Advances in heterocycles as DNA intercalating cancer drugs

References

1. Watson, JD, Crick, FHC. Molecular structure of nucleic acids: a structure for deoxyribose nucleic acid. Nature 1953;171:737–8.10.1038/171737a0Suche in Google Scholar PubMed

2. Berg, JM, Tymoczko, JL, Stryer, L, Berg, JM, Tymoczko, JL, Stryer, L. Biochemistry, 5th ed. New York: W H Freeman; 2002.Suche in Google Scholar

3. Saenger, W. Principles of nucleic acid structure [Internet]. New York: Springer-Verlag; 1984. Available from: https://www.springer.com/gp/book/9781461251903 [cited 23 Jul 2021].10.1007/978-1-4612-5190-3Suche in Google Scholar

4. Alberts, B, Johnson, A, Lewis, J, Raff, M, Roberts, K, Walter, P. Molecular biology of the cell, 4th ed. New York: Garland Science; 2002.Suche in Google Scholar

5. Ghosh, A, Bansal, M. A glossary of DNA structures from A to Z. Acta Cryst D 2003;59:620–6.10.1107/S0907444903003251Suche in Google Scholar

6. Tropp, TBE. Molecular biology: genes to proteins, 4th ed. Burlington, MA: Jones & Bartlett Publishers; 2011.Suche in Google Scholar

7. Yakovchuk, P, Protozanova, E, Frank-Kamenetskii, MD. Base-stacking and base-pairing contributions into thermal stability of the DNA double helix. Nucleic Acids Res 2006;34:564–74.10.1093/nar/gkj454Suche in Google Scholar PubMed PubMed Central

8. Russell, PJ. IGenetics [Internet]. San Francisco: Benjamin Cummings; 2002. Available from: http://archive.org/details/igenetics0000russ_v6o1 [cited 23 Jul 2021].Suche in Google Scholar

9. Hüttenhofer, A, Schattner, P, Polacek, N. Non-coding RNAs: hope or hype? Trends Genet 2005;21:289–97. Elsevier.10.1016/j.tig.2005.03.007Suche in Google Scholar PubMed

10. Munroe, SH. Diversity of antisense regulation in eukaryotes: multiple mechanisms, emerging patterns. J Cell Biochem 2004;93:664–71.10.1002/jcb.20252Suche in Google Scholar PubMed

11. Makalowska, I, Lin, C-F, Makalowski, W. Overlapping genes in vertebrate genomes. Comput Biol Chem 2005;29:1–12.10.1016/j.compbiolchem.2004.12.006Suche in Google Scholar PubMed

12. Johnson, ZI, Chisholm, SW. Properties of overlapping genes are conserved across microbial genomes. Genome Res 2004;14:2268–72.10.1101/gr.2433104Suche in Google Scholar PubMed PubMed Central

13. Lamb, RA, Horvath, CM. Diversity of coding strategies in influenza viruses. Trends Genet 1991;7:261–6.10.1016/0168-9525(91)90326-LSuche in Google Scholar PubMed PubMed Central

14. Benham, CJ, Mielke, SP. DNA mechanics. Annu Rev Biomed Eng 2005;7:21–53.10.1146/annurev.bioeng.6.062403.132016Suche in Google Scholar PubMed

15. Champoux, JJ. DNA topoisomerases: structure, function, and mechanism. Annu Rev Biochem 2001;70:369–413.10.1146/annurev.biochem.70.1.369Suche in Google Scholar PubMed

16. Wang, JC. Cellular roles of DNA topoisomerases: a molecular perspective. Nat Rev Mol Cell Biol 2002;3:430–40.10.1038/nrm831Suche in Google Scholar PubMed

17. Goff, SP, Berg, P. Construction of hybrid viruses containing SV40 and λ phage DNA segments and their propagation in cultured monkey cells. Cell 1976;9:695–705. Elsevier.10.1016/0092-8674(76)90133-1Suche in Google Scholar PubMed

18. Daniell, H, Dhingra, A. Multigene engineering: dawn of an exciting new era in biotechnology. Curr Opin Biotechnol 2002;13:136–41.10.1016/S0958-1669(02)00297-5Suche in Google Scholar

19. Job, D. Plant biotechnology in agriculture. Biochimie 2002;84:1105–10.10.1016/S0300-9084(02)00013-5Suche in Google Scholar PubMed

20. Houdebine, L-M. Transgenic animal models in biomedical research. In: Sioud, M, editor. Target discovery and validation reviews and protocols: volume 1, emerging strategies for targets and biomarker discovery, [Internet]. Totowa, NJ: Humana Press; 2007:163–202 pp. Available from: https://doi.org/10.1385/1-59745-165-7:163 [cited 23 Jul 2021].10.1385/1-59745-165-7:163Suche in Google Scholar PubMed

21. Collins, A, Morton, NE. Likelihood ratios for DNA identification. Natl Acad Sci 1994;91:6007–11.10.1073/pnas.91.13.6007Suche in Google Scholar PubMed PubMed Central

22. Baldi, P, Brunak, S. Bioinformatics: the machine learning approach, 2nd ed. Cambridge, MA: A Bradford Book; 2001.Suche in Google Scholar

23. Gusfield, D. Algorithms on strings, trees, and sequences: computer science and computational biology, 1st ed. Cambridge, England, New York: Cambridge University Press; 1997.10.1017/CBO9780511574931Suche in Google Scholar

24. Sjölander, K. Phylogenomic inference of protein molecular function: advances and challenges. Bioinformatics 2004;20:170–9.10.1093/bioinformatics/bth021Suche in Google Scholar PubMed

25. Rothemund, PWK. Folding DNA to create nanoscale shapes and patterns. Nature 2006;440:297–302.10.1038/nature04586Suche in Google Scholar PubMed

