A DC-81-indole conjugate agent suppresses melanoma A375 cell migration partially via interrupting VEGF production and stromal cell-derived factor-1α-mediated signaling

Toxicology and Applied Pharmacology

Volumn 255, Issue 2, 2011, Pages 150-159

  Hsieh, Ming Chu ^a   Hu, Wan Ping ^a   Yu, Hsin Su ^b   Wu, Wen Chuan ^b   Chang, Long Sen ^c   Kao, Ying Hsien ^d   Wang, Jeh Jeng ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^c NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

^d I SHOU UNIVERSITY   (Taiwan)

Author keywords

Angiogenic factor; IN4CPBD; Melanoma cells; SDF 1 ; Transwell migration

Indexed keywords

1,2,3,11A TETRAHYDRO 8 HYDROXY 7 METHOXY 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; CARBON; CASPASE; DNA; GELATINASE B; INDOLE DERIVATIVE; MEMBRANE PROTEIN; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; MITOGEN ACTIVATED PROTEIN KINASE P38; MYPT 1 PROTEIN; PHOSPHOTRANSFERASE INHIBITOR; PROTEIN BAX; PROTEIN BCL 2; PROTEIN KINASE B; PROTEIN P21; PROTEIN P53; RHO FACTOR; STROMAL CELL DERIVED FACTOR 1ALPHA; UNCLASSIFIED DRUG; VASCULOTROPIN;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL ASSAY; CELL CYCLE G1 PHASE; CELL CYCLE PROGRESSION; CELL CYCLE S PHASE; CELL MIGRATION; CELL MOTILITY; CHEMOTAXIS; CONTROLLED STUDY; CYTOTOXICITY; DNA CONTENT; DNA FRAGMENTATION; DOWN REGULATION; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; ENZYME LINKED IMMUNOSORBENT ASSAY; FLOW CYTOMETRY; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; MELANOMA; MITOCHONDRIAL MEMBRANE POTENTIAL; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; SIGNAL TRANSDUCTION; TRANSWELL MIGRATION ASSAY; UPREGULATION; WESTERN BLOTTING;

ANTINEOPLASTIC AGENTS; APOPTOSIS; BENZODIAZEPINES; BLOTTING, WESTERN; CASPASES; CELL CYCLE; CELL LINE, TUMOR; CELL MOVEMENT; CHEMOKINE CXCL12; FLOW CYTOMETRY; HUMANS; INDOLES; MELANOMA; ORGANOPHOSPHORUS COMPOUNDS; PROTEIN KINASE INHIBITORS; PYRROLES; SIGNAL TRANSDUCTION; VASCULAR ENDOTHELIAL GROWTH FACTOR A;

EID: 80051664165     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2011.06.008     Document Type: Article

References (41)

