Τόμος 6 (1992) – Τεύχος 2 – Άρθρο 1 – Επιθεώρηση Κλινικής Φαρμακολογίας και Φαρμακοκινητικής-Διεθνής Έκδοση – Volume 6 (1992) – Issue 2 – Article 1 – Epitheorese Klinikes Farmakologias και Farmakokinetikes-International Edition

Title Tin compounds in medicinal chemistry
Author John M. Tsangaris

Laboratory of Inorganic and General Chemistry, Department of Chemistry, University of Ioannina, Ioannina, Greece

Citation Tsangaris, J.M.: Tin compounds in medicinal chemistry, Epitheorese Klin. Farmakol. Farmakokinet. 6(2): 69-81 (1992)
Publication Date Received for publication: 5 April 1992

Accepted for publication: 15 April 1992

Full Text Language English
Order – Buy  Ηλεκτρονική Μορφή: pdf (10 €) – Digital Type: pdf (10 €) 

pharmakonpress[at]pharmakonpress[.]gr

Keywords Dentifrices, radiochemicals, hyperbilirubinaemia, cancer chemotherapy, photodynamic therapy, tin compounds.
Other Terms review article
Summary Tin compounds as SnF2, SnCl2 and Sn2P2O7 are licensed for use as additives in the dentifrices, mouthwashes and in dental cements. The same simple tin (II) compounds are used for radiopharmaceutical preparations in diagnostic scintigraphy. A plethora of tin (II) and tin (IV) compounds are researched today for use as pharmaceuticals for humans: Tin-haem for hyperbilirubinaemia, organotin compounds mainly of the general type R2SnCl2.L2, where R= alkyls and L2= ligands basically bidentate of a convenient structure for cancer chemotherapy, dichlorotin (IV) Purpurins as sensitives in cancer photodynamic therapy (PDT) and several tin compounds as antiinflammatory agents, schizonticidals, antimaiarials, amoebicidals, antimicrobials, antihelminthics and against leishmaniasis. The organotin card nostats have lower toxicity compared with the cis-platin analogs, with their activity also lower. The successful organotin antitumour agents are not yet introduced for tests involving human subjects in the clinical phase.
References 1.       Frouin, A. et Gregoire, R.: Action de retain metallique et I’oxyde d’ etain dans les infections staphylocoque. C.R. Acad. Sci (Paris), 164: 794 (1917)

2.       Kolmer, J.A., Brown, H. and Harkins, M.J.: J. Pharmacol. 43: 515 (1931)

3.       Barnes, J.M. and Stoner, H.B.: The toxicology of tin compounds. Pharmacol. Revs, 11: 211 (1959)

4.       Sadler, P.J.: Brit. Med. J. 1: 515 (1958)

5.       Sadler, P.J.: Inorganic pharmacology. Chem: Brit. 18: 182, 188(1982)

6.       Growe, P.J.: The chemotherapeutic properties of tin compounds. Drugs of the Future, 3: 255 (1987)

7.       Cardarelli, N.F.: Tin as a vital nutrient environmental ubiquity. In: Tin and Malignant Cell Growth (J.J. Zuckerman, ed.), p. 1, C.R.C. Press, Boca Raton, FL. (USA), 1988

8.       Tsangaris, J.M. and Williams, R.D.: Tin in pharmacy and nutrition. Appl. Organomet. Chem. 6:3 (1992)

9.       Muhler, J.C. and van Huysen, G.: Solubility of enamel protected by sodium fluoride and other compounds. J. Dent. Res. 26:119(1947)

10.     Howell, C.L, Gish, C.W., Smiley, R.D. and Muhler, J.C.: Effects of topically applied stannous fluoride on dental caries experience in children. J. Am. Dent. Assoc. 50: 14 (1957)

11.     Blunden, S.J., Cusack, P.A. and Hill, R.: The Industrial Uses of Tin Chemicals, Royal Society of Chemistry, London, 1985

12.     Svatum, B. and Attamadal, A.: The effect of stannous fluoride on human plaque acidogenecity in situ (Stephan curve). Acta Odontol. Sea. 36:211 (1978)

13.     Duscher, H. and Uchtmann, H.: Effects of sodium fluoride, stannous fluoride, amine hydrofluoride and sodium monofluorophosphate on the formation of precipitates adjering to bovine enamel. Caries Res. 22(2): 65 (1988)

