Cryptocaryol Structure-Activity Relationship Study of Cancer Cell Cytotoxicity and Ability to Stabilize PDCD4

ACS Medicinal Chemistry Letters

Volumn 5, Issue 5, 2014, Pages 522-526

  Cuccarese, Michael F ^a   Wang, Yanping ^a   Beuning, Penny J ^a   O'Doherty, George A ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

Author keywords

cryptocaryol SAR; cryptocaryols; PDCD4; PDCD4 stabilizer

Indexed keywords

ANTINEOPLASTIC AGENT; CAMPTOTHECIN; CRYPTOCARYOL A; CRYPTOCARYOL B; DIGITOXIN; NATURAL PRODUCT; PROGRAMMED CELL DEATH PROTEIN 4; RAPAMYCIN; TUMOR SUPPRESSOR PROTEIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CANCER INHIBITION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG POTENTIATION; DRUG SYNTHESIS; HT 29 CELL LINE; IC 50; MCF 7 CELL LINE; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN STABILITY; SENSITIZATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 84900390907     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml4005039     Document Type: Article

References (28)

1. Mochly-Rosen, D.; Das, K.; Grimes, K. V. Protein kinase C, an elusive therapeutic target? Nat. Rev. Drug. Discovery 2012, 11, 937-957
2. Watanabe, R.; Wei, L.; Huang, J. mTOR signaling, function, novel inhibitors, and therapeutic targets J. Nucl. Med. 2011, 52, 497-500
3. Cheng, J. Q.; Lindsley, C. W.; Cheng, G. Z.; Yang, H.; Nicosia, S. V. The Akt/PKB pathway: Molecular target for cancer drug discovery Oncogene 2005, 24, 7482-7492
4. Yang, H. S.; Jansen, A. P.; Nair, R.; Shibahara, K.; Verma, A. K.; Cmarik, J. L.; Colburn, N. H. A novel transformation suppressor, Pdcd4, inhibits AP-1 transactivation but not NF-kappaB or ODC transactivation Oncogene 2001, 20, 669-676
5. Schmid, T.; Bajer, M. M.; Blees, J. S.; Eifler, L. K.; Milke, L.; Rübsamen, D.; Schulz, K.; Weigert, A.; Baker, A. R.; Colburn, N. H.; Brüne, B. Inflammation-induced loss of Pdcd4 is mediated by phosphorylation-dependent degradation Carcinogenesis 2011, 32, 1427-1433
6. Palamarchuk, A.; Efanov, A.; Maximov, V.; Aqeilan, R. I.; Croce, C. M.; Pekarsky, Y. Akt phosphorylates and regulates Pdcd4 tumor suppressor protein Cancer Res. 2005, 65, 11282-11286
7. Suzuki, C.; Garces, R. G.; Edmonds, K. A.; Hiller, S.; Hyberts, S. G.; Marintchev, A.; Wagner, G. PDCD4 inhibits translation initiation by binding to elF4A using both its MA3 domains Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 3274-3279
8. Carayol, N.; Katsoulidis, E.; Sassano, A.; Altman, J. K.; Druker, B. J.; Platanias, L. C. Suppression of programmed cell death 4 (PDCD4) protein expression by BCR-ABL-regulated engagement of the mTOR/p70 S6 kinase pathway J. Biol. Chem. 2008, 283, 8601-8610
9. Dorrello, N. V.; Peschiaroli, A.; Guardavaccaro, D.; Colburn, N. H.; Sherman, N. E.; Pagano, M. S6K1- and βTRCP-mediated degradation of PDCD4 promotes protein translation and cell growth Science 2006, 314, 467-471
10. Yang, H. S.; Jansen, A. P.; Komar, A. A.; Zheng, X. J.; Merrick, W. C.; Costes, S.; Lockett, S. J.; Sonenberg, N.; Colburn, N. H. The transformation suppressor Pdcd4 is a novel eukaryotic translation initiation factor 4A binding protein that inhibits translation Mol. Cell. Biol. 2003, 23, 26-37
11. Wang, Q.; Sun, Z.; Yang, H. S. Downregulation of tumor suppressor Pdcd4 promotes invasion and activates both [beta]-catenin/Tcf and AP-1-dependent transcription in colon carcinoma cells Oncogene 2007, 27, 1527-1535
12. Göke, A.; Göke, R.; Knolle, A.; Trusheim, H.; Schmidt, H.; Wilmen, A.; Carmody, R.; Göke, B.; Chen, Y. H. DUG is a novel homologue of translation initiation factor 4G that binds eIF4A Biochem. Biophys. Res. Commun. 2002, 297, 78-82
13. Chen, Y.; Knösel, T.; Kristiansen, G.; Pietas, A.; Garber, M. E.; Matsuhashi, S.; Ozaki, I.; Petersen, I. Loss of PDCD4 expression in human lung cancer correlates with tumour progression and prognosis J. Pathol. 2003, 200, 640-646
