Literature DB >> 23715589

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

Marie-Céline Frantz1, Erin M Skoda, Joshua R Sacher, Michael W Epperly, Julie P Goff, Joel S Greenberger, Peter Wipf.   

Abstract

JP4-039 is a lead structure in a series of nitroxide conjugates that are capable of accumulating in mitochondria and scavenging reactive oxygen species (ROS). To explore structure-activity relationships (SAR), new analogs with variable nitroxide moieties were prepared. Furthermore, fluorophore-tagged analogs were synthesized and provided the opportunity for visualization in mitochondria. All analogs were tested for radioprotective and radiomitigative effects in 32Dcl3 cells.

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Year:  2013        PMID： 23715589      PMCID： PMC3729477          DOI： 10.1039/c3ob40489g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  40 in total

1.  Improvement of oral peptide bioavailability: Peptidomimetics and prodrug strategies.

Authors: 
Journal:  Adv Drug Deliv Rev       Date:  1997-09-15       Impact factor: 15.470

2.  GS-nitroxide (JP4-039)-mediated radioprotection of human Fanconi anemia cell lines.

Authors:  Mark E Bernard; Hyun Kim; Hebist Berhane; Michael W Epperly; Darcy Franicola; Xichen Zhang; Frank Houghton; Donna Shields; Hong Wang; Christopher J Bakkenist; Marie-Celine Frantz; Erin M Forbeck; Julie P Goff; Peter Wipf; Joel S Greenberger
Journal:  Radiat Res       Date:  2011-09-22       Impact factor: 2.841

3.  Two strategies for the development of mitochondrion-targeted small molecule radiation damage mitigators.

Authors:  Jean-Claude M Rwigema; Barbara Beck; Wei Wang; Alexander Doemling; Michael W Epperly; Donna Shields; Julie P Goff; Darcy Franicola; Tracy Dixon; Marie-Céline Frantz; Peter Wipf; Yulia Tyurina; Valerian E Kagan; Hong Wang; Joel S Greenberger
Journal:  Int J Radiat Oncol Biol Phys       Date:  2011-04-13       Impact factor: 7.038

4.  2-azaadamantane N-oxyl (AZADO) and 1-Me-AZADO: highly efficient organocatalysts for oxidation of alcohols.

Authors:  Masatoshi Shibuya; Masaki Tomizawa; Iwao Suzuki; Yoshiharu Iwabuchi
Journal:  J Am Chem Soc       Date:  2006-07-05       Impact factor: 15.419

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

Authors:  Carlos A Macias; Jeffrey W Chiao; Jingbo Xiao; Devinder S Arora; Yulia Y Tyurina; Russell L Delude; Peter Wipf; Valerian E Kagan; Mitchell P Fink
Journal:  Ann Surg       Date:  2007-02       Impact factor: 12.969

6.  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

7.  Amelioration of radiation esophagitis by orally administered p53/Mdm2/Mdm4 inhibitor (BEB55) or GS-nitroxide.

Authors:  Hyun Kim; Mark E Bernard; Michael W Epperly; Hongmei Shen; Andrew Amoscato; Tracy M Dixon; Alexander S Doemling; Song Li; Xiang Gao; Peter Wipf; Hong Wang; Xichen Zhang; Valerian E Kagan; Joel S Greenberger
Journal:  In Vivo       Date:  2011 Nov-Dec       Impact factor: 2.155

8.  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

9.  An expeditious entry to 9-azabicyclo[3.3.1]nonane N-oxyl (ABNO): another highly active organocatalyst for oxidation of alcohols.

Authors:  Masatoshi Shibuya; Masaki Tomizawa; Yusuke Sasano; Yoshiharu Iwabuchi
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354

Review 10.  Targeting mitochondria.

Authors:  Adam T Hoye; Jennifer E Davoren; Peter Wipf; Mitchell P Fink; Valerian E Kagan
Journal:  Acc Chem Res       Date:  2008-01       Impact factor: 22.384
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  16 in total

1.  Anti-Ferroptosis Drug Enhances Total-Body Irradiation Mitigation by Drugs that Block Apoptosis and Necroptosis.

Authors:  Stephanie Thermozier; Wen Hou; Xichen Zhang; Donna Shields; Renee Fisher; Hulya Bayir; Valerian Kagan; Jian Yu; Bing Liu; Ivet Bahar; Michael W Epperly; Peter Wipf; Hong Wang; M Saiful Huq; Joel S Greenberger
Journal:  Radiat Res       Date:  2020-03-05       Impact factor: 2.841

2.  Effectiveness of Analogs of the GS-Nitroxide, JP4-039, as Total Body Irradiation Mitigators.

Authors:  Michael W Epperly; Joshua R Sacher; Tanja Krainz; Xiaolin Zhang; Peter Wipf; Mary Liang; Renee Fisher; Song Li; Hong Wang; Joel S Greenberger
Journal:  In Vivo       Date:  2017-01-02       Impact factor: 2.155

3.  An uncharged oxetanyl sulfoxide as a covalent modifier for improving aqueous solubility.

Authors:  Erin M Skoda; Joshua R Sacher; Mustafa Z Kazancioglu; Jaideep Saha; Peter Wipf
Journal:  ACS Med Chem Lett       Date:  2014-06-27       Impact factor: 4.345

4.  The impact of ionizing radiation on placental trophoblasts.

Authors:  D J Kanter; M B O'Brien; X-H Shi; T Chu; T Mishima; S Beriwal; M W Epperly; P Wipf; J S Greenberger; Y Sadovsky
Journal:  Placenta       Date:  2014-01-02       Impact factor: 3.481

Review 5.  Therapeutic Approaches to Treat Mitochondrial Diseases: "One-Size-Fits-All" and "Precision Medicine" Strategies.

Authors:  Emanuela Bottani; Costanza Lamperti; Alessandro Prigione; Valeria Tiranti; Nicola Persico; Dario Brunetti
Journal:  Pharmaceutics       Date:  2020-11-11       Impact factor: 6.321

6.  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

Review 7.  Addressing the Symptoms or Fixing the Problem? Developing Countermeasures against Normal Tissue Radiation Injury.

Authors:  Jacqueline P Williams; Laura Calvi; Joe V Chakkalakal; Jacob N Finkelstein; M Kerry O'Banion; Edward Puzas
Journal:  Radiat Res       Date:  2016-06-22       Impact factor: 2.841

8.  Antioxidant Approaches to Management of Ionizing Irradiation Injury.

Authors:  Joel Greenberger; Valerian Kagan; Hulya Bayir; Peter Wipf; Michael Epperly
Journal:  Antioxidants (Basel)       Date:  2015-01-23

9.  4-(Nitrophenylsulfonyl)piperazines mitigate radiation damage to multiple tissues.

Authors:  Ewa D Micewicz; Kwanghee Kim; Keisuke S Iwamoto; Josephine A Ratikan; Genhong Cheng; Gayle M Boxx; Robert D Damoiseaux; Julian P Whitelegge; Piotr Ruchala; Christine Nguyen; Prabhat Purbey; Joseph Loo; Gang Deng; Michael E Jung; James W Sayre; Andrew J Norris; Dörthe Schaue; William H McBride
Journal:  PLoS One       Date:  2017-07-21       Impact factor: 3.240

10.  Mitochondrial targeted β-lapachone induces mitochondrial dysfunction and catastrophic vacuolization in cancer cells.

Authors:  Jing Ma; Chaemin Lim; Joshua R Sacher; Bennett Van Houten; Wei Qian; Peter Wipf
Journal:  Bioorg Med Chem Lett       Date:  2015-06-26       Impact factor: 2.940
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