메뉴 건너뛰기




Volumn 39, Issue 14, 1996, Pages 2819-2834

Structure-activity relationships of the didemnins

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; DIDEMNIN A; DIDEMNIN B; DIHYDROFOLATE REDUCTASE INHIBITOR; DNA POLYMERASE; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); GYRASE INHIBITOR; IMMUNOSUPPRESSIVE AGENT; RNA POLYMERASE; THYMIDYLATE SYNTHASE;

EID: 8944252332     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960048g     Document Type: Article
Times cited : (149)

References (63)
  • 4
    • 0019470678 scopus 로고
    • Structures of the Didemnins, Antiviral and Cytotoxic Depsipeptides from a Caribbean Tunicate
    • (a) Rinehart, K. L., Jr.; Gloer, J. B.; Cook, J. C., Jr.; Mizsak, S. A.; Scahill, T. A. Structures of the Didemnins, Antiviral and Cytotoxic Depsipeptides from a Caribbean Tunicate. J. Am. Chem. Soc. 1981, 103, 1857-1859.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 1857-1859
    • Rinehart Jr., K.L.1    Gloer, J.B.2    Cook Jr., J.C.3    Mizsak, S.A.4    Scahill, T.A.5
  • 7
    • 4243649195 scopus 로고
    • (c) Rinehart, K. L., Jr. Didemnins A, B, C, and Derivatives Thereof as Antiviral Agents. U.S. Patent 4,493,796, Jan 15, 1985; Chem. Abstr. 1985, 103, 76241v.
    • (1985) Chem. Abstr. , vol.103
  • 9
    • 4244053650 scopus 로고
    • Ph.D. Thesis, University of Illinois, Urbana
    • (a) Gloer, J. B. Structures of the Didemnins. Ph.D. Thesis, University of Illinois, Urbana, 1983; Chem. Abstr. 1984, 101, 122692b; Diss. Abstr. Int. B 1984, 45, 188-189.
    • (1983) Structures of the Didemnins
    • Gloer, J.B.1
  • 10
    • 8944257629 scopus 로고
    • (a) Gloer, J. B. Structures of the Didemnins. Ph.D. Thesis, University of Illinois, Urbana, 1983; Chem. Abstr. 1984, 101, 122692b; Diss. Abstr. Int. B 1984, 45, 188-189.
    • (1984) Chem. Abstr. , vol.101
  • 11
    • 4244053650 scopus 로고
    • (a) Gloer, J. B. Structures of the Didemnins. Ph.D. Thesis, University of Illinois, Urbana, 1983; Chem. Abstr. 1984, 101, 122692b; Diss. Abstr. Int. B 1984, 45, 188-189.
    • (1984) Diss. Abstr. Int. B , vol.45 , pp. 188-189
  • 14
    • 8944249317 scopus 로고
    • Didemnin and Its Biological Properties
    • Peptides, Chemistry and Biology; Marshall, G. R., Ed.; ESCOM: Leiden, and references therein
    • Rinehart, K. L. Didemnin and Its Biological Properties. In Peptides, Chemistry and Biology; Proc. 10th Am. Peptide Symposium; Marshall, G. R., Ed.; ESCOM: Leiden, 1988; pp 626-631 and references therein.
    • (1988) Proc. 10th Am. Peptide Symposium , pp. 626-631
    • Rinehart, K.L.1
  • 15
    • 0023874315 scopus 로고
    • Didemnins and Tunichlorin: Novel Natural Products from the Marine Tunicate Trididemnum solidum
    • and references therein
    • Rinehart, K. L.; Kishore V.; Bible, K. C.; Sakai, R.; Sullins, D. W.; Li, K.-M. Didemnins and Tunichlorin: Novel Natural Products From the Marine Tunicate Trididemnum solidum. J. Nat. Prod. 1988, 51, 1-21 and references therein.
    • (1988) J. Nat. Prod. , vol.51 , pp. 1-21
    • Rinehart, K.L.1    Kishore, V.2    Bible, K.C.3    Sakai, R.4    Sullins, D.W.5    Li, K.-M.6
  • 16
    • 0023113522 scopus 로고
    • In vivo Effect of Didemnin B on Two Tumors of the Rat
    • Fimiani, V. In vivo Effect of Didemnin B on Two Tumors of the Rat. Oncology 1987, 44, 42-46.
    • (1987) Oncology , vol.44 , pp. 42-46
    • Fimiani, V.1
  • 17
    • 8944236105 scopus 로고
    • NSC 325319. IND. Division of Cancer Treatment, NCI, Bethesda, MD, June
    • (a) National Cancer Institute Clinical Brochure, Didemnin B. NSC 325319. IND. Division of Cancer Treatment, NCI, Bethesda, MD, June 1984.
