Novel derivatives of spirohydantoin induce growth inhibition followed by apoptosis in leukemia cells

Biochemical Pharmacology

Volumn 77, Issue 3, 2009, Pages 348-363

  Kavitha, C V ^a   Nambiar, Mridula ^a   Ananda Kumar, C S ^b   Choudhary, Bibha ^c   Muniyappa, K ^a   Rangappa, Kanchugarakoppal S ^b   Raghavan, Sathees C ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b UNIVERSITY OF MYSORE   (India)

^c Manipal Academy of Higher Education   (India)

Author keywords

Anticancer drugs; Cell death; Chemotherapy; Cytotoxicity; DNA damage; Double strand break; Flow cytometry

Indexed keywords

8 (3,4 DICHLOROBENZYL) 1' (PENT 4 ENYL) 8 AZASPIRO[BICYCLO[3.2.1]OCTANE 3,4' IMIDAZOLIDINE] 2',5' DIONE; 8 (3,4 DIFLUOROBENZYL) 1' (PENT 4 ENYL) 8 AZASPIRO[BICYCLO[3.2.1]OCTANE 3,4' IMIDAZOLIDINE] 2',5' DIONE; CASPASE 9; DNA; FLUORESCEIN ISOTHIOCYANATE; HISTONE H3; HYDANTOIN DERIVATIVE; KU ANTIGEN; KU80 PROTEIN; LIPOCORTIN 5; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; PCNA PROTEIN; PROCASPASE 3; PROPIDIUM IODIDE; PROTEIN BAD; PROTEIN BCL 2; PROTEIN DERIVATIVE; PROTEIN P53; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER GROWTH; CANCER THERAPY; CELL ACTIVATION; CELL CYCLE; CELL CYCLE G1 PHASE; CELL STRAIN K 562; CONFOCAL MICROSCOPY; CONTROLLED STUDY; CYTOTOXICITY; DNA FRAGMENTATION; DNA REPLICATION; DOSE RESPONSE; DOWN REGULATION; DRUG INHIBITION; ENZYME ACTIVATION; FLOW CYTOMETRY; FLUORESCENCE ACTIVATED CELL SORTING; GROWTH INHIBITION; HUMAN; HUMAN CELL; LEUKEMIA CELL; MITOCHONDRION; PRIORITY JOURNAL; STAINING;

APOPTOSIS; BLOTTING, WESTERN; CELL CYCLE; CELL DIVISION; DNA REPLICATION; FLOW CYTOMETRY; HUMANS; HYDANTOINS; LEUKEMIA; MICROSCOPY, CONFOCAL;

EID: 58249144190     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2008.10.018     Document Type: Article

References (62)

