1,066
Views
9
CrossRef citations to date
0
Altmetric
Research Article

Design, synthesis and anticancer activity of oxoaporphine alkaloid derivatives

, , &
Pages 722-727 | Received 03 Jun 2013, Accepted 04 Sep 2013, Published online: 25 Jun 2014

References

  • Guinaudeau H. Aporphinoid alkaloids. V J Nat Prod 1994;57:1033–135
  • Dong XP, Mondranondra IO, Che CT, et al. Kmeriol and other aromatic constituents of Kmeria duperreana. Pharmaceut Res 1989;6:637–40
  • Warthen D, Gooden EL, Jacobson M. Tumor inhibitors: liriodenine, a cytotoxic alkaloid from Annona glabra. J Pharm Sci 1969;58:637–8
  • Rios JL, Simeon S, Villar A. Pharmacological activity of aporphinoid alkaloids. A review. Fitoterapia 1989;60:387–412
  • Clark AM, Watson ES, Ashfaq MK, Hufford CD. In vivo efficacy of antifungal oxoaporphine alkaloids in experimental disseminated candidiasis. Pharmaceut Res 1987;4:495–8
  • Hufford CD, Funderburk MJ, Morgan JM, Robertson LW. Two antimicrobial alkaloids from heartwood of Liriodendron tulipifera. J Pharm Sci 1975;64:789–92
  • Zhu WF, Zhai X, Fu QQ, et al. Design, synthesis and anticancer activity of 4-morpholinothieno[3,2-d]pyrimidine derivatives bearing arylmethylene hydrazine moiety. Chem Pharm Bull 2012;60:1037–45
  • Woo SH, Sun NJ, Cassady JM, Snapka RM. Topoisomerase II inhibition by aporphine alkaloids. Biochem Pharmacol 1999;57:1141–5
  • Zhou BN, Johnson RK, Mattern MR, et al. Isolation and biochemical characterization of a new topoisomerase I inhibitor from Ocotea leucoxylon. J Nat Prod 2000;63:217–21
  • Stevigny C, Bailly C, Quetin-Leclercq J. Cytotoxic and antitumor potentialities of aporphinoid alkaloids. Curr Med Chem Anticancer Agents 2005;5:173–82
  • Hendry LB, Mahesh VB, Bransome ED, Ewing DE. Small molecule intercalation with double stranded DNA: implications for normal gene regulation and for predicting the biological efficacy and genotoxicity of drugs and other chemicals. Mutat Res-Fund Mol Mech Mutagen 2007;623:53–71
  • Miri R, Javidnia K, Hemmateenejad B, et al. Synthesis, cytotoxicity, QSAR, and intercalation study of new diindenopyridine derivatives. Bioorg Med Chem 2004;12:2529–36
  • Wu N, Wu XW, Agama K, et al. A novel DNA topoisomerase I inhibitor with different mechanism from camptothecin induces G2/M phase cell cycle arrest to K562 Cells. Biochemistry 2010;49:10131–6
  • Reichmann ME, Rice CA, Thomas CA, Doty PA. further examination of the molecular weight and size of deoxypentose nucleic acid. J Am Chem Soc 1954;76:3047–53
  • Felsenfeld G, Hirschman SZ. A neighbor-interaction analysis of the hypochromism and spectra of DNA. J Mol Biol 1965;13:407–27
  • Kumar C, Asuncion EH. DNA binding studies and site selective fluorescence sensitization of an anthryl probe. J Am Chem Soc 1993;115:8547–53
  • Zhong W, Yu JS, Huang W, et al. Spectroscopic studies of interaction of chlorobenzylidine with DNA. Biopolymers 2001;62:315–23
  • Nicolaides DN, Papageorgiou GK, Stephanidou-Stephanatou J. Synthesis of some fused pyridine and oxazole polycyclic systems from 10-(methoxyimino)phenanthren-9-one. Tetrahedron 1989;45:4585–92
  • Van Der Puy M, Nalewajek D, Wicks GE. Controlled, regiospecific oxidation of pyridinecarboxylic acids and esters with elemental fluorine. Tetrahedron Lett 1988;29:4389–92
  • Collman JP, Decreau RA, Costanzo S. Appending a tris-imidazole ligand with a Tyr244 mimic on the distal face of bromoacetamidoporphyrin. Org Lett 2004;6:1033–6
  • Ketcha DM, Gribble GW. A convenient synthesis of 3-acylindoles via Friedel Crafts acylation of 1-(phenylsulfonyl)indole. A new route to pyridocarbazole-5,11-quinones and ellipticine. J Org Chem 1985;50:5451–7
  • Kulkarni SS, Grundt P, Kopajtic T, et al. Structure-activity relationships at monoamine transporters for a series of N-substituted 3a-(bis[4-fluorophenyl]methoxy)tropanes: comparative molecular field analysis, synthesis, and pharmacological evaluation. J Med Chem 2004;47:3388–98
  • Tang H, Wei YB, Zhang C, et al. Synthesis, biological evaluation and molecular modeling of oxoisoaporphine and oxoaporphine derivatives as new dual inhibitors of acetylcholinesterase/butyrylcholinesterase. Eur J Med Chem 2009;44:2523–32
  • Thapa U, Thapa P, Karki R, et al. Synthesis of 2,4-diaryl chromenopyridines and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship. Eur J Med Chem 2011;46:3201–9
  • Woo SH, Reynolds MC, Sun NJ, et al. Inhibition of topoisomerase II by liriodenine. Biochem Pharmacol 1997;54:467–73
  • Czarny A, Boykin DW, Wood AA, et al. Analysis of van der Waals and electrostatic contributions in the interactions of minor groove binding benzimidazoles with DNA. J Am Chem Soc 1995;117:4716–17
  • Tang H, Wang XD, Wei YB, et al. Oxoisoaporphine alkaloid derivatives: synthesis, DNA binding affinity and cytotoxicity. Eur J Med Chem 2008;43:973–80
  • Dougherty G, Pigram WJ. Spectroscopic analysis of drug-nucleic acid interactions. Crit Rev Biochem 1982;12:103–32
  • Wender PA, DeLong MA. Synthetic studies on arene-olefin cycloadditions. XII. Total synthesis of (+−)-subergorgic acid. Tetrahedron Lett 1990;31:5429–32
  • Berman HM, Young PR. The interaction of intercalating drugs with nucleic acids. Ann Rev Biophys Bio 1981;10:87–114

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.