Lactacystin. 3. Biological activity 5-9) 1) Lactacystin inhibits cell cycle progression 5) and induces neurite outgrowth in Neuro 2a cells 1).
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1 1. Discovery, producing organism and structure 1-4) was originally isolated from a broth of treptomyces lactacystinicus strain M-6519 T while screening for neurite outgrowth inducers in euro 2a, a cell line of murine neuroblastoma cells. The absolute configuration of the structure was confirmed by X-ray crystallographic analysis 2). C C 3 Chapter 1 3 C C 3 treptomyces lactacystinicus M-6519 T C 3 2. ysical data Colorless crystal. C ; mol wt ol. in 2, Me, DM, pyridine. Insol. in benzene, EtAc, CCl Biological activity 5-9) 1) inhibits cell cycle progression 5) and induces neurite outgrowth in euro 2a cells 1). Control (day 4) (1.3 µm, day 4) otomicrographs of morphological changes induced by lactacystin in euro 2a cells 2) inhibits proteasome activity 6). Proteasome exhibits three protease activities, of the three, lactacystin inhibits chymotrypsin-like activity most potently, followed by tyrpsin-like activity, but its inhibitory activity against peptidylgultamylpeptide hydrolytic activity is relatively weak
2 Chapter 1 Protein (ubstrate) Ubiquitin conjugation Ubiquitin ATP Proteolysis ATP E1, E2, E3 26 proteasome muralide 19 complex 20 proteasome 19 complex Ubiquitin Peptides Amino acids Antigen presentation The molecular structure of rat liver 26proteasome based on electron microscopy 6) Model of intracellular protein degradation mediated by the ubiquitin-proteasome system is specifically bound to the -terminal threonine residue of certain β subunits (subunit X for mammalian cells 6) and subunit β5 for yeast 8) ). Recently, it has been proposed that lactacystin is converted non-enzymatically to the β-lactone derivative (muralide), which reacts directly with the threonine active site. C C 3 3 C C 3 C 3 Proteasome α β β α 3 C 3 C C3 muralide C 3 2 Thr X (β5) 3 C C 3 C 3 C 3 2 X (β5)
3 4. tructure activity study 3) derivatives were evaluated in neurite outgrowth of euro 2a cells and growth inhibition of osteosarcoma cells. The same derivatives were found to elicit both activities, suggesting that they are based on the same mechanism. The presence of a hydroxyisobutyl group on C-5 and the 9 configuration are important, as is the 6,7R configuration of the γ-lactam ring, revealing specific structural requirements for activity. The most significant Discovery was that clasto-lactacystin β-lactone, later designated omuralide by Prof. Corey, shows almost the same activity as lactacystin 10). (A) 3 C 7 R 6 9 R C3 C 3 with R 1, R 2 but not C 3 C R 1 R 2 (B) with Et, i-pr, n-bu, Bn but not with C 3 3 C 2 7 C C 3 C 3 ummary of tructure-activity tudies of (A) and muralide (B) Chapter 1 5. Biosynthesis 11,12) C C CCoA C 2 C L-Valine IsoButyryl-CoA Methylmalonic semialdehyde CCoA Propionyl-CoA 2 C C C C L-Leucine CCoA 3 C C C 3 C 3 C 3 C C 2 L-Cysteine CCoA CCoA C Pyruvate C 2 L-erine CCoA C C () 2 C () C C 2 L,L-Cysteine
4 Chapter 1 6. Total synthesis The total synthesis of lactacystin has been reported by several groups. The following scheme is Ōmura s approach 13-15). 2 2 C 1) Cl (gas) (97%) 2) C(Me) 3 (82%) Me 2 C LMD, C (85%) C 2 Me DCC, DM, TFA, Pyridine Benzene C C 2 Me (+)-Ipc 2 B (2 steps, 70%) C 2 Me 1) 3, DM 2) acl 2 (56%) 2 C Allyl 2 C C 2 Me 1) Pd, C Ac 2) 0.1 a (82%) 2 C C 2 C 2 Allyl BPCl, Et 3 (79%) Pd(P 3 ) 4, C 2, Et 3 (81%) verall yield 14 % in 11 steps 7. Application is recognized as the most specific inhibitor of proteasome due to its mode of action. Therefore, lactacystin has been used to reveal and support the cellular proteasome functions. 1) Cell cycle: [571], [642], [667], [719], [735] 2) Apoptosis: [599], [676], [691], [692], [713], [716], [739] 3) Immunoantigen processing: [666], [667] 4) Protein degradation on ER: [593] 5) Receptor degradation: [594], [606], [653] 6) Transcription factor degradation: [643], [674], [769], 7) ther regulatory protein degradation: [618], [627], [641], [654], [670], [678], [698], [704], [752], [756], [770], [771], [780], [783], [818] 8) Anti-tumor: [750], 9) Anti-malaria: [830] 10) Anti-angiogenesis: [697] The above brackets [ ] show references for the applications (ee )
5 8. is commercially available from Kyowa Medex. 9. References 1. [455]. Ōmura et al., J. Antibiot. 44, (1991) 2. [456]. Ōmura et al., J. Antibiot. 44, (1991) 3. [760]. Tomoda et al.,yakugaku Zasshi 120, (2000) 4. [1178] A. Take et al., J. Antibiot. 68, (2015) 5. [571] M. Katagiri et al., J. Antibiot. 48, (1995) 6. G. Fenteany et al., cience 268, (1995) 7. K. Tanaka et al. J. Leukocyte Biol. 56, 571 (1994) 8. M. Groll et al., ature 386, (1997) 9. L. R. Dick et al., J. Biol. Chem. 272, (1997) 10. E. J. Corey et al., Chem. arm. Bull. 47, 1-10 (1999) 11. [546] A. akagawa et al., Tetrahedron Lett. 35, (1994) 12. [589]. Takahashi et al., J. Antibiot. 48, (1995) 13. [507] T. unazuka et al., J. Am. Chem. oc. 115, 5302 (1993) 14. [510] T. unazuka et al., Tetrahedron Lett. 34, (1993) 15. [628] T. agamitsu et al., J. Am. Chem. oc. 118, (1996) 16. L. Kozlowski et al., Tumur Biol. 22, (2001) Chapter
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