1. Nambiar M., Kari V., and Raghavan S.C. Chromosomal translocations in cancer. BBA Rev Cancer 1786 (2008) 139-152
2. Nickoloff J.A., De Haro L.P., Wray J., and Hromas R. Mechanisms of leukemia translocations. Curr Opin Hematol 15 (2008) 338-345
3. Aplan P.D. Causes of oncogenic chromosomal translocation. Trends Genet 22 (2005) 46-55
4. Rowley J.D. Chromosome translocations: dangerous liaisons revisited. Nat Rev Cancer 1 (2001) 245-250
5. Raghavan S.C., and Lieber M.R. DNA structures at chromosomal translocation sites. Bioessays 28 (2006) 480-494
6. Raghavan S.C., Swanson P.C., Wu X., Hsieh C.L., and Lieber M.R. A non-B-DNA structure at the Bcl-2 major breakpoint region is cleaved by the RAG complex. Nature 428 (2004) 88-93
7. Raghavan S.C., Kirsch I.R., and Lieber M.R. Analysis of the V(D)J recombination efficiency at lymphoid chromosomal translocation breakpoints. J Biol Chem 276 (2001) 29126-29133
8. Marculescu R., Le T., Simon P., Jaeger U., and Nadel B. V(D)J-mediated translocations in lymphoid neoplasms: a functional assessment of genomic instability by cryptic sites. J Exp Med 195 (2002) 85-98
9. Lieber M.R., Yu K., and Raghavan S.C. Roles of nonhomologous DNA end joining, V(D)J recombination, and class switch recombination in chromosomal translocations. DNA Repair (Amst) 5 (2006) 1234-1245
10. Dorsett Y., McBride K.M., Jankovic M., Gazumyan A., Thai T.H., Robbiani D.F., et al. MicroRNA-155 suppresses activation-induced cytidine deaminase-mediated Myc-Igh translocation. Immunity 28 (2008) 630-638
11. Yu K., Roy D., Bayramyan M., Haworth I.S., and Lieber M.R. Fine-structure analysis of activation-induced deaminase accessibility to class switch region R loops. Mol Cell Biol 25 (2005) 1730-1736
12. Okazaki I.M., Kotani A., and Honjo T. Role of AID in tumorigenesis. Adv Immunol 94 (2007) 245-273
13. Canadian Cancer Society-National Cancer Institute of Canada. Canadian Cancer Statistics Toronto; 2005.
14. Nowell P.C., and Hungerford D.A. A minute chromosome in human chronic granulocytic leukemia. Science 132 (1960) 1497
15. Moen M.D., McKeage K., Plosker G.L., and Siddiqui M.A. Imatinib: a review of its use in chronic myeloid leukaemia. Drugs 67 (2007) 299-320
16. Robert J., and Jarry C. Multidrug resistance reversal agents. J Med Chem 46 (2003) 4805-4817
17. Huang C., Yang S., Ge R., Sun H., Shen F., and Wang Y. ZNF23 induces apoptosis in human ovarian cancer cells. Cancer Lett 266 (2008) 135-143
18. Kohn E.A., Yoo C.J., and Eastman A. The protein kinase C inhibitor Gö6976 is a potent inhibitor of DNA damage-induced S and G2 cell cycle checkpoints. Cancer Res 63 (2003) 31-35
19. Tang D.G., and Porter A.T. Target to apoptosis: a hopeful weapon for prostate cancer. Prostate 32 (1997) 284-293
20. Buolamwini J.K. Cell cycle molecular targets in novel anticancer drug discovery. Curr Pharm Des 6 (2000) 379-392
21. Williams D.A., and Lemke T.L. Foye's principles of medicinal chemistry (2002), Lippincott Williams & Wilkins, Philadelphia
22. Kleemann A, Engel J, Kutscher B, Reichert D. Pharmaceutical substances, synthesis, patents, applications; 2001.
23. Fiallo M., Kozlowski H., and Garnier-Suillerot A. Mitomycin antitumor compounds-Part 1. CD studies on their molecular structure. Eur J Pharm Sci 12 (2001) 487-494
24. Lee J., Kim J., Koh J.S., Chung H.H., and Kim K.H. Hydantoin derivatives as non-peptidic inhibitors of Ras farnesyl transferase. Bioorg Med Chem Lett 16 (2006) 1954-1956
25. Rajic Z., Zorc B., Raic-Malic S., Ester K., Kralj M., Pavelic K., et al. Hydantoin derivatives of l- and d-amino acids: synthesis and evaluation of their antiviral and antitumoral activity. Molecules 11 (2006) 837-848
26. Carmi C., Cavazzoni A., Zuliani V., Lodola A., Bordi F., Plazzi P.V., et al. 5-Benzylidene-hydantoins as new EGFR inhibitors with antiproliferative activity. Bioorg Med Chem Lett 16 (2006) 4021-4025
27. Kirk K.L. Selective fluorination in drug design and development: an overview of biochemical rationales. Curr Top Med Chem 6 (2006) 1447-1456
28. Kirk K.L. Fluorine in medicinal chemistry: recent therapeutic applications of fluorinated small molecules. J Fluorine Chem 127 (2006) 1013-1029
29. Bégué J.-P., and Bonnet-Delpon D. Fluorine: an invaluable tool in medicinal chemistry. Actualite Chimique (2006) 83-87
30. Mueller K., Faeh C., and Diederich F. Fluorine in pharmaceuticals: looking beyond intuition. Science 317 (2007) 1881-1886
31. Swinson J. Fully functional fluorine. Pharmachem 4 (2007) 38-41
32. Isanbor C., and O'Hagan D. Fluorine in medicinal chemistry: a review of anti-cancer agents. J Fluorine Chem 127 (2006) 303-319
33. Dolzhenko A.V., Dolzhenko A.V., and Chui W.K. Advances in chemistry and biological activity of fluorinated 1,3,5-triazines. In: Gardiner I.V. (Ed). Fluorine chemistry research advances (2007), Nova Science Publishers Inc., New York 105-142
34. Ananda Kumar CS, Benaka Prasad SB, Vinaya K, Chandrappa S, Thimmegowda NR, Ranganatha SR, et al. Synthesis and antiproliferative activity of substituted diazaspiro hydantoins: a structure-activity relationship study. Invest New Drugs, doi:10.1007/s10637-008-9150-3.
