopoulos A, Alberts P, Bartfai T: Journal of Neurochemistry 39, 871 (1982)

    CAS  Google Scholar 

  231. Silver S in: Environmental Speciation and Monitoring Needs for Trace Metal-Containing Substances from Energy-Related Processes (eds Brinckman FE, Fish RH), 1981, National Bureau of Standards Special Publ 618, Washington DC, pp 301–319

    Google Scholar 

  232. Silver S in: Staphylococci and Staphylococcal Infections, Zbl Bakt Suppl 10 (ed Jeljaszewicz J), 1981, Gustav Fischer, Stuttgart, pp 5819–599

    Google Scholar 

  233. Thiel T: J Bacteriol 170, 1143 (1988)

    CAS  Google Scholar 

  234. Silver S (1984) in: Nriagu JO (ed) Changing metal cycles and human health, Springer, Berlin Heidelberg New York, p 199

    Google Scholar 

  235. Silver S, Nucifora G, Chu L, Misra TK: Trends in Biochemical Science 14, 76 (1989) and references cited therein

    CAS  Google Scholar 

  236. Rosen BP, Ambudkar SV, Borbolla MG, Chen CM, Mobley HLT, Tsujibo H, Zlotnick GW in: Prog Clin Biol Res, vol 168 (Epithelial Calcium and Phosphate Transport: Molecular and Cellular Aspects, eds Bronner F, Peterlik M), AR Liss, New York 1984, pp 219–226

    Google Scholar 

  237. Rosen BP, Weigel U, KarkariaC, Gangola P in: The Ion Pumps: Structure, Function, and Regulation (ed Stein WD), AR Liss, New York 1988, pp 105–112

    Google Scholar 

  238. Rosen BP, Weigel U, Karkaria C, Gangola P: J Biol Chem 263, 3067 (1988)

    CAS  Google Scholar 

  239. Tisa LS, Rosen BP: J Biol Chem 265, 190 (1990)

    CAS  Google Scholar 

  240. Marcovich D, Tapscott RE: J Amer Chem Soc 102, 5712 (1980) and references cited therein

    CAS  Google Scholar 

  241. Banks CH, Daniel JR, Zingaro RA: J Med Chem 22, 572 (1979)

    CAS  Google Scholar 

  242. Kenney LJ, Kaplan JH: J Biol Chem 263, 7954 (1988)

    CAS  Google Scholar 

  243. Forbush B (III): J Biol Chem 263, 7961 (1988)

    CAS  Google Scholar 

  244. Pipkin JL, Anson JF, Hinson WG, Burns ER, Casciano DA, Sheehan DM: Biochim Biophys Acta 927, 334 (1987)

    CAS  Google Scholar 

  245. Pershagen G in: Environmental Carcinogens, Selected Methods of Analysis, Vol 8, International Agency for Research on Cancer Scientific Publications, Lyons 1986, Chap 3, pp. 45–61

    Google Scholar 

  246. Pershagen G: Environmental Health Perspectives 40, 93 (1981)

    CAS  Google Scholar 

  247. Axelson A: J Toxicol Environ Health 6, 1229 (1980)

    CAS  Google Scholar 

  248. Léonard A, Lauwerys RR: Mutation Research 75, 49 (1980)

    Google Scholar 

  249. Wright D: Medical History 27, 184 (1983)

    CAS  Google Scholar 

  250. Jacobson-Kram D, Montalbano D: Environmental Mutagenesis 7, 787 (1985)

    CAS  Google Scholar 

  251. Zingaro RA: Chemica Scripta 8A, 51 (1975)

    CAS  Google Scholar 

  252. Haiduc I, Silvestru C, Coord Chem Rev 99, 253 (1990) and references cited therein.

    CAS  Google Scholar 

  253. Mirabelli CK, Hill DT, Faucette LF, McCabe FL, Girard GR, Bryan DB, Sutton BM, O'Leary Bartus J, Crooke ST, Johnson RK: J Med Chem 30, 2181 (1987)

