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Literature DB >> 19113896

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

Gary E Keck¹, Yam B Poudel, Dennie S Welch, Matthew B Kraft, Anh P Truong, Jeffrey C Stephens, Noemi Kedei, Nancy E Lewin, Peter M Blumberg.

Abstract

A close structural analogue of bryostatin 1, which differs from bryostatin 1 only by the absence of the C(30) carbomethoxy group (on the C(13) enoate of the B-ring), has been prepared by total synthesis. Biological assays reveal a crucial role for substitution in the bryostatin 1 A-ring in conferring those responses which are characteristic of bryostatin 1 and distinct from those observed with PMA.

Entities: CellLine Chemical Disease Gene Species

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Year: 2009 PMID： 19113896 PMCID： PMC2647801 DOI： 10.1021/ol8027253

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

23 in total

Review 1. The chemistry and biology of the bryostatin antitumour macrolides.

Authors: Karl J Hale; Marc G Hummersone; Soraya Manaviazar; Mark Frigerio
Journal: Nat Prod Rep Date: 2002-08 Impact factor: 13.423

2. Synthetic studies toward the bryostatins: a substrate-controlled approach to the A-ring.

Authors: Gary E Keck; Dennie S Welch; Paige K Vivian
Journal: Org Lett Date: 2006-08-17 Impact factor: 6.005

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

Authors: Paul A Wender; Vishal A Verma
Journal: Org Lett Date: 2008-06-28 Impact factor: 6.005

4. The addition of bryostatin 1 to cyclophosphamide, doxorubicin, vincristine, and prednisone (CHOP) chemotherapy improves response in a CHOP-resistant human diffuse large cell lymphoma xenograft model.

Authors: R M Mohammad; N R Wall; J A Dutcher; A M Al-Katib
Journal: Clin Cancer Res Date: 2000-12 Impact factor: 12.531

5. 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

6. Phase I study of bryostatin 1 and gemcitabine.

Authors: Basil F El-Rayes; Shirish Gadgeel; Anthony F Shields; Stephanie Manza; Patricia Lorusso; Philip A Philip
Journal: Clin Cancer Res Date: 2006-12-01 Impact factor: 12.531

7. Synthetic Studies Toward Bryostatin 1: Preparation of a C(1)-C(16) Fragment by Pyran Annulation.

Authors: Gary E Keck; Dennie S Welch; Yam B Poudel
Journal: Tetrahedron Lett Date: 2006-11-20 Impact factor: 2.415

8. 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

9. Poststroke neuronal rescue and synaptogenesis mediated in vivo by protein kinase C in adult brains.

Authors: Miao-Kun Sun; Jarin Hongpaisan; Thomas J Nelson; Daniel L Alkon
Journal: Proc Natl Acad Sci U S A Date: 2008-09-03 Impact factor: 11.205

10. 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

26 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

Review 2. Bryostatins: biological context and biotechnological prospects.

Authors: Amaro E Trindade-Silva; Grace E Lim-Fong; Koty H Sharp; Margo G Haygood
Journal: Curr Opin Biotechnol Date: 2010-12 Impact factor: 9.740

3. 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

4. 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

5. 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

6. 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

7. 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