A Formal Total Synthesis of (+)‐Apicularen A: Base‐Induced Conversion of Apicularen‐Derived Intermediates into Salicylihalamide‐Like Products.

Lewis, Arwel; Stefanuti, Ian; Swain, Simon A.; Smith, Stephen A.; Taylor, Richard J. K.

doi:10.1002/chin.200321194

Cited by 2 publications

(2 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…6). Total synthesis of these compounds were successfully reported a few years later [155][156][157] and several compounds showing similarities have been described, such as cruentaren, the oximidines or the closely related palmerolides. An excellent review on these latter compounds was published recently [133].…”

Section: Benzolactone Enamidesmentioning

confidence: 98%

Intracellular Proton Pumps as Targets in Chemotherapy: V-ATPases and Cancer

Hernández

Serrano-Bueno²,

Perez-Castiñeira³

et al. 2012

CPD

View full text Add to dashboard Cite

Cancer cells show a metabolic shift that makes them overproduce protons; this has the potential to disturb the cellular acid-base homeostasis. However, these cells show cytoplasmic alkalinisation, increased acid extrusion and endosome-dependent drug resistance. Vacuolar type ATPases (V-ATPases), together with other transporters, are responsible to a great extent for these symptoms. These multi-subunit proton pumps are involved in the control of cytosolic pH and the generation of proton gradients (positive inside) across endocellular membrane systems like Golgi, endosomes or lysosomes. In addition, in tumours, they have been shown to play an important role in the acidification of the intercellular medium. This importance makes them an attractive target to control tumour cell proliferation. In the present review we present the major characteristics of this kind of proton pumps and we provide some recent insights on their in vivo regulation. Also, we review some of the consequences that V-ATPase inhibition carries for the tumour cell, such as cell cycle arrest or cell death, and provide a brief summary of the studies related to cancer made recently with commercially available inhibitors. In the light of recent knowledge on the regulation of this proton pump, some new approaches to impair V-ATPase function are also suggested.

show abstract

Section: Benzolactone Enamidesmentioning

confidence: 98%

Intracellular Proton Pumps as Targets in Chemotherapy: V-ATPases and Cancer

Hernández

Serrano-Bueno²,

Perez-Castiñeira³

et al. 2012

CPD

View full text Add to dashboard Cite

show abstract

“…Total synthesis of benzolactone enamides was reported within a few years of their discovery. Thus, salicylihalimide A synthesis was published in the year 2000 [62], followed by lobatamide C [63] and apicularen A [64]. Apart from these representatives, this class of compounds have rendered many other chemicals that are not dealt with here but that they share a similar structure and mode of action, such as the cruentarens, the oximidines or the closely related palmerolides.…”

Section: Benzolactone Enamides: Salicylihalimides Lobatimides and Apmentioning

confidence: 99%

Intraorganellar Acidification by V-ATPases: A Target in Cell Proliferation and Cancer Therapy

Hernández¹,

Serrano

Herrera-Palau³

et al. 2010

PRA

View full text Add to dashboard Cite

Vacuolar-type ATPases are multicomponent proton pumps involved in the acidification of single membrane intracellular compartments such as endosomes and lysosomes. They couple the hydrolysis of ATP to the translocation of one to two protons across the membrane. Acidification of the lumen of single membrane organelles is a necessary factor for the correct traffic of membranes and cargo to and from the different internal compartments of a cell. Also, V-ATPases are involved in regulation of pH at the cytosol and, possibly, extracellular milieu. The inhibition of V-ATPases has been shown to induce apoptosis and cell cycle arrest in tumour cells and, therefore, chemicals that behave as inhibitors of this kind of proton pumps have been proposed as putative treatment agents against cancer and many have been patented as such. The compounds filed in patents fall into five major types: plecomacrolides, benzolactone enamides, archazolids, chondropsins and indoles. All these have proved to be apoptosis inducers in cell culture and many to be able to reduce xenograft tumor growth in murine models. The present review will summarize their general structure, origin and mechanisms of action and put them in relation to the patents registered so far for the treatment of cancer.

show abstract

A Formal Total Synthesis of (+)‐Apicularen A: Base‐Induced Conversion of Apicularen‐Derived Intermediates into Salicylihalamide‐Like Products.

Cited by 2 publications

References 1 publication

Intracellular Proton Pumps as Targets in Chemotherapy: V-ATPases and Cancer

Intracellular Proton Pumps as Targets in Chemotherapy: V-ATPases and Cancer

Intraorganellar Acidification by V-ATPases: A Target in Cell Proliferation and Cancer Therapy

Contact Info

Product

Resources

About