14.     Lim, J.K.J.: Precipitate-free, dilute aqueous solutions of stannous fluoride for topical applications. 1. Simple and mixed mediums. J. Dent. Res. 49:760 (1970)

15.     Hefti, A.F. and Huber, B.: The effect of early plaque formation gingivitis and salinary bacterial counts of mouthwashes containing hexetidine/Zinc amtnofluoride/tin or chlortexine. J. Clin. Peridontol. 14(9): 515 (1987)

16.     Elligsen, J.E. and Ekstrand, J.: J. Dent. Res. 64 (10): 1250(1985)

17.     Wright, P.S.: The effect of self lining materials on the growth of Candida albicans. J. Dent. 8:144 (1980)

18.     Elligsen, J.E.: Scanning electron microscope and electron microprobe study of reactions to stannous fluoride and stannous chloride with dental enamel. Scand. J. Dent. Res. 94(4): 299 (1986)

19.     Elligsen, J.E. and Rolla, G.: Treatment of dentin with stannous fluoride SEM and electron microscope study. Scand. J. Dent. Res. 95(4): 281 (1987)

20.     Tamizawa, Y., Ujiie, T. Sawamura, T. and Suzuki, T.: Reaction characteristics between dental enamel and tin(2+) ion. Kagaku Oyobi Koguo Butsuri Kagaku 55(12): 903(1987)

21.     Jodaikin, A. and Goldstein, S.: Possible products of tooth-amalgam in interfaces. J. Dent. 16(3): 140 (1988)

22.     Deutsch, E., Elder, R.C., Lange, B.A., Vaal, M.J. and Lay, D.G.: Structural characterization of a bridged 99mTc-Sn-dimethyl-glyoxime complex: Implications for the chemistry of 99mTc-radiopharmaceuticals prepared by the Sn(II) reduction of pertechnetate. Proc. National Acad. Sc. USA, 73:4287(1976)

see also: Libson, F.K.: Studies in technetium chemistry applied to the practice of diagnostic nuclear medecin. Ph. D. Diss. University of Cincinnati, p. 185, 1981, Diss. Abstr. 42(8): 3256 (1982)

23.     Maxon, H.R., Deutsch, E.A., Thomas, S.R., Libson, Κ., Lukes, S.J., Williams, C.C. and Ali, S.: Rhenium-186(tm)HEDP for treatment of multiple metastatic loci in bones: Human biodistribution and domestic studies. Radiology 166(2): 501 (1988)

24.     Drummond, G.S. and Kappas, A.: Prevention of neonatal hyperbilirubineamia by Sn-protoporphyrin IX, a potent competitive inhibitor of heme oxidation. Proc. National Acad. Sci. USA 73:6466 (1981)

25.     Kappas, A. and Drummond, G.S.: Synthetic metalloporphyrins: A class of compounds of pharmacological interest. BioEssays 3(6): 256 (1986)

26.     Cornelius, C.E. and Rodges, P.A.: Prevention of neonatal hyperbilirubinemia in rhesus monkeys by tin protoporphyrin. Pediat. Res. 18:728 (1984)

27.     Kappas, A., Drummond, G.S., Manola, T„ Petmezaki, S. and Valaes, T.: Sn-Protoporphyrin use in the management of hyperbilirubinemia in term newborns with direct Compositive ABO incopatibility. Pediatrics 81: 485(1988)

28.     Berglund, L„ Angelin, B., Blomstrand, R., Drummond, G. and Kappas, A.: Sn-protoporphyrin lower serum bilirubin levels, decreases biliary bilirubin output, enhances biliary heme excretion and potentialy inhibits heparin heme oxygenase activity in normal human subjects. Hepatology 8:625 (1988)

29.     Brown, N.M.: The effect of two organotin compounds on C3H-strain mice. Ph. D. Dissert. Clemson University, 1972

30.     Bulten, E.J. and Budding, H.A.: Tin compounds for the treatment of cancer. Brit. Pat. 2077266 (1981)

31.     Meinema, H.A., Liebregts, A.M.J., Budding, H.A. and Bulten, E.J.: Synthesis and evaluation of organometal-based antitumour agents of germanium and tin. Rev. Silicon, Germanium, Tin, Lead Compds 8:157 (1985)

32.     Crow, A.J., Smith, P.J. and Atassi. G.: Investigations into the antitumour activity of organotin compounds. Inorg. Chim. Acta 93:179 (1984)

