Literature DB >> 24273639

Synthesis and biological activity of NOSH-naproxen (AVT-219) and NOSH-sulindac (AVT-18A) as potent anti-inflammatory agents with chemotherapeutic potential.

Ravinder Kodela1, Mitali Chattopadhyay, Khosrow Kashfi.   

Abstract

Nitric oxide- (NO) and hydrogen sulfide- (H2S) releasing naproxen (NOSH-naproxen) and NO and H2S-releasing sulindac (NOSH-sulindac) were synthesized and their cell growth inhibitory properties were evaluated in four different human cancer cell lines. These cell lines are of adenomatous (colon, pancreas), epithelial (breast), and lymphocytic (leukemia) origin. Using HT-29 human colon cancer cells, NOSH-naproxen and NOSH-sulindac increased apoptosis, and inhibited proliferation. NOSH-naproxen caused a G0/G1 whereas NOSH-sulindac caused a G2/M block in the cell cycle. Both compounds exhibited significant anti-inflammatory properties, using the carrageenan rat paw edema model. Reconstitution and structure-activity studies representing a fairly close approximation to the intact molecule showed that NOSH-naproxen was approximately 8000-fold more potent than the sum of its parts in inhibiting cell growth. Our data suggest that these compounds merit further investigation as potential anti-cancer agents.

Entities:  

Year:  2013        PMID： 24273639      PMCID： PMC3835719          DOI： 10.1039/C3MD00185G

Source DB:  PubMed          Journal:  Medchemcomm        ISSN： 2040-2503            Impact factor:   3.597


  21 in total

Review 1.  NO-aspirins: a class of new anti-inflammatory and antithrombotic agents.

Authors:  P del Soldato; R Sorrentino; A Pinto
Journal:  Trends Pharmacol Sci       Date:  1999-08       Impact factor: 14.819

2.  Synthesis and biological activity of acetyl-protected hydroxybenzyl diethyl phosphates (EHBP) as potential chemotherapeutic agents.

Authors:  Ravinder Kodela; Mitali Chattopadhyay; Niharika Nath; Lucyna Z Cieciura; Liliya Pospishill; Daniel Boring; James A Crowell; Khosrow Kashfi
Journal:  Bioorg Med Chem Lett       Date:  2011-09-22       Impact factor: 2.823

3.  Comparison between 3-Nitrooxyphenyl acetylsalicylate (NO-ASA) and O2-(acetylsalicyloxymethyl)-1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (NONO-ASA) as safe anti-inflammatory, analgesic, antipyretic, antioxidant prodrugs.

Authors:  Mitali Chattopadhyay; Carlos A Velazquez; April Pruski; Kamran V Nia; Khaled R Abdellatif; Larry K Keefer; Khosrow Kashfi
Journal:  J Pharmacol Exp Ther       Date:  2010-08-02       Impact factor: 4.030

4.  NOSH-aspirin (NBS-1120), a novel nitric oxide- and hydrogen sulfide-releasing hybrid is a potent inhibitor of colon cancer cell growth in vitro and in a xenograft mouse model.

Authors:  Mitali Chattopadhyay; Ravinder Kodela; Kenneth R Olson; Khosrow Kashfi
Journal:  Biochem Biophys Res Commun       Date:  2012-02-16       Impact factor: 3.575

5.  Gastrointestinal safety and anti-inflammatory effects of a hydrogen sulfide-releasing diclofenac derivative in the rat.

Authors:  John L Wallace; Giuseppe Caliendo; Vincenzo Santagada; Giuseppe Cirino; Stefano Fiorucci
Journal:  Gastroenterology       Date:  2006-11-29       Impact factor: 22.682

6.  Thienopyrimidines as β3-adrenoceptor agonists: hit-to-lead optimization.

Authors:  Stefan Tasler; Roland Baumgartner; Astrid Ammendola; Josef Schachtner; Tanja Wieber; Marcus Blisse; Sandra Rath; Mirko Zaja; Philipp Klahn; Udo Quotschalla; Peter Ney
Journal:  Bioorg Med Chem Lett       Date:  2010-08-12       Impact factor: 2.823

Review 7.  NSAID-induced gastrointestinal damage and the design of GI-sparing NSAIDs.

