Literature DB >> 32450391

Synthesis and evaluation of resveratrol derivatives as fetal hemoglobin inducers.

Priscila Longhin Bosquesi1, Aylime Castanho Bolognesi Melchior1, Aline Renata Pavan1, Carolina Lanaro2, Cristiane Maria de Souza2, Radda Rusinova3, Rafael Consolin Chelucci1, Karina Pereira Barbieri1, Guilherme Felipe Dos Santos Fernandes1, Iracilda Zepone Carlos1, Olaf Sparre Andersen3, Fernando Ferreira Costa2, Jean Leandro Dos Santos4.   

Abstract

class="Chemical">Resveratrol (n class="Chemical">RVT) derivatives (10a-i) were designed, synthesized, and evaluated for their potential as gamma-globin inducers in treating Sickle Cell Disease (SCD) symptoms. All compounds were able to release NO at different levels ranging from 0 to 26.3%, while RVT did not demonstrate this effect. In vivo, the antinociceptive effect was characterized using an acetic acid-induced abdominal contortion model. All compounds exhibited different levels of protection, ranging from 5.9 to 37.3%; the compound 10a was the most potent among the series. At concentrations between 3.13 and 12.5 µM, the derivative 10a resulted in a reduction of 41.1-64.3% in the TNF-α levels in the supernatants of macrophages that were previously LPS-stimulated. This inhibitory effect was higher than that of RVT used as the control. In addition, the compound 10a and RVT induced double the production of the gamma-globin chains (γG + γA), compared to the vehicle, using CD34+ cells. Compound 10a also did not induce membrane perturbation and it was not mutagenic in the in vivo assay. Thus, compound 10a emerged as a new prototype of the gamma-globin-inducer group with additional analgesic and anti-inflammatory activities and proving to be a useful alternative to treat SCD symptoms.
Copyright © 2020 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  Epigenetic; Fetal hemoglobin inducers; Gamma-globin inducers; Nitric oxide; Resveratrol; Sickle Cell Disease

Mesh:

Substances:

Year:  2020        PMID: 32450391      PMCID: PMC8052979          DOI: 10.1016/j.bioorg.2020.103948

Source DB:  PubMed          Journal:  Bioorg Chem        ISSN: 0045-2068            Impact factor:   5.275


  48 in total

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Review 2.  Fetal haemoglobin induction in sickle cell disease.

Authors:  Alireza Paikari; Vivien A Sheehan
Journal:  Br J Haematol       Date:  2017-11-16       Impact factor: 6.998

3.  The abdominal constriction response and its suppression by analgesic drugs in the mouse.

Authors:  H O Collier; L C Dinneen; C A Johnson; C Schneider
Journal:  Br J Pharmacol Chemother       Date:  1968-02

4.  Design, synthesis, and pharmacological evaluation of novel hybrid compounds to treat sickle cell disease symptoms.

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Journal:  J Med Chem       Date:  2011-07-25       Impact factor: 7.446

5.  Furoxans as nitric oxide donors. 4-Phenyl-3-furoxancarbonitrile: thiol-mediated nitric oxide release and biological evaluation.

Authors:  C Medana; G Ermondi; R Fruttero; A Di Stilo; C Ferretti; A Gasco
Journal:  J Med Chem       Date:  1994-12-09       Impact factor: 7.446

6.  A thalidomide-hydroxyurea hybrid increases HbF production in sickle cell mice and reduces the release of proinflammatory cytokines in cultured monocytes.

Authors:  Carolina Lanaro; Carla F Franco-Penteado; Fabio H Silva; Kleber Y Fertrin; Jean Leandro Dos Santos; Marlene Wade; Shobha Yerigenahally; Thais R de Melo; Chung Man Chin; Abdullah Kutlar; Steffen E Meiler; Fernando Ferreira Costa
Journal:  Exp Hematol       Date:  2017-11-03       Impact factor: 3.084

7.  Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor.