    • (1984) National Cancer Institute Clinical Brochure, Didemnin B
  • 19
    • 0023745136 scopus 로고
    • Phase I Clinical and Pharmacokinetic Investigation of Didemnin B, a Cyclic Depsipeptide
    • (c) Dorr, F. A.; Kuhn, J. G.; Phillips, J.; Von Hoff, D. D. Phase I Clinical and Pharmacokinetic Investigation of Didemnin B, a Cyclic Depsipeptide. Eur. J. Cancer Clin. Oncol. 1988, 24, 1699-1706.
    • (1988) Eur. J. Cancer Clin. Oncol. , vol.24 , pp. 1699-1706
    • Dorr, F.A.1    Kuhn, J.G.2    Phillips, J.3    Von Hoff, D.D.4
  • 21
    • 0027056934 scopus 로고
    • New Anti-cancer Agents in Phase I/II
    • (e) Queisser, W. New Anti-cancer Agents in Phase I/II. Onkologie 1992, 15, 454-462.
    • (1992) Onkologie , vol.15 , pp. 454-462
    • Queisser, W.1
  • 22
    • 0027452805 scopus 로고
    • A Phase II Trial of Didemnin B (NSC #325319) in Patients with Previously Treated Epithelial Ovarian Cancer. A Gynecologic Oncology Group Study
    • (f) Malfetano, J. H.; Blessing, J. A.; Jacobs, A. J. A Phase II Trial of Didemnin B (NSC #325319) in Patients with Previously Treated Epithelial Ovarian Cancer. A Gynecologic Oncology Group Study. Am. J. Clin. Oncol. 1993, 16, 47-49.
    • (1993) Am. J. Clin. Oncol. , vol.16 , pp. 47-49
    • Malfetano, J.H.1    Blessing, J.A.2    Jacobs, A.J.3
  • 23
    • 0009685301 scopus 로고
    • Didemnin B. NSC 325319. IND 24505. Division of Cancer Treatment, NCI, Bethesda, MD, August
    • Annual Report to the Food and Drug Administration. Didemnin B. NSC 325319. IND 24505. Division of Cancer Treatment, NCI, Bethesda, MD, August 1994.
    • (1994) Annual Report to the Food and Drug Administration
  • 25
    • 0028300782 scopus 로고
    • GTP-dependent Binding of the Antiproliferative Agent Didemnin to Elongation Factor 1α
    • (b) Crews, C. M.; Collins, J. L.; Lane, W. S.; Snapper, M. L.; Schreiber, S. L. GTP-dependent Binding of the Antiproliferative Agent Didemnin to Elongation Factor 1α. J. Biol. Chem. 1994, 269, 15411-15414.
    • (1994) J. Biol. Chem. , vol.269 , pp. 15411-15414
    • Crews, C.M.1    Collins, J.L.2    Lane, W.S.3    Snapper, M.L.4    Schreiber, S.L.5
  • 26
    • 0029114876 scopus 로고
    • Mechanism of Protein-Synthesis Inhibition by Didemnin-B In-vitro
    • (c) SirDeshpande, B. V.; Toogood, P. L. Mechanism of Protein-Synthesis Inhibition by Didemnin-B In-vitro. Biochemistry 1995, 34, 9177-9184.
    • (1995) Biochemistry , vol.34 , pp. 9177-9184
    • SirDeshpande, B.V.1    Toogood, P.L.2
  • 27
    • 0028815543 scopus 로고
    • Didemnin-B Induces Cell-Death by Apoptosis-The Fastest Induction of Apoptosis Ever Described
    • (d) Grubb, D. R.; Wolvetang, E. J.; Lowen, A. Didemnin-B Induces Cell-Death by Apoptosis-The Fastest Induction of Apoptosis Ever Described. Biochem. Biophys. Res. Commun. 1995, 215, 1130-1136.
    • (1995) Biochem. Biophys. Res. Commun. , vol.215 , pp. 1130-1136
    • Grubb, D.R.1    Wolvetang, E.J.2    Lowen, A.3
  • 28
    • 0021079226 scopus 로고
    • Didemnins A and B. Effectiveness Against Cutaneous Herpes simplex Virus in Mice
    • Weed, S. D.; Stringfellow, D. A. Didemnins A and B. Effectiveness Against Cutaneous Herpes simplex Virus in Mice. Antiviral Res. 1983, 3, 269-274.