35. Ananda Kumar CS, Kavitha CV, Vinaya K, Benaka Prasad SB, Thimmegowda NR, Chandrappa S, et al. Synthesis and in vitro cytotoxic evaluation of novel diazaspiro bicyclo hydantoin derivatives in human leukemia cells: a SAR study. Invest New Drugs, doi:10.1007/S10637-008-9179-3.
36. Freimoser F.M., Jakob C.A., Aebi M., and Tuor U. The MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay is a fast and reliable method for colorimetric determination of fungal cell densities. Appl Environ Microbiol 65 (1999) 3727-3729
37. Korzeniewski C., and Callewaert D.M. An enzyme-release assay for natural cytotoxicity. J Immunol Methods 64 (1983) 313-320
38. Singh N.P., McCoy M.T., Tice R.R., and Schneider E.L. A simple technique for quantitation of low levels of DNA damage in individual cells. Exp Cell Res 175 (1988) 184-191
39. Ioannou Y.A., and Chen F.W. Quantitation of DNA fragmentation in apoptosis. Nucleic Acids Res 24 (1996) 992-993
40. Kaufmann S.H., Desnoyers S., Ottaviano Y., Davidson N.E., and Poirier G.G. Specific proteolytic cleavage of poly(ADP-ribose) polymerase: an early marker of chemotherapy-induced apoptosis. Cancer Res 53 (1993) 3976-3985
41. Miranda C.L., Stevens J.F., Helmrich A., Henderson M.C., Rodriguez R.J., Yang Y.-H., et al. Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines. Food Chem Toxicol 37 (1999) 271-285
42. Sakayama K., Mashima N., Kidani T., Miyazaki T., Yamamoto H., and Masuno H. Effect of cortisol on cell proliferation and the expression of lipoprotein lipase and vascular endothelial growth factor in a human osteosarcoma cell line. Cancer Chemother Pharmacol 61 (2008) 471-479
43. Nowak S.J., and Corces V.G. Phosphorylation of histone H3: a balancing act between chromosome condensation and transcriptional activation. Trends Genet 20 (2004) 214-220
44. Anselmi C., Ettorre A., Andreassi M., Centini M., Neri P., and Di Stefano A.D. In vitro induction of apoptosis vs. necrosis by widely used preservatives: 2-phenoxyethanol, a mixture of isothiazolinones, imidazolidinyl urea and 1,2-pentanediol. Biochem Pharmacol 63 (2002) 437-453
45. Reed J.C. Bcl-2-family proteins and hematologic malignancies:history and future prospects. Blood 111 (2008) 3322-3330
46. Kelekar A., and Thompson C.B. Bcl-2-family proteins: the role of the BH3 domain in apoptosis. Trends Cell Biol 8 (1998) 324-330
47. Westphal S., and Kalthoff H. Apoptosis: targets in pancreatic cancer. Mol Cancer (2003) 2
48. Ahsan H., Reagan-Shaw S., Breur J., and Ahmad N. Sanguinarine induces apoptosis of human pancreatic carcinoma AsPC-1 and BxPC-3 cells via modulations in Bcl-2 family proteins. Cancer Lett 249 (2007) 198-208
49. Thornberry N.A. Caspases: key mediators of apoptosis. Chem Biol 5 (1998) R97-R103
50. Nicholson D.W., and Thornberry N.A. Caspases: killer proteases. Trends Biochem Sci 22 (1997) 299-306
51. Kim J.W., Won J., Sohn S., and Joe C.O. DNA-binding activity of the N-terminal cleavage product of poly(ADP-ribose) polymerase is required for UV mediated apoptosis. J Cell Sci 113 (2000) 955-961
52. Dong M., Nio Y., Yamasawa K., Toga T., Yue L., and Harada T. p53 alteration is not an independent prognostic indicator, but affects the efficacy of adjuvant chemotherapy in human pancreatic cancer. J Surg Oncol 82 (2003) 111-120
53. Polyak K., Waldman T., He T.C., Kinzler K.W., and Vogelstein B. Genetic determinants of p53-induced apoptosis and growth arrest. Genes Dev 10 (1996) 1945-1952
54. Rho J.K., Choi Y.J., Ryoo B.-Y., Na I.I., Yang S.H., Kim C.H., et al. p53 enhances gefitinib-induced growth inhibition and apoptosis by regulation of Fas in non-small cell lung cancer. Cancer Res 67 (2007) 1163-1169
55. Miyahsita T., and Reed J.C. Tumor suppressor p53 is a direct transcriptional activator of the human bax gene. Cell 80 (1995) 293-299
56. Friesen C., Herr I., Krammer P.H., and Debatin K.M. Involvement of the CD95 (APO-1/FAS) receptor/ligand system in drug-induced apoptosis in leukemia cells. Nat Med 2 (1996) 574-577
57. Hefferin M.L., and Tomkinson A.E. Mechanism of DNA double-strand break repair by non-homologous end joining. DNA Repair (Amst) 4 (2005) 639-648
58. Lieber M.R. The mechanism of human nonhomologous DNA end joining. J Biol Chem 283 (2008) 1-5
59. Chiruvella K.K., Sankaran S.K., Singh M., Nambiar M., and Raghavan S.C. Mechanism of DNA double-strand break repair. ICFAI J Biotechnol 1 (2007) 7-22
60. Gama V., Yoshida T., Gomez J.A., Basile D.P., Mayo L.D., Haas A.L., et al. Involvement of the ubiquitin pathway in decreasing Ku70 levels in response to drug-induced apoptosis. Exp Cell Res 312 (2006) 488-499
61. Lee J.-C., Lee C.-H., Su C.-L., Huang C.-W., Liu H.-S., Lin C.-N., et al. Justicidin A decreases the level of cytosolic Ku70 leading to apoptosis in human colorectal cancer cells. Carcinogenesis 26 (2005) 1716-1730
62. Cohen H.Y., Lavu S., Bitterman K.J., Hekking B., Imahiyerobo T.A., Miller C., et al. Acetylation of the C terminus of Ku 70 by CBP and PCAF controls Bax-mediated apoptosis. Mol Cell 13 (2004) 627-638