33.    Crow, A.J., Smith, P.J., Cardin, C.J., Parge, H.E. and Smith, F.E.: Possible pre-dissociation of organotin dihalide complexes. Relationship between antitumour activity and structure. Cancer Lett. 24:45 (1984)

34.     Kabanos, T.A., Keramidas, A.D., Mentzafos, D., Russo, U., Terzis, A. and Tsangaris, J.M.: Synthesis, structural and physical studies of tin(IV) complexes with 2-(2-pyridyljbenzimidazole (pbi). J. Chem. Soc. Dalt. Trans, in press

35.     Kopf-Maier, P., Janiak, C. and Schumann, H.: Monomeric air stable metallocenes of main-group elements as antitumour agents. Inorg. Chim. Acta 152:75 (1988)

36.     Barbieri, R., Pelterito, L., Russi, G. and LoGuidice, M.T.: The antitumor activity of diorganotin(IV) complexes with adenine and glycylglycine. Inorg. Chim. Acta 66: L34- L40 (1982)

37.     Barbieri, R. and Ruisi, G.: The antitumour activity and the structure of diphenyltin(IV) bis adeninate. Nato Adv. Workshop on the effect of Tin upon malignant cell growth, Brussells, Abstr. P02, 1989

38.     Huber, F., Roge, G., Carl, L., Atassi, G., Spreafico, F., Filippeschi, S., Barbieri, R., Silvestrl, A., Rivarola, E„ Ruisi, G., DiBianco, F. and Alonzo, G.: Studies on the antitumour activity of di- and tri-organotin IV) complexes of amino acids and related compounds of 2-mercaptoethane sulphonate and of purine-6-thiol. J. Chem. Soc. Dalt. Trans. 523 (1985)

39.     Saxena, A. and Tandon, J.P.: Antitumour activity of some diorganotin and tin(IV) complexes of Schiff bases. Cancer Lett. 19:73 (1983)

40.     Keller, H.J., Keppler, B., Kruger, U. and Dobbins, E.: Antineoplastic effect of metal complexes and their use in medecin. Eur. P. 49486 (1982)

41.     Cardarelli, N.F., Cardarelli, B.N., Libby, E.B. and Dobbins, E.: Organotin implications in anticarcinogenesis effects of several organotin on tumour growth rate in mice. Austral. Exp. Biol. Med. Set. 62:209 (1984)

42.     Cardarelli, N.F. and Kanakkanatt, S.V.: Tin steroids and their use as antineoplastic agents. U.S.P. 4541956 (1985)

43.     Barbieri, R„ Silvestri, AS., Filippeschi, S., Magistrelli, M. and Huber, F.: Studies on the antitumour activity of complexes of R2Sn(IV) with penicillamine enantiomers and with 3-thlopropanic acid and correlation with structural aspects. Inorg. Chim. Acta 177:141 (1990)

44.     Meriem, A., Willem, R., Meumer-Piret, J. and Gielen, M.: Diorganotin derivatives of substituted iminoacetic acids: Synthesis spectroscopic characterization, x-rays structure analysis in vitro and in vivo antitumour activity. Nato Adv. Research Workshop on the effect of Tin upon malignant cell growth. Brussels, abstr. P13,1989

45.     Narajanan, V.L., Nasr, M. and Pauli, K.D.: Computer assisted structure antileukemic activity correlations of organotin compounds and initial exploration of their potential anti-HIV activity. In: Tin-Based Antitumour Drugs. Nato ASI series, p. 201, Springer Verlag Berlin, 1990

46.     Gielen, M., Willem, Κ., Maneilla, T., Ramharter, J. and Joosen, E.: In: Tin and Malignant Cell Growth (J.J. Zuckerman, ed.), CRC Press, Clevelant, 1988

47.     Carrara, M., Zampirou, S., Voltarel, G., Sindellari, L. and Trincia, L.: Inhibitory properties of tin(IV) diethyl- dithiocarbonates on tumoral cell growth. Pharmacol. Res. Commun. 20: 61 (1988)

48.     Furlani, A., Scarcia, V., Cherchi, V., Sindellari, L. and Preti, C.: Tin carbodithiates as cytostatic agents. Nato Adv. Workshop on the Effect of Tin upon Malignant Cell growth, abstr. P04, Brussels, 1989

