Literature DB >> 22356735

Diazeniumdiolated carbamates: a novel class of nitric oxide donors.

Rahul S Nandurdikar1, Anna E Maciag, Zhao Cao, Larry K Keefer, Joseph E Saavedra.   

Abstract

We report an indirect method for synthesis of previously inaccessible diazeniumdiolated carbamates. Synthesis involves use of previously reported triisopropylsilyloxymethylated isopropylamine diazeniumdiolate (TOM-ylated IPA/NO). These novel diazeniumdiolated carbamate prodrugs upon activation release nitric oxide (NO) similar to their secondary amine counterparts. They are also efficient sources of intracellular NO. These prodrugs may have potential applications as therapeutic NO-donors. Copyright Â
© 2012 Elsevier Ltd. All rights reserved.

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Year:  2012        PMID： 22356735      PMCID： PMC3298570          DOI： 10.1016/j.bmc.2012.01.046

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  10 in total

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Authors:  Nazareno Paolocci; Tatsuo Katori; Hunter C Champion; Marcus E St John; Katrina M Miranda; Jon M Fukuto; David A Wink; David A Kass
Journal:  Proc Natl Acad Sci U S A       Date:  2003-04-18       Impact factor: 11.205

Review 2.  Nitric oxide: physiology, pathophysiology, and pharmacology.

Authors:  S Moncada; R M Palmer; E A Higgs
Journal:  Pharmacol Rev       Date:  1991-06       Impact factor: 25.468

3.  O(2)-Vinyl 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate protection against D-galactosamine/endotoxin-induced hepatotoxicity in mice: genomic analysis using microarrays.

Authors:  Jie Liu; Joseph E Saavedra; Tong Lu; Jian-Guo Song; James Clark; Michael P Waalkes; Larry K Keefer
Journal:  J Pharmacol Exp Ther       Date:  2002-01       Impact factor: 4.030

4.  Novel protection-deprotection strategies in diazeniumdiolate chemistry: synthesis of V-IPA/NO.

Authors:  Rahul S Nandurdikar; Larry K Keefer; Joseph E Saavedra
Journal:  Chem Commun (Camb)       Date:  2011-05-10       Impact factor: 6.222

5.  HNO and NO release from a primary amine-based diazeniumdiolate as a function of pH.

Authors:  Debra J Salmon; Claudia L Torres de Holding; Lynta Thomas; Kyle V Peterson; Gens P Goodman; Joseph E Saavedra; Aloka Srinivasan; Keith M Davies; Larry K Keefer; Katrina M Miranda
Journal:  Inorg Chem       Date:  2011-03-15       Impact factor: 5.165

Review 6.  Fluorescent and luminescent probes for measurement of oxidative and nitrosative species in cells and tissues: progress, pitfalls, and prospects.

Authors:  Peter Wardman
Journal:  Free Radic Biol Med       Date:  2007-07-10       Impact factor: 7.376

7.  Dual mechanisms of HNO generation by a nitroxyl prodrug of the diazeniumdiolate (NONOate) class.

Authors:  Daniela Andrei; Debra J Salmon; Sonia Donzelli; Azadeh Wahab; John R Klose; Michael L Citro; Joseph E Saavedra; David A Wink; Katrina M Miranda; Larry K Keefer
Journal:  J Am Chem Soc       Date:  2010-10-29       Impact factor: 15.419

Review 8.  The nitric oxide prodrug JS-K and its structural analogues as cancer therapeutic agents.

Authors:  Anna E Maciag; Joseph E Saavedra; Harinath Chakrapani
Journal:  Anticancer Agents Med Chem       Date:  2009-09-01       Impact factor: 2.505

9.  Prodrugs of nitroxyl as potential aldehyde dehydrogenase inhibitors vis-a-vis vascular smooth muscle relaxants.

Authors:  H T Nagasawa; S P Kawle; J A Elberling; E G DeMaster; J M Fukuto
Journal:  J Med Chem       Date:  1995-05-26       Impact factor: 7.446

Review 10.  Fifty years of diazeniumdiolate research. From laboratory curiosity to broad-spectrum biomedical advances.

Authors:  Larry K Keefer
Journal:  ACS Chem Biol       Date:  2011-09-30       Impact factor: 5.100
  10 in total
  5 in total

Review 1.  The dichotomous role of H2S in cancer cell biology? Déjà vu all over again.

Authors:  Khosrow Kashfi
Journal:  Biochem Pharmacol       Date:  2018-02-14       Impact factor: 5.858

Review 2.  The evolving landscape for cellular nitric oxide and hydrogen sulfide delivery systems: A new era of customized medications.

Authors:  Kearsley M Dillon; Ryan J Carrazzone; John B Matson; Khosrow Kashfi
Journal:  Biochem Pharmacol       Date:  2020-03-26       Impact factor: 5.858

3.  Nitric oxide modulators: an emerging class of medicinal agents.

Authors:  S R Deshpande; K Satyanarayana; M N A Rao; K V Pai
Journal:  Indian J Pharm Sci       Date:  2012-11       Impact factor: 0.975

4.  Direct reaction of amides with nitric oxide to form diazeniumdiolates.

Authors:  Ryan J Holland; John R Klose; Jeffrey R Deschamps; Zhao Cao; Larry K Keefer; Joseph E Saavedra
Journal:  J Org Chem       Date:  2014-09-22       Impact factor: 4.354

5.  Combination of betulinic acid with diazen-1-ium-1,2-diolate nitric oxide moiety donating a novel anticancer candidate.

Authors:  Laiyin Zhang; Shuangxing Hou; Bo Li; Jianjian Pan; Liping Jiang; Guiying Zhou; Hong Gu; Caixing Zhao; Huiping Lu; Fenfen Ma
Journal:  Onco Targets Ther       Date:  2018-01-15       Impact factor: 4.147
  5 in total

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