Browse > Article

Selective Cytotoxicity of Novel Platinum(II) Coordination Complexes Containing DL-2-Hydroxy 3-Methylbutyric Acid  

정지창 (경희대학교 의과대학 약리학 교실)
홍언표 (경희대학교 의과대학 약학대학)
최승기 (포천중문의과대학 약리학교실)
장성구 (경희대학교 의과대학 비뇨기과학 교실)
육창수 (경희대학교 의과대학 약학대학)
노영수 (경희대학교 의과대학 약학대학)
Publication Information
Biomolecules & Therapeutics / v.11, no.2, 2003 , pp. 91-98 More about this Journal
Abstract
A new series of highly water soluble platinum(II) complexes[Pt(II)(DL-2-hydroxy-3-methylbutyrate)(trans-l-1,2-dimninocyc1ohexane)] (PC-1) and [Pt(II)DL-2-hydroxy-3-methylbutyrate](cis-1,2-diaminocyclohexane)](PC-2) were synthesized and characterized by their elemental analysis and by various spectroscopic techniques [infrared(IR), $^{13}C$-nuclear magnetic resonance (NMR)]. In vitro antitumor activity of new Pt(II)complexes was tested against MKN-45, MKN/ADM and MKN/CDDP human gastric adenocarcinoma cell lines using colorimetric MTT[3-(4,5-dimethyl thiazol-2-yl)-2,5-diphenyltetrazoliumbromide] assay for cell survival and proliferation. PC-1 and PC-2 showed active against MKN-45/P, MKN/ADM and MKN/CDDP human gastric cancer cell lines, and the antitumor activity of these compounds were comparable or superior to that of cisplatin. The nephrotoxicities of PC-1 and PC-2 were found quite less then that of cisplatin using MTT and [$^3H$] thymidine uptake tests in rabbit proximal tubule cells, human kidney cortical cells human renal cortical tissues. Based on these results, these novel platinum(II) complex compounds(PC-1 & PC-2) represent a valuable lead in the development of the new anticancer chemotherapeutic agents capable of improving antitumor activity and low nephrotoxicity.
Keywords
Selective cytotoxicity; Human gastric adenocarcinoma cells; Nephrotoxicity; Platinum coordination complex;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Chung. S. D., Alavi, N., Livingston, D., Hiler, S. and Taub, M. (1982). Characterization of primary rabbit kidney cultures that express proximal tubule functions in a hormonally defined dedium, J Cell Biol 95, 118-126   DOI   ScienceOn
2 Clear, M. J., and Hoeschele, J. D. (1973). Antitumor platinum compound : Relationship between structure and activity. Platinum Metals Review 17, 2-10
3 Connors, T. A., Jones, M. and Ross, W. C. J. (1972). New platinum complexes with antitumor activity. Chem Bioi Interact 5, 415-420   DOI   ScienceOn
4 Cook, W. F. and Pickering, G. W. (1958). A rapid method for separating glomeruli from rahbit kidney. Nature 182, 1103-1104   DOI   ScienceOn
5 Day, R. S., Ziolkowski, C H. J. and Scudiero, D. A. (1980). Defective repair of alkylated DNA by human tumor and SV40-transfonued human cell strains. Nature 288, 124-129
6 Jung, J. C., Lee, S. M., Kadakia, N. and Taub, M.(1992). Growth and function of primal rabbit kidney proximal tubule cells in glucose-free serum-free medium J. Cellular Physiol 150, 243-249   DOI
7 Jung, J. C., Lee, M. H., Chang. S. G. and Rho, Y.S.(1995). Antitumor activity and nephrotoxicity of the novel platinum(Il) complex. Korean J Pharmacology 31, 1. 103-109
8 Adrie, C M., Dijk, M. and Lohman, H. M. (1984). Induction and repair of DNA cross-links in Chinese hamster ovary cells treated with various platinum coordination compounds in relation to platinum binding to DNA, cytotoxicity mutagenecity, and antitumor activity. Cancer Res 44, 2043-2051
9 Jung, J. C., Chung, J. H., Chang, S. G., and Rho, Y. S. (2000). Selective Cytotoxicity of a Novel platinum(II) coordination complex on human bladder cancer cell lines and normal kidney cells. Kor J Physiol & Pharmacal. 4, 159-167
10 Jung, J. C., Yim, S. V., Park, S. J., Chung, J. H., Ko, K. C., Chang, S. G. and Rho, Y. S. (1996). In vitro antitumor activity and nephrotoxicity of the novel platinumrIl) coordination complex containing cis-DACH/diphosphine. The Korean J Pharmacal 32, 93-102
11 Appleton, T. G., Bennett, M. A. and Tomkins, I. B. (1976). Effect of chelatering size on spectroscopic and chemical properties of methylplatinum(II) complexes of the ditertiary phosphines Ph$_{2}P[CH_{2}]nPPh_{2}$ (n = 1,2 or 3) JCS Dalton 439-446.