26. Andersen, ES, Dong, M, Nielsen, MM, Jahn, K, Subramani, R, Mamdouh, W, et al.. Self-assembly of a nanoscale DNA box with a controllable lid. Nature 2009;459:73–6.10.1038/nature07971Suche in Google Scholar PubMed

27. Aldaye, FA, Palmer, AL, Sleiman, HF. Assembling materials with DNA as the guide. Science 2008;321:1795–9.10.1126/science.1154533Suche in Google Scholar PubMed

28. Wing, R, Drew, H, Takano, T, Broka, C, Tanaka, S, Itakura, K, et al.. Crystal structure analysis of a complete turn of B-DNA. Nature 1980;287:755–8.10.1038/287755a0Suche in Google Scholar PubMed

29. Wang, JC. Helical repeat of DNA in solution. Natl Acad Sci 1979;76:200–3.10.1073/pnas.76.1.200Suche in Google Scholar PubMed PubMed Central

30. Hamilton, P, Arya, D. Natural product DNA major groove binders. Nat Prod Rep 2011;29:134–43.10.1039/C1NP00054CSuche in Google Scholar PubMed

31. Richards, AD, Rodger, A. Synthetic metallomolecules as agents for the control of DNA structure. Chem Soc Rev 2007;36:471–83.10.1039/B609495CSuche in Google Scholar

32. Schatzschneider, U. Metallointercalators and metalloinsertors: structural requirements for DNA recognition and anticancer activity. Met Ions Life Sci 2018;18:387–436. http://books/9783110470734/9783110470734-020/9783110470734-020.xml.10.1515/9783110470734-014Suche in Google Scholar PubMed

33. Denny, WA. Acridine derivatives as chemotherapeutic agents. Curr Med Chem 2002;9:1655–65.10.2174/0929867023369277Suche in Google Scholar PubMed

34. DeJong, ES, Chang, C, Gilson, MK, Marino, JP. Proflavine acts as a rev inhibitor by targeting the high-affinity rev binding site of the rev responsive element of HIV-1. Biochemistry 2003;42:8035–46.10.1021/bi034252zSuche in Google Scholar PubMed

35. Browning, CH, Gulbransen, R, Kennaway, EL, Thornton, LHD. Flavine and brilliant green, powerful antiseptics with low toxicity to the tissues: their use in the treatment of infected wounds. Br Med J 1917;1:73–8.10.1136/bmj.1.2925.73Suche in Google Scholar PubMed PubMed Central

36. Denny, WA, Baguley, BC, Cain, BF, Waring, MJ. Antitumour acridines. In: Neidle, S, Waring, MJ, editors. Molecular aspects of anti-cancer drug action [Internet]. London: Macmillan Education UK; 1983:1–34 pp.10.1007/978-1-349-06010-8_1Suche in Google Scholar

37. Gatasheh, MK, Kannan, S, Hemalatha, K, Imrana, N. Proflavine an acridine DNA intercalating agent and strong antimicrobial possessing potential properties of carcinogen. Karbala Int J Mod Sci 2017;3:272–8.10.1016/j.kijoms.2017.07.003Suche in Google Scholar

38. Zhang, M-S, Niu, F-W, Li, K. Proflavin suppresses the growth of human osteosarcoma MG63 cells through apoptosis and autophagy. Oncol Lett 2015;10:463–8.10.3892/ol.2015.3206Suche in Google Scholar PubMed PubMed Central

39. Sasikala, WD, Mukherjee, A. Intercalation and de-intercalation pathway of proflavine through the minor and major grooves of DNA: roles of water and entropy. Phys Chem Chem Phys 2013;15:6446–55.10.1039/c3cp50501dSuche in Google Scholar PubMed

40. Janovec, L, Sabolová, D, Kožurková, M, Paulíková, H, Kristian, P, Ungvarský, J, et al.. Synthesis, DNA interaction, and cytotoxic activity of a novel proflavine−dithiazolidinone pharmacophore. Bioconjugate Chem 2007;18:93–100.10.1021/bc060168vSuche in Google Scholar PubMed

41. Kožurková, M, Sabolová, D, Janovec, L, Mikeš, J, Koval’, J, Ungvarský, J, et al.. Cytotoxic activity of proflavine diureas: synthesis, antitumor, evaluation and DNA binding properties of 1′,1″-(acridin-3,6-diyl)-3′,3″-dialkyldiureas. Bioorg Med Chem 2008;16:3976–84.10.1016/j.bmc.2008.01.026Suche in Google Scholar PubMed

42. Benchabane, Y, Di Giorgio, C, Boyer, G, Sabatier, A-S, Allegro, D, Peyrot, V, et al.. Photo-inducible cytotoxic and clastogenic activities of 3,6-di-substituted acridines obtained by acylation of proflavine. Eur J Med Chem 2009;44:2459–67.10.1016/j.ejmech.2009.01.010Suche in Google Scholar PubMed

43. Plsikova, J, Janovec, L, Koval, J, Ungvarsky, J, Mikes, J, Jendzelovsky, R, et al.. 3,6-Bis(3-alkylguanidino)acridines as DNA-intercalating antitumor agents. Eur J Med Chem 2012;57:283–95.10.1016/j.ejmech.2012.09.020Suche in Google Scholar PubMed

44. Borst, P. Ethidium DNA agarose gel electrophoresis: how it started. IUBMB Life 2005;57:745–7.10.1080/15216540500380855Suche in Google Scholar PubMed

45. Stevenson, P, Sones, KR, Gicheru, MM, Mwangi, EK. Comparison of isometamidium chloride and homidium bromide as prophylactic drugs for trypanosomiasis in cattle at Nguruman, Kenya. Acta Trop 1995;59:77–84.10.1016/0001-706X(94)00080-KSuche in Google Scholar

