Literature DB >> 21539315

Antineoplastic agents. 590. X-ray crystal structure of dolastatin 16 and syntheses of the dolamethylleuine and dolaphenvaline units.

George R Pettit1, Thomas H Smith, Jun-Ping Xu, Delbert L Herald, Erik J Flahive, Collin R Anderson, Paul E Belcher, John C Knight.   

Abstract

Three advances necessary to bring dolastatin 16 (1) into full-scale preclinical development as an anticancer drug have been accomplished. The X-ray crystal structure of dolastatin 16 has been solved, which allowed stereoselective syntheses of its two new amino acid units, dolamethylleuine (Dml) and dolaphenvaline (Dpv), to be completed. The X-ray crystal structures of synthetic Z-Dml and TFA-Dpv have also been completed.

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Year:  2011        PMID： 21539315      PMCID： PMC3111978          DOI： 10.1021/np100877h

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  18 in total

1.  Isolation of four new cyclic depsipeptides, antanapeptins A-D, and dolastatin 16 from a Madagascan collection of Lyngbya majuscula.

Authors:  Lisa M Nogle; William H Gerwick
Journal:  J Nat Prod       Date:  2002-01       Impact factor: 4.050

2.  Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa.

Authors:  Junji Kimura; Yuuki Takada; Tomoko Inayoshi; Yoichi Nakao; Gilles Goetz; Wesley Y Yoshida; Paul J Scheuer
Journal:  J Org Chem       Date:  2002-03-22       Impact factor: 4.354

3.  Isolation of dolastatin 10 from the marine cyanobacterium Symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1.

Authors:  H Luesch; R E Moore; V J Paul; S L Mooberry; T H Corbett
Journal:  J Nat Prod       Date:  2001-07       Impact factor: 4.050

4.  Asymmetric chelated Claisen rearrangements in the presence of chiral ligands--scope and limitations.

Authors:  Uli Kazmaier; Heike Mues; Achim Krebs
Journal:  Chemistry       Date:  2002-04-15       Impact factor: 5.236

5.  Effect of auristatin PHE on microtubule integrity and nuclear localization in Cryptococcus neoformans.

Authors:  Tanja Woyke; Robert W Roberson; George R Pettit; Günther Winkelmann; Robin K Pettit
Journal:  Antimicrob Agents Chemother       Date:  2002-12       Impact factor: 5.191

6.  Somamides A and B, two new depsipeptide analogues of dolastatin 13 from a Fijian cyanobacterial assemblage of Lyngbya majuscula and Schizothrix species.

Authors:  L M Nogle; R T Williamson; W H Gerwick
Journal:  J Nat Prod       Date:  2001-06       Impact factor: 4.050

7.  Potentiation of the activity of cisplatin in a human colon tumour xenograft model by auristatin PYE, a structural modification of dolastatin 10.

Authors:  Ekatherine M Prokopiou; Patricia A Cooper; George R Pettit; Michael C Bibby; Steven D Shnyder
Journal:  Mol Med Rep       Date:  2010 Mar-Apr       Impact factor: 2.952

8.  Total synthesis of epothilones B and D: stannane equivalents for beta-keto ester dianions.

Authors:  Gary E Keck; Robert L Giles; Victor J Cee; Carrie A Wager; Tao Yu; Matthew B Kraft
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

9.  Isolation, structure determination, and biological activity of dolastatin 12 and lyngbyastatin 1 from Lyngbya majuscula/Schizothrix calcicola cyanobacterial assemblages.

Authors:  G G Harrigan; W Y Yoshida; R E Moore; D G Nagle; P U Park; J Biggs; V J Paul; S L Mooberry; T H Corbett; F A Valeriote
Journal:  J Nat Prod       Date:  1998-10       Impact factor: 4.050

10.  Differential gene expression in auristatin PHE-treated Cryptococcus neoformans.

Authors:  Tanja Woyke; Michael E Berens; Dominique B Hoelzinger; George R Pettit; Günther Winkelmann; Robin K Pettit
Journal:  Antimicrob Agents Chemother       Date:  2004-02       Impact factor: 5.191
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  2 in total

Review 1.  Marine Mollusk-Derived Agents with Antiproliferative Activity as Promising Anticancer Agents to Overcome Chemotherapy Resistance.

Authors:  Maria Letizia Ciavatta; Florence Lefranc; Marianna Carbone; Ernesto Mollo; Margherita Gavagnin; Tania Betancourt; Ramesh Dasari; Alexander Kornienko; Robert Kiss
Journal:  Med Res Rev       Date:  2016-12-07       Impact factor: 12.944

2.  Effective Synthesis and Antifouling Activity of Dolastatin 16 Derivatives.

Authors:  Loida O Casalme; Keisuke Katayama; Yoshiki Hayakawa; Kensuke Nakamura; Arisa Yamauchi; Yasuyuki Nogata; Erina Yoshimura; Fuyuhiko Matsuda; Taiki Umezawa
Journal:  Mar Drugs       Date:  2022-02-04       Impact factor: 5.118
  2 in total

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