12 Baek, M. S., Rho, Y. S., Jung, J. C., Chang, S. G., Normura, M., Miyamoto, K. I. (1977). Antitumor activity and nephrotoxicity of a novel platinum complex, [l,2-bis(diphenylphosphine) propane](trans-I-DACH) platinum dinitrate, Anticancer Research 17, 995-960
13 Bodenner, D. L., Dedon, P. C., Katz, J. C., and Borch, R. F. (1986). : Selective protection against cis-diaminedichlore platinum (II) induced toxicity in kidney, gut and hone marrow by diethyl-dithiocarbamate. Cancer Res 46(6), 2751-2757.
14 Bradley, M, O., Patterson, S. and Zwelling, L. A. (1982). Thiourea prevents cytotoxicity and mutagenicity, but not sister chromatid exchanges in V79 cells treated with cisdiaminedichloroplatinum(II). Mutai Res 96, 67-74
15 Rho, Y. S., Lee, K. T., Jung, J. C. and Chang, S. G. (1996). In vitro cytotoxicity of Pt(II) complexes containing ethylenediamine in rabbit kidney proximal tubular and human renal cortical cell. Yakhak Hoeji 40, 218-224
16 Rho, Y. S., Kim, S. A., Jung, J. C, Shin, C. C. and Chang, S.G. (2002). Anticancer cytotoxicity and nephrotoxicity of the new platinum(II) complexes containing diaminocyclohexane and glycolic acid. Int J Oncology 20, 929
17 Ettinger, L. T., Gaynon, P. S. and Krailo, M. D. (1994). A phase II study of carboplatin in children with recurrent or progressive solid tumors. A report from the childrens group. Cancer 73, 1297-1302   DOI   ScienceOn
18 Ridgway, H. J., Speer, R. J. and Hall, J. M. (1977). Analogs of sulfato 1,2-diaminocyclohexane platinum(II) : Modifications in leaving ligands. J Clin Hematol Oncol 7,220-227
19 Dobyan, D. C, Levi, J., Jacobs, C. (1980). Mechanism of cisplatinum nephrotoxicity. J Pharmacol Exp Ther 213(3), 551-556
20 Einhorn, L. H. and Donohue, J. (1977). Cis-dismminedichloroplatinum, vinblastine and bleomycin combination chemotherapy in disseminated testicular cancer, Ann Intern Med 87, 293-328   DOI   ScienceOn
21 Fields, K. K., Zorsky, P. E. and Hiernenz, J. W. (1994). Ifosfamide carboplatin and etoposide: a new regimen with a broad spectrum of activity. J Clin Oncol 12, 544-552   DOI
22 Glover, D., Glick, J. H.. Weiler, C. (1986). Phase I/lI trials of WR-2721 and cis-platinum, Int J Radiat Oneal Biol Phys 12(8), 1509-1512   DOI   ScienceOn
23 Gonzales-Vitale, J. C., Hayes, D. M. and Sternberg, S. S. (1977). The renal pathology in clinical trials of cis-platinum. Cancer 39, 1362-1371   DOI   ScienceOn
24 Inagaki, K. and Kidani, Y. (1986). Differences in binding of 1,2-diaminocyclohexane platinum(ll) isomers with d(GPG). lnorg Chem 25, 1-5   DOI
25 Jones, B. R., Bhalla, R. B., Mladek, J. (1980). Comparison methods of evaluating nephrotoxicity of cis-platinum. Clin Phamacol Ther 27(4), 557-562   DOI   ScienceOn