46. Kramer, MJ, Grunberg, E. Effect of ethidium bromide against transplantable tumors in mice and rats. Chemotherapy 1973;19:254–8.10.1159/000221462Suche in Google Scholar PubMed

47. Nishiwaki, H, Miura, M, Imai, K, Ohno, R, Kawashima, K, Ezaki, K, et al.. Experimental studies on the antitumor effect of ethidium bromide and related substances. Cancer Res 1974;34:2699–703.Suche in Google Scholar

48. Galindo-Murillo, R, Cheatham, TEIII. Ethidium bromide interactions with DNA: an exploration of a classic DNA–ligand complex with unbiased molecular dynamics simulations. Nucleic Acids Res 2021;49:3735–47.10.1093/nar/gkab143Suche in Google Scholar PubMed PubMed Central

49. Banerjee, A, Majumder, P, Sanyal, S, Singh, J, Jana, K, Das, C, et al.. The DNA intercalators ethidium bromide and propidium iodide also bind to core histones. FEBS Open Bio. 2014;4:251–9.10.1016/j.fob.2014.02.006Suche in Google Scholar PubMed PubMed Central

50. Vardevanyan, PO, Antonyan, AP, Parsadanyan, MA, Shahinyan, MA, Melkonyan, GA. Behavior of ethidium bromide-hoechst 33258-DNA and ethidium bromide-methylene blue-DNA triple systems by means of UV melting. Int J Spectrosc 2015;2015:e586231.10.1155/2015/586231Suche in Google Scholar

51. Scaria, PV, Shafer, RH. Binding of ethidium bromide to a DNA triple helix. Evidence for intercalation. J Biol Chem 1991;266:5417–23.10.1016/S0021-9258(19)67611-8Suche in Google Scholar

52. Ravina, E. The evolution of drug discovery: from traditional medicines to modern drugs. Hoboken, NJ: John Wiley & Sons; 2011.Suche in Google Scholar

53. Buchholz, TA, Stivers, DN, Stec, J, Ayers, M, Clark, E, Bolt, A, et al.. Global gene expression changes during neoadjuvant chemotherapy for human breast cancer. Cancer J 2002;8:461–8.10.1097/00130404-200211000-00010Suche in Google Scholar PubMed

54. Minotti, G, Menna, P, Salvatorelli, E, Cairo, G, Gianni, L. Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity. Pharmacol Rev 2004;56:185–229.10.1124/pr.56.2.6Suche in Google Scholar PubMed

55. Gewirtz, DA. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem Pharmacol 1999;57:727–41.10.1016/S0006-2952(98)00307-4Suche in Google Scholar PubMed

56. Ashley, N, Poulton, J. Mitochondrial DNA is a direct target of anti-cancer anthracycline drugs. Biochem Biophys Res Commun 2009;378:450–5.10.1016/j.bbrc.2008.11.059Suche in Google Scholar PubMed

57. Ibsen, S, Zahavy, E, Wrasdilo, W, Berns, M, Chan, M, Esener, S. A novel doxorubicin prodrug with controllable photolysis activation for cancer chemotherapy. Pharm Res 2010;27:1848–60.10.1007/s11095-010-0183-xSuche in Google Scholar PubMed PubMed Central

58. Surendiran, A, Sandhiya, S, Pradhan, SC, Adithan, C. Novel applications of nanotechnology in medicine. Indian J Med Res 2009;130:689–701.Suche in Google Scholar

59. Chouhan, R, Bajpai, A. Real time in vitro studies of doxorubicin release from PHEMA nanoparticles. J Nanobiotechnol 2009;7:5.10.1186/1477-3155-7-5Suche in Google Scholar PubMed PubMed Central

60. Ahmad, MZ, Akhter, S, Jain, GK, Rahman, M, Pathan, SA, Ahmad, FJ, et al.. Metallic nanoparticles: technology overview & drug delivery applications in oncology. Expert Opin Drug Deliv 2010;7:927–42.10.1517/17425247.2010.498473Suche in Google Scholar PubMed

61. Andhariya, N, Chudasama, B, Mehta, RV, Upadhyay, RV. Biodegradable thermoresponsive polymeric magnetic nanoparticles: a new drug delivery platform for doxorubicin. J Nanopart Res 2011;13:1677–88.10.1007/s11051-010-9921-6Suche in Google Scholar

62. Varaprasad, K, Ravindra, S, Reddy, NN, Vimala, K, Raju, KM. Design and development of temperature sensitive porous poly(NIPAAm-AMPS) hydrogels for drug release of doxorubicin – a cancer chemotherapy drug. J Appl Polym Sci 2010;116:3593–602.10.1002/app.31917Suche in Google Scholar

63. Zhu, S, Hong, M, Zhang, L, Tang, G, Jiang, Y, Pei, Y. PEGylated PAMAM dendrimer-doxorubicin conjugates: in vitro evaluation and in vivo tumor accumulation. Pharm Res (N Y) 2010;27:161–74.10.1007/s11095-009-9992-1Suche in Google Scholar PubMed

64. Muthu, MS, Rajesh, CV, Mishra, A, Singh, S. Stimulus-responsive targeted nanomicelles for effective cancer therapy. Nanomedicine 2009;4:657–67.10.2217/nnm.09.44Suche in Google Scholar PubMed

65. Doijad, RC, Manvi, FV, Swati, S, Rony, MS. Niosomal drug delivery of cisplatin: development and characterization. Indian Drugs 2008;45:713–8.Suche in Google Scholar

66. Sudhamani, T, Priyadarisini, N, Radhakrishnan, M. Proniosomes—a promising drug carriers. Int J Pharmtech Res 2010;2:1446–54.Suche in Google Scholar

