Perspectives of antimony compounds in oncology

Acta Pharmacologica Sinica

Volumn 29, Issue 8, 2008, Pages 881-890

  Sharma, Pankaj ^a   Perez, Diego ^a   Cabrera, Armando ^a   Rosas, Noe ^a   Arias, Jose Luis ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Antimony; Antitumoral; Leishminiatic drugs; Organoantimony

Indexed keywords

2 SELENOPHENYLSTIBENE 3 METHYL 2 THIENYLSTIBINE; AMINE; ANTILEISHMANIAL AGENT; ANTIMONY DERIVATIVE; ANTIMONY GLUCONATE; ANTIMONY TARTRATE; CARBOPLATIN; CEFALEXIN; CISPLATIN; CYCLOPHOSPHAMIDE; DIPHENYLDITHIOPHOSPHONIC ACID DIISOPROPYLDITHIOPHOSPHORIC ACID; INTERFERON; MEGLUMINE ANTIMONATE; NITRILOACETATE; ORGANOMETALLIC COMPOUND; PENTETIC ACID; PLATINUM DERIVATIVE; POLYAMINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; STIBOCAPTATE; STIBOGLUCONATE SODIUM; STIBOPHEN; SURAMIN; TUNGSTEN DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; COMPLEX FORMATION; DRUG ACTIVITY; DRUG STRUCTURE; HUMAN; NONHUMAN; REVIEW; SARCOMA; SCREENING;

ANIMALS; ANTIMONY; ANTINEOPLASTIC AGENTS; HUMANS; ORGANOMETALLIC COMPOUNDS;

EID: 49349110707     PISSN: 16714083     EISSN: 17457254     Source Type: Journal    
DOI: 10.1111/j.1745-7254.2008.00818.x     Document Type: Review

References (61)

