Literature DB >> 19419164

The bryostatin 1 A-ring acetate is not the critical determinant for antagonism of phorbol ester-induced biological responses.

Gary E Keck1, Wei Li, Matthew B Kraft, Noemi Kedei, Nancy E Lewin, Peter M Blumberg.   

Abstract

The contribution of the A-ring C(7) acetate to the function of bryostatin 1 has been investigated through synthesis and biological evaluation of an analogue incorporating this feature into the bryopyran core structure. No enhanced binding affinity for protein kinase C (PKC) was observed, relative to previously characterized analogues lacking the C(7) acetate. Functional assays showed biological responses characteristic of those induced by the phorbol ester PMA and distinctly different from those observed with bryostatin 1.

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Year:  2009        PMID： 19419164      PMCID： PMC3075950          DOI： 10.1021/ol900585t

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


  17 in total

Review 1.  The protein kinase complement of the human genome.

Authors:  G Manning; D B Whyte; R Martinez; T Hunter; S Sudarsanam
Journal:  Science       Date:  2002-12-06       Impact factor: 47.728

2.  The practical synthesis of a novel and highly potent analogue of bryostatin.

Authors:  Paul A Wender; Jeremy L Baryza; Chad E Bennett; F Christopher Bi; Stacey E Brenner; Michael O Clarke; Joshua C Horan; Cindy Kan; Emmanuel Lacôte; Blaise Lippa; Peter G Nell; Tim M Turner
Journal:  J Am Chem Soc       Date:  2002-11-20       Impact factor: 15.419

Review 3.  Protein kinase C as a therapeutic target.

Authors:  Beverly A Teicher
Journal:  Clin Cancer Res       Date:  2006-09-15       Impact factor: 12.531

4.  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

5.  Targeting protein kinase C and "non-kinase" phorbol ester receptors: emerging concepts and therapeutic implications.

Authors:  Marcelo G Kazanietz
Journal:  Biochim Biophys Acta       Date:  2005-09-12

Review 6.  Protein kinase C and the development of diabetic vascular complications.

Authors:  K J Way; N Katai; G L King
Journal:  Diabet Med       Date:  2001-12       Impact factor: 4.359

7.  The in vivo effect of bryostatin-1 on paclitaxel-induced tumor growth, mitotic entry, and blood flow.

Authors:  J A Koutcher; M Motwani; K L Zakian; X K Li; C Matei; J P Dyke; D Ballon; H H Yoo; G K Schwartz
Journal:  Clin Cancer Res       Date:  2000-04       Impact factor: 12.531

8.  Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters.

Authors:  M Castagna; Y Takai; K Kaibuchi; K Sano; U Kikkawa; Y Nishizuka
Journal:  J Biol Chem       Date:  1982-07-10       Impact factor: 5.157

9.  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

10.  Divergent effects of bryostatin 1 and phorbol myristate acetate on cell cycle arrest and maturation in human myelomonocytic leukemia cells (U937).

Authors:  J A Vrana; A M Saunders; S P Chellappan; S Grant
Journal:  Differentiation       Date:  1998-05       Impact factor: 3.880
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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.  Total synthesis of bryostatin 1.

Authors:  Gary E Keck; Yam B Poudel; Thomas J Cummins; Arnab Rudra; Jonathan A Covel
Journal:  J Am Chem Soc       Date:  2010-12-22       Impact factor: 15.419

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 Several Bryostatin Analogues Bearing a Diacylglycerol Lactone C-Ring.

Authors:  David O Baumann; Kevin M McGowan; Noemi Kedei; Megan L Peach; Peter M Blumberg; Gary E Keck
Journal:  J Org Chem       Date:  2016-08-23       Impact factor: 4.354

6.  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

7.  Total synthesis of bryostatin 9.

Authors:  Paul A Wender; Adam J Schrier
Journal:  J Am Chem Soc       Date:  2011-05-27       Impact factor: 15.419

8.  The quest for supernatural products: the impact of total synthesis in complex natural products medicinal chemistry.

Authors:  Zhi-Chen Wu; Dale L Boger
Journal:  Nat Prod Rep       Date:  2020-11-10       Impact factor: 13.423

9.  Comparison of transcriptional response to phorbol ester, bryostatin 1, and bryostatin analogs in LNCaP and U937 cancer cell lines provides insight into their differential mechanism of action.

Authors:  N Kedei; A Telek; A M Michalowski; M B Kraft; W Li; Y B Poudel; A Rudra; M E Petersen; G E Keck; P M Blumberg
Journal:  Biochem Pharmacol       Date:  2012-11-09       Impact factor: 5.858

10.  Evaluation of Chromane-Based Bryostatin Analogues Prepared via Hydrogen-Mediated C-C Bond Formation: Potency Does Not Confer Bryostatin-like Biology.

Authors:  John M Ketcham; Ivan Volchkov; Te-Yu Chen; Peter M Blumberg; Noemi Kedei; Nancy E Lewin; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-09-27       Impact factor: 15.419
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