67. Kruger, M, Beyer, U, Schumacher, P, Unger, C, Zahn, H, Kartz, F. Synthesis and stability of four maleimide derivatives of the anticancer drug doxorubicin for the preparation of chemoimmunoconjugates. Chem Pharmaceut Bull 1997;45:399–401.10.1248/cpb.45.399Suche in Google Scholar

68. Chhikara, BS, Jean N, S, Mandal, D, Kumar, A, Parang, K. Fatty acyl amide derivatives of doxorubicin: synthesis and in vitro anticancer activities. Eur J Med Chem 2011;46:2037–42.10.1016/j.ejmech.2011.02.056Suche in Google Scholar PubMed

69. Chhikara, BS, Mandal, D, Parang, K. Synthesis, anticancer activities, and cellular uptake studies of lipophilic derivatives of doxorubicin succinate. J Med Chem 2012;55:1500–10.10.1021/jm201653uSuche in Google Scholar PubMed

70. Marczak, A, Denel-Bobrowska, M, Rogalska, A, Łukawska, M, Oszczapowicz, I. Cytotoxicity and induction of apoptosis by formamidinodoxorubicins in comparison to doxorubicin in human ovarian adenocarcinoma cells. Environ Toxicol Pharmacol 2015;39:369–83.10.1016/j.etap.2014.11.023Suche in Google Scholar PubMed

71. Mielczarek-Puta, M, Struga, M, Roszkowski, P. Synthesis and anticancer effects of conjugates of doxorubicin and unsaturated fatty acids (LNA and DHA). Med Chem Res 2019;28:2153–64.10.1007/s00044-019-02443-0Suche in Google Scholar

72. Kratz, F, Ehling, G, Kauffmann, H-M, Unger, C, Acute and repeat-dose toxicity studies of the (6-maleimidocaproyl)hydrazone derivative of doxorubicin (DOXO-EMCH), an albumin-binding prodrug of the anticancer agent doxorubicin. Hum Exp Toxicol 2007;26:19–35.10.1177/0960327107073825Suche in Google Scholar PubMed

73. Di Meo, C, Cilurzo, F, Licciardi, M, Scialabba, C, Sabia, R, Paolino, D, et al.. Polyaspartamide-doxorubicin conjugate as potential prodrug for anticancer therapy. Pharm Res 2015;32:1557–69.10.1007/s11095-014-1557-2Suche in Google Scholar PubMed

74. Rabbani-Chadegani, A, Keyvani-Ghamsari, S, Zarkar, N. Spectroscopic studies of dactinomycin and vinorelbine binding to deoxyribonucleic acid and chromatin. Spectrochim Acta Mol Biomol Spectrosc 2011;84:62–7.10.1016/j.saa.2011.08.064Suche in Google Scholar PubMed

75. Soper, JT. Gestational trophoblastic disease. Obstet Gynecol 2006;108:176–87.10.1097/01.AOG.0000224697.31138.a1Suche in Google Scholar PubMed

76. Eiriksson, L, Wells, T, Steed, H, Schepansky, A, Capstick, V, Hoskins, P, et al.. Combined methotrexate–dactinomycin: an effective therapy for low-risk gestational trophoblastic neoplasia. Gynecol Oncol 2012;124:553–7.10.1016/j.ygyno.2011.10.036Suche in Google Scholar PubMed

77. Beziat, G, Tavitian, S, Bertoli, S, Huguet, F, Largeaud, L, Luquet, I, et al.. Dactinomycin in acute myeloid leukemia with NPM1 mutations. Eur J Haematol 2020;105:302–7.10.1111/ejh.13438Suche in Google Scholar PubMed

78. Hecht, SM. Bleomycin: new perspectives on the mechanism of action. J Nat Prod 2000;63:158–68.10.1021/np990549fSuche in Google Scholar PubMed

79. Burger, RM, Peisach, J, Horwitz, SB. Activated bleomycin. A transient complex of drug, iron, and oxygen that degrades DNA. J Biol Chem 1981;256:11636–44.10.1016/S0021-9258(19)68452-8Suche in Google Scholar

80. Roy, B, Tang, C, Alam, MP, Hecht, SM. DNA methylation reduces binding and cleavage by bleomycin. Biochemistry 2014;53:6103–12.10.1021/bi5010848Suche in Google Scholar PubMed PubMed Central

81. Neidle, S. Molecular aspects of anticancer drug DNA interactions. Boca Raton, FL: CRC Press; 1994.10.1007/978-1-349-13330-7Suche in Google Scholar

82. Chen, J, Stubbe, J. Bleomycins: towards better therapeutics. Nat Rev Cancer 2005;5:102–12.10.1038/nrc1547Suche in Google Scholar PubMed

83. Brahim, S, Abid, K, Kenani, A. Role of carbohydrate moiety of bleomycin-A2 in caspase-3 activation and internucleosomal chromatin fragmentation in apoptosis of laryngeal carcinoma cells. Cell Biol Int 2008;32:171–7.10.1016/j.cellbi.2007.08.032Suche in Google Scholar PubMed

84. Gimonet, D, Landais, E, Bobichon, H, Coninx, P, Liautaud-Roger, F. Induction of apoptosis by bleomycin in p53-null HL-60 leukemia cells. Int J Oncol 2004;24:313–9.10.3892/ijo.24.2.313Suche in Google Scholar

85. Cort, A, Timur, M, Ozdemir, E, Kucuksayan, E, Ozben, T. Synergistic anticancer activity of curcumin and bleomycin: an in vitro study using human malignant testicular germ cells. Mol Med Rep 2012;5:1481–6.Suche in Google Scholar

86. Belehradek, M, Domenge, C, Luboinski, B, Orlowski, S, Belehradek, J, Mir, LM. Electrochemotherapy, a new antitumor treatment. First clinical phase I-II trial. Cancer 1993;72:3694–700.10.1002/1097-0142(19931215)72:12<3694::AID-CNCR2820721222>3.0.CO;2-2Suche in Google Scholar