Authors:  Syuhei Nakao; Miyuki Mabuchi; Shenglan Wang; Yoko Kogure; Tadashi Shimizu; Koichi Noguchi; Akito Tanaka; Yi Dai
Journal:  Bioorg Med Chem Lett       Date:  2017-05-22       Impact factor: 2.823

8.  Sickle red cells as danger signals on proinflammatory gene expression, leukotriene B4 and interleukin-1 beta production in peripheral blood mononuclear cell.

Authors:  Thassila N Pitanga; Ricardo R Oliveira; Dalila L Zanette; Caroline C Guarda; Rayra P Santiago; Sanzio S Santana; Valma M L Nascimento; Jonilson B Lima; Graziele Q Carvalho; Vitor V Maffili; Magda O S Carvalho; Luiz C J Alcântara; Valéria M Borges; Marilda S Goncalves
Journal:  Cytokine       Date:  2016-04-02       Impact factor: 3.861

9.  Analgesic and Anti-Inflammatory Activities of Resveratrol through Classic Models in Mice and Rats.

Authors:  Guangxi Wang; Zhiqiang Hu; Xu Song; Qiankun Cui; Qiuting Fu; Renyong Jia; Yuanfeng Zou; Lixia Li; Zhongqiong Yin
Journal:  Evid Based Complement Alternat Med       Date:  2017-03-13       Impact factor: 2.629

10.  A general mechanism for drug promiscuity: Studies with amiodarone and other antiarrhythmics.

Authors:  Radda Rusinova; Roger E Koeppe; Olaf S Andersen
Journal:  J Gen Physiol       Date:  2015-11-16       Impact factor: 4.086

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  6 in total

Review 1.  Fetal hemoglobin in sickle cell anemia.

Authors:  Martin H Steinberg
Journal:  Blood       Date:  2020-11-19       Impact factor: 22.113

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Authors:  Mandrita Mukherjee; Motiur Rahaman; Suman Kumar Ray; Praphulla Chandra Shukla; Tuphan Kanti Dolai; Nishant Chakravorty
Journal:  Mol Biol Rep       Date:  2021-11-25       Impact factor: 2.316

3.  Resveratrol-nitric oxide donor hybrid effect on priapism in sickle cell and nitric oxide-deficient mouse.

Authors:  Andressa Kely Pinheiro; Dalila Andrade Pereira; Jean Leandro Dos Santos; Fabiano Beraldi Calmasini; Eduardo Costa Alexandre; Leonardo Oliveira Reis; Arthur L Burnett; Fernando Ferreira Costa; Fábio Henrique Silva
Journal:  PLoS One       Date:  2022-06-02       Impact factor: 3.752

4.  Synthesis and pharmacological evaluation of pomalidomide derivatives useful for sickle cell disease treatment.

Authors:  Thais Regina Ferreira de Melo; Brian M Dulmovits; Guilherme Felipe Dos Santos Fernandes; Cristiane M de Souza; Carolina Lanaro; Minghzu He; Yousef Al Abed; Man Chin Chung; Lionel Blanc; Fernando Ferreira Costa; Jean Leandro Dos Santos
Journal:  Bioorg Chem       Date:  2021-06-10       Impact factor: 5.307

5.  Perspectives and challenges to discovering hemoglobin-inducing agents in Sickle Cell Disease.

Authors:  Aline Renata Pavan; Juliana Romano Lopes; Carlos Henrique Lima Imperador; Chung Man Chin; Jean Leandro Dos Santos
Journal:  Front Med (Lausanne)       Date:  2022-09-08

6.  Design, synthesis and biological evaluation of N-oxide derivatives with potent in vivo antileishmanial activity.

Authors:  Leandro da Costa Clementino; Guilherme Felipe Santos Fernandes; Igor Muccilo Prokopczyk; Wilquer Castro Laurindo; Danyelle Toyama; Bruno Pereira Motta; Amanda Martins Baviera; Flávio Henrique-Silva; Jean Leandro Dos Santos; Marcia A S Graminha
Journal:  PLoS One       Date:  2021-11-01       Impact factor: 3.240

  6 in total

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