Literature DB >> 21452836

Large-scale asymmetric synthesis of the bioprotective agent JP4-039 and analogs.

Marie-Céline Frantz1, Joshua G Pierce, Joan M Pierce, Li Kangying, Wan Qingwei, Matthew Johnson, Peter Wipf.   

Abstract

JP4-039 is a novel nitroxide conjugate capable of crossing lipid bilayer membranes and scavenging reactive oxygen species (ROS). An efficient and scalable one-pot hydrozirconation-transmetalation-imine addition methodology has been developed for its asymmetric preparation. Furthermore, this versatile methodology allows for the synthesis of cyclopropyl and fluorinated analogs of the parent lead structure.

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Year:  2011        PMID： 21452836      PMCID： PMC3089766          DOI： 10.1021/ol200567p

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


  32 in total

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Authors:  Sejal J Patel; Timothy F Jamison
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Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

4.  Treatment with a novel hemigramicidin-TEMPO conjugate prolongs survival in a rat model of lethal hemorrhagic shock.

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5.  Electrostatic versus steric effects in peptidomimicry: synthesis and secondary structure analysis of gramicidin S analogues with (E)-alkene peptide isosteres.

Authors:  Jingbo Xiao; Bernard Weisblum; Peter Wipf
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

6.  Oxidative lipidomics of hyperoxic acute lung injury: mass spectrometric characterization of cardiolipin and phosphatidylserine peroxidation.

Authors:  Yulia Y Tyurina; Vladimir A Tyurin; A Murat Kaynar; Valentyna I Kapralova; Karla Wasserloos; Jin Li; Mackenzie Mosher; Lindsay Wright; Peter Wipf; Simon Watkins; Bruce R Pitt; Valerian E Kagan
Journal:  Am J Physiol Lung Cell Mol Physiol       Date:  2010-04-23       Impact factor: 5.464

7.  The mitochondria-targeted nitroxide JP4-039 augments potentially lethal irradiation damage repair.

Authors:  Malolan S Rajagopalan; Kanika Gupta; Michael W Epperly; Darcy Franicola; Xichen Zhang; Hong Wang; Hong Zhao; Vladimir A Tyurin; Joshua G Pierce; Valerian E Kagan; Peter Wipf; Anthony J Kanai; Joel S Greenberger
Journal:  In Vivo       Date:  2009 Sep-Oct       Impact factor: 2.155

8.  Following an ISES lead: the first examples of asymmetric Ni(0)-mediated allylic amination.

Authors:  David B Berkowitz; Gourhari Maiti
Journal:  Org Lett       Date:  2004-08-05       Impact factor: 6.005

Review 9.  Targeting mitochondria.

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Journal:  Acc Chem Res       Date:  2008-01       Impact factor: 22.384

10.  Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity.

Authors:  Carolyn E Anderson; Larry E Overman
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419
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  17 in total

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Journal:  Radiat Res       Date:  2013-10-14       Impact factor: 2.841

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4.  A Topical Mitochondria-Targeted Redox-Cycling Nitroxide Mitigates Oxidative Stress-Induced Skin Damage.

Authors:  Rhonda M Brand; Michael W Epperly; J Mark Stottlemyer; Erin M Skoda; Xiang Gao; Song Li; Saiful Huq; Peter Wipf; Valerian E Kagan; Joel S Greenberger; Louis D Falo
Journal:  J Invest Dermatol       Date:  2016-10-26       Impact factor: 8.551

5.  Continuous One Year Oral Administration of the Radiation Mitigator, MMS350, after Total-Body Irradiation, Restores Bone Marrow Stromal Cell Proliferative Capacity and Reduces Senescence in Fanconi Anemia (Fanca-/-) Mice.

Authors:  Aranee Sivananthan; Donna Shields; Renee Fisher; Wen Hou; Xichen Zhang; Darcy Franicola; Michael W Epperly; Peter Wipf; Joel S Greenberger
Journal:  Radiat Res       Date:  2018-11-30       Impact factor: 2.841

6.  Allylic Amines as Key Building Blocks in the Synthesis of (E)-Alkene Peptide Isosteres.

Authors:  Erin M Skoda; Gary C Davis; Peter Wipf
Journal:  Org Process Res Dev       Date:  2012       Impact factor: 3.317

7.  Synthesis and Optimization of Nitroxide-Based Inhibitors of Ferroptotic Cell Death in Cancer Cells and Macrophages.

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Journal:  ACS Med Chem Lett       Date:  2022-02-04       Impact factor: 4.345

8.  Nanoassembly of surfactants with interfacial drug-interactive motifs as tailor-designed drug carriers.

Authors:  Xiang Gao; Yixian Huang; Alexander M Makhov; Michael Epperly; Jianqin Lu; Sheila Grab; Peijun Zhang; Lisa Rohan; Xiang-Qun Xie; Peter Wipf; Joel Greenberger; Song Li
Journal:  Mol Pharm       Date:  2012-12-17       Impact factor: 4.939

9.  Synthesis of analogs of the radiation mitigator JP4-039 and visualization of BODIPY derivatives in mitochondria.

Authors:  Marie-Céline Frantz; Erin M Skoda; Joshua R Sacher; Michael W Epperly; Julie P Goff; Joel S Greenberger; Peter Wipf
Journal:  Org Biomol Chem       Date:  2013-07-07       Impact factor: 3.876

10.  The mitochondrial-targeted reactive species scavenger JP4-039 prevents sulfite-induced alterations in antioxidant defenses, energy transfer, and cell death signaling in striatum of rats.

Authors:  Nícolas Manzke Glänzel; Mateus Grings; Nevton Teixeira da Rosa-Junior; Leila Maria Cereta de Carvalho; Al-Walid Mohsen; Peter Wipf; Moacir Wajner; Jerry Vockley; Guilhian Leipnitz
Journal:  J Inherit Metab Dis       Date:  2020-09-14       Impact factor: 4.982
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