87. Larkin, JO, Collins, CG, Aarons, S, Tangney, M, Whelan, M, O’Reily, S, et al.. Electrochemotherapy: aspects of preclinical development and early clinical experience. Ann Surg 2007;245:469–79.10.1097/01.sla.0000250419.36053.33Suche in Google Scholar

88. Mir, LM, Tounekti, O, Orlowski, S. Bleomycin: revival of an old drug. Gen Pharmacol 1996;27:745–8.10.1016/0306-3623(95)02101-9Suche in Google Scholar

89. Mir, LM. Bases and rationale of the electrochemotherapy. Eur J Cancer Suppl 2006;4:38–44.10.1016/j.ejcsup.2006.08.005Suche in Google Scholar

90. Coleman, AJ, Saunders, JE. A review of the physical properties and biological effects of the high amplitude acoustic fields used in extracorporeal lithotripsy. Ultrasonics 1993;31:75–89.10.1016/0041-624X(93)90037-ZSuche in Google Scholar

91. Tachibana, K, Uchida, T, Tamura, K, Eguchi, H, Yamashita, N, Ogawa, K. Enhanced cytotoxic effect of Ara-C by low intensity ultrasound to HL-60 cells. Cancer Lett 2000;149:189–94.10.1016/S0304-3835(99)00358-4Suche in Google Scholar

92. Yu, T, Wang, Z, Jiang, S. Potentiation of cytotoxicity of adriamycin on human ovarian carcinoma cell line 3AO by low-level ultrasound. Ultrasonics 2001;39:307–9.10.1016/S0041-624X(01)00051-8Suche in Google Scholar

93. Tachibana, K, Uchida, T, Ogawa, K, Yamashita, N, Tamura, K. Induction of cell-membrane porosity by ultrasound. Lancet 1999;353:1409.10.1016/S0140-6736(99)01244-1Suche in Google Scholar PubMed

94. Tomizawa, M, Ebara, M, Saisho, H, Sakiyama, S, Tagawa, M. Irradiation with ultrasound of low output intensity increased chemosensitivity of subcutaneous solid tumors to an anti-cancer agent. Cancer Lett 2001;173:31–5.10.1016/S0304-3835(01)00687-5Suche in Google Scholar PubMed

95. Larkin, JO, Casey, GD, Tangney, M, Cashman, J, Collins, CG, Soden, DM, et al.. Effective tumor treatment using optimized ultrasound-mediated delivery of bleomycin. Ultrasound Med Biol 2008;34:406–13.10.1016/j.ultrasmedbio.2007.09.005Suche in Google Scholar PubMed

96. Sleijfer, S. Bleomycin-induced pneumonitis. Chest 2001;120:617–24.10.1378/chest.120.2.617Suche in Google Scholar PubMed

97. Yaoxian, W, Hui, Y, Yunyan, Z, Yanqin, L, Xin, G, Xiaoke, W. Emodin induces apoptosis of human cervical cancer hela cells via intrinsic mitochondrial and extrinsic death receptor pathway. Cancer Cell Int 2013;13:71.10.1186/1475-2867-13-71Suche in Google Scholar PubMed PubMed Central

98. Fujimoto, J. Novel strategy of anti-angiogenic therapy for uterine cervical carcinomas. Anticancer Res 2009;29:2665–9.Suche in Google Scholar

99. Vorechovsky, I, Munzarova, M, Lokaj, J. Increased bleomycin-induced chromosome damage in lymphocytes of patients with common variable immunodeficiency indicates an involvement of chromosomal instability in their cancer predisposition. Cancer Immunol Immunother 1989;29:303–6.10.1007/BF00199219Suche in Google Scholar PubMed

100. Hay, J, Shahzeidi, S, Laurent, G. Mechanisms of bleomycin-induced lung damage. Arch Toxicol 1991;65:81–94.10.1007/BF02034932Suche in Google Scholar PubMed

101. Athar, M, Back, JH, Tang, X, Kim, KH, Kopelovich, L, Bickers, DR, et al.. Resveratrol: a review of preclinical studies for human cancer prevention. Toxicol Appl Pharmacol 2007;224:274–83.10.1016/j.taap.2006.12.025Suche in Google Scholar PubMed PubMed Central

102. Khan, N, Mukhtar, H. Multitargeted therapy of cancer by green tea polyphenols. Cancer Lett 2008;269:269–80.10.1016/j.canlet.2008.04.014Suche in Google Scholar PubMed PubMed Central

103. Hoffman, R, Graham, L, Newlands, ES. Enhanced anti-proliferative action of busulphan by quercetin on the human leukaemia cell line K562. Br J Cancer 1989;59:347–8.10.1038/bjc.1989.68Suche in Google Scholar PubMed PubMed Central

104. Scambia, G, Ranelletti, FO, Panici, PB, De Vincenzo, R, Bonanno, G, Ferrandina, G, et al.. Quercetin potentiates the effect of adriamycin in a multidrug-resistant MCF-7 human breast-cancer cell line: P-glycoprotein as a possible target. Cancer Chemother Pharmacol 1994;34:459–64.10.1007/BF00685655Suche in Google Scholar PubMed

105. Kaiserová, H, Šimůnek, T, van der Vijgh, WJF, Bast, A, Kvasničková, E. Flavonoids as protectors against doxorubicin cardiotoxicity: role of iron chelation, antioxidant activity and inhibition of carbonyl reductase. Biochim Biophys Acta 2007;1772:1065–74.10.1016/j.bbadis.2007.05.002Suche in Google Scholar PubMed

106. Hosseinimehr, SJ, Rostamnejad, M, Ghaffarirad, V. Epicatechin enhances anti-proliferative effect of bleomycin in ovarian cancer cell. Res Mol Med 2013;1:24–7.10.18869/acadpub.rmm.1.3.25Suche in Google Scholar

