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Chemical Compound Review

Didemnin B     N-[1-[[13-butan-2-yl-12- hydroxy-20-[(4...

Synonyms: AGN-PC-00GIAO, Neuro_000164, NSC-333841, NSC333841, AC1LB3VX
 
 
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Disease relevance of Didemnin B

 

Psychiatry related information on Didemnin B

  • Fluorescent analogues (DB1 and TA1) of the secondary metabolites didemnin B (DB) and tamandarin A (TA) were synthesized to investigate the potential chemical defense mechanisms of tunicates in the family Didemnidae [6].
 

High impact information on Didemnin B

  • Our initial investigation of didemnin B resulted in the discovery of its GTP-dependent binding of the translation elongation factor EF1 alpha [7].
  • Mitotic cells were the least sensitive to didemnin B, and cells became more sensitive as they progressed into G1 and S phase [8].
  • Didemnin B inhibited the in vitro growth of B16 greater than L1210 greater than V-79 cells = human foreskin fibroblast = 9L greater than Chinese hamster ovary cells [8].
  • The marine natural product, didemnin B, is a 7-amino acid, cyclic depsipeptide that inhibits G1 cell cycle progression at nanomolar concentrations by undefined mechanisms [9].
  • Addition of CsA or DB 2 hr after PRL had no effect on PRL-stimulated ODC activity detectable at 6 hr, but addition of either as late as 6 hr still affected the extent of mitogenesis [2].
 

Chemical compound and disease context of Didemnin B

  • The [N,O-Me(2)Tyr(5)]residue of didemnin B was replaced with L-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) and L-1,2,3,4-tetrahydro-7-methoxyisoquinoline-3-carboxylic acid (MeO-Tic), which mimic the N,O-dimethylated tyrosine while constraining the conformation of the molecule [10].
  • A randomized phase II trial of trimetrexate or didemnin B for the treatment of metastatic or recurrent squamous carcinoma of the uterine cervix: a Southwest Oncology Group trial [11].
 

Biological context of Didemnin B

 

Anatomical context of Didemnin B

  • Didemnin B, a branched cyclic peptolide described to have immunosuppressive, anti-tumour, and anti-viral properties, induces rapid apoptosis in a range of mammalian cell lines [12].
  • 3H-thymidine incorporation (4 hr) by freshly harvested bone marrow leukocytes from DB-treated mice (0.025, 0.05, and 0.10 mg/kg/day x 7 days) was enhanced up to 40% over control (P less than .05), while bone marrow cellularity was increased 200% (P less than .01).(ABSTRACT TRUNCATED AT 400 WORDS)[13]
  • Anti-sheep red blood cell (SRBC) hemagglutinating antibody (hAb) production was induced by i.p. injection of 5 x 10(7) SRBC in CB6F1 mice (5/group) treated with vehicle or DB once/day for six days [13].
  • Didemnin B (DB) is a 7-amino-acid, cyclic polypeptide with potent (10(7)-10(10)M) antiproliferative effects in vivo and in vitro against a variety of viruses and tumor cell lines [17].
  • Kinetic studies showed that by 24 hr after a single i.p. injection of DB (1.0 mg/kg), blood leukocyte, granulocyte, and lymphocyte counts were elevated by 2.5-, 3-, and 2-fold, respectively, but declined rapidly thereafter [13].
 

Associations of Didemnin B with other chemical compounds

  • These observations suggest that didemnin B prevents translocation by stabilizing aminoacyl-tRNA bound to the ribosomal A-site, similar to the antibiotic kirromycin, and consistent with the known affinity of didemnins for elongation factor eEF-1 alpha [Crews et al. (1994) J. Biol. Chem. 269, 15411] [18].
  • Unlike kirromycin, didemnin B does not prevent peptide bond formation, so inhibition is observed only at the translocation step [18].
  • Nordidemnin (NorD), a cyclodepsipeptide isolated from marine invertebrates, exhibits antiproliferative and antitumoral properties identical to didemnin B on many cell lines [19].
  • In vitro distribution of diacetyl didemnin B in human blood cells and plasma [20].
  • With the brush border membrane vesicles prepared from the rat kidney cortex, didemnin B and its parent compound, didemnin A function neither as a K+-specific ionophore nor as an ionophore for Na+ ions while other depsipeptide antibiotics such as valinomycin and gramicidin promote transmembrane movement of K+ and Na+ ions, respectively [21].
 

Gene context of Didemnin B

 

