Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate

Nature Chemistry

Volumn 5, Issue 6, 2013, Pages 510-517

  Li, Jing ^a   Cisar, Justin S ^b   Zhou, Cong Ying ^a   Vera, Brunilda ^c   Williams, Howard ^a   Rodríguez, Abimael D ^c   Cravatt, Benjamin F ^b   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; ANTINEOPLASTIC AGENT; AZIRIDINE; AZIRIDINE DERIVATIVE; BIOLOGICAL PRODUCT; DITERPENE; EUPALMERIN ACETATE; RHODIUM;

AMINATION; ARTICLE; CATALYSIS; CELL STRAIN HL 60; CELL SURVIVAL; CHEMISTRY; DRUG EFFECT; HUMAN; PROTEOMICS; STRUCTURE ACTIVITY RELATION;

ALKENES; ALKYNES; AMINATION; ANTINEOPLASTIC AGENTS; AZIRIDINES; BIOLOGICAL AGENTS; CATALYSIS; CELL SURVIVAL; DITERPENES; HL-60 CELLS; HUMANS; PROTEOMICS; RHODIUM; STRUCTURE ACTIVITY RELATIONSHIP;

MLCS; MLOWN;

EID: 84879074474     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1653     Document Type: Article

References (49)

1. Li, J. W-H. & Vederas, J. C. Drug discovery and natural products: end of an era or an endless frontier? Science 325, 161-165 (2009).
2. Newhouse, T., Baran, P. S. & Hoffmann, R. W. The economies of synthesis. Chem. Soc. Rev. 38, 3010-3021 (2009).
3. Schreiber, S. L. Organic synthesis toward small-molecule probes and drugs, special feature. Proc. Natl Acad. Sci. USA 108, 6699-6822 (2011).
4. Koehn, F. E. High impact technologies for natural products screening. Prog. Drug Res. 65, 177-210 (2008).
5. Newman, D. J. & Cragg, G. M. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J. Nat. Prod. 75, 311-335 (2012).
6. Burdine, L. & Kodadek, T. Target identification in chemical genomics: the (often) missing link. Chem. Biol. 11, 593-597 (2004).
7. Carlson, E. E. Natural products as chemical probes. ACS Chem. Biol. 5, 639-653 (2010).
8. Hopkins, A. L. & Groom, C. R. The druggable genome. Nature Rev. Drug Discov. 1, 727-730 (2002).
9. Kanoh, N. et al. Immobilization of natural products on glass slides by using a photoaffinity reaction and the detection of protein-small-molecule interactions. Angew Chem. Int. Ed. 42, 5584-5587 (2003).
10. Piggott, A. M. & Karuso, P. Quality, not quantity: the role of natural products and chemical proteomics in modern drug discovery. Comb. Chem. High Throughput Screening 7, 607-630 (2004).
11. Terstappen, G. C., Schlüpen, C., Raggiaschi, R. & Gaviraghi, G. Target deconvolution strategies in drug discovery. Nature Rev. Drug Discov. 6, 891-903 (2007).
12. Peddibhotla, S., Dang, Y., Liu, J. O. & Romo, D. Simultaneous arming and structure/activity studies of natural products employing O-H insertions: an expedient and versatile strategy for natural products-based chemical genetics. J. Am. Chem. Soc. 129, 12222-12231 (2007).
13. Chamni, S. et al. Diazo reagents with small steric footprints for simultaneous arming/SAR studies of alcohol-containing natural products via OH insertion. ACS Chem. Biol. 6, 1175-1181 (2011).
14. 3-catalyzed arene iodination. Org. Lett. 12, 2104-2107 (2010).
15. Robles, O., Serna-Saldívar, S. O., Gutiérrez-Uribe, J. A. & Romo, D. Cyclopropanations of olefin-containing natural products for simultaneous arming and structure activity studies. Org. Lett. 14, 1394-1397 (2012).
16. Davies, H. M. L. & Manning, J. R. Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion. Nature 451, 417-424 (2008).
17. Fiori, K. W. & Du Bois, J. Catalytic intermolecular amination of C-H bonds: method development and mechanistic insights. J. Am. Chem. Soc. 129, 562-568 (2007).
18. Zalatan, D. N. & Du Bois, J. Understanding the differential performance of Rh2(esp)2 as a catalyst for C-H amination. J. Am. Chem. Soc. 131, 7558-7559 (2009).
19. Lebel, H. & Huard, K. De novo synthesis of Troc-protected amines: intermolecular rhodium-catalyzed C-H animation with N-tosyloxycarbamates. Org. Lett. 9, 639-642 (2007).
20. Guthikonda, K. & Du Bois, J. A unique and highly efficient method for catalytic olefin aziridination. J. Am. Chem. Soc. 124, 13672-13673 (2002).
21. Lebel, H., Spitz, C., Leogane, O., Trudel, C. & Parmentier, M. Stereoselective rhodium-catalyzed amination of alkenes. Org. Lett. 13, 5460-5463 (2011).
22. Appendino, G., Tron, G. C., Jarevång, T. & Sterner O. Unnatural natural products from the transannular cyclization of lathyrane diterpenes. Org Lett. 3, 1609-1612 (2001).
23. Lewis, C. A. & Miller, S. J. Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts. Angew Chem. Int. Ed. 45, 5616-5619 (2006).