49.     Crow, A.J.: The antitumour activity of tin compounds. In: Metal Based Antitumour Drugs (M. Gielen, ed.), p. 103, Freund Publ. House Ltd., London, 1989

50.     Hondrellis, V., Perlepes, S.P. and Tsangaris, J.M.: Preparation and characterization of new tin(II) and tin(IV) and mixed-oxidation state tin complexes with amide ligands. Nato Adv. Research Workshop in the effect of Tin upon Malignant Cell Growth, Abstr. P05, Brussels, 1989

51.     Perlepes, S.P., Hondrellis, V., Tsangaris, J.M. and Russo, U.: Complexation of tin with amide ligands; two cases of mixed oxidation state tin complexes. Inorg. Chim. Acta 189: 213 (1991)

52.     Teraoka, M.: Distribution of 24 elements in the internal organs of normal males and the metallic workers in Japan. Arch. Environ. Health. 36: 155 (1981)

53.     Sherman, L.R., Bilgicer, K.I, and Cardarelli, N.F.: Analysis of tin in mouse and human organs. J. Nutr. Growth and Cancer 2: 107 (1985)

54.     Cardarelli, N.F., Quitter, B.N., Allen, A., Dobbins, E., Libby, E.P., Hager, P. and Sherman, L.R.: Organotin implications in anticarcinogenesis. Backround and thymus involvement. Austral. J. Exp. Biol. Med. Sci. 62: 179(1984)

55.     Cardarelli, N.F.: Implications In cancer prophylaxis and other physiology processes. In: Tin as a Vital Nutrient (N.F. Cardarelli, ed.), CRC Press, Boca Raton, FL, 1985

56.     T.D. Luckey, ed.: Thymic Hormones, Univ. Park Press, Baltimore, 1973

57.     Cardarelli, N.F., Cardarelli, B.N. and Marrioneaux, M.: Tin as a vital trace element. J. Nutr. Growth and Cancer 1:183 (1983)

58.     Cardarelli, N.N., Cardarelli, B.N., Libby, E.P. and Dobbins, E.: Organotin implications in anticarcinogenesis. Effect of several organotins on tumour growth rate in mice. Austral. J. Exp. Biol. Med. Sci. 62:209 (1984)

59.     Cardarelli, N.F.: The role of tin hormones in senescence: A hypothesis. In: Tin-based Antitumour Drugs (M. Gielen, ed.), vol. 37, p. 115, Nato ASI Series, 1989

60.     Williams, D.R.: Metal, ligand and cancer. Chem. Rev. 72:203(1972)

61.     H. Siegel (ed.): Metal Ions in Biological Systems. Vol. II, Metal Complexes as Anticancer Agents, M. Dekker, N.Y., 1980

62.     Albert, A.: The molecular basis of drug action. Chem. Intern. 3:19(1980)

63.     Sherman, S.E., Gilson, D., Wang, J. and Lippard, S.J.: X-rays structure of the major adduct of the anticancer drug cisplatin with DNA: cis-[Pt(NH3)2(pGpG)]. Science 230:412(1985)

64.     Penninks, A.H., Bol-Shoenmakers, M. and Seinen, W.: Cellular interaction of organotin compounds in relation to their antitumour activity. In: Tin-based Antitumour Drugs (M. Gielen, ed.), vol. H37, p. 169, Nato ASI Series, Springer, Verlag, Berlin, 1990

65.     Crowe, A.J.: Tin compounds and their potential on pharmaceutical agents. In: Tin-based Antitumour Drugs (M. Gielen, ed.). Vol. H37, p. 69, Nato ASI Series, Springer, Verlag, Berlin, 1990

66.     Barnes,J.M. and Stoner, H.B.: Toxic properties of some dialkyl and trialkyl tin salts. Brit. J. Ind. Med. 15: 15 (1958)

67.     Pottier, R.H.: Past, present and future of photosensitizers. In: Photosensitisation (G. Moreno, R.H. Pottier and T.G. Truscott, eds), p. 1, Springer Verlag, Berlin, 1988

68.     Morgan, A.R., Garbo, G.M., Keck, R.W. and Selman, S.H.: In vivo cytotoxicity of metalopurpurins to bladder tumours. In: Photosensitisation (G. Moreno, R.H. Pottier and T.G. Truscott, eds), p. 475, Springer-Verlag, Berlin, 1988