1. Bartolome R.A., Galvez B.G., Longo N., Baleux F., Van Muijen G.N., Sanchez-Mateos P., Arroyo A.G., Teixido J. Stromal cell-derived factor-1alpha promotes melanoma cell invasion across basement membranes involving stimulation of membrane-type 1 matrix metalloproteinase and Rho GTPase activities. Cancer Res. 2004, 64:2534-2543.
2. Boehme K.A., Kulikov R., Blattner C. p53 stabilization in response to DNA damage requires Akt/PKB and DNA-PK. Proc. Natl. Acad. Sci. U.S.A. 2008, 105:7785-7790.
3. Chang H.R., Huang H.P., Kao Y.L., Chen S.L., Wu S.W., Hung T.W., Lian J.D., Wang C.J. The suppressive effect of Rho kinase inhibitor, Y-27632, on oncogenic Ras/RhoA induced invasion/migration of human bladder cancer TSGH cells. Chem. Biol. Interact. 2010, 183:172-180.
4. Chou W.W., Guh J.Y., Tsai J.F., Hwang C.C., Chiou S.J., Chuang L.Y. Arecoline-induced phosphorylated p53 and p21(WAF1) protein expression is dependent on ATM/ATR and phosphatidylinositol-3-kinase in clone-9 cells. J. Cell. Biochem. 2009, 107:408-417.
5. Erhard H., Rietveld F.J., van Altena M.C., Brocker E.B., Ruiter D.J., de Waal R.M. Transition of horizontal to vertical growth phase melanoma is accompanied by induction of vascular endothelial growth factor expression and angiogenesis. Melanoma Res. 1997, 7(Suppl. 2):S19-S26.
6. Gassmann P., Haier J., Schluter K., Domikowsky B., Wendel C., Wiesner U., Kubitza R., Engers R., Schneider S.W., Homey B., Muller A. CXCR4 regulates the early extravasation of metastatic tumor cells in vivo. Neoplasia 2009, 11:651-661.
7. Ge X., Fu Y.M., Meadows G.G. U0126, a mitogen-activated protein kinase kinase inhibitor, inhibits the invasion of human A375 melanoma cells. Cancer Lett. 2002, 179:133-140.
8. Graells J., Vinyals A., Figueras A., Llorens A., Moreno A., Marcoval J., Gonzalez F.J., Fabra A. Overproduction of VEGF concomitantly expressed with its receptors promotes growth and survival of melanoma cells through MAPK and PI3K signaling. J. Invest. Dermatol. 2004, 123:1151-1161.
9. Haass N.K., Smalley K.S., Li L., Herlyn M. Adhesion, migration and communication in melanocytes and melanoma. Pigment Cell Res. 2005, 18:150-159.
10. Hofmann U.B., Westphal J.R., Van Muijen G.N., Ruiter D.J. Matrix metalloproteinases in human melanoma. J. Invest. Dermatol. 2000, 115:337-344.
11. Hu W.P., Wang J.J., Lin F.L., Lin Y.C., Lin S.R., Hsu M.H. An efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepine. Synthesis of the antibiotic DC-81. J. Org. Chem. 2001, 66:2881-2883.
12. Hu W.P., Yu H.S., Chen Y.C., Wang J.J. Biological evaluation of an antibiotic DC-81-indole conjugate agent in human melanoma cell lines. Kaohsiung J. Med. Sci. 2003, 19:6-12.
13. Hu W.P., Yu H.S., Sung P.J., Tsai F.Y., Shen Y.K., Chang L.S., Wang J.J. DC-81-indole conjugate agent induces mitochondria mediated apoptosis in human melanoma A375 cells. Chem. Res. Toxicol. 2007, 20:905-912.
14. Hu W.P., Tsai F.Y., Yu H.S., Sung P.J., Chang L.S., Wang J.J. Induction of apoptosis by DC-81-indole conjugate agent through NF-kappaB and JNK/AP-1 pathway. Chem. Res. Toxicol. 2008, 21:1330-1336.
15. Hurley L.H. Pyrrolo(1,4)benzodiazepine antitumor antibiotics. Comparative aspects of anthramycin, tomaymycin and sibiromycin. J. Antibiot. (Tokyo) 1977, 30:349-370.
16. Kao Y.H., Yu C.L., Chang L.W., Yu H.S. Low concentrations of arsenic induce vascular endothelial growth factor and nitric oxide release and stimulate angiogenesis in vitro. Chem. Res. Toxicol. 2003, 16:460-468.
17. Kim S.Y., Lee C.H., Midura B.V., Yeung C., Mendoza A., Hong S.H., Ren L., Wong D., Korz W., Merzouk A., Salari H., Zhang H., Hwang S.T., Khanna C., Helman L.J. Inhibition of the CXCR4/CXCL12 chemokine pathway reduces the development of murine pulmonary metastases. Clin. Exp. Metastasis 2008, 25:201-211.
18. Kucerova L., Matuskova M., Hlubinova K., Altanerova V., Altaner C. Tumor cell behaviour modulation by mesenchymal stromal cells. Mol. Cancer 2010, 9:129.
19. Lee C.H., Hu W.P., Hong C.H., Yu H.S., Liao W.T., Chen C.Y., Chen Y.L., Chen B.H., Chen G.S., Wang J.J. Pyrrolo[2,1-c][1,4]benzodiazepine and indole conjugate (IN6CPBD) has better efficacy and superior safety than the mother compound DC-81 in suppressing the growth of established melanoma in vivo. Chem. Biol. Interact. 2009, 180:360-367.
20. Liu B., Earl H.M., Baban D., Shoaibi M., Fabra A., Kerr D.J., Seymour L.W. Melanoma cell lines express VEGF receptor KDR and respond to exogenously added VEGF. Biochem. Biophys. Res. Commun. 1995, 217:721-727.