24. Miao, H. et al. Ring-opening and ring-closing reactions of a shikimic acidderived substrate leading to diverse small molecules. J. Comb. Chem. 9, 245-253 (2007).
25. Li, F. et al. Iminonitroso Diels-Alder reactions for efficient derivatization and functionalization of complex diene-containing natural products. Org Lett. 15, 2923-2926 (2007).
26. Du Bois, J. Rhodium-catalyzed C-H amination: versatile methodology for the selective preparation of amines and amine derivatives. Chemtracts: Org. Chem. 18, 1-13 (2005).
27. Trost, B. M., Boyle, O., Torres, W. & Ameriks, M. K. Development of a flexible strategy towards FR900482 and mitomycins. Chem. Eur. J. 17, 7890-7903 (2011).
28. Gangapuram, M. & Redda, K. K. Synthesis of substituted N-[4(5-methyl/phenyl-1, 3, 4-oxadiazol-2-yl)-3,6-diphydropyridin-1(2H)-yl] benzamide sulfonamides as anti-inflammatory and anti-cancer agents. J. Heterocycl. Chem. 46, 309-316 (2009).
29. Balthaser, B. R., Maloney, M. C., Beeler, A. B., Porco, J. A. & Snyder, J. K. Remodeling of the natural product fumagillol employing a reaction discovery approach. Nature Chem. 3, 969-973 (2011).
30. Huigens, R.W. III, et al. A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products. Nature Chem. 5, 195-202 (2013).
31. Jordan, P. A. & Miller, S. J. An approach to the site-selective deoxygenation of hydroxy groups based on catalytic phosphoramidite transfer. Angew Chem. Int. Ed. 51, 2907-2911 (2012).
32. Schreiber, K., Schneider, G. & Sembdner, G. Gibberelline-IX: Epoxydation von einigen gibberellinen. Tetrahedron 22, 1437-1444 (1966).
33. Dong, Q., Anderson, C. E. & Ciufolini, M. A. Reductive cleavage of troc groups under neutral conditions with cadmium-lead couple. Tetrahedron Lett. 36, 5681-5682 (1995).
34. Shoemaker, R. H. The NCI60 human tumour cell line anticancer drug screen. Nature Rev. Cancer 6, 813-823 (2006).
35. 2-terminal kinase pathway. Mol. Cancer Ther. 6, 184-192 (2007).
36. Rostovtsev, V. V., Green, L. G., Fokin, V. V. & Sharpless, K. B. A stepwise Hüisgen cycloaddition process: copper(I)-catalyzed regioselective 'ligation' of azides and terminal alkynes. Angew Chem. Int. Ed. 41, 2596-2599 (2002).
37. Weerapana, E. et al. Quantitative reactivity profiling predicts functional cysteines in proteomes. Nature 468, 790-795 (2010).
38. Everley, P. A. et al. Assessing enzyme activities using stable isotope labeling and mass spectrometry. Mol. Cell Proteom. 6, 1771-1777 (2007).
39. Cisar, J. S. & Cravatt, B. F. Fully functionalized small-molecule probes for integrated phenotypic screening and target identification. J. Am. Chem. Soc. 134, 10385-10388 (2012).
40. Ong, S. E. et al. Identifying the proteins to which small-molecule probes and drugs bind in cells. Proc. Natl Acad. Sci. USA 106, 4617-4622 (2009).
41. 5b (CYB5B). Mol. Cancer 9, 14 (2010).
42. Cathcart, M. C. et al. Examination of thromboxane synthase as a prognostic factor and therapeutic target in non-small cell lung cancer. Mol. Cancer 10, 25 (2011).
43. Wang, J. H. H. et al. Derlin-1 is overexpressed in human breast carcinoma and protects cancer cells from endoplasmic reticulum stress-induced apoptosis. Breast Cancer Res. 10, R7 (2008).
44. Simamura, E. S. H., Hatta, T. & Hirai, K. J. Mitochondrial voltage-dependent anion channels (VDACs) as novel pharmacological targets for anti-cancer agents. Bioenerg. Biomembr. 40, 213-217 (2008).
45. Wang, C. M. C., Belinson, J. L., Vaziri, S., Ganapathi, R. & Sengupta, S. Role of the 18:1 lysophosphatidic acid-ovarian cancer immunoreactive antigen domain containing 1 (OCIAD)-integrin axis in generating late-stage ovarian cancer. Mol. Cancer Ther. 9, 1709-1718 (2010).
46. 3 carbons. J. Am. Chem. Soc. 134, 2547-2550 (2012).
47. Dai, H-X., Stephan, A. F., Plummer, M. S., Zhang, Y-H. & Yu, J-Q. Divergent C-H functionalizations directed by sulfonamide pharmacophores: late-stage diversification as a tool for drug discovery. J. Am. Chem. Soc. 133, 7222-7228 (2011).
48. Masahiro, A., Hisanor, N. & Shuinchi, H. Catalytic C-H activation in total synthesis of natural products. Chem. Sci. J. Curr. Rev. 5, 175-191 (2011).
49. Tayo, L. L., Lu, B., Cruz, L. J. & Yates, J. R. Proteomic analysis provides insights on venom processing in Conus textile. J. Proteome Res. 9, 2292-2301 (2010).