Literature DB >> 19954250

High lipophilicity of meta Mn(III) N-alkylpyridylporphyrin-based superoxide dismutase mimics compensates for their lower antioxidant potency and makes them as effective as ortho analogues in protecting superoxide dismutase-deficient Escherichia coli.

Ivan Kos1, Ludmil Benov, Ivan Spasojević, Júlio S Rebouças, Ines Batinić-Haberle.   

Abstract

Lipophilicity/bioavailibility of Mn(III) N-alkylpyridylporphyrin-based superoxide dismutase (SOD) mimics has a major impact on their in vivo ability to suppress oxidative stress. Meta isomers are less potent SOD mimics than ortho analogues but are 10-fold more lipophilic and more planar. Enhanced lipophilicity contributes to their higher accumulation in cytosol of SOD-deficient Escherichia coli, compensating for their lower potency; consequently, both isomers exert similar-to-identical protection of SOD-deficient E. coli. Thus meta isomers may be prospective therapeutics as are ortho porphyrins.

Entities:  

Mesh:

Substances:

Year:  2009        PMID: 19954250      PMCID: PMC2920616          DOI: 10.1021/jm900576g

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  26 in total

1.  Complementation of SOD-deficient Escherichia coli by manganese porphyrin mimics of superoxide dismutase activity.

Authors:  Ayako Okado-Matsumoto; Ines Batinić-Haberle; Irwin Fridovich
Journal:  Free Radic Biol Med       Date:  2004-08-01       Impact factor: 7.376

2.  Protein measurement with the Folin phenol reagent.

Authors:  O H LOWRY; N J ROSEBROUGH; A L FARR; R J RANDALL
Journal:  J Biol Chem       Date:  1951-11       Impact factor: 5.157

3.  The identification of primary sites of superoxide and hydrogen peroxide formation in the aerobic respiratory chain and sulfite reductase complex of Escherichia coli.

Authors:  K R Messner; J A Imlay
Journal:  J Biol Chem       Date:  1999-04-09       Impact factor: 5.157

4.  A mechanism-based antioxidant approach for the reduction of skin carcinogenesis.

Authors:  Yunfeng Zhao; Luksana Chaiswing; Terry D Oberley; Ines Batinic-Haberle; William St Clair; Charles J Epstein; Daret St Clair
Journal:  Cancer Res       Date:  2005-02-15       Impact factor: 12.701

5.  A manganese porphyrin superoxide dismutase mimetic enhances tumor radioresponsiveness.

Authors:  Benjamin J Moeller; Ines Batinic-Haberle; Ivan Spasojevic; Zahid N Rabbani; Mitchell S Anscher; Zeljko Vujaskovic; Mark W Dewhirst
Journal:  Int J Radiat Oncol Biol Phys       Date:  2005-10-01       Impact factor: 7.038

6.  Redox modulation of oxidative stress by Mn porphyrin-based therapeutics: the effect of charge distribution.

Authors:  Júlio S Rebouças; Ivan Spasojević; Daryono H Tjahjono; Arlette Richaud; Francisco Méndez; Ludmil Benov; Ines Batinić-Haberle
Journal:  Dalton Trans       Date:  2008-01-07       Impact factor: 4.390

Review 7.  Cellular defenses against superoxide and hydrogen peroxide.

Authors:  James A Imlay
Journal:  Annu Rev Biochem       Date:  2008       Impact factor: 23.643

8.  Manganese porphyrin reduces renal injury and mitochondrial damage during ischemia/reperfusion.

Authors:  Hamida Saba; Ines Batinic-Haberle; Shankar Munusamy; Tanecia Mitchell; Cheryl Lichti; Judit Megyesi; Lee Ann MacMillan-Crow
Journal:  Free Radic Biol Med       Date:  2007-02-28       Impact factor: 7.376

9.  Comparison of two Mn porphyrin-based mimics of superoxide dismutase in pulmonary radioprotection.

Authors:  Benjamin Gauter-Fleckenstein; Katharina Fleckenstein; Kouros Owzar; Chen Jiang; Ines Batinic-Haberle; Zeljko Vujaskovic
Journal:  Free Radic Biol Med       Date:  2007-11-21       Impact factor: 7.376

10.  Isolation of superoxide dismutase mutants in Escherichia coli: is superoxide dismutase necessary for aerobic life?

Authors:  A Carlioz; D Touati
Journal:  EMBO J       Date:  1986-03       Impact factor: 11.598

View more
  27 in total

Review 1.  Design of Mn porphyrins for treating oxidative stress injuries and their redox-based regulation of cellular transcriptional activities.

