Arsenic-based drugs: From fowler's solution to modern anticancer chemotherapy

Topics in Organometallic Chemistry

Volumn 32, Issue , 2010, Pages 1-20

  Gibaud, Stéphane ^a   Jaouen, Gérard ^b  

^a UNIVERSITÉ DE LORRAINE   (France)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

Atoxyl; Leukemia; Melarsoprol; Salvarsan; Syphilis; Trypanosomiasis; Tryparsamide

Indexed keywords

EID: 77956671923     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-3-642-13185-1_1     Document Type: Article

References (106)

1. Ralph SJ (2008) Arsenic-based antineoplastic drugs and their mechanisms of action. Met Based Drugs 2008:260146
2. Li S, Luo X (2003) Compendium of materia medica. Foreign Languages Press, Beijing
3. Jackson R, Grainge JW (1975) Arsenic and cancer. Can Med Assoc J 113:396-401
4. Evens AM, Tallman MS, Gartenhaus RB (2004) The potential of arsenic trioxide in the treatment of malignant disease: past, present, and future. Leuk Res 28:891-900
5. Lipscomb JD (1877) Improvement in remedy for fevers. US Patent 186,141
6. Ramsaur MH (1869) Improved medical compound. US Patent 92,209
7. Lentilius R (1684) Ephémérides des curieux de la nature. Dec. 11, an 3 - Obs. 46
8. Friceius M (1710) Cap 2. Tractus de Virtute Venenorum Medica
9. Frank J (1835) Encyclopédie des Sciences Médicales ou traité général méthodique et complet des diverses branches de lart de guérir. Deuxième division, Médecine : pathologie médicale. Bureau de lEncyclopédie, Paris
10. Fowler T (1786) Medical reports on the effects of arsenic in the cure of agues, remittent fevers and perodic headaches
11. Hunt T (1848) Minimum fatal dose of arsenic. Prov Med Surg J 12:445
12. Hunt T (1848) On Dr. Castles case of supposed poisoning by Fowlers solution. Prov Med Surg J 12:391
13. Bouteille B, Oukem O, Bisser S et al (2003) Treatment perspectives for human African trypanosomiasis. Fundam Clin Pharmacol 17:171-181
14. Steverding D (2008) The history of African trypanosomiasis. Parasit Vectors 1:3
15. Livingstone D (1858) Arsenic as a remedy for the tse tse bite. Br Med J 1:360-361
16. Manchester K (2001) Antoine Béchamp: père de la biologie. Oui ou non? Endeavour 25:68-73
17. Béchamp A (1863) De laction de la chaleur sur larséniate daniline et de la formation dun anilide de lacide arsénique. Compt Rend 56:1172-1175
18. Thomas H (1905) Some experiments in the treatment of trypanosmiasis. Br Med J 1:1140-1143
19. Scherber G (1907) The atoxyl treatment of syphilis. Wien Klin Wochenschr 20:1165-1172
20. Blumenthal F (1902) Uber Metaarsensaureanilid (atoxyl). Med Woche 3:163
21. Ehrlich P, Bertheim A (1907) Uber p-Aminophenylarsinsäure. Ber Dtsch Chem Ges 40:3292-3297
22. Anonymous (1910) Action of Atoxyl on Eyes. Cal State J Med 8:384
23. Knopf H, Fabian R (1909) Further results of Atoxyl treatment. Berl Klin Wochenschr 46:99-101
24. Jacobs WA, Heidelberger M (1919) Aromatic arsenic compounds. II. The amides and alkylamides of N-arylglycine arsonic acids. J Am Chem Soc 41:1809-1821
25. Pearce L (1925) Tryparsamide treatment of African sleeping sickness. Science 61:90-92
26. Pearce L (1921) Treatment of human trypanosomiasis with tryparsamide (sodium salt of N-phenylglycineamide-p-arsonic acid). J Exp Med 34(1):1-104
27. Hawking F (1941) Drug resistance acquired during the treatment of sleeping sickness with tryparsamide and with Bayer 205. Am J Trop Med 21:469-475
28. Friedheim EAH (1944) Trypanocidal and spirochetocidal arsenicals derived from s-triazine. J Am Chem Soc 66:1775-1778
29. Friedheim EAH (1942) Substituted [1,3,5-triazinyl-(6)]-aminophenyl- arsonic acids and process for manufacture of same. US Patent 2,295,574