    CAS  Google Scholar 

  254. Mirabelli CK, Johnson RK, Hill DT, Faucette LF, Girard GR, Kuo GY, Sung CM, Crooke ST: J Med Chem 29, 218 (1986)

    CAS  Google Scholar 

  255. Jarrett PS, Ni Dhubhghaill OM, Sadler PJ, unpublished results

    Google Scholar 

  256. Berners-Price SJ, Sadler PJ: Struct Bonding 70, 27 (1988) and references cited therein

    CAS  Google Scholar 

  257. Hoke GD, Rush GF, Bossard GE, McArdle JV, Jenson BD, Mirabelli CK: J Biol Chem 263, 11203 (1988)

    CAS  Google Scholar 

  258. Kirschner S, Wei YK, Francis D, Bergman JG: J Med Chem 9, 369 (1966)

    CAS  Google Scholar 

  259. Köpf-Maier P, Klapötke T: Inorg Chim Acta 152, 49 (1988)

    Google Scholar 

  260. Gupta P, O'Marro S, Rinaldo CR, Ho M: 5th International Conference on AIDS, Montreal 1989, Section C, M.C.P 133.

    Google Scholar 

  261. Jasmin C, Chermann JC, Herve G, Teze A, Souchay P, Boy-Loustau C, Raybaud N, Sinoussi F, Raynaud M: J Nat Cancer Inst 53, 469 (1974)

    CAS  Google Scholar 

  262. Edmonds JS, Francesconi KA, Cannon JR, Raston CL, Skelton BW, White AH: Tet Lett 18, 1543 (1977)

    Google Scholar 

  263. Edmonds JS, Francesconi KA: Nature 289, 602 (1981)

    CAS  Google Scholar 

  264. Nisizawa K, Noda H, Kikuchi R, Watanabe T: Hydrobiologia 151–152, 5 (1987)

    CAS  Google Scholar 

  265. Maher W, Butler E: Applied Organometallic Chemistry 2, 191 (1988) and references cited therein

    CAS  Google Scholar 

  266. Edmonds JS, Francesconi KA: Appl Organometallic Chemistry 2, 297 (1988)

    CAS  Google Scholar 

  267. Edmonds JS, Francesconi KA: Experientia 43, 553 (1987)

    CAS  Google Scholar 

  268. Phillips DJH, Depledge MH: Water Science Technology 18, 213 (1986)

    CAS  Google Scholar 

  269. Edmonds JS, Francesconi KA: J Chem Soc Perkin Trans I, 2375 (1983)

    Google Scholar 

  270. Edmonds JS, Francesconi KA in: The biological alkylation of heavy elements (eds Craig PJ, Glocking F), Royal Society of Chemistry, London 1988, pp 138–141 and references cited therein

    Google Scholar 

  271. Edmonds JS, Francesconi KA, Hansen JA: Experientia 38, 643 (1982)

    CAS  Google Scholar 

  272. Norin H, Christakopoulos A: Chemosphere 11, 287 (1982)

    CAS  Google Scholar 

  273. Hanaoka K, Yamamoto H, Kawashima K, Tagawa S, Kaise T: Appl Organomet Chem. 2, 371 (1988)

    CAS  Google Scholar 

  274. Maher WA: Biological Trace Element Research 6, 159 (1984)

    CAS  Google Scholar 

  275. Vahter M, Marfante E, Dencker L: Science of the Total Environment 30, 197 (1983)

    CAS  Google Scholar 

  276. Cannon JR, Saunders JB, Toia RF: Science of the Total Environment 31, 181 (1983)

    CAS  Google Scholar 

  277. Irvin TR, Irgolic KJ: Applied Organometallic Chemistry 2, 509 (1988)

    CAS  Google Scholar 

  278. Yancy PH, Clarke ME, Hand SC, Bowlus RD, Somero GN: Science 217, 1214 (1982)

    Google Scholar 

  279. Dévai I, Felföldy L, Wittner I, Plósz S: Nature 333, 343 (1988)

    Google Scholar 

  280. Berners-Price SJ, Mirabelli CK, Johnson RK, Mattern MR, McCabe FL, Faucette LF, Sung C-H, Mong S-M, Sadler PJ, Crooke ST: Cancer Research 46, 5486 (1986)

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Springer-Verlag

About this chapter

Cite this chapter

Ni Dhubhghaill, O.M., Sadler, P.J. (1991). The structure and reactivity of arsenic compounds: Biological activity and drug design. In: Bioinorganic Chemistry. Structure and Bonding, vol 78. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-54261-2_3

Download citation

  • DOI: https://doi.org/10.1007/3-540-54261-2_3

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-54261-2

  • Online ISBN: 978-3-540-47535-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics