Summary
The chemical aspects of organometallic bismuth(Ill) compounds are discussed with respect to the stability of the metal-carbon σ bond, their low dipole moments, and the limited solubility of these complexes in hydrophilic solvents. A new Bi heterocycle, which is of potential interest in terms of stability and solution behaviour, was shown to exist as an intermediate under the conditions in the mass spectrometer.
Although generally bismuth organic compounds are extremely toxic, in the 1970s they became important as biocides and this is still being investigated. They have also been discussed as irritation causing chemical warfare agents. While their application in chemotherapy never became very widespread because antibiotics were discovered, in the last few years the antitumor activity of some derivatives has been reported.
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Abbreviations
- BE :
-
bond energy
- IC :
-
inhibition concentration
- MIC :
-
minimal inhibition concentration
- χ :
-
electronegativity (Allred and Rochow)
- X :
-
halogen, pseudohalogen=F, Cl, Br, CN
- Me:
-
CH3
- Et:
-
C2H5
- Bu:
-
C4H9
- Ph:
-
C6H5
- Ac:
-
CH3COO
- MS:
-
mass spectrometry
References
American Cyanamid Co. (1965) Br. P. 1.003.685
American Cyanamid Co. (1964/1968) U.S.P. 3.395.212
Ammedick E (1980) Bausteine der Chemie. Militärchemie — eine Einführung. VEB Deutscher Verlag Grundstoffindustrie, Leipzig
Bagramyan SB, Babayan EA, Dartyan RM (1975) Long-term effects of single-dose and chronic administration of copper and bismuth on laboratory animals. Biol Zh Arm 28:56–62
Coates GE, Green MLH, Wade K (1967) Organometallic compounds, vol 1, chapt 5. Methuen, London
Delmas-Marsalet P, Arné B (1949) A case of bismuth poisoning. J Med Bord Sud-Quest 126:76
Dub M (1968) Organometallic compounds: methods of synthesis, physical constants and chemical reactions; compounds of arsenic, antimony and bismuth, vol 3. Springer, Berlin Heidelberg New York
Dyson GM (1928) Bismuth in pharmacy and chemistry. Pharm J 120:242–244
Ehrlich P (1910) Vorträge über die Behandlung der Syphilis mit dem Ehrlichschen Präparat 606. Berl Klin Wochenschr 47:1996
Elschenbroich C, Salzen A (1986) Organometallchemie. Teubner, Stuttgart
Giemsa G (1924) Über die chemotherapeutische Wirkung des Arsens, Antimons und Wismuths. Z Angew Chem37:765–788
Gross FJ (American Cyanamid Co.) (1962/1965) U.S.P. 3.197.314
Gross FJ (American Cyanamid Co.) (1964/1968) U.S.P. 3.395.212
Gross R, Schölmerich P (1973) Lehrbuch der Inneren Medizin. Schattauer, Stuttgart
Haiduc I, Zuckerman JJ (1985) Basic organometallic chemistry. de Gruyter, Berlin New York
Klapötke T (1987a) Synthese, spektroskopische Charakterisierung und bakterizide Wirksamkeit neuer Organylbis(thiophenolato)bismut(III)-Komplexe. J Organomet Chem331:299–307
Klapötke T (1987b) Synthesis and characterization of novel chalcogen and pnictogen coordinated Bi(III) complexes — the first Se,Se′ coordinated Bi metallacycle. Polyhedron 6:1593–1597
Klapötke T (1987c) Biological activity of novel bismuth chalcogenolate complexes (seminar). Maritime Inorganic Discussion Weekend, Sackville, New Brunswick, Canada
Klapötke T (1987d) Biologische Aktivität neuer Bismut(III)organylchalkogenolat-Komplexe (Poster). 21. GDCh-Hauptversammlung, Berlin
Klapötke T (1988) Methylbis(thiomethanolato)bismut(III) —Synthese, Charakterisierung und mikrobiologische Aktivität. Monatsh Chem (in press)
Klapötke T, Gowik P (1987) Methylbis(2,6-dichlorthiophenolato)bismut(III) — Synthese, fungizide und bakterizide Aktivität. Z Naturforsch 42b:940–942
Köpf H, Klapötke T, Köpf-Maier P (1986) Titanocene mercaptoanilinium derivatives as new antitumor agents (seminar). INOR 132, ACS National Meeting, Anaheim, Calif
Köpf-Maier P (1987) Cytostatische nicht-Platinmetall-Komplexe: neue Perspektiven für die Krebsbehandlung? Naturwissenschaften 74:374–382
Köpf-Maier P, Klapötke T (1988) Antitumor activity of some organometallic bismuth(III)thiolates. Inorg Chim Acta152 No. 1; 49–52
Kooistra JA (Procter and Gamble Co.) (1970/74) U.S.P. 3.852.441
Kuschinsky G, Lüllmann H (1974) Lehrbuch der Pharmakologie. Thieme, Stuttgart
Langer HG (Dow Chemical Co.) (1964/69) U.S.P. 3.442.922
Lecoq H (1937) Role des arsines, stibines et bismuthines en toxicologie. J Pharm. Belg 19:173–181
Leebrick JR (M&T Chemicals, Inc.) (1962/65) U.S.P. 3.239.411
Leebrick JR (M&T Chemicals, Inc.) (1962/66) U.S.P. 3.247.050
McCombie H, Saunders BC (1947) Toxic organo-lead compounds. Nature 159:491–494
Meyer RJ, Pietsch EHE (1952) Arsen. Gmelin Handbuch der anorganischen Chemie, vol 17. Springer, Berlin Heidelberg New York
M&T Chemicals, Inc. (1964a) Neth. Appl. 6.405.308
M&T Chemicals, Inc. (1964b) Neth. Appl. 6.405.309
Pschyrembel (1982) Klinisches Wörterbuch. de Gruyter, Berlin New York
Pyman FL (1935) Some lines of chemotherapeutic research. Chem Ind: 580–585
Raiziss GW, Severac M, Moetsch JC (1934) Toxicity of various compounds of bismuth used in the therapy of syphilis. J Chemother 10:77–87
Rosenberg B, Camp Lvan, Krigas T (1965) Inhibition of cell division inEscherichia coli by electrolysis products from a platinum electrode. Nature 205:698
Rosenberg B, Camp Lvan, Grimley EB, Thomson AJ (1967a) The inhibition of growth or cell division inEscherichia coli by different ionic species of platinum(IV) complexes. J Biol Chem 242:1347
Rosenberg B, Renshaw E, Camp Lvan, Hartwick J, Drobuik J (1967b) Platinum-induced filamentous growth inEscherichia coli. J Bacteriol 93:716
Rosenberg B, Camp Lvan, Trosko JE, Mansour VH (1969) Platinum compounds: a new class of potent antitumor agents. Nature 222:385–386
Rosenberg B (1985) Fundamental studies with cisplatin. Cancer 55:2303
Saggers DT (Fisons Ltd) (1970) D.P. 2.005.409
Smith JD (1973) Arsenic, antimony and bismuth. In: Bailar JC, Emeléus HJ, Nyholm Sir R, Trotman-Dickenson AF (eds) Comprehensive inorganic chemistry, vol 2. Pergamon Press, Oxford, pp 622–671
Sollmann T, Seifter J (1939) Pharmacology of trimethylbismuth. J Pharmacol 67:17–49
Stöhr R (1985) Chemische Kampfstoffe und Schutz vor chemischen Kampfstoffen. Militärverlag der DDR, Berlin
Strube I, Stolz R, Remane H (1986) Geschichte der Chemie. VEB Deutscher Verlag der Wissenschaften, Berlin
Wallhäuser KH (1984) Praxis der Sterilisation — Desinfektion — Konservierung. Thieme, Stuttgart
Wieber M (1977) Bismut-Organische Verbindungen. Gmelin Handbuch der anorganischen Chemie, vol 47. Springer, Berlin Heidelberg New York
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Klapötke, T. Biological activity of organometallic bismuth compounds. Biol Metals 1, 69–76 (1988). https://doi.org/10.1007/BF01138064
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DOI: https://doi.org/10.1007/BF01138064