Natural products as probes of cell biology: 20 Years of didemnin research

Medicinal Research Reviews

Volumn 22, Issue 2, 2002, Pages 102-145

  Vera, Matthew D ^a   Joullie, Madeleine M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Apoptosis; Biological activity; Clinical studies; Didemnins; Mechanism of action

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; CYCLOSPORIN A; DEHYDRODIDEMNIN B; DIDEMNIN A; DIDEMNIN B; DIDEMNIN C; DIDEMNIN M; IMMUNOSUPPRESSIVE AGENT; NORDIDEMNIN B; TACROLIMUS; TAMANDARIN A; TAMANDARIN B; UNCLASSIFIED DRUG; VIDARABINE;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; APOPTOSIS; CELL CYCLE; CELL GROWTH; CELL PROLIFERATION; CLINICAL TRIAL; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IMMUNE RESPONSE; IMMUNOSUPPRESSIVE TREATMENT; IN VITRO STUDY; IN VIVO STUDY; INHIBITION KINETICS; LETHAL DOSE; LIVER TOXICITY; MONKEY; NONHUMAN; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; APOPTOSIS; CHROMATOGRAPHY, AFFINITY; CLINICAL TRIALS; DEPSIPEPTIDES; HUMANS; IMMUNOSUPPRESSIVE AGENTS; PEPTIDES, CYCLIC; PHOTOAFFINITY LABELS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0036178591     PISSN: 01986325     EISSN: None     Source Type: Journal    
DOI: 10.1002/med.10003     Document Type: Review

References (146)

