Akt-dependent anabolic activity of natural and synthetic brassinosteroids in rat skeletal muscle cells

Journal of Medicinal Chemistry

Volumn 54, Issue 12, 2011, Pages 4057-4066

  Esposito, Debora ^a   Rathinasabapathy, Thirumurugan ^a   Poulev, Alexander ^a   Komarnytsky, Slavko ^a,b   Raskin, Ilya ^a  

^a RUTGERS UNIVERSITY   (United States)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

22BETA,23BETA HYDROXYLATED BRASSINOSTEROID; 3ALPHA FLUOROHOMOBRASINOLIDE; 3ALPHA HOMOCASTASTERONE; 6 AZA HOMOBRASSINOLIDE; 7 AZA HOMOBRASSINOLIDE; BRASSINOSTEROID; EPIBRASSINOLIDE; HOMOBRASSINOLIDE; HOMOCASTASTERONE; PROTEIN KINASE B; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CYTOTOXICITY; DRUG EFFICACY; DRUG SYNTHESIS; FIBROBLAST; HORMONE ACTION; MUSCLE CELL; NONHUMAN; PHARMACOGENOMICS; PROTEIN PHOSPHORYLATION; PROTEIN SYNTHESIS; RAT; SIGNAL TRANSDUCTION; SKELETAL MUSCLE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANABOLIC AGENTS; ANIMALS; CELL LINE; CELL SURVIVAL; CHOLESTANONES; MICE; MUSCLE, SKELETAL; PHOSPHORYLATION; PROTO-ONCOGENE PROTEINS C-AKT; RATS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79959446441     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200028h     Document Type: Article

References (45)

