Literature DB >> 1454834

Additional antitumor ecteinascidins from a Caribbean tunicate: crystal structures and activities in vivo.

R Sakai1, K L Rinehart, Y Guan, A H Wang.   

Abstract

Ecteinascidins (Ets), isolated from the Caribbean tunicate Ecteinascidia turbinata, protect mice in vivo against P388 lymphoma, B16 melanoma, M5076 ovarian sarcoma, Lewis lung carcinoma, and the LX-1 human lung and MX-1 human mammary carcinoma xenografts. Crystal structures of two tris(tetrahydroisoquinoline) Ets were investigated with single crystals of the 21-O-methyl-N12-formyl derivative of Et 729 and the natural N12-oxide of Et 743. Representatives of an additional class of Ets, Et 722 and Et 736, isolated from the same organism, were assigned tetrahydro-beta-carboline-substituted bis(tetrahydroisoquinoline) structures by NMR and fast atom bombardment MS spectra.

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Year:  1992        PMID： 1454834      PMCID： PMC50570          DOI： 10.1073/pnas.89.23.11456

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  11 in total

Review 1.  Bioactive compounds from aquatic and terrestrial sources.

Authors:  K L Rinehart; T G Holt; N L Fregeau; P A Keifer; G R Wilson; T J Perun; R Sakai; A G Thompson; J G Stroh; L S Shield
Journal:  J Nat Prod       Date:  1990 Jul-Aug       Impact factor: 4.050

2.  Facile formation of a crosslinked adduct between DNA and the daunorubicin derivative MAR70 mediated by formaldehyde: molecular structure of the MAR70-d(CGTnACG) covalent adduct.

Authors:  Y G Gao; Y C Liaw; Y K Li; G A van der Marel; J H van Boom; A H Wang
Journal:  Proc Natl Acad Sci U S A       Date:  1991-06-01       Impact factor: 11.205

3.  Mode of action of saframycin A, a novel heterocyclic quinone antibiotic. Inhibition of RNA synthesis in vivo and in vitro.

Authors:  K Ishiguro; S Sakiyama; K Takahashi; T Arai
Journal:  Biochemistry       Date:  1978-06-27       Impact factor: 3.162

4.  Formaldehyde cross-links daunorubicin and DNA efficiently: HPLC and X-ray diffraction studies.

Authors:  A H Wang; Y G Gao; Y C Liaw; Y K Li
Journal:  Biochemistry       Date:  1991-04-23       Impact factor: 3.162

5.  DNA sequence specificity of the pyrrolo[1,4]benzodiazepine antitumor antibiotics. Methidiumpropyl-EDTA-iron(II) footprinting analysis of DNA binding sites for anthramycin and related drugs.

Authors:  R P Hertzberg; S M Hecht; V L Reynolds; I J Molineux; L H Hurley
Journal:  Biochemistry       Date:  1986-03-25       Impact factor: 3.162

6.  Mode of action of saframycin antitumor antibiotics: sequence selectivities in the covalent binding of saframycins A and S to deoxyribonucleic acid.

Authors:  K E Rao; J W Lown
Journal:  Chem Res Toxicol       Date:  1990 May-Jun       Impact factor: 3.739

7.  The in vitro interaction of naphthyridinomycin with deoxyribonucleic acids.

Authors:  M J Zmijewski; K Miller-Hatch; M Mikolajczak
Journal:  Chem Biol Interact       Date:  1985-01       Impact factor: 5.192

8.  Molecular mechanisms of binding and single-strand scission of deoxyribonucleic acid by the antitumor antibiotics saframycins A and C.

Authors:  J W Lown; A V Joshua; J S Lee
Journal:  Biochemistry       Date:  1982-02-02       Impact factor: 3.162

9.  Molecular structure, conformation and interactions of antitumor antibiotic cyanonaphthridinomycin, a covalent binder of DNA.

Authors:  S K Arora; M B Cox
Journal:  J Biomol Struct Dyn       Date:  1988-12

10.  Naphthyridinomycin-DNA adducts: a molecular modeling study.

Authors:  M B Cox; P Arjunan; S K Arora
Journal:  J Antibiot (Tokyo)       Date:  1991-08       Impact factor: 2.649
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  18 in total

1.  Poisoning of human DNA topoisomerase I by ecteinascidin 743, an anticancer drug that selectively alkylates DNA in the minor groove.

Authors:  Y Takebayashi; P Pourquier; A Yoshida; G Kohlhagen; Y Pommier
Journal:  Proc Natl Acad Sci U S A       Date:  1999-06-22       Impact factor: 11.205

2.  Interference of transcriptional activation by the antineoplastic drug ecteinascidin-743.

Authors:  M Minuzzo; S Marchini; M Broggini; G Faircloth; M D'Incalci; R Mantovani
Journal:  Proc Natl Acad Sci U S A       Date:  2000-06-06       Impact factor: 11.205

Review 3.  Drug development from marine natural products.

Authors:  Tadeusz F Molinski; Doralyn S Dalisay; Sarah L Lievens; Jonel P Saludes
Journal:  Nat Rev Drug Discov       Date:  2008-12-19       Impact factor: 84.694

Review 4.  Ecteinascidins. A review of the chemistry, biology and clinical utility of potent tetrahydroisoquinoline antitumor antibiotics.

Authors:  V H Le; M Inai; R M Williams; T Kan
Journal:  Nat Prod Rep       Date:  2015-02       Impact factor: 13.423

Review 5.  Life in cellulose houses: symbiotic bacterial biosynthesis of ascidian drugs and drug leads.

Authors:  Eric W Schmidt; Mohamed S Donia
Journal:  Curr Opin Biotechnol       Date:  2010-11-01       Impact factor: 9.740

6.  Phthalascidin, a synthetic antitumor agent with potency and mode of action comparable to ecteinascidin 743.

Authors:  E J Martinez; T Owa; S L Schreiber; E J Corey
Journal:  Proc Natl Acad Sci U S A       Date:  1999-03-30       Impact factor: 11.205

Review 7.  Enriching cancer pharmacology with drugs of marine origin.

Authors:  Paula C Jimenez; Diego V Wilke; Paola C Branco; Anelize Bauermeister; Paula Rezende-Teixeira; Susana P Gaudêncio; Leticia V Costa-Lotufo
Journal:  Br J Pharmacol       Date:  2019-12-23       Impact factor: 8.739

Review 8.  Ewing's sarcoma: standard and experimental treatment options.

Authors:  Vivek Subbiah; Pete Anderson; Alexander J Lazar; Emily Burdett; Kevin Raymond; Joseph A Ludwig
Journal:  Curr Treat Options Oncol       Date:  2009-06-17

9.  Replication and homologous recombination repair regulate DNA double-strand break formation by the antitumor alkylator ecteinascidin 743.

Authors:  Daniele Grazziotin Soares; Alexandre E Escargueil; Virginie Poindessous; Alain Sarasin; Aimery de Gramont; Diego Bonatto; João Antonio Pêgas Henriques; Annette K Larsen
Journal:  Proc Natl Acad Sci U S A       Date:  2007-07-26       Impact factor: 11.205

10.  Von Hippel-Lindau-coupled and transcription-coupled nucleotide excision repair-dependent degradation of RNA polymerase II in response to trabectedin.

Authors:  Gregory J Aune; Kazutaka Takagi; Olivier Sordet; Josée Guirouilh-Barbat; Smitha Antony; Vilhelm A Bohr; Yves Pommier
Journal:  Clin Cancer Res       Date:  2008-10-15       Impact factor: 12.531
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