30. Doak G, Steinman H, Eagle H (1944) Arsenoso compounds containing amide groups. J Am Chem Soc 66:194-197
31. Banks C, Gruhzit O, Tillitson E et al (1944) Arylaminoheterocycles. III. Arsenicals of anilinotriazines. J Am Chem Soc 66:1771-1775
32. Jonchère H, Gomer J, Reynaud R (1953) Contribution à létude de produits à radical mélaminyl dans le traitement de la trypanosomiase humaine. Bull Soc Pathol Exot 46:386-396
33. Friedheim EAH (1948) Melarsen oxide in the treatment of human African trypanosomiasis. Ann Trop Med 42:357-363
34. Peters R, Stocken L, Thompson R (1945) British Anti-Lewisite (BAL). Nature 156:616-619
35. Friedheim EAH (1953) Heterocyclic metal and sulfur organic compounds. US Patent 2,664,432
36. Gibaud S, Alfonsi R, Mutzenhardt P et al (2006) (2-Phenyl-[1, 3, 2] dithiarsolan-4-yl)- methanol derivatives show in vitro antileukemic activity. J Organomet Chem 691:1081-1084
37. Friedheim EAH (1952) Propylene glycol solution of arsenic medicaments. US Patent 3,593,434
38. Watson HJC (1962) Mel W: A field trial in the treatment of Trypanosoma gambiense sleeping sickness. Trans R Soc Trop Med Hyg 56:231-235
39. Watson HJC (1965) Mel W: final report on a field trial in the treatment of Trypanosoma gambiense sleeping sickness. Trans R Soc Trop Med Hyg 59:163-170
40. Loiseau PM, Lubert P, Wolf JG (2000) Contribution of dithiol ligands to In vitro and In vivo trypanocidal activities of dithiaarsanes and investigation of ligand exchange in an aqueous solution. Antimicrob Agents Chemother 44:2954-2961
41. Pépin J, Milord F, Khonde A et al (1994) Gambiense trypanosomiasis: frequency of, and risk factors for, failure of melarsoprol therapy. Trans R Soc Trop Med Hyg 88:447-452
42. Pépin J, Milord F (1991) African trypanosomiasis and drug-induced encephalopathy: risk factors and pathogenesis. Trans R Soc Trop Med Hyg 85:222-224
43. Kennedy PGE (2006) Diagnostic and neuropathogenesis issues in human African trypanosomiasis. Int J Parasitol 36:505-512
44. Adams JH, Haller L, Boa FY et al (1986) Human African trypanosomiasis (T.b. gambiense): a study of 16 fatal cases of sleeping sickness with some observations on acute reactive arsenical encephalopathy. Neuropathol Appl Neurobiol 12:81-94
45. Friedheim EAH (1951) Mel B in the treatment of tryparsamide resistant T. gambiense sleeping sickness: observations on drug resistance in the trypanosomes of the French Cameroon. Am J Trop Med Hyg 31:218-226
46. Friedheim EAH (1949) Mel B in the treatment of human trypasonomiasis. Am J Trop Med Hyg 29:173-180
47. Burri C, Nkunku S, Merolle A et al (2000) Efficacy of new, concise schedule for melarsoprol in treatment of sleeping sickness caused by Trypanosoma brucei gambiense: a randomised trial. Lancet 355:1419-1425
48. Pépin J, Mpia B (2006) Randomized controlled trial of three regimens of melarsoprol in the treatment of Trypanosoma brucei gambiense trypanosomiasis. Trans R Soc Trop Med Hyg 100:437-441
49. Pépin J, Milord F, Guern C et al (1989) Trial of prednisolone for prevention of melarsoprolinduced encephalopathy in gambiense sleeping sickness. Lancet 1:1246-1250 (Pubitemid 19140336)
50. Carter NS, Fairlamb AH (1993) Arsenical-resistant trypanosomes lack an unusual adenosine transporter. Nature 361:173-176
51. Balasegaram M, Young H, Chappuis F et al (2009) Effectiveness of melarsoprol and eflornithine as first-line regimens for gambiense sleeping sickness in nine Médecins Sans Frontières programmes. Trans R Soc Trop Med Hyg 103:280-290
52. Jennings FW (1993) Combination chemotherapy of CNS trypanosomiasis. Acta Trop 54:205-213