1. Desoize B. Metals and metal compounds in cancer treatment. Anticancer Res 2004 24 : 1529 44.
2. Rosenberg B, Van Camp L, Trosko JE, Mansour VH. Platinum compounds: a new class of potent antitumour agents. Nature 1969 222 : 385 6.
3. Allen TM. Ligand-targeted therapeutics in anticancer therapy. Nat Rev Cancer 2002 2 : 750 63.
4. Gielen M, editor. Metal based antitumour drugs. London : Freund Publishing House Ltd 1988.
5. Keppler BK, editor. Metal complexes in cancer chemotherapy. Weinheim Germany : VCH 1993. p 1 8.
6. Köpf-Maier P. Complexes of metals other than platinum as antitumour agents. Eur J Clin Pharmacol 1994 47 : 1 16.
7. Barnard CFJ, Fricker SP, Vaughan OJ. Medical applications of inorganic chemicals. In Thompson D, editor. Insights into specialty inorganic chemicals. Cambridge : Royal Society of Chemistry 1995. p 35 60.
8. Sadler PJ, Guo Z. Metal complexes in medicine: design and mechanism of action. Pure Appl Chem 1998 70 : 863 71.
9. Guo Z, Sadler PJ. Metals in medicine. Angew Chem Int Ed Engl 1999 38 : 1512 31.
10. Meriem A, Willem R, Biesemans M, Mahieu B, Vos de D, Lelievald P, et al. Synthesis, characterization and in vitro antitumour activity of dibutyltin(IV) derivatives of some aromatic carboxylic acids, including aspirin. Appl Organomet Chem 1991 5 : 195 201.
11. Brutkiewicz RR, Suzuki F. Biological activities and antitumour mechanism of an immunopotentiating organogermanium compound, Ge-132 (review). In Vivo 1987 1 : 189 204.
12. Celaries B, Gielen M, Vos de D, Rima G. In vitro antitumour activity of some organogermanium radioprotectors. Appl Organomet Chem 2003 17 : 191 3.
13. Gielen M, Willem R, Bouhdid A, Vos de D, Inventors; Pharmachemie B.V., asignee., Preparation of Aaromatic fluorine-containing organotin compounds as anti-tumour agents. Eur Patent 5 700 921 1996 Mar 13.
14. Gielen M, Willem R, Biesemans M, Kemmer M, Vos de D, Inventors; Pharmachemie B.V., asignee, Antitumour tin poly oxaalkanecarboxylates, preparation thereof, and compositions containing them. PCT Int Appl 17 006 583 2000 Feb 10.
15. Tabassum S, Pettinari CJ. Chemical and biotechnological developments in organotin cancerchemotherapy. J Organomet Chem 2006 691 : 1761 6.
16. Duffin J, Camping BJ. Therapy and disease concepts: the history (and future) of antimony in cancer. J Hist Med 2002 57 : 61 78.
17. Tiekink ERT. Antimony and bismuth compounds in oncology. Crit Rev Onco Hemat 2002 42 : 217 24.
18. Tracy JW, Webster LT. Drugs used in the chemotherapy of protozoal infections. In : Hardman JG, Limbird LE, Molinoff PB, Ruddon RW, Gilman AG. editors. The pharmacological basis of therapeutics, 9th ed. New York : Mcgraw-Hill 1995 p 987 1008.
19. Berman DJ. Chemotherapy for Leishmaniasis: boichemical mechanisms, clinical efficacy, and future strategies. Rev Infect Dis 1988 10 : 560 86.
20. Tester-Dalderup CBM. Antiprotozoal drugs. In : Dukes MNG, editor. Meyler′s side effects of drugs, 13th ed. Amsterdam : Elsevier 1996 p 799 842.
21. Lee MB, Gilbert HM. Current approaches to Leishmaniasis. Infect Med 1999 16 : 37 45.
22. Lugo A, Anez N, Petit de Pena Y, Burguera JL, Burguera M. Antimony determination in tissues and blood serum of hamsters infected with Leishmania garnhami and treated with meglumine antimoniate. Annals Trop Med Parasitol 1994 88 : 37 41.
23. Demicheli C, Frézard F, Lecouvey M, Garnier-Suillerot A. Antimony(V) complex formation with adenine nucleosides in aqueous solution. Biochim Biophys Acta 2002 1570 : 192 8.
24. Hsu B, Chou CH, Chen JT, Shen ML. Studies on antitumour action of antimony-complexones. Chin Med J 1963 82 : 155 63.
25. Hsu B, Chou CH, Chen JT, Shen ML. Studies on antitumour action of antimony complexones. Acta Unio Intern Contra Cancrum 1964 20 : 245 8.
26. Hsu B, Kao YS, Tsai JS, Chou CH, Liu MC, Shen ML, et al. Pharmacological studies of several new antitumour agents. Sci Sin 1964 13 : 789 800.
27. Jasmin C, Cherman JC, Herve G, Teze A, Souchay P, Boy- Loustau C, et al. In vivo inhibition of murine leukemia and sarcoma viruses by the heteropolyanion 5-tungsto-2-antimoniate J Natl Cancer Inst 1974 53 : 469 74.
28. Lidereau R, Bouchet C, Sinoussi F, Saracino R, Cherman JC. Current Chemotherapy Proc 1978 2 : 1323 6.
29. Joesten MD, Najjar R, Hebrank G. Metal complexes of alkylating agents-(III). Complexes by cyclophosphamides. Polyhedron 1982 1 : 637 9.
30. 2O(M=Na+,NH4+., pdta=propylenediaminetetraacetic acid). Inorg Chim Acta 1995 232 : 161 5.
31. 2O (dtpa=diethylenetriaminepenta acetic acid). Main Group Metal Chem 1997 20 : 169 80.
32. 4, Na., n=1,2). Pharm Chem J 2005 39 : 119 21.
33. Tofazzal M, Tarafder H, Ali AM, Elias MS, Crouse K, Silong S. Coordination chemistry and biological activity of bidentate and quadridentate nitrogen- sulphur donor ligands and their complexes. Trans Met Chem 2000 25 : 706 10.
34. Hadjikakou SK, Antoniadis CD, Hadjiliadis N, Kubicki M, Binolis J, Karkaounas S, et al. Synthesis and characterization of new water stable antimony(III) complex with pyrimidine-2-thione and in vitro biological study. Inorg Chim Acta 2005 358 : 2861 6.
