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Combretastatin dinitrogen-substituted stilbene analogues as tubulin-binding and vascular-disrupting agents

Siles, Rogelio; Ackley, J Freeland; Hadimani, Mallinath B; Hall, John J; Mugabe, Benon E; Guddneppanavar, Rajsekhar; Monk, Keith A; Chapuis, Jean-Charles; Pettit, George R and Chaplin, David J, et al. (2008) In Journal of Natural Products 71(3). p.313-320
Abstract
Several stilbenoid compounds having structural similarity to the combretastatin group of natural products and characterized by the incorporation of two nitrogen-bearing groups (amine, nitro, serinamide) have been prepared by chemical synthesis and evaluated in terms of biochemical and biological activity. The 2',3'-diamino B-ring analogue 17 demonstrated remarkable cytotoxicity against selected human cancer cell lines in vitro (average GI(50) = 13.9 nM) and also showed good activity in regard to inhibition of tubulin assembly (IC50 = 2.8 mu M). In addition, a single dose (10 mg/kg) of compound 17 caused a 40% tumor-selective blood flow shutdown in tumor-bearing SCID mice at 24 h, thus suggesting the potential value of this compound and its... (More)
Several stilbenoid compounds having structural similarity to the combretastatin group of natural products and characterized by the incorporation of two nitrogen-bearing groups (amine, nitro, serinamide) have been prepared by chemical synthesis and evaluated in terms of biochemical and biological activity. The 2',3'-diamino B-ring analogue 17 demonstrated remarkable cytotoxicity against selected human cancer cell lines in vitro (average GI(50) = 13.9 nM) and also showed good activity in regard to inhibition of tubulin assembly (IC50 = 2.8 mu M). In addition, a single dose (10 mg/kg) of compound 17 caused a 40% tumor-selective blood flow shutdown in tumor-bearing SCID mice at 24 h, thus suggesting the potential value of this compound and its corresponding salt formulations as new vascular-disrupting agents. (Less)
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Natural Products
volume
71
issue
3
pages
313 - 320
publisher
The American Chemical Society
external identifiers
  • wos:000254544900004
  • scopus:42249093853
ISSN
0163-3864
DOI
10.1021/np070377j
language
English
LU publication?
yes
id
c1b1f65a-b29d-4462-bac2-d1fb17232194 (old id 1182954)
date added to LUP
2008-09-02 09:50:18
date last changed
2017-08-27 04:52:36
@article{c1b1f65a-b29d-4462-bac2-d1fb17232194,
  abstract     = {Several stilbenoid compounds having structural similarity to the combretastatin group of natural products and characterized by the incorporation of two nitrogen-bearing groups (amine, nitro, serinamide) have been prepared by chemical synthesis and evaluated in terms of biochemical and biological activity. The 2',3'-diamino B-ring analogue 17 demonstrated remarkable cytotoxicity against selected human cancer cell lines in vitro (average GI(50) = 13.9 nM) and also showed good activity in regard to inhibition of tubulin assembly (IC50 = 2.8 mu M). In addition, a single dose (10 mg/kg) of compound 17 caused a 40% tumor-selective blood flow shutdown in tumor-bearing SCID mice at 24 h, thus suggesting the potential value of this compound and its corresponding salt formulations as new vascular-disrupting agents.},
  author       = {Siles, Rogelio and Ackley, J Freeland and Hadimani, Mallinath B and Hall, John J and Mugabe, Benon E and Guddneppanavar, Rajsekhar and Monk, Keith A and Chapuis, Jean-Charles and Pettit, George R and Chaplin, David J and Edvardsen, Klaus and Trawick, Mary Lynn and Garner, Charles M and Pinney, Kevin G},
  issn         = {0163-3864},
  language     = {eng},
  number       = {3},
  pages        = {313--320},
  publisher    = {The American Chemical Society},
  series       = {Journal of Natural Products},
  title        = {Combretastatin dinitrogen-substituted stilbene analogues as tubulin-binding and vascular-disrupting agents},
  url          = {http://dx.doi.org/10.1021/np070377j},
  volume       = {71},
  year         = {2008},
}