26 Susan, J. B., and Peter, J. S. (1987). Phosphines in medicine. Chemistry in Britain June: 541-547.
27 Tashiro, T. (1988). The mechanism of antitumor action of platinum complexes. Jap J Chem 4, 684
28 Ward, J. M., Young, D. M., Fauvie, K. A., Wolpert, M. K., Davis, R. and Guarino, A. M. (1976). Comparative nephrotoxicity of platinum cancer chemotherapeutic agent. Cancer Chemother Rep 60, 1675-198I
29 Levi, J., Jacobs, C, Kalman, S. M., McTigue, M., Wincer, M. W. (1980). Mechanism of cis-platinum nephrotoxicity. I Effects of sulfhydryl group in rat kidney. J Pharmacol Exp Ther 213(3), 545-550.
30 Kidani, Y. (1985). Development of antitumor platinum complexes. Yakugaku Zasshi 105(10), 909-914   DOI
31 Meijer, S., Mulder, N. H., Sleijfer, D. T. and Schraffordt, K. H. (1982). Nephrotoxicity of cisplatinum during remissioninduction and maintenance chemotherapy of testicula carcinoma, Cancer Chemother PharmacoI 8(1), 27-30   DOI   ScienceOn
32 Mortine, T. J. and Borch, R. F. (1988). Quiescent LLC-PK$_{1}$ cells as a model for cis-diaminedichloroplatinum(II) nephrotoxicity and modulation by thio rescue by agents. Cancer Res 48, 6017, 24-29
33 Mossman, T (1973). Rapid colorimetric assay for cellular growth and survival: application and cytotoxic assays. J Immunol Methods 65, 55-61   DOI   ScienceOn
34 Munchausen, L. L. (1974). The chemical and biological effects of cis-dichlorodiamine platinum(II), and antitumor agent, on DNA. Proc Natl Acad Sci USA 71, 4519
35 Porter, G. A. and Bennet, W. M. (1981). Toxic nephropathies: In the kidney(2nd.ed). Saunders Co. Philadelphia pp. 2045-2108
36 Reslova, S. (1971). The induction of lysogenic strains of Escherichia coli by cis-dichlorodiammineplatnum(II). Chem Biol Interact 4, 66-74   DOI   ScienceOn
37 Royer-Pokora, B., Gordon, L. K. and Haseltine, W. A. (1981). Use of endonuclease III to determine the site of stable lesions in defined sequences of DNA: the cyclobutane dimmer and cis-and trans-dichlorodiamineplatinum(II) examples. Nucleic Acids Res 9, 4595-4609   DOI   ScienceOn
38 Rosenberg, B. (1975). Possible mechanism for the antitumor activity of platinum coordination complexes. Cancer Chemother Rep 59, 589-595
39 Rosenberg, B., Van Camp, L., Krigas, T. (1965). Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode. Nature 205,698-707   DOI   ScienceOn
40 Rosenberg, B., Van Camp, L., Grimley, E. B. and Thomson, A. J. (1967)- The inhibition of growth or cell division in Escherichia coli by different ionic species of platinum complexes. J Biol Chem 242, 1347-1352
41 Shimoyama, Y., Kubota, T. and Watanabe, M. (1989). Predictability of in vivo chemosnesitivity by in vitro MTT assay with reference to the clonogenic assay. J Surg Oncol 41, 12-18   DOI   ScienceOn
42 Sorenson, C. M. and Eastman, A. (1988). Mechanism of cisdiaminedichloroplatinum(Il)-induced cytotoxicity: Role of G2 arrest and DNA double-strand breaks. Cancer Res 48, 4484-4488
43 Stone, P. J., Kelman, A. D. and Sinex, E M. (1974). Specific binding of antitumor drug cis-Pt(NH$_{3})_{2}Cl_{2}$ to DNA rich in guanine and cytosine. Nature 251, 736   DOI   ScienceOn
44 Zhong, L. F., Zhang, M., Ma, S. L. and Xia, Y. X. (1990). Protection against cisplatin induced lipid peroxidation and kidney damage by procaine in rats. Arch Toxicol 64, 599-600   DOI   ScienceOn
45 Zhang, J. G., Zhang, L. F., Zhang, M. and Xia, Y. X. (1922). Protection effects of procaine on oxidative stress and toxicities of renal cortical slices from rats caused by cisplatin in vitro. Arch Toxicol 66, 354-358   DOI   ScienceOn