1. Drugs from the sea. The search continues
2. The didemnins: Biological properties, chemistry, and total synthesis
3. Toxins from ascidians
4. Synthetic studies of biologically-active marine cyclopeptides
5. Antitumor compounds from tunicates
6. Didemnins: Antiviral and antitumor depsipeptides from a Caribbean Tunicate
7. Structures of the didemnins, antiviral and cytotoxic depsipeptides from a Caribbean Tunicate
8. Seven new didemnins from the marine tunicate Trididemnum solidum
9. Antineoplastic activity of didemnin congeners: Nordidemnin and modified chain analogues
10. Isodidemnine-1, a cytotoxic cyclodepsipeptide isolated from a tunicate, Trididemnum Cyanophorum (Didemnidae)
11. Total synthesis of didemnins A, B, and C
12. Crystal and molecular structure of didemnin B, an antiviral and cytotoxic depsipeptide
13. Didemnin B.: Comparative study and conformational approach in solution
14. In vitro activity of aplidine, a new marine-derived anti-cancer compound, on freshly explanted clonogenic human tumour cells and haematopoietic precursor cells
15. Structure-activity relationships of the didemnins
16. The Complete spectral assignment of didemnin H, a new constituent of the tunicate Trididemnum Cyanophorum
17. 4]didemnin B; two new natural didemnins with a modified macrocycle
18. Phase II clinical and pharmacological study of didemnin B in patients with metastatic breast cancer
19. Tamandarins A and B: New cytotoxic depsipeptides from a Brazilian ascidian of the family Didemnidae
20. 2]-modified didemnin B from the tunicate Trididemnum cyanophorum
21. Defense of ascidians and their conspicuous larvae: Adult versus larval chemical defenses
22. Didemnin B. The first marine compound entering clinical trials as an antineoplastic agent
23. Inhibition of RNA viruses in vitro and in Rift Valley Fever-Infected Mice by didemnins A and B
24. Antitumor activity of didemnin B in the human tumor stem cell assay
25. Didemnin A inhibits the in vitro replication of dengue virus types 1, 2, and 3
26. Antiviral and antitumor compounds from tunicates
27. Didemnins A and B. Effectiveness against cutaneous herpes simplex virus in mice
28. Treatment of rabies in mice and foxes with antiviral compounds
29. Mechanism of action of didemnin B, a depsipeptide from the sea
30. In vivo effect of Didemnin B on two tumors of the rat
31. Application of a new preclinical drug screening system for cancer of the large bowel
32. Dual effects of nordidemnin on WRK1 Cells: Inhibition of phosphoinositide metabolism and cell proliferation
33. Antiproliferative effect of dehydrodidemnin B (DDB), a depsipeptide isolated from Mediterranean tunicates
34. Effect of dehydrodidemnin B on human colon carcinoma cell lines
35. Macrocyclic immunomodulators
36. Chemistry and biology of the immunophilins and their immunosuppressive ligands
37. Molecular recognition of immunophiklins and immunophilin-ligand complexes
38. Natural products as probes of cellular function: Studies of immunophilins
39. The cell cycle, signal transduction, and immunophilin-ligand complexes
40. Synthesis, structure, and mechanism in immunophilin research
41. Didemnin B: A new immunosuppressive cyclic peptide with potent activity in vitro and in vivo
42. Didemnin B: An immunosuppressive cyclic peptide that stimulates murine antibody responses in vivo and in vitro
43. Inhibition of T-lymphocyte proliferation by the cyclic polypeptide didemnin B: No inhibition of lymphokine stimulation
44. Mechanism of protein synthesis inhibition by didemnin B in vitro
45. Didemnin B prolongs rat heart allograft survival
46. Efficacy of didemnin B in suppressing allograft rejection in mice and rats
47. The effect of two new immunosuppressive agents, FK506 and didemnin B, in murine pregnancy
48. A comparison of the inhibitory effects of immunosuppressive agents cyclosporine, tetranactin, and didemnin B on human T cell responses in vitro
49. Prolongation of skin allograft survival in mice by didemnin B
50. Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill
51. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assay
52. Synthesis of new didemnin B analogs for investigations of structure/biological activity relationships
53. Phase I clinical and pharmacokinetic investigation of didemnin B, a cyclic depsipeptide
54. Phase I/II clinical trial of didemnin B in non-small-cell lung cancer: Neuromuscular toxicity is dose-limiting
55. A phase I clinical trial of didemnin B
56. Phase I clinical study of didemnin B
57. A phase II trial of didemnin B in patients with previously treated epithelial ovarian cancer
58. Phase II clinical trial of didemnin B in previously treated small cell lung cancer
59. Didemnin B in favorable histology non-Hodgkin's lymphoma: A phase II study of the national cancer institute of canada clinical trials group
60. A phase II study of Didemnin B (NSC 325319) in advanced malignant melanoma: An eastern cooperative oncology group study (PB687)
61. A phase II trial of didemnin B (NSC #335319) in patients with advanced squamous cell carcinoma of the cervix: A gynecologic oncology group study
62. Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides
63. Total synthesis of the didemnins-I. Synthesis of the peptolide ring
64. Total synthesis of the didemnins-II. Synthesis of didemnin A, B, C, and prolyldidemnin A
65. Total synthesis of the didemnins; III. Synthesis of protected (2R, 3S)-Alloisoleucine and (3S, 4R, 5S)-isostatine derivatives-amino acids from hydroxy acids
66. Total synthesis of the didemnins; IV. Synthesis of the peptolide ring and construction of the side chain
67. 5] Didemnin B
68. Efficient total synthesis of didemnins A and B
69. Total synthesis and structural investigations of didemnins A, B, and C
