The Crucial Role of Divalent Metal Ions in the DNA-Acting Efficacy and Inhibition of the Transcription of Dimeric Chromomycin A3

PLoS ONE

Volumn 7, Issue 9, 2012, Pages

  Hsu, Chun Wei ^a   Chuang, Show Mei ^a   Wu, Wen Ling ^a   Hou, Ming Hon ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMOMYCIN A3; COBALT; DNA; FERRIC ION; MYC PROTEIN; NICKEL;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CANCER CELL CULTURE; CELL KINETICS; CHELATION; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DNA CLEAVAGE; DNA STRAND BREAKAGE; DRUG CONFORMATION; DRUG CYTOTOXICITY; DRUG DNA BINDING; DRUG EFFICACY; GENETIC STABILITY; HUMAN; HUMAN CELL; IN VITRO STUDY; INHIBITION KINETICS; METAL BINDING; NONHUMAN; SURFACE PLASMON RESONANCE; TRANSCRIPTION TERMINATION; ULTRAVIOLET SPECTROSCOPY;

CATIONS, DIVALENT; CELL LINE, TUMOR; CELL SURVIVAL; CHROMOMYCIN A3; DIMERIZATION; DNA; HUMANS; KINETICS; METALS; MODELS, MOLECULAR; NUCLEIC ACID DENATURATION; NUCLEIC ACID HETERODUPLEXES; PLASMIDS; PROTEIN CONFORMATION; PROTO-ONCOGENE PROTEINS C-MYC; SURFACE PLASMON RESONANCE; TRANSCRIPTION, GENETIC; TRANSITION TEMPERATURE;

EID: 84866314865     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0043792     Document Type: Article

References (51)