1. Bajguz, A.; Tretyn, A. The chemical characteristic and distribution of brassinosteroids in plants Phytochemistry 2003, 62, 1027-1046 (Pubitemid 36323474)
2. Losel, R.; Wehling, M. Nongenomic actions of steroid hormones Nature Rev. Mol. Cell Biol. 2003, 4, 46-56 (Pubitemid 36077256)
3. Clouse, S. D. Brassinosteroids. Plant counterparts to animal steroid hormones? Vitam. Horm. 2002, 65, 195-223 (Pubitemid 135763176)
4. Mussig, C. Brassinosteroid-promoted growth Plant Biol. (Stuttgart, Ger.) 2005, 7, 110-117 (Pubitemid 40564544)
5. Wang, Z. Y.; Seto, H.; Fujioka, S.; Yoshida, S.; Chory, J. BRI1 is a critical component of a plasma-membrane receptor for plant steroids Nature 2001, 410, 380-383 (Pubitemid 32246056)
6. Nam, K. H.; Li, J. BRI1/BAK1, a receptor kinase pair mediating brassinosteroid signaling Cell 2002, 110, 203-212 (Pubitemid 34876548)
7. Takatsuto, S.; Ikekawa, N. Synthesis and activity of plant growth-promoting steroids, (22 R,23 R,24 S)-28-homobrassinosteroids, with modifications in rings A and B J. Chem. Soc., Perkin Trans. 1984, 1, 439-447
8. Bajguz, A. Effect of brassinosteroids on nucleic acids and protein content in cultured cells of Chlorella vulgaris Plant Physiol. Biochem. 2000, 38, 209-215 (Pubitemid 30199505)
9. Kartal, G.; Temel, A.; Arican, E.; Gozukirmizi, N. Effects of brassinosteroids on barley root growth, antioxidant system and cell division Plant Growth Regul. 2009, 58, 261-267
10. Kulaeva, O. N.; Burkhanova, E. A.; Fedina, A. B.; Khokhlova, V. A.; Bokebayeva, G. A.; Vorbrodt, H. M.; Adam, G. n. Effect of Brassinosteroids on Protein Synthesis and Plant-Cell Ultrastructure under Stress Conditions. In Brassinosteroids; American Chemical Society: Washington, DC, 2009; pp 141-155.
11. Massey, A. P.; Pore, V. S.; Hazra, B. G. New route for the synthesis of (22 S,23 S)-28-homobrassinolide Synthesis 2003, 3, 426-430 (Pubitemid 36343874)
12. Ramirez, J. A.; Brosa, C.; Galagovsky, L. R. Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6 Phytochemistry 2005, 66, 581-587 (Pubitemid 40249658)
13. Kuzmitsky, B. B.; Mizulo, N. A. Study of acute toxicity of epibrassinolide and its preparative forms Tech. Rep. - Acad. Sci. Belarus, Minsk 1991, 1-44
14. Murkunde, Y. V.; Balakrishna Murthy, P. Developmental toxicity of homobrassinolide in wistar rats Int. J. Toxicol. 2010, 29, 517-522
15. Malikova, J.; Swaczynova, J.; Kolar, Z.; Strnad, M. Anticancer and antiproliferative activity of natural brassinosteroids Phytochemistry 2008, 69, 418-426
16. Wachsman, M. B.; Ramírez, J. A.; L.B., T.; Galagovsky, L. R.; Coto, C. E. Antiviral activity of natural and synthetic brassinosteroids Curr. Med. Chem. Anti-Infect. Agents 2004, 3, 163-179 (Pubitemid 38854997)
17. Andersen, D. L.; Back, T. G.; Janzen, L.; Michalak, K.; Pharis, R. P.; Sung, G. C. Design, synthesis, and bioactivity of the first nonsteroidal mimetics of brassinolide J. Org. Chem. 2001, 66, 7129-7141 (Pubitemid 32983103)
18. Baron, D. L.; Luo, W.; Janzen, L.; Pharis, R. P.; Back, T. G. Structure-activity studies of brassinolide b-ring analogues Phytochemistry 1998, 49, 1849-1858 (Pubitemid 28563788)
19. Romero-Avila, M.; de Dios-Bravo, G.; Mendez-Stivalet, J. M.; Rodriguez-Sotres, R.; Iglesias-Arteaga, M. A. Synthesis and biological activity of furostanic analogues of brassinosteroids bearing the 5alpha-hydroxy-6-oxo moiety Steroids 2007, 72, 955-959 (Pubitemid 47603252)
20. Esposito, D.; Rathinasabapathy, T.; Poulev, A.; Komarnytsky, S.; Raskin, I. Anabolic effect of plant brassinosteroid. Unpublished results.
21. Hajduch, E.; Alessi, D. R.; Hemmings, B. A.; Hundal, H. S. Constitutive activation of protein kinase B alpha by membrane targeting promotes glucose and system A amino acid transport, protein synthesis, and inactivation of glycogen synthase kinase 3 in L6 muscle cells Diabetes 1998, 47, 1006-1013 (Pubitemid 28294540)
22. Zullo, M. A. T.; Adam, G. Brassinosteroid phytohormones - structure, bioactivity and applications Braz. J. Plant Physiol. 2002, 14, 143-181 (Pubitemid 36224671)
23. Adler, J. H.; Grebenok, R. J. Biosynthesis and distribution of insect-molting hormones in plants - a review Lipids 1995, 30, 257-262
24. Bathori, M.; Toth, N.; Hunyadi, A.; Marki, A.; Zador, E. Phytoecdysteroids and anabolic-androgenic steroids - structure and effects on humans Curr. Med. Chem. 2008, 15, 75-91 (Pubitemid 351234629)