53. Pépin J, Ethier L, Kazadi C et al (1992) The impact of human immunodeficiency virus infection on the epidemiology and treatment of Trypanosoma brucei gambiense sleeping sickness in Nioki, Zaire. Am J Trop Med Hyg 47:133-140
54. Kennedy PGE (2008) The continuing problem of human African trypanosomiasis (sleeping sickness). Ann Neurol 64:116-126
55. Harper K, Ocampo P, Steiner B et al (2008) On the origin of the treponematoses: a phylogenetic approach. PLoS Negl Trop Dis 2:e148
56. Ehrlich P, Bertheim A (1911) Derivatives of oxyarylarsinic acids and process of making same. US Patent 986,148
57. Christiansen WG (1920) Hypophosporous acid preparation of arsphenamine. (3, 3-diamino-4, 4-dihydroxy-arseno-benzene dihydrochloride. J Am Chem Soc 42:2402-2405
58. Lloyd NC, Morgan HW, Nicholson BK et al (2005) The composition of Ehrlichs Salvarsan: resolution of a century-old debate. Angew Chem Int Ed 44:941-944
59. Pariser RJ (2008) Syphilis rules. Clin Dermatol 26:399-410
60. Anonymous (1911) Salvarsan, new indications. Cal State J Med 9:265-266
61. Kaufmann SHE (2008) Paul Ehrlich: founder of chemotherapy. Nat Rev Drug Discov 7:373
62. Kolmer J, Schamberg J (1912) Experimental studies on the administration of salvarsan by mouth to animals and man. J Exp Med 15:498-509
63. Fleming A, Florey HW, Bodenham DC et al (1944) Discussion on penicillin. Proc R Soc Med 37:101-112
64. Chain E, Florey HW (1944) Penicillin. Endeavour 3:3-14
65. Chain E, Florey HW, Gardner AD et al (1940) Penicillin as a chemotherapeutic agent. Lancet 2:226-228
66. Florey HW, Chain E (1945) Penicillin: demonstration of its value as a chemotherapeutic agent. Preliminary report of a new method. Med Rec (1866-1922) 158:217-219
67. Florey HW (1944) Penicillin: a survey. Br Med J 2:169-170
68. Heatley NG (1945) Administration of penicillin by mouth. Lancet 1:590-591
69. Ehrlich P, Karrer P, Georg Speyer H (1915) Arseno-metallic compounds. Ber Dtsch Chem Ges 48:1634-1644
70. Raiziss GW, Kremens A (1926) Arseno-bismuth compound and process of making same. US Patent 1,605,691
71. Stokes JH, Chambers SO (1927) Bismuth arsphenamine sulphonate. J Am Med Assoc 89:1500
72. Rayburn CR, Boyd TM (1931) The treatment of neurosyphilis - Observations on 393 patients over a period of five years. Am J Syph 15:168-184
73. World Health Organisation (1997) Weekly epidemiological record 72:97-100
74. Gunn H (1918) Amebiasis: its radical cure with combined emetin and salvarsan products. Cal State J Med 16:240-244
75. Fourneau E (1925) Relation between chemical constitution and therapeutic action. In: Union Internationale de chimie pure et appliquée (ed.) Comptes rendus de la sixième conférence internationale de la chimie, Bucarest
76. James DM (1949) The relation between the effect of certain therapeutic agents on infusoria and on pathogenic protozoa. Ann Trop Med Parasitol 43:164-173
77. David NA, Anderson HH, Koch DA et al (1932) Comparative toxicity and protozoacidal action of acetarsone, carbarsone and certain related quinquevalent arsenical compounds. Proc Soc Exp Biol Med 29:125-128
78. Chopra RN, Sen B, Sen G (1935) Amibiarson in the treatment of chronic intestinal amebiasis. Ind Med Gaz 70:324-328
79. Anonymous. (1971) Food additives. Carbarsone (not USP) in combination with bacitracin methylene disalicylate. Fed Regist 36:24001-24002
80. Schneider J, Dupoux R, Montezin G (1957) Traitement de lamibiase intestinale par le diphetarsone-spiramycine (6 753 RP). Bull Soc Pathol Exot Filiales 50:600-606
81. Elsdondew R, Powell SP, Wilmot AJ (1957) Diphetarsone in the treatment of acute amoebic dysentery. J Trop Med Hyg 60:16-18
82. Schneider J, Biguet J, Machez J (1960) Treatment of oxyuriasis by diphetarsone-spiramycin and by diphetarsone. Therapie 15:648-654