21. Longo-Imedio M.I., Longo N., Trevino I., Lazaro P., Sanchez-Mateos P. Clinical significance of CXCR3 and CXCR4 expression in primary melanoma. Int. J. Cancer 2005, 117:861-865.
22. Mann K.K., Colombo M., Miller W.H. Arsenic trioxide decreases AKT protein in a caspase-dependent manner. Mol. Cancer Ther. 2008, 7:1680-1687.
23. Martin D., Salinas M., Fujita N., Tsuruo T., Cuadrado A. Ceramide and reactive oxygen species generated by H2O2 induce caspase-3-independent degradation of Akt/protein kinase B. J. Biol. Chem. 2002, 277:42943-42952.
24. Melnikova V.O., Dobroff A.S., Zigler M., Villares G.J., Braeuer R.R., Wang H., Huang L., Bar-Eli M. CREB inhibits AP-2alpha expression to regulate the malignant phenotype of melanoma. PLoS One 2010, 5:e12452.
25. Merighi S., Benini A., Mirandola P., Gessi S., Varani K., Leung E., Maclennan S., Borea P.A. A3 adenosine receptor activation inhibits cell proliferation via phosphatidylinositol 3-kinase/Akt-dependent inhibition of the extracellular signal-regulated kinase 1/2 phosphorylation in A375 human melanoma cells. J. Biol. Chem. 2005, 280:19516-19526.
26. Muller A., Homey B., Soto H., Ge N., Catron D., Buchanan M.E., McClanahan T., Murphy E., Yuan W., Wagner S.N., Barrera J.L., Mohar A., Verastegui E., Zlotnik A. Involvement of chemokine receptors in breast cancer metastasis. Nature 2001, 410:50-56.
27. Murakami T., Maki W., Cardones A.R., Fang H., Tun Kyi A., Nestle F.O., Hwang S.T. Expression of CXC chemokine receptor-4 enhances the pulmonary metastatic potential of murine B16 melanoma cells. Cancer Res. 2002, 62:7328-7334.
28. Payne A.S., Cornelius L.A. The role of chemokines in melanoma tumor growth and metastasis. J. Invest. Dermatol. 2002, 118:915-922.
29. Riesterer O., Zingg D., Hummerjohann J., Bodis S., Pruschy M. Degradation of PKB/Akt protein by inhibition of the VEGF receptor/mTOR pathway in endothelial cells. Oncogene 2004, 23:4624-4635.
30. Robledo M.M., Bartolome R.A., Longo N., Rodriguez-Frade J.M., Mellado M., Longo I., van Muijen G.N., Sanchez-Mateos P., Teixido J. Expression of functional chemokine receptors CXCR3 and CXCR4 on human melanoma cells. J. Biol. Chem. 2001, 276:45098-45105.
31. Routhier A., Astuccio M., Lahey D., Monfredo N., Johnson A., Callahan W., Partington A., Fellows K., Ouellette L., Zhidro S., Goodrow C., Smith A., Sullivan K., Simone P., Le L., Vezuli B., Zohni M., West E., Gleason D., Bryan B. Pharmacological inhibition of Rho-kinase signaling with Y-27632 blocks melanoma tumor growth. Oncol. Rep. 2010, 23:861-867.
32. Salmaggi A., Maderna E., Calatozzolo C., Gaviani P., Canazza A., Milanesi I., Silvani A., DiMeco F., Carbone A., Pollo B. CXCL12, CXCR4 and CXCR7 expression in brain metastases. Cancer Biol. Ther. 2009, 8:1608-1614.
33. Salven P., Heikkila P., Joensuu H. Enhanced expression of vascular endothelial growth factor in metastatic melanoma. Br. J. Cancer 1997, 76:930-934.
34. Srivastava A., Hughes L.E., Woodcock J.P., Laidler P. Vascularity in cutaneous melanoma detected by Doppler sonography and histology: correlation with tumour behaviour. Br. J. Cancer 1989, 59:89-91.
35. Thurston D.E., Bose D.S., Howard P.W., Jenkins T.C., Leoni A., Baraldi P.G., Guiotto A., Cacciari B., Kelland L.R., Foloppe M.P., Rault S. Effect of A-ring modifications on the DNA-binding behavior and cytotoxicity of pyrrolo[2,1-c][1,4]benzodiazepines. J. Med. Chem. 1999, 42:1951-1964.
36. Vaishnav D., Jambal P., Reusch J.E., Pugazhenthi S. SP600125, an inhibitor of c-jun N-terminal kinase, activates CREB by a p38 MAPK-mediated pathway. Biochem. Biophys. Res. Commun. 2003, 307:855-860.
37. Wang J.J., Shen Y.K., Hu W.P., Hsieh M.C., Lin F.L., Hsu M.K., Hsu M.H. Design, synthesis, and biological evaluation of pyrrolo[2,1-c][1,4]benzodiazepine and indole conjugates as anticancer agents. J. Med. Chem. 2006, 49:1442-1449.
38. Wu H., Goel V., Haluska F.G. PTEN signaling pathways in melanoma. Oncogene 2003, 22:3113-3122.
39. Yoon S.O., Shin S., Lee H.J., Chun H.K., Chung A.S. Isoginkgetin inhibits tumor cell invasion by regulating phosphatidylinositol 3-kinase/Akt-dependent matrix metalloproteinase-9 expression. Mol. Cancer Ther. 2006, 5:2666-2675.
40. Yuecheng Y., Xiaoyan X. Stromal-cell derived factor-1 regulates epithelial ovarian cancer cell invasion by activating matrix metalloproteinase-9 and matrix metalloproteinase-2. Eur. J. Cancer Prev. 2007, 16:430-435.
41. Zhivotovsky B., Kroemer G. Apoptosis and genomic instability. Nat. Rev. Mol. Cell Biol. 2004, 5:752-762.