70. Total syntheses and biological investigations of tamandarins A and B, and tamandarin A analogs
71. The first total synthesis of (-)-tamandarin A
72. 2]Didemnin M
73. Total synthesis of tamandarin B
74. Synthesis of the cyclodepsipeptide nordidemnin B, a cytotoxic minor product isolated from the sea tunicate Trididemnum cyanophorum
75. An improved synthesis of β-keto ester units in didemnins, using 2,2′-carbonyl-Bis(3,5-diazo-4-methyl-1,2,4-oxadiazolidine)
76. Total synthesis of dehydrodidemnin B. Use of uronium and phosphonium salt coupling reagents in peptide synthesis in solution
77. Applications of fast atom bombardment mass spectrometry
78. Synthetic studies of didemnins. I. Revision of the stereochemistry of the hydroxyisovalerylpropionyl (HIP) unit
79. 13C NMR spectroscopy
80. Assignment of proton and carbon NMR signals of didemnin A in solution
81. The complete spectral assignment of didemnin B and nordidemnin B
82. Crystal and molecular structure of didemnin A, an antiviral depsipeptide
83. The cyclic depsipeptide backbone of the didemnins
84. Conformational analysis of didemnins. A multidisciplinary approach by means of X-ray, NMR, molecular dynamics, and molecular mechanics techniques
85. 7] Didemnin B determined by NMR spectroscopy and refined by MD calculation
86. Conformational analysis of dehydrodidemnin B (Aplidine) by NMR spectroscopy and molecular mechanics/dynamics calculations
87. Synthesis and cytostatic activities of Didemnin derivatives
88. Regulation of protein synthesis by antitumor peptides
89. Structure-activity relationships of sidechain modified didemnins
90. A specific binding site in Nb2 Node lymphoma cells mediates the effects of didemnin B, an immunosuppressive cyclic peptide
91. Synthetic routes to a constrained ring analog of didemnin B
92. Stereoselective synthesis of a conformationally restricted β-hydroxy-γ-amino acid
93. Total synthesis of a conformationally constrained Didemnin B analog
94. 5] didemnin B
95. 5]-didemnin B
96. A simple method for displaying the hydropathic character of a protein
97. Structure-activity relationships of the didemnins
98. Understanding and controlling the cell cycle with natural products
99. Biochemical and cellular effects of didemnins A and B
100. Prolactin-dependent mitogenesis in Nb 2 node lymphoma cells: Effects of immunosuppressive cyclopeptides
101. Multiwavelength videomicrofluorometric study of cytotoxic properties of a marine peptide, didemnin B, using adriamycin as reference compound
102. Multiwavelength videomicrofluorometric study of cytotoxic effects of a marine peptide, didemnin B, on normal and MDR resistant CCRF-CEM cell lines
103. In vitro distribution of diacetyl didemnin B in human blood cells and plasma
104. Inhibition of protein synthesis by didemnins: Cell potency and SAR
105. Inhibition of protein synthesis by didemnin B is not sufficient to induce apoptosis in human mammary carcinoma (MCF7) cells
106. Didemnin B inhibits biological effects of tumor promoting phorbol esters on mouse skin, as well as phosphorylation of a 100 kD protien in mouse epidermis cytosol
107. The immunosuppressant FK-506, like cyclosporins and didemnin B, inhibits calmodulin-dependent phosphorylation of the elongation factor 2 in vitro and biological effects of the phorbol ester TPA on mouse skin in vivo
108. GTP-dependent binding of the antiproliferative agent didemnin to elongation factor 1α
109. Didemnin B inhibits polypeptide elongation in cell-free translation systems
110. Inhibition of protein synthesis by didemnin B: How EF-1α mediates inhibition of translocation
111. Further evidence that elongation factor 1 remains bound to ribosomes during peptide chain elongation
112. A new concept of the function of elongation factor 1 in peptide chain elongation
113. Characterization of the elongation factors from calf brain. 3. Propeties of the GTPase activity of EF-1α and mode of action of kirromycin
114. Didemnin binds to the protein palmitoyl thioesterase responsible for infantile neuronal ceroid lipofuscinosis
115. The antiproliferative agent didemnin B uncompetitively inhibits palmitoyl protein thioesterase
116. Didemnin B induces cell death by apoptosis: The fastest induction of apoptosis ever described
117. Apoptosis and disease: Regulation and clinical relevance of programmed cell death
118. Apoptosis, p53 and tumor cell sensitivity to anticancer agents
119. Protein tyrosine kinase inhibitors prevent didemnin B-induced apoptosis in HL-60 cells
120. Unspecific activation of caspases during the induction of apoptosis by didemnin B in human cell lines
121. Mitochondrial cytochrome c release is caspasedependent and does not involve mitochondrial permeability transition in didemnin B-induced apoptosis
122. Rapamycin inhibits Didemnin B-induced apoptosis in human HL-60 Cells: Evidence for the possible involvement of FK506-binding protein 25
123. Effect of Nordidemnin on the cell cycle of sea urchin embryos. Role in synthesis and phosphorylation of proteins and in polyphosphoinositide rurnover in mitosis progression
124. A new paclitaxel photoaffinity analog with a 3-(4-benzoylphenyl)propanoyl probe for characterization of drugbinding sites on tubulin and P-Glycoprotein
125. Benzophenone photophores in biochemistry
126. Chemical reagents in photoaffinity labeling
127. Synthesis and biological evaluation of didemnin photoaffinity analogs
128. Some practical considerations and applications of the National Cancer Institute in vitro Anticancer Drug Discovery Screen
129. 3]didemnins as potential affinity ligands
130. Fluorescent taxoids
131. First total synthesis of a fluorescent didemnin
132. Total syntheses and biological investigations of tamandarin compounds