Authors:  Ines Batinic-Haberle; Ivan Spasojevic; Hubert M Tse; Artak Tovmasyan; Zrinka Rajic; Daret K St Clair; Zeljko Vujaskovic; Mark W Dewhirst; Jon D Piganelli
Journal:  Amino Acids       Date:  2010-05-16       Impact factor: 3.520

Review 2.  A combination of two antioxidants (an SOD mimic and ascorbate) produces a pro-oxidative effect forcing Escherichia coli to adapt via induction of oxyR regulon.

Authors:  Ines Batinic-Haberle; Zrinka Rajic; Ludmil Benov
Journal:  Anticancer Agents Med Chem       Date:  2011-05-01       Impact factor: 2.505

3.  Acid-base and electrochemical properties of manganese meso(ortho- and meta-N-ethylpyridyl)porphyrins: potentiometric, spectrophotometric and spectroelectrochemical study of protolytic and redox equilibria.

Authors:  Tin Weitner; Ana Budimir; Ivan Kos; Ines Batinić-Haberle; Mladen Biruš
Journal:  Dalton Trans       Date:  2010-11-04       Impact factor: 4.390

Review 4.  Diverse functions of cationic Mn(III) N-substituted pyridylporphyrins, recognized as SOD mimics.

Authors:  Ines Batinic-Haberle; Zrinka Rajic; Artak Tovmasyan; Julio S Reboucas; Xiaodong Ye; Kam W Leong; Mark W Dewhirst; Zeljko Vujaskovic; Ludmil Benov; Ivan Spasojevic
Journal:  Free Radic Biol Med       Date:  2011-05-06       Impact factor: 7.376

5.  Mn porphyrin in combination with ascorbate acts as a pro-oxidant and mediates caspase-independent cancer cell death.

Authors:  Myron K Evans; Artak Tovmasyan; Ines Batinic-Haberle; Gayathri R Devi
Journal:  Free Radic Biol Med       Date:  2013-12-12       Impact factor: 7.376

6.  Challenges encountered during development of Mn porphyrin-based, potent redox-active drug and superoxide dismutase mimic, MnTnBuOE-2-PyP5+, and its alkoxyalkyl analogues.

Authors:  Zrinka Rajic; Artak Tovmasyan; Otávio L de Santana; Isabelle N Peixoto; Ivan Spasojevic; Silmar A do Monte; Elizete Ventura; Júlio S Rebouças; Ines Batinic-Haberle
Journal:  J Inorg Biochem       Date:  2017-01-05       Impact factor: 4.155

7.  Effect of molecular characteristics on cellular uptake, subcellular localization, and phototoxicity of Zn(II) N-alkylpyridylporphyrins.

Authors:  Rima Ezzeddine; Anwar Al-Banaw; Artak Tovmasyan; James D Craik; Ines Batinic-Haberle; Ludmil T Benov
Journal:  J Biol Chem       Date:  2013-11-08       Impact factor: 5.157

Review 8.  Superoxide dismutase mimics: chemistry, pharmacology, and therapeutic potential.

Authors:  Ines Batinić-Haberle; Júlio S Rebouças; Ivan Spasojević
Journal:  Antioxid Redox Signal       Date:  2010-09-15       Impact factor: 8.401

Review 9.  Simple biological systems for assessing the activity of superoxide dismutase mimics.

Authors:  Artak Tovmasyan; Julio S Reboucas; Ludmil Benov
Journal:  Antioxid Redox Signal       Date:  2013-10-19       Impact factor: 8.401

Review 10.  SOD therapeutics: latest insights into their structure-activity relationships and impact on the cellular redox-based signaling pathways.

Authors:  Ines Batinic-Haberle; Artak Tovmasyan; Emily R H Roberts; Zeljko Vujaskovic; Kam W Leong; Ivan Spasojevic
Journal:  Antioxid Redox Signal       Date:  2013-10-01       Impact factor: 8.401

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.