107. Alshatwi, AA, Periasamy, VS, Athinarayanan, J, Elango, R. Synergistic anticancer activity of dietary tea polyphenols and bleomycin hydrochloride in human cervical cancer cell: caspase-dependent and independent apoptotic pathways. Chem Biol Interact 2016;247:1–10.10.1016/j.cbi.2016.01.012Suche in Google Scholar PubMed

108. Lo, Y-L. A potential daidzein derivative enhances cytotoxicity of epirubicin on human colon adenocarcinoma Caco-2 cells. Int J Mol Sci 2013;14:158–76.10.3390/ijms14010158Suche in Google Scholar PubMed PubMed Central

109. Chang, T-S. Two potent suicide substrates of mushroom tyrosinase:7 ,8,4’-trihydroxyisoflavone and 5 ,7,8,4’-tetrahydroxyisoflavone. J Agric Food Chem 2007;55:2010–5.10.1021/jf063095iSuche in Google Scholar PubMed

110. Chang, T-S, Ding, H-Y, Tai, SS-K, Wu, C-Y. Mushroom tyrosinase inhibitory effects of isoflavones isolated from soygerm koji fermented with Aspergillus oryzae BCRC 32288. Food Chem 2007;105:1430–8.10.1016/j.foodchem.2007.05.019Suche in Google Scholar

111. Tai, SS-K, Lin, C-G, Wu, M-H, Chang, T-S. Evaluation of depigmenting activity by 8-hydroxydaidzein in mouse B16 melanoma cells and human volunteers. Int J Mol Sci 2009;10:4257–66.10.3390/ijms10104257Suche in Google Scholar PubMed PubMed Central

112. Kulling, SE, Honig, DM, Simat, TJ, Metzler, M. Oxidative in vitro metabolism of the soy phytoestrogens daidzein and genistein. J Agric Food Chem 2000;48:4963–72.10.1021/jf000524iSuche in Google Scholar PubMed

113. Chen, J, Lin, H, Hu, M. Absorption and metabolism of genistein and its five isoflavone analogs in the human intestinal Caco-2 model. Cancer Chemother Pharmacol 2005;55:159–69.10.1007/s00280-004-0842-xSuche in Google Scholar PubMed

114. Hirota, A, Taki, S, Kawaii, S, Yano, M, Abe, N. 1,1-Diphenyl-2-picrylhydrazyl radical-scavenging compounds from soybean miso and antiproliferative activity of isoflavones from soybean miso toward the cancer cell lines. Biosci Biotechnol Biochem 2000;64:1038–40.10.1271/bbb.64.1038Suche in Google Scholar PubMed

115. Park, J-S, Kim, DH, Lee, JK, Lee, JY, Kim, DH, Kim, HK, et al.. Natural ortho-dihydroxyisoflavone derivatives from aged Korean fermented soybean paste as potent tyrosinase and melanin formation inhibitors. Bioorg Med Chem Lett 2010;20:1162–4.10.1016/j.bmcl.2009.12.021Suche in Google Scholar PubMed

116. Chang, T-L. Inhibitory effect of flavonoids on 26S proteasome activity. J Agric Food Chem 2009;57:9706–15.10.1021/jf9017492Suche in Google Scholar PubMed

117. Hedlund, TE, Bokhoven, A, Johannes, WU, Nordeen, SK, Ogden, LG. Prostatic fluid concentrations of isoflavonoids in soy consumers are sufficient to inhibit growth of benign and malignant prostatic epithelial cells in vitro. Prostate 2006;66:557–66.10.1002/pros.20380Suche in Google Scholar PubMed

118. Chang, T-S. An updated review of tyrosinase inhibitors. Int J Mol Sci 2009;10:2440–75.10.3390/ijms10062440Suche in Google Scholar PubMed PubMed Central

119. Hirota, A, Inaba, M, Chen, Y-C, Abe, N, Taki, S, Yano, M, et al.. Isolation of 8-hydroxyglycitein and 6-hydroxydaidzein from soybean miso. Biosci Biotechnol Biochem 2004;68:1372–4.10.1271/bbb.68.1372Suche in Google Scholar PubMed

120. Pasut, G, Scaramuzza, S, Schiavon, O, Mendichi, R, Veronese, FM. PEG-epirubicin conjugates with high drug loading. J Bioact Compat Polym 2005;20:213–30.10.1177/0883911505053377Suche in Google Scholar

121. Kmiecik, SW, Krzyścik, MA, Filip-Psurska, B, Wietrzyk, J, Boratyński, J, Goszczyński, TM. Methotrexate and epirubicin conjugates as potential antitumor drugs. Adv Exp Med Biol 2017;71:618–23.10.5604/01.3001.0010.3842Suche in Google Scholar PubMed

122. Ansari, L, Jaafari, MR, Bastami, TR, Malaekeh-Nikouei, B. Improved anticancer efficacy of epirubicin by magnetic mesoporous silica nanoparticles: in vitro and in vivo studies. Artif Cells Nanomed Biotechnol 2018;46:594–606.10.1080/21691401.2018.1464461Suche in Google Scholar PubMed

123. Tiwari, G, Sharma, D. Electronic structure, spectra analysis and nano-range interactions of mitoxantrone with RNA base pairs: an anticancer drug. Mater Today Proc 2020;29:844–9.10.1016/j.matpr.2020.05.014Suche in Google Scholar

124. Qin, J, Kunda, NM, Qiao, G, Tulla, K, Prabhakar, BS, Maker, AV. Vaccination with mitoxantrone-treated primary colon cancer cells enhances tumor-infiltrating lymphocytes and clinical responses in colorectal liver metastases. J Surg Res 2019;233:57–64.10.1016/j.jss.2018.07.068Suche in Google Scholar PubMed

