Literature DB >> 24332494

Synthesis, biological evaluation and SAR of 3-benzoates of ingenol for treatment of actinic keratosis and non-melanoma skin cancer.

Gunnar Grue-Sørensen1, Xifu Liang1, Kristoffer Månsson1, Per Vedsø1, Morten Dahl Sørensen1, Anke Soor1, Martin Stahlhut2, Malene Bertelsen2, Karen Margrethe Engell3, Thomas Högberg4.   

Abstract

Ingenol 3-benzoates were investigated with respect to chemical stability, pro-inflammatory effects, cell death induction and PKCδ activation. A correlation between structure, chemical stability and biological activity was found and compared to ingenol mebutate (ingenol 3-angelate) used for field treatment of actinic keratosis. We also provided further support for involvement of PKCδ for induction of oxidative burst and cytokine release. Molecular modeling and dynamics calculations corroborated the essential interactions between key compounds and C1 domain of PKCδ.
Copyright © 2013 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Cell death induction; Cytokine release; Ingenol 3-benzoates; Molecular modeling; Oxidative burst; PKCδ activation

Mesh：

Substances：

Year:  2013        PMID： 24332494     DOI： 10.1016/j.bmcl.2013.11.073

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  6 in total

1.  [Successful treatment of Bowen disease with ingenol mebutate].

Authors:  S A Braun; B Homey; P A Gerber
Journal:  Hautarzt       Date:  2014-10       Impact factor: 0.751

2.  Prodrugs of PKC modulators show enhanced HIV latency reversal and an expanded therapeutic window.

Authors:  Jack L Sloane; Nancy L Benner; Katherine N Keenan; Xiaoyu Zang; Mohamed S A Soliman; Xiaomeng Wu; Melanie Dimapasoc; Tae-Wook Chun; Matthew D Marsden; Jerome A Zack; Paul A Wender
Journal:  Proc Natl Acad Sci U S A       Date:  2020-05-05       Impact factor: 11.205

3.  Chemical Proteomics Identifies SLC25A20 as a Functional Target of the Ingenol Class of Actinic Keratosis Drugs.

Authors:  Christopher G Parker; Christian A Kuttruff; Andrea Galmozzi; Lars Jørgensen; Chien-Hung Yeh; Daniel J Hermanson; Yujia Wang; Marta Artola; Steven J McKerrall; Christopher M Josyln; Bjarne Nørremark; Georg Dünstl; Jakob Felding; Enrique Saez; Phil S Baran; Benjamin F Cravatt
Journal:  ACS Cent Sci       Date:  2017-12-06       Impact factor: 14.553

4.  Ingol and Ingenol-Type Diterpenes from Euphorbia trigona Miller with Keratinocyte Inhibitory Activity.

Authors:  Reham Hammadi; Norbert Kúsz; Csilla Zsuzsanna Dávid; Zoltán Behány; László Papp; Lajos Kemény; Judit Hohmann; Lóránt Lakatos; Andrea Vasas
Journal:  Plants (Basel)       Date:  2021-06-14

5.  C-H Oxidation of Ingenanes Enables Potent and Selective Protein Kinase C Isoform Activation.

Authors:  Yehua Jin; Chien-Hung Yeh; Christian A Kuttruff; Lars Jørgensen; Georg Dünstl; Jakob Felding; Swaminathan R Natarajan; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-29       Impact factor: 15.336

6.  Ingenol Disoxate: A Novel 4-Isoxazolecarboxylate Ester of Ingenol with Improved Properties for Treatment of Actinic Keratosis and Other Non-Melanoma Skin Cancers.

Authors:  Malene Bertelsen; Martin Stahlhut; Gunnar Grue-Sørensen; Xifu Liang; Gitte Bach Christensen; Kresten Skak; Karen Margrethe Engell; Thomas Högberg
Journal:  Dermatol Ther (Heidelb)       Date:  2016-08-08
  6 in total

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