25. Takatsuto, S.; Ikekawa, N.; Morishita, T.; Abe, H. Structure-activity relationship of brassinosteroids with respect to the A/B-ring functional groups Chem. Pharm. Bull. 1987, 35, 211-216
26. Anastasia, M.; Allevi, P.; Brasca, M. G.; Ciuffreda, P.; Fiechi, A. Synthesis of (2 R,3 S,22 S,23 S)-2,3,22,23-tetrahydroxy-B-homo-6-aza-5a- stigmastan-7-one, an aza analogue of brassinolide Gazz. Chim. Ital. 1984, 114, 159-161
27. Galagovsky, L. R.; Gros, E. G.; Ramirez, J. A. Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide Phytochemistry 2001, 58, 973-980 (Pubitemid 33086226)
28. Mykhaylyk, O. M.; Kotzuruba, A. V.; Buchanevich, O. M.; Korduban, A. M.; Meged, E. F.; Gulaya, N. M. Signal transduction of erythrocytes after specific binding of ecdysterone and cholesterol immobilized on nanodispersed magnetite J. Magn. Magn. Mater. 2001, 225, 226-234 (Pubitemid 32335301)
29. Rommel, C.; Bodine, S. C.; Clarke, B. A.; Rossman, R.; Nunez, L.; Stitt, T. N.; Yancopoulos, G. D.; Glass, D. J. Mediation of IGF-1-induced skeletal myotube hypertrophy by PI(3)K/Akt/mTOR and PI(3)K/Akt/GSK3 pathways Nature Cell Biol. 2001, 3, 1009-1013 (Pubitemid 34428746)
30. Gorelick-Feldman, J.; Maclean, D.; Ilic, N.; Poulev, A.; Lila, M. A.; Cheng, D.; Raskin, I. Phytoecdysteroids increase protein synthesis in skeletal muscle cells J. Agric. Food Chem. 2008, 56, 3532-3537 (Pubitemid 351860149)
31. Strosberg, A. D. Structure, function, and regulation of the three beta-adrenergic receptors Obes. Res. 1995, 3 (Suppl 4) 501S-505S
32. Saini, A.; Al-Shanti, N.; Stewart, C. C2 skeletal myoblast survival, death, proliferation and differentiation: regulation by Adra1d Cell. Physiol. Biochem. 2010, 25, 253-262
33. Kou, K.; Rotwein, P. Transcriptional activation of the insulin-like growth factor-II gene during myoblast differentiation Mol. Endocrinol. 1993, 7, 291-302 (Pubitemid 23066872)
34. Alzhanov, D. T.; McInerney, S. F.; Rotwein, P. Long-range interactions regulate Igf2 gene transcription during skeletal muscle differentiation J. Biol. Chem. 2010, 285, 38969-38977
35. Lee, P. D.; Giudice, L. C.; Conover, C. A.; Powell, D. R. Insulin-like growth factor binding protein-1: recent findings and new directions Proc. Soc. Exp. Biol. Med. 1997, 216, 319-357
36. Challiss, R. A.; Arch, J. R.; Newsholme, E. A. The rate of substrate cycling between fructose 6-phosphate and fructose 1,6-bisphosphate in skeletal muscle Biochem. J. 1984, 221, 153-161 (Pubitemid 14082302)
37. Lai, K. M.; Gonzalez, M.; Poueymirou, W. T.; Kline, W. O.; Na, E.; Zlotchenko, E.; Stitt, T. N.; Economides, A. N.; Yancopoulos, G. D.; Glass, D. J. Conditional activation of akt in adult skeletal muscle induces rapid hypertrophy Mol. Cell. Biol. 2004, 24, 9295-9304 (Pubitemid 39391668)
38. Izumiya, Y.; Hopkins, T.; Morris, C.; Sato, K.; Zeng, L.; Viereck, J.; Hamilton, J. A.; Ouchi, N.; LeBrasseur, N. K.; Walsh, K. Fast/Glycolytic muscle fiber growth reduces fat mass and improves metabolic parameters in obese mice Cell Metab. 2008, 7, 159-172 (Pubitemid 351168553)
39. Blaauw, B.; Canato, M.; Agatea, L.; Toniolo, L.; Mammucari, C.; Masiero, E.; Abraham, R.; Sandri, M.; Schiaffino, S.; Reggiani, C. Inducible activation of Akt increases skeletal muscle mass and force without satellite cell activation FASEB J. 2009, 23, 3896-3905
40. Solomon, A. M.; Bouloux, P. M. Modifying muscle mass - the endocrine perspective J. Endocrinol. 2006, 191, 349-360 (Pubitemid 44830610)
41. Mandel, J. L.; Pearson, M. L. Insulin stimulates myogenesis in a rat myoblast line Nature 1974, 251, 618-620
42. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 1983, 65, 55-63 (Pubitemid 14203433)
43. Montgomery, J. L.; Harper, W. M., Jr.; Miller, M. F.; Morrow, K. J., Jr.; Blanton, J. R., Jr. Measurement of protein synthesis and degradation in C2C2) myoblasts using extracts of muscle from hormone treated bovine Methods Cell Sci. 2002, 24, 123-129 (Pubitemid 36916740)
44. Fawcett, J.; Hamel, F. G.; Duckworth, W. C. Characterization of the inhibition of protein degradation by insulin in L6 cells Arch. Biochem. Biophys. 2001, 385, 357-363 (Pubitemid 32989293)
45. Komarnytsky, S.; Cook, A.; Raskin, I. Potato protease inhibitors inhibit food intake and increase circulating cholecystokinin levels by a trypsin-dependent mechanism Int. J. Obes. 2011, 35, 236-243