125. Wang, AY, Weiner, H, Green, M, Chang, H, Fulton, N, Larson, RA, et al.. A phase I study of selinexor in combination with high-dose cytarabine and mitoxantrone for remission induction in patients with acute myeloid leukemia. J Hematol Oncol 2018;11:4.10.1186/s13045-017-0550-8Suche in Google Scholar PubMed PubMed Central

126. Ge, C, Wang, Y, Feng, Y, Wang, S, Zhang, K, Xu, X, et al.. Suppression of oxidative phosphorylation and IDH2 sensitizes colorectal cancer to a naphthalimide derivative and mitoxantrone. Cancer Lett 2021;519:30–45.10.1016/j.canlet.2021.06.015Suche in Google Scholar PubMed

127. Perillo, E, Allard-Vannier, E, Falanga, A, Stiuso, P, Vitiello, MT, Galdiero, M, et al.. Quantitative and qualitative effect of gH625 on the nanoliposome-mediated delivery of mitoxantrone anticancer drug to HeLa cells. Int J Pharm 2015;488:59–66.10.1016/j.ijpharm.2015.04.039Suche in Google Scholar PubMed

128. Blasiak, J, Gloc, E, Warszawski, M. A comparison of the in vitro genotoxicity of anticancer drugs idarubicin and mitoxantrone. Acta Biochim Pol 2002;49:145–55.10.18388/abp.2002_3831Suche in Google Scholar

129. Garbett, N, Graves, D. Extending nature’s leads: the anticancer agent ellipticine. Curr Med Chem Anticancer Agents 2004;4:149–72.10.2174/1568011043482070Suche in Google Scholar PubMed

130. Kohn, KW, Waring, MJ, Glaubiger, D, Friedman, CA. Intercalative binding of ellipticine to DNA. Cancer Res 1975;35:71–6.Suche in Google Scholar

131. Purciolas, M, Canals, A, Coll, M, Aymamí, J. The anticancer agent ellipticine unwinds DNA by intercalative binding in an orientation parallel to base pairs. Acta Crystallogr D 2005;61:1009–12.10.1107/S0907444905015404Suche in Google Scholar PubMed

132. Chu, Y, Hsu, M-T. Ellipticine increase the superhelical density of intracellular SV40 DNA by intercalation. Nucleic Acids Res 1992;20:4033–8.10.1093/nar/20.15.4033Suche in Google Scholar PubMed PubMed Central

133. Froelich-Ammon, SJ, Patchan, MW, Osheroff, N, Thompson, RB. Topoisomerase II binds to ellipticine in the absence or presence of DNA: characterization of enzyme∙drug interactions by fluorescence spectroscopy (∗). J Biol Chem 1995;270:14998–5004.10.1074/jbc.270.25.14998Suche in Google Scholar PubMed

134. Knölker, H-J, Reddy, KR. Isolation and synthesis of biologically active carbazole alkaloids. Chem Rev 2002;102:4303–428.10.1021/cr020059jSuche in Google Scholar PubMed

135. Schmidt, AW, Reddy, KR, Knölker, H-J. Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids. Chem Rev 2012;112:3193–328.10.1021/cr200447sSuche in Google Scholar PubMed

136. Pearson, WH. Advances in heterocyclic natural product synthesis. Stamford, CT: Jai Press; 1991.Suche in Google Scholar

137. Saulnier, MG, Gribble, GW. An efficient synthesis of ellipticine. J Org Chem 1982;47:2810–2.10.1021/jo00135a034Suche in Google Scholar

138. Ramkumar, N, Nagarajan, R. Total synthesis of ellipticine quinones, olivacine, and calothrixin B. J Org Chem 2014;79:736–41.10.1021/jo402593wSuche in Google Scholar PubMed

139. Ramkumar, N, Nagarajan, R. A new route to the synthesis of ellipticine quinone from isatin. Tetrahedron Lett 2014;55:1104–6.10.1016/j.tetlet.2013.12.098Suche in Google Scholar

140. Bernardo, PH, Chai, CLL, Heath, GA, Mahon, PJ, Smith, GD, Waring, P, et al.. Synthesis, electrochemistry, and bioactivity of the cyanobacterial calothrixins and related quinones. J Med Chem 2004;47:4958–63.10.1021/jm049625oSuche in Google Scholar PubMed

141. Nishiyama, T, Hatae, N, Mizutani, M, Yoshimura, T, Kitamura, T, Miyano, M, et al.. Concise synthesis and antiproliferative activity evaluation of ellipticine quinone and its analogs. Eur J Med Chem 2017;136:1–13.10.1016/j.ejmech.2017.04.071Suche in Google Scholar PubMed

142. Mousset, D, Rabot, R, Bouyssou, P, Coudert, G, Gillaizeau, I. Synthesis and biological evaluation of novel benzoxazinic analogues of ellipticine. Tetrahedron Lett 2010;51:3987–90.10.1016/j.tetlet.2010.05.123Suche in Google Scholar

143. Chabane, H, Lamazzi, C, Thiéry, V, Guillaumet, G, Besson, T. Synthesis of novel 2-cyanothiazolocarbazoles analogues of ellipticine. Tetrahedron Lett 2002;43:2483–6.10.1016/S0040-4039(02)00353-2Suche in Google Scholar

144. Braña, MF, Castellano, JM, Morán, M, Pérez de Vega, MJ, Romerdahl, CR, Qian, XD, et al.. Bis-naphthalimides: a new class of antitumor agents. Anti Cancer Drug Des 1993;8:257–68.Suche in Google Scholar