14. Jansen, A. P.; Camalier, C. E.; Stark, C.; Colburn, N. H. Characterization of programmed cell death 4 in multiple human cancers reveals a novel enhancer of drug sensitivity Mol. Cancer Ther. 2004, 3, 103-110
15. Lankat-Buttgereit, B.; Göke, R. Programmed cell death protein 4 (PDCD4): A novel target for antineoplastic therapy? Biol. Cell 2003, 95, 515-519
16. Sonenberg, N.; Pause, A. Signal trnasduction: Protein synthesis and oncogenesis meet again Science 2006, 314, 428-429
17. Schmid, T.; Jansen, A. P.; Baker, A. R.; Hegamyer, G.; Hagan, J. P.; Colburn, N. H. Translation inhibitor PDCD4 is targeted for degradation during tumor promotion Cancer Res. 2008, 68, 1254-1260
18. Buck, E.; Eyzaguirre, A.; Brown, E.; Petti, F.; McCormack, S.; Haley, J. D.; Iwata, K. K.; Gibson, N. W.; Griffin, G. Rapamycin synergizes with the epidermal growth factor receptor inhibitor erlotinib in non-small-cell lung, pancreatic, colon, and breast tumors Mol. Cancer Ther. 2006, 5, 2676-2684
19. Sehgal, S. N. Rapamune (RAPA, rapamycin, sirolimus): mechanism of action immunosuppressive effect results from blockade of signal transduction and inhibition of cell cycle progression Clin. Biochem. 1998, 31, 335-340
20. Wang, Y.; O'Doherty, G. A.; Cryptocaryols, A.; Total, B. Cryptocaryols A and B: Total Syntheses, Stereochemical Revision, Structure Elucidation, and Structure-Activity Relationship J. Am. Chem. Soc. 2013, 135, 9334-9337
21. For other PDCD4 stablizers, see: Zhao, L.-X.; Huang, S.-X.; Tang, S.-K.; Jiang, C.-L.; Duan, Y.; Beutler, J. A.; Henrich, C. J.; McMahon, J. B.; Schmid, T.; Blees, J. S.; Colburn, N. H.; Rajski, S. R.; Shen, B. Actinopolysporins A-C and tubercidin as a PDCD4 stabilizer from the halophilic actinomycete actinopolyspora erythraea YIM 90600 J. Nat. Prod. 2011, 74, 1990-1995
22. Grkovic, T.; Blees, J. S.; Colburn, N. H.; Schmid, T.; Thomas, C. L.; Henrich, C. J.; McMahon, J. B.; Gustafson, K. R. Cryptocaryols A-H, α-pyrone-containing 1,3-polyols from Cryptocarya sp. implicated in stabilizing the tumor suppressor Pdcd4 J. Nat. Prod. 2011, 74, 1015-1020
23. Pongrakhannon, V.; Stueckle, T. A.; Wang, H.-Y. L.; O'Doherty, G. A.; Dinu, C. Z.; Chanvorachote, P.; Rojanasakul, Y. Monosaccharide digitoxin derivatives sensitize human non-small cell lung cancer cells to anoikis through Mcl-1 proteasomal degradation Biochem. Pharmacol. 2013, 10.1016/j.bcp.2013.10. 027
24. Hinds, J. W.; McKenna, S. B.; Sharif, E. U.; Wang, H.-Y. L.; Akhmedov, N. G.; O'Doherty, G. A. C3′/C4′-Stereochemical effects of digitoxigenin α- l -/α- d -glycoside in cancer cytotoxicity ChemMedChem 2013, 8, 63-69
25. Wang, H.-Y. L.; Wu, B.; Zhang, Q.; Kang, S.-W.; Rojanasakul, Y.; O'Doherty, G. A. C5′-Alkyl substitution effects on digitoxigenin α- l -glycoside cancer cytotoxicity ACS Med. Chem. Lett. 2011, 2, 259-263
26. Iyer, A.; Zhou, M.; Azad, N.; Elbaz, H.; Wang, L.; Rogalsky, D. K.; Rojanasakul, Y.; O'Doherty, G. A.; Langenhan, J. M. A direct comparison of the anticancer activities of digitoxin MeON-neoglycosides and O-glycosides: Oligosaccharide chain length-dependant induction of caspase-9-mediated apoptosis ACS Med. Chem. Lett. 2010, 1, 326-330
27. Blees, J. S.; Bokesch, H. R.; Rubsamen, D.; Schulz, K.; Milke, L.; Bajer, M. M.; Gustafson, K. R.; Henrich, C. J.; McMahon, J. B.; Colburn, N. H.; Schmid, T.; Brune, B. Erioflorin stabilizes the tumor suppressor PDCD4 by inhibiting its interaction with the E3-ligase beta-TrCP1 PLoS One 2012, 7, e46567
28. Cuccarese, M. F.; Singh, A.; Amiji, M.; O'Doherty, G. A.; Novel, A. Use of gentamicin in the ROS-mediated sensitization of NCI-H460 lung cancer cells to various anticancer agents ACS Chem. Biol. 2013, 6, 2771-2777