Novel combretastatin analogues endowed with antitumor activity

Journal of Medicinal Chemistry

Volumn 49, Issue 11, 2006, Pages 3143-3152

  Simoni, Daniele ^a   Romagnoli, Romeo ^a   Baruchello, Riccardo ^a   Rondanin, Riccardo ^a   Rizzi, Michele ^a   Pavani, Maria Giovanna ^a   Alloatti, Domenico ^b   Giannini, Giuseppe ^b   Marcellini, Marcella ^b   Riccioni, Teresa ^b   Castorina, Massimo ^b   Guglielmi, Mario B ^b   Bucci, Federica ^b   Carminati, Paolo ^b   Pisano, Claudio ^b  

^a UNIVERSITY OF FERRARA   (Italy)

^b Sigma Tau SpA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; COLCHICINE; COMBRETASTATIN; PRODRUG; ST 2151; ST 2179; TUBULIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; AREA UNDER THE CURVE; ARTICLE; CANCER CELL CULTURE; CELL CYCLE ARREST; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG CYTOTOXICITY; DRUG HALF LIFE; ENDOTHELIUM CELL; FEMALE; HUMAN; HUMAN CELL; IC 50; IMMUNOFLUORESCENCE; MICROTUBULE ASSEMBLY; MOUSE; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZOFURANS; BIBENZYLS; BINDING, COMPETITIVE; BIOPOLYMERS; CELL LINE, TUMOR; CELL NUCLEUS; COLCHICINE; ENDOTHELIAL CELLS; ENDOTHELIUM, VASCULAR; FEMALE; HUMANS; MICE; MICE, NUDE; MICROTUBULES; PHOSPHORIC ACID ESTERS; PRODRUGS; STEREOISOMERISM; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES; TUBULIN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 33744785404     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0510732     Document Type: Article

References (38)