    • (1983) Antiviral Res. , vol.3 , pp. 269-274
    • Weed, S.D.1    Stringfellow, D.A.2
  • 29
    • 0020461050 scopus 로고
    • Inhibition of RNA Viruses in Vitro and in Rift Valley Fever-Infected Mice by Didemnins A and B
    • Canonico, P. G.; Pannier, W. L.; Huggins, J. W.; Rinehart, K. L., Jr. Inhibition of RNA Viruses in Vitro and in Rift Valley Fever-Infected Mice by Didemnins A and B. Antimicrob. Agents Chemother. 1982, 22, 696-697.
    • (1982) Antimicrob. Agents Chemother. , vol.22 , pp. 696-697
    • Canonico, P.G.1    Pannier, W.L.2    Huggins, J.W.3    Rinehart Jr., K.L.4
  • 30
    • 0021824736 scopus 로고
    • Didemnin B: A New Immunosuppressive Cyclic Peptide with Potent Activity in Vitro and In Vivo
    • Montgomery, D. W.; Zukoski, C. F. Didemnin B: A New Immunosuppressive Cyclic Peptide with Potent Activity in Vitro and In Vivo. Transplantation 1985, 40, 49-56.
    • (1985) Transplantation , vol.40 , pp. 49-56
    • Montgomery, D.W.1    Zukoski, C.F.2
  • 31
    • 0023129614 scopus 로고
    • 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. Didemnin B: An Immunosuppressive Cyclic Peptide that Stimulates Murine Hemagglutinating Antibody Responses and Induces Leukocytosis In Vivo. Transplantation 1987, 43, 133-139.
    • (1987) Transplantation , vol.43 , pp. 133-139
    • Montgomery, D.W.1    Celniker, A.2    Zukoski, C.F.3
  • 32
    • 8944224559 scopus 로고
    • Efficacy of Didemnin B Therapy in Prolonging Cardiac Allograft Survival in Mice and Rats
    • Abstract 9006
    • Yuh, D. D.; Zurcher, B.; Rulifson, E.; Morris, R. E. Efficacy of Didemnin B Therapy in Prolonging Cardiac Allograft Survival in Mice and Rats. FASEB J. 1988, 2, Abstract 9006.
    • (1988) FASEB J. , vol.2
    • Yuh, D.D.1    Zurcher, B.2    Rulifson, E.3    Morris, R.E.4
  • 33
    • 0025970199 scopus 로고
    • Antineoplastic Activity of Didemnin Congeners: Nordidemnin and Modified Chain Analogues
    • Jouin, P.; Poncet, J.; Dufour, M.-N.; Aumelas, A.; Pantaloni, A. Antineoplastic Activity of Didemnin Congeners: Nordidemnin and Modified Chain Analogues. J. Med. Chem. 1991, 34, 486-491.
    • (1991) J. Med. Chem. , vol.34 , pp. 486-491
    • Jouin, P.1    Poncet, J.2    Dufour, M.-N.3    Aumelas, A.4    Pantaloni, A.5
  • 34
  • 35
    • 0027967358 scopus 로고
    • Synthesis of New Didemnin B Analogues for Investigation of Structure/Biological Activity Relationships
    • Mayer, S. C.; Ramanjulu, J.; Vera, M. D.; Pfizenmayer, A. J.; Joullié, M. M. Synthesis of New Didemnin B Analogues for Investigation of Structure/Biological Activity Relationships. J. Org. Chem. 1994, 59, 5192-5205.
    • (1994) J. Org. Chem. , vol.59 , pp. 5192-5205
    • Mayer, S.C.1    Ramanjulu, J.2    Vera, M.D.3    Pfizenmayer, A.J.4    Joullié, M.M.5
  • 36
    • 0028917624 scopus 로고
    • Seven New Didemnins from the Marine Tunicate Trididemnum solidum
    • (a) Sakai, R.; Stroh, J. G.; Sullins, D. W.; Rinehart, K. L. Seven New Didemnins from the Marine Tunicate Trididemnum solidum. J. Am. Chem. Soc. 1995, 117, 3734-3748.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 3734-3748
    • Sakai, R.1    Stroh, J.G.2    Sullins, D.W.3    Rinehart, K.L.4
  • 38
    • 0004034476 scopus 로고
    • (b) Rinehart, K. L. Pharmaceutical Compositions Containing Didemnins. U.S. Patent 5,294,603. Mar. 15,1994; Chem. Abstr. 1994, 121, P887m.
