Literature DB >> 18588309

The design, synthesis, and evaluation of C7 diversified bryostatin analogs reveals a hot spot for PKC affinity.

Paul A Wender1, Vishal A Verma.   

Abstract

The first series of systematically varied C7-functionalized bryostatin analogs (12 members in all) have been synthesized through an efficient and convergent route. A new hotspot for PKC affinity, not present in the natural products, has been discovered, allowing for affinity control and potentially for selective regulation of PKC isozymes. Several analogs exhibit single-digit nanomolar affinity to PKC and display superior activity compared to bryostatin against the leukemia cell line K562.

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Year:  2008        PMID： 18588309      PMCID： PMC2730840          DOI： 10.1021/ol801235h

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  26 in total

1.  Design, synthesis, and biological evaluation of a potent, PKC selective, B-ring analog of bryostatin.

Authors:  Paul A Wender; Vishal A Verma
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

2.  Identification of the putative bryostatin polyketide synthase gene cluster from "Candidatus Endobugula sertula", the uncultivated microbial symbiont of the marine bryozoan Bugula neritina.

Authors:  Sebastian Sudek; Nicole B Lopanik; Laura E Waggoner; Mark Hildebrand; Christine Anderson; Haibin Liu; Amrish Patel; David H Sherman; Margo G Haygood
Journal:  J Nat Prod       Date:  2007-01       Impact factor: 4.050

3.  A structural basis for enhancement of long-term associative memory in single dendritic spines regulated by PKC.

Authors:  Jarin Hongpaisan; Daniel L Alkon
Journal:  Proc Natl Acad Sci U S A       Date:  2007-12-04       Impact factor: 11.205

4.  A multi-center phase II study of sequential paclitaxel and bryostatin-1 (NSC 339555) in patients with untreated, advanced gastric or gastroesophageal junction adenocarcinoma.

Authors:  Jaffer A Ajani; Yixing Jiang; Josephine Faust; Baochong B Chang; Linus Ho; James C Yao; Steven Rousey; Shaker Dakhil; Richard C Cherny; Catherine Craig; Archie Bleyer
Journal:  Invest New Drugs       Date:  2006-07       Impact factor: 3.850

5.  Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.

Authors:  Gary E Keck; Jonathan A Covel; Tobias Schiff; Tao Yu
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

6.  Effect of CD40 ligand and other immunomodulators on Pneumocystis carinii infection in rat model.

Authors:  H S Oz; W T Hughes; J E Rehg; E K Thomas
Journal:  Microb Pathog       Date:  2000-09       Impact factor: 3.738

Review 7.  Function-oriented synthesis, step economy, and drug design.

Authors:  Paul A Wender; Vishal A Verma; Thomas J Paxton; Thomas H Pillow
Journal:  Acc Chem Res       Date:  2007-12-27       Impact factor: 22.384

8.  Therapeutic effects of PKC activators in Alzheimer's disease transgenic mice.

Authors:  René Etcheberrigaray; Mathew Tan; Ilse Dewachter; Cuno Kuipéri; Ingrid Van der Auwera; Stefaan Wera; Lixin Qiao; Barry Bank; Thomas J Nelson; Alan P Kozikowski; Fred Van Leuven; Daniel L Alkon
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-19       Impact factor: 11.205

9.  Potent cytotoxins produced by a microbial symbiont protect host larvae from predation.

Authors:  Nicole Lopanik; Niels Lindquist; Nancy Targett
Journal:  Oecologia       Date:  2004-01-28       Impact factor: 3.225

10.  Modulation of resistance to ara-C by bryostatin in fresh blast cells from patients with AML.

Authors:  A W Elgie; J M Sargent; P Alton; G J Peters; P Noordhuis; C J Williamson; C G Taylor
Journal:  Leuk Res       Date:  1998-04       Impact factor: 3.156
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  19 in total

1.  Translating Nature's Library: The Bryostatins and Function-Oriented Synthesis.

Authors:  Paul A Wender; Brian A Loy; Adam J Schrier
Journal:  Isr J Chem       Date:  2011-03-24       Impact factor: 3.333

2.  Substitution on the A-ring confers to bryopyran analogues the unique biological activity characteristic of bryostatins and distinct from that of the phorbol esters.

Authors:  Gary E Keck; Yam B Poudel; Dennie S Welch; Matthew B Kraft; Anh P Truong; Jeffrey C Stephens; Noemi Kedei; Nancy E Lewin; Peter M Blumberg
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

3.  Total synthesis of bryostatin 16 using a Pd-catalyzed diyne coupling as macrocyclization method and synthesis of C20-epi-bryostatin 7 as a potent anticancer agent.

Authors:  Barry M Trost; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2010-11-02       Impact factor: 15.419

4.  Design, synthesis, and evaluation of potent bryostatin analogs that modulate PKC translocation selectivity.

Authors:  Paul A Wender; Jeremy L Baryza; Stacey E Brenner; Brian A DeChristopher; Brian A Loy; Adam J Schrier; Vishal A Verma
Journal:  Proc Natl Acad Sci U S A       Date:  2011-03-17       Impact factor: 11.205

5.  Synthesis and Biological Evaluation of Fluorescent Bryostatin Analogues.

Authors:  Thomas J Cummins; Noemi Kedei; Agnes Czikora; Nancy E Lewin; Sharon Kirk; Mark E Petersen; Kevin M McGowan; Jin-Qiu Chen; Xiaoling Luo; Randall C Johnson; Sarangan Ravichandran; Peter M Blumberg; Gary E Keck
Journal:  Chembiochem       Date:  2018-03-25       Impact factor: 3.164

6.  The synthetic bryostatin analog Merle 23 dissects distinct mechanisms of bryostatin activity in the LNCaP human prostate cancer cell line.

Authors:  Noemi Kedei; Andrea Telek; Alexandra Czap; Emanuel S Lubart; Gabriella Czifra; Dazhi Yang; Jinqiu Chen; Tyler Morrison; Paul K Goldsmith; Langston Lim; Poonam Mannan; Susan H Garfield; Matthew B Kraft; Wei Li; Gary E Keck; Peter M Blumberg
Journal:  Biochem Pharmacol       Date:  2011-03-30       Impact factor: 5.858

7.  Total synthesis of bryostatin 7 via C-C bond-forming hydrogenation.

Authors:  Yu Lu; Sang Kook Woo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-08-11       Impact factor: 15.419

8.  A cellular model of Alzheimer's disease therapeutic efficacy: PKC activation reverses Abeta-induced biomarker abnormality on cultured fibroblasts.

Authors:  Tapan K Khan; Thomas J Nelson; Vishal A Verma; Paul A Wender; Daniel L Alkon
Journal:  Neurobiol Dis       Date:  2009-02-20       Impact factor: 5.996

9.  Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches.

Authors:  Barry M Trost; Guangbin Dong
Journal:  Nature       Date:  2008-11-27       Impact factor: 49.962

10.  Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.

Authors:  Yu Lu; Michael J Krische
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005
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