1. Denekamp, J. Angiogenesis, neovascular proliferation and vascular pathophysiology as targets for cancer therapy. Br. J. Radiol. 1993, 66, 181-196.
2. Burrows, F. J.; Thorpe, P. E. Vascular targeting-A new approach to the therapy of solid tumors. Pharmacol. Ther. 1994, 64, 155-174.
3. Siemann, D. W.; Chaplin, D. J.; Horsman, M. R. Vascular-targeting therapies for treatment of malignant disease. Cancer 2004, 100, 2491-2499.
4. Feron, O. Targeting the tumor vascular compartment to improve conventional cancer therapy. Trends Pharmacol. Sci. 2004, 25, 536-542.
5. Murata, R.; Siemann, D. W.; Overgaard, J.; Horsman, M. R. Improved tumor response by combining radiation and the vascular-damaging drug 5,6-dimethylxanthenone-4-acetic acid. Radiat. Res. 2001, 156, 503-509.
6. Horsman, M. R.; Murata, R. Combination of vascular targeting agents with thermal or radiation therapy. Int. J. Radiat. Oncol. Biol. Phys. 2002, 54, 1518-1523.
7. Pedley, R. B.; El-Emir, E.; Flynn, A. A.; Boxer, G. M.; Dearling, J.; Raleigh, J. A.; Hill, S. A.; Stuart, S.; Motha, R.; Begent, R. H. Synergy between vascular targeting agents and antibody-directed therapy. Int. J. Radiat. Oncol. Biol. Phys. 2002, 54, 1524-1531.
8. Wedge, S. R.; Kendrew, J.; Ogilvie, D. J.; Hennequin, L. F.; Brave, S. R.; Ryan, A. J.; Ashton, S. E.; Calvete, J. A.; Blakey, D. C. Combination of the VEGF receptor tyrosine kinase inhibitor ZD6474 and vascular-targeting agent ZD6126 produces an enhanced antitumor response. Proc. Am. Assoc. Cancer Res. 2002, 43, 1081-1083.
9. Pettit, G. R.; Cragg, G. M.; Herald, D. L.; Schmidt, J. M.; Lobavanijaya, P. Isolation and structure of combretastatin. Can. J. Chem. 1982, 60, 1347-1376.
10. Hamel, E.; Lin, C. M. Interactions of combretastatin, a new plant-derived antimitotic agent with tubulin. Biochem. Pharmacol. 1983, 32, 3864-3867.
11. Lin, C. M.; Singh, S. B.; Chu, P. S.; Dempcy, R. O.; Schmidt, J. M.; Pettit, G. R.; Hamel, E. Interactions of tubulin with potent natural and synthetic analogs of the antimitotic agent combretastatin: A structure-activity study. Mol. Pharmacol. 1988, 34, 200-208.
12. Lin, C. M.; Ho, H. H.; Pettit, G. R. Antimitotic natural products combretastatin A-4 and combretastatin A-2: Studies on the mechanism of their inhibition of the binding of colchicine to tubulin. Biochemistry 1989, 28, 6984-6991.
13. Pettit, G. R.; Singh, S. B.; Hamel, E.; Lin, C. M.; Alberts, D. S.; Garcia-Kendall, D. Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4. Experientia 1989, 45, 209-211.
14. Boye, O.; Brossi, A. In The Alkaloids; Brossi, A., Cordell, G. A., Eds.; Academic: New York, 1992; Vol. 41, pp 125-178.
15. Griggs, J.; Metcalfe, J. C.; Hesketh, R. Targeting tumour vasculature: The development of combretastatin A4. Lancet Oncol. 2001, 2, 82-87.
16. Chaplin, D. J.; Hill, S. A. The development of Combretastatin A4 phosphate as a vascular targeting agent. Int. J. Radiat. Oncol. Biol. Phys. 2002, 54, 1491-1496.
17. Pettit, G. R.; Temple, C. Jr.; Narayanan, V. L.; Varma, R.; Boyd, M. R.; Rener, G. A.; Bansal, N. Antineoplastic agents 322. Synthesis of combretastatin A-4 prodrugs. Anti-Cancer Drug Des. 1995, 10, 299-309.
18. Hadimani, M. B.; Hua, J.; Jonklaas, M. D.; Kessler, R. J.; Sheng, Y.; Olivares, A.; Tanpure, R. P.; Weiser, A.; Zhang, J.; Edvardsen, K.; Kane, R. R.; Pinney, K. G. Synthesis, in vitro, and in vivo evaluation of phosphate ester derivatives of combretastatin A-4. Bioorg. Med. Chem. Lett. 2003, 13, 1505-1508.
19. Sheng, Y.; Hua, J.; Pinney, K. G.; Garner, C. M.; Kane, R. R.; Prezioso, J. A.; Chaplin, D. J.; Edvardsen, K. Combretastatin family member OXI4503 induces tumor vascular collapse through the induction of endothelial apoptosis. Int. J. Cancer 2004, 111 (4), 604-610.
20. Nam, N. H. Combretastatin A-4 analogues as antimitotic antitumor agents. Curr. Med. Chem. 2003, 10, 1697-1722 and references therein.
21. Simoni, D.; Grisolla, G.; Giannini, G.; Roberti, M.; Rondanin, R.; Piccagli, L.; Baruchello, R.; Rossi, R.; Romagnoli, R.; Invidiata, F. P.; Grimaudo, S.; Jung, M. K.; Hamel, E.; Gebbia, N.; Crosta, L.; Abbadessa, V.; Di Cristina, A.; Dusonschet, L.; Meli, M.; Tolomeo, M. Heterocyclic and phenyl double-bond-locked combretastatin analogues possessing potent apoptosis-inducing activity in HL60 and in MDR cell lines. J. Med. Chem. 2005, 48, 723-736.