    • (1994) Chem. Abstr. , vol.121
  • 40
    • 0003296257 scopus 로고
    • Rinehart K. L.; Lithgow-Bertelloni, A. M. Novel Antiviral and Cytotoxic Agent. PCT Int. Pat. Appl. WO 91.04985, Apr. 18, 1991; GB Appl. 89/22,026, Sept. 29, 1989; Chem Abstr. 1991, 115, 248086q.
    • (1991) Chem Abstr. , vol.115
  • 41
  • 43
    • 85077634689 scopus 로고
    • The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
    • Mitsunobu, O. The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products. Synthesis 1981, 1-28.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 44
    • 0028353050 scopus 로고
    • The Complete Spectral Assignment of Didemnin H, a New Constituent of the Tunicate Trididemnum Cyanophorum
    • 1,20 we shall retain our previous nomenclature.
    • (1994) Tetrahedron Lett. , vol.25 , pp. 4345-4348
    • Boulanger1
  • 46
    • 0019465788 scopus 로고
    • Synthesis and Biological Effects of Acyclic Pyrimidine Nucleoside Analogues
    • (b) Schroeder, A. C.; Hughes, R. G., Jr.; Bloch, A. Synthesis and Biological Effects of Acyclic Pyrimidine Nucleoside Analogues. J. Med. Chem. 1981, 24, 1078-1083.
    • (1981) J. Med. Chem. , vol.24 , pp. 1078-1083
    • Schroeder, A.C.1    Hughes Jr., R.G.2    Bloch, A.3
  • 47
    • 0021224710 scopus 로고
    • A Novel Antitumor Antibiotic. 3. Mode of Action
    • Tomita, F.; Takahashi, K.; Tamaoki, T. Quinocarcin, A Novel Antitumor Antibiotic. 3. Mode of Action. J. Antibiot. 1984, 37, 1268-1272.
    • (1984) J. Antibiot. , vol.37 , pp. 1268-1272
    • Tomita, F.1    Takahashi, K.2    Quinocarcin, T.T.3
  • 49
    • 0022340594 scopus 로고
    • Camptothecin Induces Protein-linked DNA Breaks via Mammalian DNA Topoisomerase I
    • Hsiang, Y.-H.; Hertzberg, R.; Hecht, S.; Liu, L. F. Camptothecin Induces Protein-linked DNA Breaks via Mammalian DNA Topoisomerase I. J. Biol. Chem. 1985, 260, 14873-14878.
    • (1985) J. Biol. Chem. , vol.260 , pp. 14873-14878
    • Hsiang, Y.-H.1    Hertzberg, R.2    Hecht, S.3    Liu, L.F.4
  • 50
    • 0020492979 scopus 로고
    • Inhibition of Dihydrofolate Reductase: Effect of Reduced Nicotinamide Adenine Dinucleotide Phosphate on the Selectivity and Affinity of Diaminobenzylpyrimidines
    • Baccanari, D. P.; Daluge, S.; King, R. W. Inhibition of Dihydrofolate Reductase: Effect of Reduced Nicotinamide Adenine Dinucleotide Phosphate on the Selectivity and Affinity of Diaminobenzylpyrimidines. Biochemistry 1982, 21, 5068-5075.
    • (1982) Biochemistry , vol.21 , pp. 5068-5075
    • Baccanari, D.P.1    Daluge, S.2    King, R.W.3
  • 51
    • 0015210983 scopus 로고
    • Thymidylate Synthetase from Amethopterin-Resistant Lactobacillus casei
    • Dunlap, R. B.; Harding, N. G. L.; Huennekens, F. M. Thymidylate Synthetase from Amethopterin-Resistant Lactobacillus casei. Biochemistry 1971, 10, 88-97.
    • (1971) Biochemistry , vol.10 , pp. 88-97
    • Dunlap, R.B.1    Harding, N.G.L.2    Huennekens, F.M.3
  • 52
    • 0020375548 scopus 로고
    • Inhibitors of Adenosine Deaminase
    • Agarwal, R. P. Inhibitors of Adenosine Deaminase. Pharmacol. Ther. 1982, 17, 399-429.
    • (1982) Pharmacol. Ther. , vol.17 , pp. 399-429
    • Agarwal, R.P.1
  • 53
    • 0002396942 scopus 로고
    • Analysis of Cytotoxic T Cell Responses
    • Weir, D. M., Ed.; Blackwell Scientific Publications: Boston, Chapter 68
    • Simpson, E.; Chandler, P. Analysis of Cytotoxic T Cell Responses. In Volume 2: Cellular Immunology; Weir, D. M., Ed.; Blackwell Scientific Publications: Boston, 1986; Chapter 68.