Authors:  John L Wallace; Linda Vong
Journal:  Curr Opin Investig Drugs       Date:  2008-11

8.  Site-directed mutagenesis on human cystathionine-gamma-lyase reveals insights into the modulation of H2S production.

Authors:  Shufen Huang; Jia Hui Chua; Wen Shan Yew; J Sivaraman; Philip K Moore; Choon-Hong Tan; Lih-Wen Deng
Journal:  J Mol Biol       Date:  2009-12-01       Impact factor: 5.469

9.  NOSH-Aspirin: A Novel Nitric Oxide-Hydrogen Sulfide-Releasing Hybrid: A New Class of Anti-inflammatory Pharmaceuticals.

Authors:  Ravinder Kodela; Mitali Chattopadhyay; Khosrow Kashfi
Journal:  ACS Med Chem Lett       Date:  2012-01-28       Impact factor: 4.345

Review 10.  Is hydrogen sulfide a circulating "gasotransmitter" in vertebrate blood?

Authors:  Kenneth R Olson
Journal:  Biochim Biophys Acta       Date:  2009-04-08
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  15 in total

1.  NOSH-aspirin (NBS-1120), a novel nitric oxide- and hydrogen sulfide-releasing hybrid has enhanced chemo-preventive properties compared to aspirin, is gastrointestinal safe with all the classic therapeutic indications.

Authors:  Ravinder Kodela; Mitali Chattopadhyay; Carlos A Velázquez-Martínez; Khosrow Kashfi
Journal:  Biochem Pharmacol       Date:  2015-09-21       Impact factor: 5.858

Review 2.  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

3.  Synthesis and anti-cancer potential of the positional isomers of NOSH-aspirin (NBS-1120) a dual nitric oxide and hydrogen sulfide releasing hybrid.

Authors:  Federica Vannini; Andrew C MacKessack-Leitch; Erin K Eschbach; Mitali Chattopadhyay; Ravinder Kodela; Khosrow Kashfi
Journal:  Bioorg Med Chem Lett       Date:  2015-08-14       Impact factor: 2.823

Review 4.  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

Review 5.  The therapeutic potential of cystathionine β-synthetase/hydrogen sulfide inhibition in cancer.

Authors:  Mark R Hellmich; Ciro Coletta; Celia Chao; Csaba Szabo
Journal:  Antioxid Redox Signal       Date:  2014-06-20       Impact factor: 8.401

Review 6.  International Union of Basic and Clinical Pharmacology. CII: Pharmacological Modulation of H2S Levels: H2S Donors and H2S Biosynthesis Inhibitors.

Authors:  Csaba Szabo; Andreas Papapetropoulos
Journal:  Pharmacol Rev       Date:  2017-10       Impact factor: 25.468

7.  NOSH-sulindac (AVT-18A) is a novel nitric oxide- and hydrogen sulfide-releasing hybrid that is gastrointestinal safe and has potent anti-inflammatory, analgesic, antipyretic, anti-platelet, and anti-cancer properties.

Authors:  Khosrow Kashfi; Mitali Chattopadhyay; Ravinder Kodela
Journal:  Redox Biol       Date:  2015-08-14       Impact factor: 11.799

Review 8.  Hydrogen sulfide and polysulfides as signaling molecules.

Authors:  Hideo Kimura
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2015       Impact factor: 3.493

Review 9.  Role of Hydrogen Sulfide in Ischemia-Reperfusion Injury.

Authors:  Dongdong Wu; Jun Wang; Hui Li; Mengzhou Xue; Ailing Ji; Yanzhang Li
Journal:  Oxid Med Cell Longev       Date:  2015-05-12       Impact factor: 6.543

10.  Gastrointestinal safety, chemotherapeutic potential, and classic pharmacological profile of NOSH-naproxen (AVT-219) a dual NO- and H2S-releasing hybrid.

Authors:  Mitali Chattopadhyay; Ravinder Kodela; Pascale L Duvalsaint; Khosrow Kashfi
Journal:  Pharmacol Res Perspect       Date:  2016-03-04
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