1. Slavik M, Carter SK, (1975) Chromomycin A3, mithramycin, and olivomycin: antitumor antibiotics of related structure. Adv Pharmacol Chemother 12: 1-30.
2. Foley JF, Lemon HM, Miller DM, Kessinger A, (1972) The treatment of metastatic testicular tumors. J Urol 108: 439-442.
3. Du Priest RW, Fletcher WS, (1973) Chemotherapy of testicular germinal tumors. Oncology 28: 147-163.
4. Hou MH, Lu WJ, Lin HY, Yuann JM, (2008) Studies of sequence-specific DNA binding, DNA cleavage, and topoisomerase I inhibition by the dimeric chromomycin A3 complexed with Fe(II). Biochemistry 47: 5493-5502.
5. Zajac AJ, Phillips PE, (1985) Paget's disease of bone: clinical features and treatment. Clin Exp Rheumatol 3: 75-88.
6. Zihlif M, Catchpoole DR, Stewart BW, Wakelin LP, (2010) Effects of DNA minor groove binding agents on global gene expression. Cancer Genomics Proteomics 7: 323-330.
7. Bianchi N, Rutigliano C, Passadore M, Tomassetti M, Pippo L, et al. (1997) Targeting of the HIV-1 long terminal repeat with chromomycin potentiates the inhibitory effects of a triplex-forming oligonucleotide on Sp1-DNA interactions and in vitro transcription. Biochem J 326 (Pt 3):: 919-927.
8. Chatterjee S, Zaman K, Ryu H, Conforto A, Ratan RR, (2001) Sequence-selective DNA binding drugs mithramycin A and chromomycin A3 are potent inhibitors of neuronal apoptosis induced by oxidative stress and DNA damage in cortical neurons. Ann Neurol 49: 345-354.
9. Bianchi N, Osti F, Rutigliano C, Corradini FG, Borsetti E, et al. (1999) The DNA-binding drugs mithramycin and chromomycin are powerful inducers of erythroid differentiation of human K562 cells. Br J Haematol 104: 258-265.
10. Ming LJ, (2003) Structure and function of "metalloantibiotics". Med Res Rev 23: 697-762.
11. Chakrabarti S, Aich P, Sarker D, Bhattacharyya D, Dasgupta D, (2000) Role of Mg2+ in the interaction of anticancer antibiotic, chromomycin A3 with DNA: does neutral antibiotic bind DNA in absence of the metal ion? J Biomol Struct Dyn 18: 209-218.
12. Aich P, Sen R, Dasgupta D, (1992) Role of magnesium ion in the interaction between chromomycin A3 and DNA: binding of chromomycin A3-Mg2+ complexes with DNA. Biochemistry 31: 2988-2997.
13. Devi PG, Pal S, Banerjee R, Dasgupta D, (2007) Association of antitumor antibiotics, mithramycin and chromomycin, with Zn(II). J Inorg Biochem 101: 127-137.
14. Sastry M, Patel DJ, (1993) Solution structure of the mithramycin dimer-DNA complex. Biochemistry 32: 6588-6604.
15. Sastry M, Fiala R, Patel DJ, (1995) Solution structure of mithramycin dimers bound to partially overlapping sites on DNA. J Mol Biol 251: 674-689.
16. Gochin M, (2000) A high-resolution structure of a DNA-chromomycin-Co(II) complex determined from pseudocontact shifts in nuclear magnetic resonance. Structure Fold Des 8: 441-452.
17. Gao XL, Mirau P, Patel DJ, (1992) Structure refinement of the chromomycin dimer-DNA oligomer complex in solution. J Mol Biol 223: 259-279.
18. Keniry MA, Banville DL, Simmonds PM, Shafer R, (1993) Nuclear magnetic resonance comparison of the binding sites of mithramycin and chromomycin on the self-complementary oligonucleotide d(ACCCGGGT)2. Evidence that the saccharide chains have a role in sequence specificity. J Mol Biol 231: 753-767.
19. Hou MH, Robinson H, Gao YG, Wang AH, (2004) Crystal structure of the [Mg2+-(chromomycin A3)2]-d(TTGGCCAA)2 complex reveals GGCC binding specificity of the drug dimer chelated by a metal ion. Nucleic Acids Res 32: 2214-2222.
20. Itzhaki L, Weinberger S, Livnah N, Berman E, (1990) A unique binding cavity for divalent cations in the DNA-metal-chromomycin A3 complex. Biopolymers 29: 481-489.
21. Lu WJ, Wang HM, Yuann JM, Huang CY, Hou MH, (2009) The impact of spermine competition on the efficacy of DNA-binding Fe(II), Co(II), and Cu(II) complexes of dimeric chromomycin A(3). J Inorg Biochem 103: 1626-1633.
22. Majee S, Sen R, Guha S, Bhattacharyya D, Dasgupta D, (1997) Differential interactions of the Mg2+ complexes of chromomycin A3 and mithramycin with poly(dG-dC) x poly(dC-dG) and poly(dG) x poly(dC). Biochemistry 36: 2291-2299.
23. Cantor CR, Tinoco I, (1965) Absorption and optical rotatory dispersion of seven trinucleoside diphosphates. J Mol Biol 13: 65-77.
24. Hou MH, Wang AH, (2005) Mithramycin forms a stable dimeric complex by chelating with Fe(II): DNA-interacting characteristics, cellular permeation and cytotoxicity. Nucleic Acids Res 33: 1352-1361.
25. Chang YM, Chen CM, Hou MH, (2012) Conformational Changes in DNA upon Ligand Binding Monitored by Circular Dichroism. International Journal of Molecular Sciences 13: 3394-3413.
