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Literature DB >> 15987196

Apoptolidins B and C: isolation, structure determination, and biological activity.

Paul A Wender¹, Martin Sukopp, Kate Longcore.

Abstract

[reaction: see text] Apoptolidin (1) is a promising new therapeutic lead that exhibits remarkable selectivity against cancer cells relative to normal cells. We report the isolation, characterization, solution structure, stability, and biological activity of two new members of this family: apoptolidins B (2) and C (3). These new agents are found to have antiproliferative activity on par with or better than apoptolidin itself in an assay with H292 lung cancer cells.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2005 PMID： 15987196 PMCID： PMC2533581 DOI： 10.1021/ol051074o

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

16 in total

1. Toward a structure-activity relationship for apoptolidin: selective functionalization of the hydroxyl group array.

Authors: Paul A Wender; Orion D Jankowski; Elie A Tabet; Haruo Seto
Journal: Org Lett Date: 2003-02-20 Impact factor: 6.005

2. Synthesis of termini-differentiated 6-carbon stereotetrads: an alkylative oxidation strategy for preparation of the c21-c26 segment of apoptolidin(1).

Authors: Yuzhong Chen; Jerry B Evarts; Eduardo Torres; Philip L Fuchs
Journal: Org Lett Date: 2002-10-17 Impact factor: 6.005

3. Total synthesis of apoptolidin: construction of enantiomerically pure fragments.

Authors: K C Nicolaou; Konstantina C Fylaktakidou; Holger Monenschein; Yiwei Li; Bernd Weyershausen; Helen J Mitchell; Heng-xu Wei; Prasuna Guntupalli; David Hepworth; Kazuyuki Sugita
Journal: J Am Chem Soc Date: 2003-12-17 Impact factor: 15.419

4. Facile synthetic access to and biological evaluation of the macrocyclic core of apoptolidin.

Authors: Paul A Wender; Orion D Jankowski; Elie A Tabet; Haruo Seto
Journal: Org Lett Date: 2003-06-26 Impact factor: 6.005

5. Structure-activity relationships within a family of selectively cytotoxic macrolide natural products.

Authors: A R Salomon; Y Zhang; H Seto; C Khosla
Journal: Org Lett Date: 2001-01-11 Impact factor: 6.005

6. Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase.

Authors: A R Salomon; D W Voehringer; L A Herzenberg; C Khosla
Journal: Chem Biol Date: 2001-01

7. Synthesis of the apoptosis inducing agent apoptolidin. Assembly of the C(16)-C(28) fragment.

Authors: G A Sulikowski; W M Lee; B Jin; B Wu
Journal: Org Lett Date: 2000-05-18 Impact factor: 6.005

8. Understanding and exploiting the mechanistic basis for selectivity of polyketide inhibitors of F(0)F(1)-ATPase.

Authors: A R Salomon; D W Voehringer; L A Herzenberg; C Khosla
Journal: Proc Natl Acad Sci U S A Date: 2000-12-19 Impact factor: 11.205

9. Toward a stable apoptolidin derivative: identification of isoapoptolidin and selective deglycosylation of apoptolidin.

Authors: James D Pennington; Howard J Williams; Arthur R Salomon; Gary A Sulikowski
Journal: Org Lett Date: 2002-10-31 Impact factor: 6.005

10. Isoapoptolidin: structure and activity of the ring-expanded isomer of apoptolidin.

Authors: Paul A Wender; Aaron V Gulledge; Orion D Jankowski; Haruo Seto
Journal: Org Lett Date: 2002-10-31 Impact factor: 6.005

12 in total

1. Biosynthesis of the Apoptolidins in Nocardiopsis sp. FU 40.

Authors: Yu Du; Dagmara K Derewacz; Sean M Deguire; Jesse Teske; Jacques Ravel; Gary A Sulikowski; Brian O Bachmann
Journal: Tetrahedron Date: 2011-09-02 Impact factor: 2.457

Review 2. Natural products and other inhibitors of F₁F_O ATP synthase.

Authors: Bhargav A Patel; Terin L D'Amico; Brian S J Blagg
Journal: Eur J Med Chem Date: 2020-09-03 Impact factor: 6.514

3. Fluorescent probes of the apoptolidins and their utility in cellular localization studies.

Authors: Sean M DeGuire; David C Earl; Yu Du; Brenda A Crews; Aaron T Jacobs; Alessandro Ustione; Cristina Daniel; Katherine M Chong; Lawrence J Marnett; David W Piston; Brian O Bachmann; Gary A Sulikowski
Journal: Angew Chem Int Ed Engl Date: 2014-11-27 Impact factor: 15.336

4. Amycolatopsins A-C: antimycobacterial glycosylated polyketide macrolides from the Australian soil Amycolatopsis sp. MST-108494.

Authors: Zeinab G Khalil; Angela A Salim; Daniel Vuong; Andrew Crombie; Ernest Lacey; Antje Blumenthal; Robert J Capon
Journal: J Antibiot (Tokyo) Date: 2017-10-25 Impact factor: 2.649

Apoptolidins B and C: isolation, structure determination, and biological activity.

1. Toward a structure-activity relationship for apoptolidin: selective functionalization of the hydroxyl group array.

2. Synthesis of termini-differentiated 6-carbon stereotetrads: an alkylative oxidation strategy for preparation of the c21-c26 segment of apoptolidin(1).

3. Total synthesis of apoptolidin: construction of enantiomerically pure fragments.

4. Facile synthetic access to and biological evaluation of the macrocyclic core of apoptolidin.

5. Structure-activity relationships within a family of selectively cytotoxic macrolide natural products.

6. Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase.

7. Synthesis of the apoptosis inducing agent apoptolidin. Assembly of the C(16)-C(28) fragment.

8. Understanding and exploiting the mechanistic basis for selectivity of polyketide inhibitors of F(0)F(1)-ATPase.

9. Toward a stable apoptolidin derivative: identification of isoapoptolidin and selective deglycosylation of apoptolidin.

10. Isoapoptolidin: structure and activity of the ring-expanded isomer of apoptolidin.

1. Biosynthesis of the Apoptolidins in Nocardiopsis sp. FU 40.

Review 2. Natural products and other inhibitors of F₁F_O ATP synthase.

3. Fluorescent probes of the apoptolidins and their utility in cellular localization studies.

4. Amycolatopsins A-C: antimycobacterial glycosylated polyketide macrolides from the Australian soil Amycolatopsis sp. MST-108494.

5. Light-induced isomerization of apoptolidin a leads to inversion of C2-C3 double bond geometry.

6. The use of fluorescently-tagged apoptolidins in cellular uptake and response studies.

7. Apoptolidins E and F, new glycosylated macrolactones isolated from Nocardiopsis sp.

8. An approach to the site-selective diversification of apoptolidin A with peptide-based catalysts.

9. Correlation of F0F1-ATPase inhibition and antiproliferative activity of apoptolidin analogues.

10. Combined chemical and biosynthetic route to access a new apoptolidin congener.

Review 2. Natural products and other inhibitors of F1FO ATP synthase.

Review 2. Natural products and other inhibitors of F₁F_O ATP synthase.