Analytical, diagnostic and therapeutic context of Didemnin B

References

  1. Didemnins: antiviral and antitumor depsipeptides from a caribbean tunicate. Rinehart, K.L., Gloer, J.B., Hughes, R.G., Renis, H.E., McGovren, J.P., Swynenberg, E.B., Stringfellow, D.A., Kuentzel, S.L., Li, L.H. Science (1981) [Pubmed]
  2. Prolactin-dependent mitogenesis in Nb 2 node lymphoma cells: effects of immunosuppressive cyclopeptides. Russell, D.H., Buckley, A.R., Montgomery, D.W., Larson, N.A., Gout, P.W., Beer, C.T., Putnam, C.W., Zukoski, C.F., Kibler, R. J. Immunol. (1987) [Pubmed]
  3. Antitumor compounds from tunicates. Rinehart, K.L. Medicinal research reviews. (2000) [Pubmed]
  4. Antineoplastic activity of didemnin congeners: nordidemnin and modified chain analogues. Jouin, P., Poncet, J., Dufour, M.N., Aumelas, A., Pantaloni, A., Cros, S., François, G. J. Med. Chem. (1991) [Pubmed]
  5. A comparison of the inhibitory effects of immunosuppressive agents cyclosporine, tetranactin, and didemnin B on human T cell responses in vitro. Teunissen, M.B., Pistoor, F.H., Rongen, H.A., Kapsenberg, M.L., Bos, J.D. Transplantation (1992) [Pubmed]
  6. Chemical defense in ascidians of the didemnidae family. Joullié, M.M., Leonard, M.S., Portonovo, P., Liang, B., Ding, X., La Clair, J.J. Bioconjug. Chem. (2003) [Pubmed]
  7. Didemnin binds to the protein palmitoyl thioesterase responsible for infantile neuronal ceroid lipofuscinosis. Crews, C.M., Lane, W.S., Schreiber, S.L. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  8. Biochemical and cellular effects of didemnins A and B. Crampton, S.L., Adams, E.G., Kuentzel, S.L., Li, L.H., Badiner, G., Bhuyan, B.K. Cancer Res. (1984) [Pubmed]
  9. GTP-dependent binding of the antiproliferative agent didemnin to elongation factor 1 alpha. Crews, C.M., Collins, J.L., Lane, W.S., Snapper, M.L., Schreiber, S.L. J. Biol. Chem. (1994) [Pubmed]
  10. Total syntheses of conformationally constrained didemnin B analogues. replacements of N,O-dimethyltyrosine with L-1,2,3,4-tetrahydroisoquinoline and L-1,2,3,4-tetrahydro-7-methoxyisoquinoline. Tarver, J.E., Pfizenmayer, A.J., Joullié, M.M. J. Org. Chem. (2001) [Pubmed]
  11. A randomized phase II trial of trimetrexate or didemnin B for the treatment of metastatic or recurrent squamous carcinoma of the uterine cervix: a Southwest Oncology Group trial. Weiss, G.R., Liu, P.Y., O'Sullivan, J., Alberts, D.S., Brown, T.D., Neefe, J.R., Hutchins, L.F. Gynecol. Oncol. (1992) [Pubmed]
  12. Mitochondrial cytochrome c release is caspase-dependent and does not involve mitochondrial permeability transition in didemnin B-induced apoptosis. Grubb, D.R., Ly, J.D., Vaillant, F., Johnson, K.L., Lawen, A. Oncogene (2001) [Pubmed]
  13. Didemnin B--an immunosuppressive cyclic peptide that stimulates murine hemagglutinating antibody responses and induces leukocytosis in vivo. Montgomery, D.W., Celniker, A., Zukoski, C.F. Transplantation (1987) [Pubmed]
  14. Phase II clinical and pharmacological study of didemnin B in patients with metastatic breast cancer. Benvenuto, J.A., Newman, R.A., Bignami, G.S., Raybould, T.J., Raber, M.N., Esparza, L., Walters, R.S. Investigational new drugs. (1992) [Pubmed]
  15. Didemnin B in favourable histology non-Hodgkin's lymphoma. A phase II study of the National Cancer Institute of Canada Clinical Trials Group. Goss, G., Muldal, A., Lohmann, R., Taylor, M., Lopez, P., Armitage, G., Steward, W.P. Investigational new drugs. (1995) [Pubmed]
  16. Cytotoxicity and neurocytotoxicity of new marine anticancer agents evaluated using in vitro assays. Geldof, A.A., Mastbergen, S.C., Henrar, R.E., Faircloth, G.T. Cancer Chemother. Pharmacol. (1999) [Pubmed]
  17. Didemnin B: a new immunosuppressive cyclic peptide with potent activity in vitro and in vivo. Montgomery, D.W., Zukoski, C.F. Transplantation (1985) [Pubmed]
  18. Mechanism of protein synthesis inhibition by didemnin B in vitro. SirDeshpande, B.V., Toogood, P.L. Biochemistry (1995) [Pubmed]
  19. Dual effects of nordidemnin on WRK1 cells: inhibition of phosphoinositide metabolism and cell proliferation. Dominice, C., Dufour, M.N., Patino, N., Manzoni, O., Grazzini, E., Jouin, P., Guillon, G. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  20. In vitro distribution of diacetyl didemnin B in human blood cells and plasma. Phillips, J.L., Schwartz, R., Von Hoff, D.D. Cancer Invest. (1989) [Pubmed]
  21. Mechanism of action of didemnin B, a depsipeptide from the sea. Li, L.H., Timmins, L.G., Wallace, T.L., Krueger, W.C., Prairie, M.D., Im, W.B. Cancer Lett. (1984) [Pubmed]
  22. Inhibition of T-lymphocyte proliferation by the cyclic polypeptide didemnin B: no inhibition of lymphokine stimulation. Legrue, S.J., Sheu, T.L., Carson, D.D., Laidlaw, J.L., Sanduja, S.K. Lymphokine Res. (1988) [Pubmed]
  23. Rapamycin inhibits didemnin B-induced apoptosis in human HL-60 cells: evidence for the possible involvement of FK506-binding protein 25. Johnson, K.L., Lawen, A. Immunol. Cell Biol. (1999) [Pubmed]
  24. The antiproliferative agent didemnin B uncompetitively inhibits palmitoyl protein thioesterase. Meng, L., Sin, N., Crews, C.M. Biochemistry (1998) [Pubmed]
  25. Phase II evaluation of didemnin B in hormonally refractory metastatic prostate cancer. A Southwest Oncology Group study. Williamson, S.K., Wolf, M.K., Eisenberger, M.A., O'Rourke, M., Brannon, W., Crawford, E.D. Investigational new drugs. (1995) [Pubmed]
  26. Prolongation of skin allograft survival in mice by didemnin B. Alfrey, E.J., Zukoski, C.F., Montgomery, D.W. Transplantation (1992) [Pubmed]
  27. In vivo effect of didemnin B on two tumors of the rat. Fimiani, V. Oncology (1987) [Pubmed]
 
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