145. Villalona-Calero, MA, Eder, JP, Toppmeyer, DL, Allen, LF, Fram, R, Velagapudi, R, et al.. Phase I and pharmacokinetic study of LU79553, a DNA intercalating bisnaphthalimide, in patients with solid malignancies. J Clin Oncol 2001;19:857–69.10.1200/JCO.2001.19.3.857Suche in Google Scholar PubMed

146. Bailly, C, Braña, M, Waring, MJ. Sequence-selective intercalation of antitumour bis-naphthalimides into DNA. Eur J Biochem 1996;240:195–208.10.1111/j.1432-1033.1996.0195h.xSuche in Google Scholar PubMed

147. Braña, MF, Cacho, M, García, MA, de Pascual-Teresa, B, Ramos, A, Domínguez, MT, et al.. New analogues of amonafide and elinafide, containing aromatic heterocycles:synthesis ,antitumor activity ,molecular modeling ,and DNA binding properties. J Med Chem 2004;47:1391–9.10.1021/jm0308850Suche in Google Scholar PubMed

148. Wadler, S, Tenteromano, L, Cazenave, L, Sparano, JA, Greenwald, ES, Rozenblit, A, et al.. Phase II trial of echinomycin in patients with advanced or recurrent colorectal cancer. Cancer Chemother Pharmacol 1994;34:266–9.10.1007/BF00685088Suche in Google Scholar PubMed

149. Kim, YB, Kim, YH, Park, JY, Kim, SK. Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues. Bioorg Med Chem Lett 2004;14:541–4.10.1016/j.bmcl.2003.09.086Suche in Google Scholar PubMed

150. Wang, Y, Liu, Y, Tang, F, Bernot, KM, Schore, R, Marcucci, G, et al.. Echinomycin protects mice against relapsed acute myeloid leukemia without adverse effect on hematopoietic stem cells. Blood 2014;124:1127–35.10.1182/blood-2013-12-544221Suche in Google Scholar PubMed PubMed Central

151. Park, JY, Ryang, YS, Shim, KY, Lee, JI, Kim, HS, Kim, YH, et al.. Molecular signaling cascade in DNA bisintercalator, echinomycin-induced apoptosis of HT-29 cells: evidence of the apoptotic process via activation of the cytochrome c-ERK-caspase-3 pathway. Int J Biochem Cell Biol 2006;38:244–54.10.1016/j.biocel.2005.09.003Suche in Google Scholar PubMed

152. Zeglis, BM, Pierre, VC, Barton, JK. Metallo-intercalators and metallo-insertors. Chem Commun 2007;2007:4565–79.10.1039/b710949kSuche in Google Scholar PubMed PubMed Central

153. Gill, MR, Thomas, JA. Ruthenium(II) polypyridyl complexes and DNA—from structural probes to cellular imaging and therapeutics. Chem Soc Rev 2012;41:3179–92.10.1039/c2cs15299aSuche in Google Scholar PubMed

154. Pages, BJ, Ang, DL, Wright, EP, Aldrich-Wright, JR. Metal complex interactions with DNA. Dalton Trans 2015;44:3505–26.10.1039/C4DT02700KSuche in Google Scholar PubMed

155. Liu, Y-J, Zeng, C-H, Huang, H-L, He, L-X, Wu, F-H. Synthesis, DNA-binding, photocleavage, cytotoxicity and antioxidant activity of ruthenium (II) polypyridyl complexes. Eur J Med Chem 2010;45:564–71.10.1016/j.ejmech.2009.10.043Suche in Google Scholar PubMed

156. Pierre, VC, Kaiser, JT, Barton, JK. Insights into finding a mismatch through the structure of a mispaired DNA bound by a rhodium intercalator. Proc Natl Acad Sci U S A 2007;104:429–34.10.1073/pnas.0610170104Suche in Google Scholar PubMed PubMed Central

157. Junicke, H, Hart, JR, Kisko, J, Glebov, O, Kirsch, IR, Barton, JK. A rhodium(III) complex for high-affinity DNA base-pair mismatch recognition. Proc Natl Acad Sci U S A 2003;100:3737–42.10.1073/pnas.0537194100Suche in Google Scholar PubMed PubMed Central

158. Hart, JR, Glebov, O, Ernst, RJ, Kirsch, IR, Barton, JK. DNA mismatch-specific targeting and hypersensitivity of mismatch-repair-deficient cells to bulky rhodium(III) intercalators. Natl Acad Sci 2006;103:15359–63.10.1073/pnas.0607576103Suche in Google Scholar PubMed PubMed Central

159. Vargiu, AV, Magistrato, A. Detecting DNA mismatches with metallo-insertors: a molecular simulation study. Inorg Chem 2012;51:2046–57.10.1021/ic201659vSuche in Google Scholar PubMed

160. Raman, N, Rajakumar, R. Bis-amide transition metal complexes: isomerism and DNA interaction study. Spectrochim Acta A Mol Biomol Spectrosc 2014;120:428–36.10.1016/j.saa.2013.10.037Suche in Google Scholar PubMed

161. Polyanskaya, TV, Kazhdan, I, Motley, DM, Walmsley, JA. Synthesis, characterization and cytotoxicity studies of palladium(II)-proflavine complexes. J Inorg Biochem 2010;104:1205–13.10.1016/j.jinorgbio.2010.07.010Suche in Google Scholar PubMed PubMed Central

162. Barry, NPE, Sadler, PJ. Exploration of the medical periodic table: towards new targets. Chem Commun 2013;49:5106–31.10.1039/c3cc41143eSuche in Google Scholar PubMed

163. Adımcılar, V, Çeşme, M, Şenel, P, Danış, İ, Ünal, D, Gölcü, A. Comparative study of cytotoxic activities, DNA binding and molecular docking interactions of anticancer agent epirubicin and its novel copper complex. J Mol Struct 2021;1232:130072.10.1016/j.molstruc.2021.130072Suche in Google Scholar