69.     Arakawa, V. and Wada, O.: Inhibition of carrageenan edema formation by organotin compounds. Biophys. Comm. 725; 59 (1989)

70.     Wasi, N., Singh, H.B., Cajanane, A. and Raichowdary, A.N.: Synthesis of metal complexes of antimalarial drugs and in vitro evaluation of their activity against Plasmodium falciparum. Inorg. Chim. Acta 135(2): 133 (1987)

71.     Saxena, A.K., Koaker, J.K., Tandon, J.P. and Dass, S.R.: Studies of organotin-Schiff base complexes as new potential ameobicidal agents. J. Toxicol. Environ. Health 10(4-5): 709(1982)

72.     Samgupta, A.K. and Gupta, A.A.: Synthesis of some indole derivatives as potential antibacterial agents. Ind. J. Chem. Sect. B. (Orgamed. Chem.) 22 (3): 263 (1983)

73.     Peters, W., Trotter, E.R. and Robinson, B.L.: The experimental chemotherapy of leishmaniasis. VII. Drug response of L. major and L. mexicana amazonensis with an analysis of promising chemical leads to new anti-leishmanian agents. Ann. Trop. Med. Parasitol. 74: 321 (1980)

74.     Tareeva, A.I. and Borodina, G.M.: Comparative study of antihelminthic properties common to some organic tin compounds. Farmakol. Toksikol. 30:207 (1967)

75.     Nagel, F.J.: Antimicrobial composition. Canad. P. 158157{1983), Chem. Abstr. 99:67466n

76.     Ladanyi, P.: Composition and preparation of an antimicrobial agent. French P. 2482860 (1981). Chem. Abstr. 96: P110163v, P129814e

77.     Gucklhorm, I.R.: Antimicrobials in cosmetics, part 8, 9. Mfg Chemist Aerosol News 42:34 (1971)

78.     Melin, Chr.: Hair dye composition containing vegetable extracts. French P. 2453434 (1984). Chem. Abstr. 102: 119424f

79.     Schroeber, H.A., Balassa, J.J. and Timpton, I.H.: Abnormal trace elements in man: Tin. J. Chron. Dis. 17: 483(1964)

80.     Laughlin, R.D. Jr. and Linden, O.: Fate and effects on organotin compounds. Ambio 14(2): 88 (1985)

81.     Mitchell, D.C.: Vitamin supplements and diet pills. U.S.P. 4588717(1986). Chem. Abstr. 105:102602b

82.     Saxema, A.K. and Huber, F.: Organotin compounds and cancer chemotherapy. Coord. Chem. Review 95: 109 (1989)

Relative Papers

Online ISSN 1011-6575

Άρθρα Δημοσιευμένα σε αυτό το Περιοδικό Καταχωρούνται στα:

Articles published in this Journal are Indexed or Abstracted in: • Chemical Abstracts • Elsevier’s Bibliographic Databases: Scopus, EMBASE, EMBiology, Elsevier BIOBASE SCImago Journal and Country Rank Factor

Τι είναι η Επιθεώρηση Κλινικής Φαρμακολογίας και Φαρμακοκινητικής-Διεθνής Έκδοση-Οδηγίες προς τους Συγγραφείς – 
What is Epitheorese Klinikes Farmakologias 
και Farmakokinetikes-International Edition-Instrunctions to Authors

Άρθρα Δημοσιευμένα στην Επιθεώρηση Κλινικής Φαρμακολογίας και Φαρμακοκινητικής-Διεθνής Έκδοση – 
Articles Published in Epitheorese Klinikes Farmakologias 
και Farmakokinetikes-International Edition

Συντακτικη Επιτροπή-Editorial Board

ΕΤΗΣΙΑ ΣΥΝΔΡΟΜΗ 1992 – ANNUAL SUBSCRIPTION 1992
Γλώσσα Πλήρους Κειμένου – Full Text Language Αγγλικά – English
Παραγγελία – Αγορά – Order – Buy Ηλεκτρονική Μορφή: pdf (70 €) – Digital Type: pdf (70 €)

pharmakonpress[at]pharmakonpress[.]gr

Έντυπη Μορφή (70 € + έξοδα αποστολής) – Printed Type (70 € + shipping)

pharmakonpress[at]pharmakonpress[.]gr

 

 

 

Bookmark the permalink.

Comments are closed.