22. Maya, A. B. S.; Perez-Melero, C.; Mateo, C.; Alonso, D.; Fernandez, J. L.; Gajate, C.; Mollinedo, F.; Pelaez, R.; Caballero, E.; Medarde, M. Further naphthylcombretastatins. An investigation on the role of naphthalene moiety. J. Med. Chem. 2005, 48, 556-568.
23. Flynn, B. L.; Hamel, E.; Jung, M. K. One-pot synthesis of benzo[b]furan and indole inhibitors of tubulin polymerization. J. Med Chem. 2002, 45, 2670-2673.
24. Pinney, K. G.; Bounds, A. D.; Dingerman, K. M.; Mocharla, V. P.; Pettit, G. P.; Bai, R.; Hamel, H. A new anti-tubulin agent containing the benzo[b]thiophene ring system. Bioorg. Med. Chem. Lett. 1999, 9, 1081-1086.
25. Combretastatin Derivatives with Cytotoxic Action. Patent RM2003A000355. Daniele Simoni, Romeo Romagnoli, Giuseppe Giannini, Domenico Aloatti, Claudio Pisano.
26. Howard, T. T.; Lingerfelt, B. M.; Purnell, B. L.; Scott, A. E.; Price, C. A.; Townes, H. M.; McNulty, L.; Handl, H. L.; Summerville, K.; Hudson, S. J.; Bowen, J. P.; Kiakos, K.; Hartley, J. A.; Lee, M. Novel furano analogues of duocarmycin C1 and C2: Design, synthesis, and biological evaluation of seco-iso-cyclopropylfurano[2,3-e]indoline (seco-iso-CFI) and seco-cyclopropyltetrahydrofurano[2,3-f]quinoline (seco-CFQ) analogues. Bioorg. Med. Chem. 2002, 10, 2941-2952 and references therein.
27. Batt, D. G.; Jones, D. G.; La Greca, S. Regioselectivity in the acid-catalyzed isomerization of 2-substituted 1,4-dihydro-I,4-epoxynaphthalenes. J. Org. Chem. 1991, 56, 6704-6708.
28. Horii, Z.; Katagi, T.; Tamura, Y.; Tanaka, T.; Yamawaki, Y. Synthetic studies on Sorigenins. III. Syntheses of 4-methoxynaphtho[2,3-c]-furan-1(3H)-one and 5-methoxynaphtho[1,2-c]furan-3(IH)-one. Chem. Pharm. Bull. 1962, 10, 898-901.
29. Gabbutt, C. D.; Hepworth, J. D.; Heron, B. M.; Thomas, D. A.; Kilner, C.; Partington, S. M. Synthesis and photochromic properties of methoxy substituted 2,2-diaryl-2H-naphtho(1,2-e)pyrans. Heterocycles 2004, 65, 567-582.
30. Silverstein, E. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds; John Wiley and Sons: New York, 1981; pp 264-265.
31. Pettit, G. R.; Anderson, C. R.; Herald, D. L.; Jung, M. K.; Lee, D. J.; Hamel, E.; Pettit, R. K. Antineoplastic agents. 487. Synthesis and biological evaluation of the antineoplastic agent 3,4-methylenedioxy-5,4′-dimethoxy- 3′-amino-Z-stilbene and derived amino acid amides. J. Med. Chem. 2003, 46, 525-531.
32. Pettit, G. R.; Moser, B. R.; Boyd, M. R.; Schmidt, J. M.; Pettit, R. K.; Chapuis, J. C. Antineoplastic agents 460. Synthesis of combretastatin A-2 prodrugs. Anti-Cancer Drug Des. 2001, 16, 185-193.
33. Cushman, M.; Nagarathnam, D.; Gopal, D.; Chakraborti, A. K.; Lin, C. M.; Hamel, E. Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization. J. Med. Chem. 1991, 34, 2579-2588.
34. Cushman, M.; Nagarathnam, D.; Gopal, D.; He, H.-M.; Lin, C. M.; Hamel, E. Synthesis and evaluation of analogues of (Z)-1-(4-methoxyphenyl)-2-(3,4,5- trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents. J. Med. Chem. 1992, 55, 2293-2306.
35. Kirwan, I. G.; Loadman, P. M.; Swaine, D. J.; Anthoney, D. A.; Pettit, G. R.; Lippert, J. W., III; Shnyder, S. D.; Cooper, P. A.; Bibby, M. C. Comparative preclinical pharmacokinetic and metabolic studies of the combretastatin prodrugs combretastatin A4 phosphate and A1 phosphate. Clin. Cancer Res. 2004, 10, 1446-1453.
36. Folkman, J.; Haudenschild, C. C.; Zetter, B. R. Long-term culture of capillary endothelial cells. Proc. Natl. Acad. Sci. U.S.A. 1979, 76 (10), 5217-5221.
37. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R.; New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 1990, 82 (13), 1107-1112.
38. Tahir, S. K.; Han, E. K-H.; Credo, B.; Jae, H.-S.; Pietenpol, J. A.; Scatena, C. D.; Wu-Wong, J. R.; Frost, D.; Sham, H.; Rosenberg, S. H.; Ng, S.-C. A-204197, a new tubulin-binding agent with antimitotic activity in tumor cell lines resistant to known microtubule inhibitors. Cancer Res. 2001, 61, 5480-5485.