35. Ozturk II, Hadjikakou SK, Hadjiliadis N, Kourkoumelis N, Kubicki M, Baril M, et al. Synthesis, structural characterization, and biological studies of new antimony (III) complexes with thiones. The influence of the solvent on the geometry of the complexes. Inorg Chem 2007 46 : 8652 61.
36. Xu S, Guo G, Wang J, Huang Y. Effects of potassium antimonyl tartrate on proliferation and apoptosis in vitro of human gastric cancer. Disi Junyi Daxue Xuebao 2004 25 : 1464 6.
37. Salerno M, Suillerot AG. Resistance to arsenic-and antimony based drugs. Bioinorg Chem Appl 2003 1 : 189 98.
38. Yu W, Sun B, Chai Y, Zhao Z, Liu X, Ji Z, et al. Apoptosis of acute promyelocytic leukemia cell NB4 induced by different kinds of antimonials. Disi Junyi Daxue Xuebao 2003 24 : 338 41.
39. Pathak MK, Hu X, Yi T. Effects of sodium stibogluconate on differenciation and proliferation of human myeloid leukemia in vitro. Leukemia 2002 16 : 2285 91.
40. Muller S, Miller WH, Dejean A. Trivalent antimonials induce degradation of the PML-RARa oncoprotein and reorganization of the promyelocytic leukemia nuclear bodies in acute promyelocytic leukemia NB4 cells. Blood 1998 92 : 4308 16.
41. Yi T, Pathak MK, Lindner DJ, Ketterer MF, Farver C, Borden EC. Anticancer activity of sodium stibogluconate in synergy with IFNs. J Immunol 2002 169 : 5978 85.
42. Fan K, Zhou M, Pathak MK, Lidner DJ, Aluntas CJ, Tuohy VK, et al. Sodium Stibogluconate interacts with IL-2 in anti-Renca tumour action via T cell-dependent mechanism in connection with induction of tumour-infiltrating macrophages. J Immunol 2005 169 : 7003 8.
43. Yu W, Sun B, Chai Y, Zhao Z, Liu X, Ji Z, et al. Apoptotic induction of acute promyelocytic leukemia cell NB4 by antimony trioxide. Xibao Yu Fenzi Mianyixue Zazhi 2002 18 : 592 4.
44. Yi T. Inhibition of protein tyrosine phosphatase by leishmaniasis agents and their use in combination with cytokines for treatment of cancer and other diseases. PCT Int Appl 2003 144.
45. Silvestru C, Socaciu C, Bara A, Haiduc I. The first organoantimony (III) compounds possessing antitumour properties: diphenylantimony(III) derivatives of dithiophosphorus ligands. Anticancer Res 1990 10 : 803 4.
46. Bara A, Socaciu C, Silvestru C, Haiduc I. Activity of some diphenyltin(IV) and diphenylantimony(III) derivatives on in vitro and in vivo Ehrlich ascites tumour Antitumour organometallics. Anticancer Res 1991 11 : 1651 6.
47. Socaciu C, Bara A, Silvestru C, Haiduc I. Antitumour organometallics. II. Inhibitory effects of two diphenyl-anti-mony (III) dithiophosphorus derivatives on in vitro and in vivo Ehrlich ascites tumour. In Vivo 1991 5 : 425 8.
48. Keppler BK, Silvestru C, Haiduc I. Antitumour organometallics. III. In vivo activity of diphenylantimony(III) and diorganotin (IV) dithiophosphorus derivatives against P388 leukemia. Metal-Based Drugs 1994 1 : 73 7.
49. Socaciu C, Pasca I, Silvestru C, Bara A., Haiduc I. Antitumour organometallics. IV. The mutagenic potential of some diphenylantimony(III) dithiophosphorus derivatives. Metal-Based Drugs 1994 1 : 291 7.
50. Sharma P, Rosas N, Cabrera A, Toscano A, Silva MJ, Pérez D, et al. First synthesis and structural report on selenophen-2-yl containing pnictogens: Biological Activities of tris (selenophen-2-yl)stibine. J Organomet Chem 2005 690 : 3286 91.
51. Sharma P, Rosas N, Cabrera A, Toscano A, Silva MJ, Hernández S, et al. Substituted thienyl stibines and bismuthines: syntheses, structures and cytotoxicity. Appl Organomet Chem 2005 19 : 1121 6.
52. 3(Y=H, Me, MeO). Appl Organomet Chem 1995 9 : 597 607.
53. Carraher CE Jr., Nass MD, Giron DJ, Cerutis DR. Structrual and biological characterization of antimony(V) polyamines. J Macromol Sci Chem 1983 19 : 1101 20.
54. Wang GC, Xiao J, Lu Y, Li JS, Cui JR, Wang RQ, et al. Synthesis, crystal structures and in vitro antitumour activities of some arylantimony derivatives of analogues of demethylcantharimide. J Organomet Chem 2004 689 : 1631 8.
55. Wang GC, Lu YN, Xiao J, Yu L, Song HB, Li JS, et al. Synthesis, Crystal structure and in vitro antitumour activities of some organoantimony arylhydroxamates. J Organomet Chem 2005 690 : 151 6.
56. Li JS, Ma YQ, Cui JR, Wang RQ. Synthesis and in vitro antitumour activity of some tetraphenylantimony derivatives of exo-7-oxa-bicyclo [2,2,1]heptane(ene)-3- arylamide -2-acid. Appl Organomet Chem 2001 15 : 639 45.
57. Li JS, Ma YQ, Yu L, Cui JR, Wang RQ. Synthesis, spectroscopic characterization, and in vitro antitumour activity of tetrapheny-lantimony derivatives of analogs of demethylcantharidin and demethyl- dehydrogencantharidin. Synth React Inorg Met Org Chem 2002 32 : 583 93.
58. Ma YQ, Li JS. Synthesis and in vitro antitumour activity of triarylantomony di (triphenylgermanyl propionates). Main Group Met Chem 2001 24 : 235 8.
59. 3. Polyhedron 2004 23 : 823 9.
60. Yu L, Ma YQ, Wang GC, Li JS. Synthesis and in vitro antitumour activity of some triarylantimony di(N-phenylglycinates). Heteroatom Chem 2004 15 : 32 6.
61. Slegmann-Louda DW, Carraher CE Jr., Quinones Q, McBride G. Preliminary evaluation of organoarsenic and organoantimony polymers derived from cephalexin as potential anticancer drugs. PMSE Preprints 2003 88 : 390 2.