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Literature DB >> 16468718

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

Paul A Wender¹, Orion D Jankowski, Kate Longcore, Elie A Tabet, Haruo Seto, Taijiro Tomikawa.

Abstract

[structure: see text] Apoptolidin (1) exhibits potent and highly selective apoptosis inducing activity against sensitive cancer cell lines and is hypothesized to act by inhibition of mitochondrial F(0)F(1)-ATP synthase. A series of apoptolidin derivatives, including a new intermolecular Diels-Alder adduct, were analyzed for antiproliferative activity in E1A-transformed rat fibroblasts. Potent F(0)F(1)-ATPase inhibition was not a sufficient determinant of antiproliferative activity for several analogues, suggesting the existence of a secondary biological target or more complex mode of action for apoptolidin.

Entities: Chemical Disease Species

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Year: 2006 PMID： 16468718 PMCID： PMC2533578 DOI： 10.1021/ol052800q

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

19 in total

1. Total synthesis of apoptolidin: completion of the synthesis and analogue synthesis and evaluation.

Authors: K C Nicolaou; Yiwei Li; Kazuyuki Sugita; Holger Monenschein; Prasuna Guntupalli; Helen J Mitchell; Konstantina C Fylaktakidou; Dionisios Vourloumis; Paraskevi Giannakakou; Aurora O'Brate
Journal: J Am Chem Soc Date: 2003-12-17 Impact factor: 15.419

2. 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

3. Enantioselective synthesis of apoptolidinone: exploiting the versatility of thiazolidinethione chiral auxiliaries.

Authors: Michael T Crimmins; Hamish S Christie; Kleem Chaudhary; Alan Long
Journal: J Am Chem Soc Date: 2005-10-12 Impact factor: 15.419

4. Apoptolidin, a new apoptosis inducer in transformed cells from Nocardiopsis sp.

Authors: J W Kim; H Adachi; K Shin-ya; Y Hayakawa; H Seto
Journal: J Antibiot (Tokyo) Date: 1997-07 Impact factor: 2.649

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. 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

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

Authors: Paul A Wender; Martin Sukopp; Kate Longcore
Journal: Org Lett Date: 2005-07-07 Impact factor: 6.005

9. ATP depletion rather than mitochondrial depolarization mediates hepatocyte killing after metabolic inhibition.

Authors: A L Nieminen; A K Saylor; B Herman; J J Lemasters
Journal: Am J Physiol Date: 1994-07

10. Enantioselective preparation of the C1-C11 fragment of apoptolidin.

Authors: William D Paquette; Richard E Taylor
Journal: Org Lett Date: 2004-01-08 Impact factor: 6.005

11 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

Review 3. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Authors: Christopher R Shugrue; Scott J Miller
Journal: Chem Rev Date: 2017-06-05 Impact factor: 60.622

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

Authors: Brian O Bachmann; Ruth McNees; Bruce J Melancon; Victor P Ghidu; Rachel Clark; Brenda C Crews; Sean M Deguire; Lawrence J Marnett; Gary A Sulikowski
Journal: Org Lett Date: 2010-07-02 Impact factor: 6.005

5. Mitochondrial Side Effects of Surgical Prophylactic Antibiotics Ceftriaxone and Rifaximin Lead to Bowel Mucosal Damage.

Authors: Bálint Baráth; Dávid K Jász; Tamara Horváth; Bence Baráth; Gergely Maróti; Gerda Strifler; Gabriella Varga; Lilla Sándor; Domonkos Perényi; Szabolcs Tallósy; Tibor Donka; Péter Jávor; Mihály Boros; Petra Hartmann
Journal: Int J Mol Sci Date: 2022-05-03 Impact factor: 6.208

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

1. Total synthesis of apoptolidin: completion of the synthesis and analogue synthesis and evaluation.

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

3. Enantioselective synthesis of apoptolidinone: exploiting the versatility of thiazolidinethione chiral auxiliaries.

4. Apoptolidin, a new apoptosis inducer in transformed cells from Nocardiopsis sp.

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

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

9. ATP depletion rather than mitochondrial depolarization mediates hepatocyte killing after metabolic inhibition.

10. Enantioselective preparation of the C1-C11 fragment of apoptolidin.

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

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

Review 3. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

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

5. Mitochondrial Side Effects of Surgical Prophylactic Antibiotics Ceftriaxone and Rifaximin Lead to Bowel Mucosal Damage.

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

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

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

9. Synthesis and evaluation of the cytotoxicity of apoptolidinones A and D.

Review 10. Why All the Fuss about Oxidative Phosphorylation (OXPHOS)?

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

Review 3. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Review 10. Why All the Fuss about Oxidative Phosphorylation (OXPHOS)?

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