83. Friedheim EAH (1949) A five day peroral treatment of yaws with stb, a new trivalent arsenical. Am J Trop Med Hyg 29(suppl 1):185
84. Anonyme (1953) New and nonofficial remedies; arsthinol. J Am Med Assoc 152:531
85. Abernathy CO, Liu YP, Longfellow D et al (1999) Arsenic: health effects, mechanisms of actions, and research issues. Environ Health Perspect 107:593-597
86. Stohrer G (1991) Arsenic: opportunity for risk assessment. Arch Toxicol 65:525-531
87. Cutler E, Bradford E (1878) Action of iron, cod liver oil and arsenic on globular richness of the blood. Am J Med Sci 75:74-84
88. Stockman R (1898) The action of arsenic on the bone-marrow and blood. J Physiol 23:376-382
89. Forkner C, Scott T (1931) Arsenic as a therapeutic agent in chronic myelogenous leukemia. J Am Med Assoc 97:3-5
90. Rontgen W (1896) On a new kind of rays. Science 3:227-231
91. Senn N (1903) Case of spleno-medullary leukemia successfully treated by the use of roentgen ray. Med Rec NY 63:281
92. Wang ZY (2001) Arsenic compounds as anticancer agents. Cancer Chemother Pharmacol 48 (suppl 1):S72-S76
93. Sun HD, Li H, Ma L et al (1992) Treatment of acute promyelocytic leukemia by Ailing-1 therapy (in Chinese). Chin J Integr Trad Med West Med 12:170-172
94. Zhang P, Wang SY, Lu LH et al (1996) Arsenic trioxide-treated 72 cases of acute promyelocytic leukemia (in Chinese). Clin J Hematol 17:58-62
95. Lu DP, Qiu JY, Jiang B et al (2002) Tetra-arsenic tetra-sulfide for the treatment of acute promyelocytic leukemia: a pilot report. Blood 99:3136-3143
96. Soignet SL, Tong WP, Hirschfeld S et al (1999) Clinical study of an organic arsenical, melarsoprol, in patients with advanced leukemia. Cancer Chemother Pharmacol 44:417-421
97. Soignet SL, Maslak P, Wang ZG et al (1998) Complete remission after treatment of acute promyelocytic leukemia with arsenic trioxide. N Engl J Med 339:1341-1348
98. Warrell R, Soignet S, Maslak P et al (1998) Initial western study of arsenic trioxide (As2O3) in acute promyelocytic leukemia (APL). Proc Am Soc Clin Oncol 17:6a
99. Chen GQ, Zhu J, Shi XG et al (1996) In vitro studies on cellular and molecular mechanisms of arsenic trioxide (As2O3) in the treatment of acute promyelocytic leukemia: As2O3 induces NB4 cell apoptosis with downregulation of Bcl-2 expression and modulation of PMLRARa/ PML proteins. Blood 88:1052-1061
100. Dai J, Weinberg RS, Waxman S et al (1999) Malignant cells can be sensitized to undergo growth inhibition and apoptosis by arsenic trioxide through modulation of the glutathione redox system. Blood 93:268-277
101. Jing Y, Dai J, Chalmers-Redman RME et al (1999) Arsenic trioxide selectively induces acute promyelocytic leukemia cell apoptosis via a hydrogen peroxide-dependent pathway. Blood 94:2102-2111
102. Schmidt A, Koppelt J, Neustadt M et al (2007) Mass spectrometric evidence for different complexes of peptides and proteins with arsenic (III), arsenic (V), copper (II), and zinc (II) species. Rapid Commun Mass Spectrom 21:153-163
103. Rousselot P, Labaume S, Marolleau JP et al (1999) Arsenic trioxide and melarsoprol induce apoptosis in plasma cell lines and in plasma cells from myeloma patients. Cancer Res 59:1041-1048
104. Wang ZG, Rivi R, Delva L et al (1998) Arsenic trioxide and melarsoprol induce programmed cell death in myeloid leukemia cell lines and function in a PML and PML-RARalpha independent manner. Blood 92:1497-1504
105. Konig A, Wrazel L, Warrell RP et al (1997) Comparative activity of melarsoprol and arsenic trioxide in chronic B- cell leukemia lines. Blood 90:562-570
106. De Los SJ, Thomas G (2007) Anemia correction in malignancy management: threat or opportunity? Gynecol Oncol 105:517-529