26. Yuann JM, Tseng WH, Lin HY, Hou MH, (2012) The effects of loop size on Sac7d-hairpin DNA interactions. Biochim Biophys Acta 1824: 1009-1015.
27. Marky LA, Breslauer KJ, (1987) Calculating thermodynamic data for transitions of any molecularity from equilibrium melting curves. Biopolymers 26: 1601-1620.
28. Hou MH, Lin SB, Yuann JM, Lin WC, Wang AH, et al. (2001) Effects of polyamines on the thermal stability and formation kinetics of DNA duplexes with abnormal structure. Nucleic Acids Res 29: 5121-5128.
29. Shiraishi H, Kataoka M, Morita Y, Umemoto J, (1993) Interactions of hydroxyl radicals with tris (hydroxymethyl) aminomethane and Good's buffers containing hydroxymethyl or hydroxyethyl residues produce formaldehyde. Free Radic Res Commun 19: 315-321.
30. Cons BM, Fox KR, (1989) Interaction of mithramycin with metal ions and DNA. Biochem Biophys Res Commun 160: 517-524.
31. Huang HW, Li D, Cowan JA, (1995) Biostructural chemistry of magnesium. regulation of mithramycin-DNA interactions by Mg2+ coordination. Biochimie 77: 729-738.
32. Song YM, Wu Q, Yang PJ, Luan NN, Wang LF, et al. (2006) DNA Binding and cleavage activity of Ni(II) complex with all-trans retinoic acid. J Inorg Biochem 100: 1685-1691.
33. Piestrzeniewicz M, Studzian K, Wilmanska D, Plucienniczak G, Gniazdowski M, (1998) Effect of DNA-interacting drugs on phage T7 RNA polymerase. Acta Biochim Pol 45: 127-132.
34. Gambari R, Feriotto G, Rutigliano C, Bianchi N, Mischiati C, (2000) Biospecific interaction analysis (BIA) of low-molecular weight DNA-binding drugs. J Pharmacol Exp Ther 294: 370-377.
35. Scott D, Rohr J, Bae Y, (2011) Nanoparticulate formulations of mithramycin analogs for enhanced cytotoxicity. Int J Nanomedicine 6: 2757-2767.
36. Seznec J, Silkenstedt B, Naumann U, (2011) Therapeutic effects of the Sp1 inhibitor mithramycin A in glioblastoma. J Neurooncol 101: 365-377.
37. Remsing LL, Bahadori HR, Carbone GM, McGuffie EM, Catapano CV, et al. (2003) Inhibition of c-src transcription by mithramycin: structure-activity relationships of biosynthetically produced mithramycin analogues using the c-src promoter as target. Biochemistry 42: 8313-8324.
38. Gao Y, Jia Z, Kong X, Li Q, Chang DZ, et al. (2011) Combining betulinic acid and mithramycin a effectively suppresses pancreatic cancer by inhibiting proliferation, invasion, and angiogenesis. Cancer Res 71: 5182-5193.
39. Barcelo F, Ortiz-Lombardia M, Martorell M, Oliver M, Mendez C, et al. (2010) DNA binding characteristics of mithramycin and chromomycin analogues obtained by combinatorial biosynthesis. Biochemistry 49: 10543-10552.
40. Lahiri S, Takao T, Devi PG, Ghosh S, Ghosh A, et al. (2012) Association of aureolic acid antibiotic, chromomycin A3 with Cu(2+) and its negative effect upon DNA binding property of the antibiotic. Biometals 25: 435-450.
41. Hou MH, Lu WJ, Huang CY, Fan RJ, Yuann JM, (2009) Effects of polyamines on the DNA-reactive properties of dimeric mithramycin complexed with cobalt(II): implications for anticancer therapy. Biochemistry 48: 4691-4698.
42. Lai MM, (2001) RNA polymerase as an antiviral target of hepatitis C virus. Antivir Chem Chemother 12 Suppl 1: 143-147.
43. Merkel O, Wacht N, Sifft E, Melchardt T, Hamacher F, et al. (2012) Actinomycin D induces p53-independent cell death and prolongs survival in high-risk chronic lymphocytic leukemia. Leukemia.
44. White RJ, Phillips DR, (1989) Sequence-dependent termination of bacteriophage T7 transcription in vitro by DNA-binding drugs. Biochemistry 28: 4277-4283.
45. Reusser F, (1975) Steffimycin B, a DNA binding agent. Biochim Biophys Acta 383: 266-273.
46. Safe S, Abdelrahim M, (2005) Sp transcription factor family and its role in cancer. Eur J Cancer 41: 2438-2448.
47. Campbell VW, Davin D, Thomas S, Jones D, Roesel J, et al. (1994) The G-C specific DNA binding drug, mithramycin, selectively inhibits transcription of the C-MYC and C-HA-RAS genes in regenerating liver. Am J Med Sci 307: 167-172.
48. Hardenbol P, Van Dyke MW, (1992) In vitro inhibition of c-myc transcription by mithramycin. Biochem Biophys Res Commun 185: 553-558.
49. Rey NA, Neves A, Silva PP, Paula FC, Silveira JN, et al. (2009) A synthetic dinuclear copper(II) hydrolase and its potential as antitumoral: cytotoxicity, cellular uptake, and DNA cleavage. J Inorg Biochem 103: 1323-1330.
50. Wang HF, Shen R, Tang N, (2009) Synthesis and characterization of the Zn(II) and Cu(II) piperidinyl isoeuxanthone complexes: DNA-binding and cytotoxic activity. Eur J Med Chem 44: 4509-4515.
51. Chen S, Zhang Y, Hecht SM, (2011) p-Thiophenylalanine-induced DNA cleavage and religation activity of a modified vaccinia topoisomerase IB. Biochemistry 50: 9340-9351.