Full-text resources of PSJD and other databases are now available in the new Library of Science.
Visit https://bibliotekanauki.pl

PL EN


Preferences help
enabled [disable] Abstract
Number of results

Journal

2009 | 7 | 3 | 569-575

Article title

Synthesis, DNA-binding and antiproliferative activity of N-(Nitrogen heterocyclic) norcantharidin acylamide acid

Content

Title variants

Languages of publication

EN

Abstracts

EN
Two novel norcantharidin acylamide acids (HL1=N-pyrimidine norcantharidin acylamide acid, C12H13N3O4; HL2=N-pyridine norcantharidin acylamide acid, C13H14N2O4) were synthesized by a reaction of norcantharidin(NCTD) with 2-aminopyrimidine and 2-aminopyridine, respectively. Their structures were characterized by elemental analysis, IR, UV and 1 H NMR. Fluorescence titration and viscosity measurements indicated that HL1, HL2 and HL3 (HL3=N-phenyl norcantharidin acylamide acid, C14H15NO4) can bind calf thymus DNA via partial intercalation. The liner Stern-Volmer quenching constant Ksv values for HL1, HL2 and HL3 were 2.05 × 104 L mol−1, 1.15 × 104 L mol−1 and 8.30×103 L mol−1, respectively. Two compounds containing heterocycle of HL1 and HL2 have been found to cleave pBR322 plasmid DNA at physiological pH and temperature. The test of antiproliferation activity showed that the compounds had moderate to strong antiproliferative ability against the tested cell lines except of HL3 against the SMMC7721 cell line. The results indicated that the heterocycle attached to the norcantharidin was favorable to antiproliferative activity. This result was consistent with the DNA binding experiment. [...]

Publisher

Journal

Year

Volume

7

Issue

3

Pages

569-575

Physical description

Dates

published
1 - 9 - 2009
online
21 - 6 - 2009

Contributors

author
author
author
author
  • Institute of Matria Medica, Zhejiang Academy of Medical Sciences, Hangzhou, 310013, China

References

  • [1] I. Kostova, G. Momekov, T. Tzanova, M. Karaivanova, Bioinorg.Chem. Appl. 2006, 25651 (2006)
  • [2] B.D. Wang, Z.Y. Yang, Q. Wang, T.K. Cai, P. Crewdsonc, Bioorg. Med. Chem. 14, 1880 (2006) http://dx.doi.org/10.1016/j.bmc.2005.10.031[Crossref]
  • [3] T.M. Ehrman, D.J. Barlow, P.J. Hylands, J. Chem. Inf. Model. 47, 2316 (2007) http://dx.doi.org/10.1021/ci700155t[Crossref]
  • [4] L. Janovec, D. Sabolova, M. Kozurkova, H. Paulikova, P. Kristian, J. Ungvarsky, E. Moravcikova, M. Bajdichova, D. Podhradsky, J. Imrich, Bioconjugate Chem. 18, 93 (2007) http://dx.doi.org/10.1021/bc060168v[Crossref]
  • [5] S.K.H. Huan, H.H. Lee, D.Z. Liu, C.C. Wu, C.C. Wang, Toxicology 223, 136 (2006) http://dx.doi.org/10.1016/j.tox.2006.03.012[Crossref]
  • [6] T. Efferth, R. Rauh, S. Kahl, M. Tomicic, H. Bochzelt, M.E. Tome, M.M. Briehl, R. Bauer, B. Kaina, Biochem. Pharmacol. 69, 811 (2005) http://dx.doi.org/10.1016/j.bcp.2004.12.003[Crossref]
  • [7] A. McCluskey, M.C. Bowyer, E. Collins, A.T.R. Sim, J.A. Sakoff, M.L. Baldwin, Bioorg. Med. Chem. Lett. 10, 1687 (2000) http://dx.doi.org/10.1016/S0960-894X(00)00323-1[Crossref]
  • [8] G.S. Wang, J. Ethnopharmacol. 26, 147 (1989) http://dx.doi.org/10.1016/0378-8741(89)90062-7[Crossref]
  • [9] A. McCluskey, A.T.R. Sim, J.A. Sakoff, J. Med. Chem. 45, 1151 (2002) http://dx.doi.org/10.1021/jm010066k[Crossref]
  • [10] T.A. Hill, S.G. Stewart, S.P. Ackland, J. Gilbert, B. Sauer, J.A. Sakoff, A. McCluskey, Bioorg. Med. Chem. 15, 6126 (2007) http://dx.doi.org/10.1016/j.bmc.2007.06.034[Crossref]
  • [11] X. W. Liu, J. Li, H. Li, K.C. Zheng, H. Chao, L.N. Ji, J. Inorg. Biochem. 99, 2372 (2005) http://dx.doi.org/10.1016/j.jinorgbio.2005.09.004[Crossref]
  • [12] S.G. Stewart, T.A. Hill, J. Gilbert, S.P. Ackland, J.A. Sakoff, A. McCluskey, Bioorg. Med. Chem. 15, 7301 (2007) http://dx.doi.org/10.1016/j.bmc.2007.08.028[Crossref]
  • [13] X.L. Zheng, H.X. Sun, X.L. Liu, Y.X. Chen, B.C. Qian, Acta Pharmacol. Sin. 25, 1090 (2004)
  • [14] N. Niklas, O. Walter, R. Alsfasser, Eur. J. Inorg. Chem. 1723 (2000)
  • [15] M. Bakir, O. Green, W.H. Mulder, J. Mol. Struct. 873, 17 (2008) http://dx.doi.org/10.1016/j.molstruc.2007.03.001[Crossref]
  • [16] J.B. Chaires, N. Dattagupta, D.M. Crothers, Biochemistry 21, 3933 (1982) http://dx.doi.org/10.1021/bi00260a005[Crossref]
  • [17] A.K.D Mesmaeker, G. Orellana, J.K. Barton, N.J. Turro, Photochem. Photobiol. 52, 461 (1990) http://dx.doi.org/10.1111/j.1751-1097.1990.tb01787.x[Crossref]
  • [18] J.Z. Wu, L. Yuan, J.F. Wu, J. Inorg. Biochem. 99, 2211 (2005) http://dx.doi.org/10.1016/j.jinorgbio.2005.08.002[Crossref]
  • [19] J.R. Lakowicz, G. Weber, Biochemistry 12, 4161 (1973) http://dx.doi.org/10.1021/bi00745a020[Crossref]
  • [20] B.C. Baguley, M.L. Bret, Biochemistry 23, 937 (1984) http://dx.doi.org/10.1021/bi00300a022[Crossref]
  • [21] S. Satyanarayana, J.C. Dabrowiak, J.B. Chaires, Biochemistry 32, 2573 (1993) http://dx.doi.org/10.1021/bi00061a015[Crossref]
  • [22] J.M. Kelly, A.B. Tossi, D.J. McConnell, C. ObUigin, Nucleic Acids Res. 13, 6017 (1985) http://dx.doi.org/10.1093/nar/13.17.6017[Crossref]
  • [23] M.A. Chowdhury, F. Huq, A. Abdullah, P. Beale, K. Fisher, J. Inorg. Biochem. 99, 1098 (2005) http://dx.doi.org/10.1016/j.jinorgbio.2005.02.002[Crossref]
  • [24] Y. Baba, N. Hirukawa, N. Tanohira, M. Sodeoka, J. Am. Chem. Soc. 125, 9740 (2003) http://dx.doi.org/10.1021/ja034694y[Crossref]

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_s11532-009-0058-3
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.