    • (1986) Volume 2: Cellular Immunology , vol.2
    • Simpson, E.1    Chandler, P.2
  • 55
    • 0024602364 scopus 로고
    • Conformational Analysis of Didemnins. A Multidisciplinary Approach by Means of X-Ray, NMR, Molecular-Dynamics, and Molecular-Mechanics Techniques
    • Kessler, H.; Will, M.; Antel, J.; Beck, H.; Sheldrick, G. M. Conformational Analysis of Didemnins. A Multidisciplinary Approach by Means of X-Ray, NMR, Molecular-Dynamics, and Molecular-Mechanics Techniques. Helv. Chim. Acta 1989, 72, 530-555.
    • (1989) Helv. Chim. Acta , vol.72 , pp. 530-555
    • Kessler, H.1    Will, M.2    Antel, J.3    Beck, H.4    Sheldrick, G.M.5
  • 56
    • 0023879011 scopus 로고
    • Inhibition of T-Lymphocyte Proliferation by the Cyclic Polypeptide Didemnin B: No Inhibition of Lymphokine Stimulation
    • Lagrue, S. J.; Sheu. T.-L.; Carson, D. D.; Laidlaw, J. L..; Sanduja, S. K. Inhibition of T-Lymphocyte Proliferation by the Cyclic Polypeptide Didemnin B: No Inhibition of Lymphokine Stimulation. Lymphokine Res. 1988, 7, 21-29.
    • (1988) Lymphokine Res. , vol.7 , pp. 21-29
    • Lagrue, S.J.1    Sheu, T.-L.2    Carson, D.D.3    Laidlaw, J.L.4    Sanduja, S.K.5
  • 57
    • 0026575583 scopus 로고
    • Natural Products as Probes of Cellular Function: Studies of Immunophilins
    • Rosen, M. K.; Schreiber, S. L. Natural Products as Probes of Cellular Function: Studies of Immunophilins. Angew. Chem., Int. Ed. Engl. 1992, 31, 384-400.
    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 384-400
    • Rosen, M.K.1    Schreiber, S.L.2
  • 58
    • 0026030568 scopus 로고
    • Chemistry and Biology of the Immunophilins and Their Immunosuppressive Ligands
    • Schreiber, S. L. Chemistry and Biology of the Immunophilins and Their Immunosuppressive Ligands. Science 1991, 251, 283-287.
    • (1991) Science , vol.251 , pp. 283-287
    • Schreiber, S.L.1
  • 59
    • 0015825024 scopus 로고
    • The Involvment of LD-and SD-Region Differences in MLC and CML: A Three-Cell Experiment
    • Schendel, D. J.; Alter, B. J.; Bach, F. H. The Involvment of LD-and SD-Region Differences in MLC and CML: A Three-Cell Experiment. Transplant. Proc. 1973, 5, 1651-1655.
    • (1973) Transplant. Proc. , vol.5 , pp. 1651-1655
    • Schendel, D.J.1    Alter, B.J.2    Bach, F.H.3
  • 60
    • 0024231152 scopus 로고
    • A Simple Screening Procedure for the Quantitative Measurement of Cytotoxicity to Resting Primary Lymphocyte Cultures
    • Faircloth, G. T.; Stewart, D.; Clement, J. J. A Simple Screening Procedure for the Quantitative Measurement of Cytotoxicity to Resting Primary Lymphocyte Cultures. J. Tissue Cult. Meth. 1988, 11, 201-205.
    • (1988) J. Tissue Cult. Meth. , vol.11 , pp. 201-205
    • Faircloth, G.T.1    Stewart, D.2    Clement, J.J.3
  • 61
    • 0002509825 scopus 로고
    • Mitogen-Induced Responses
    • Mishell, B. B., Shiigi, S. M., Eds.; W. H. Freeman: San Francisco, Chapter 6.2
    • Bradley, L. M. Mitogen-Induced Responses. In Selected Methods in Cellular Immunology; Mishell, B. B., Shiigi, S. M., Eds.; W. H. Freeman: San Francisco, 1980; Chapter 6.2, pp 156-161.
    • (1980) Selected Methods in Cellular Immunology , pp. 156-161
    • Bradley, L.M.1
  • 62
    • 0001723343 scopus 로고
    • Graft Versus Host Reactions: Their Natural History and Applicability as Tools of Research
    • Simonsen, M. Graft Versus Host Reactions: Their Natural History and Applicability as Tools of Research. Progr. Allergy 1962, 6, 349-467.
    • (1962) Progr. Allergy , vol.6 , pp. 349-467
    • Simonsen, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.