Literature DB >> 12620066

A novel atypical retinoid endowed with proapoptotic and antitumor activity.

Raffaella Cincinelli1, Sabrina Dallavalle, Lucio Merlini, Sergio Penco, Claudio Pisano, Paolo Carminati, Giuseppe Giannini, Loredana Vesci, Carlo Gaetano, Barbara Illy, Valentina Zuco, Rosanna Supino, Franco Zunino.   

Abstract

The novel atypical retinoid E-3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid (ST1926, 4) exhibited a potent antiproliferative activity on a large panel of human tumor cells. Despite almost complete loss of ability to activate RARs, the compound was an effective apoptosis inducer and surprisingly produced DNA damage, that likely contributes to the proapoptotic activity. Following oral administration, 4 was well tolerated and caused tumor growth inhibition in the ovarian carcinoma, A2780/DX, and in the human melanoma, MeWo, growing in nude mice, thus supporting the therapeutic interest of the novel agent.

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Year:  2003        PMID: 12620066     DOI: 10.1021/jm025593y

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


  12 in total

1.  Enhanced cell cycle perturbation and apoptosis mediate the synergistic effects of ST1926 and ATRA in neuroblastoma preclinical models.

Authors:  Angela Maria Di Francesco; Paolo Ubezio; Anna Rita Torella; Daniela Meco; Filomena Pierri; Giuseppe Barone; Gabriella Cusano; Claudio Pisano; Maurizio D'Incalci; Riccardo Riccardi
Journal:  Invest New Drugs       Date:  2011-06-03       Impact factor: 3.850

2.  Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.

Authors:  Santiago Pérez-Rodríguez; Maria A Ortiz; Raquel Pereira; Fátima Rodríguez-Barrios; Angel R de Lera; F Javier Piedrafita
Journal:  Eur J Med Chem       Date:  2009-01-20       Impact factor: 6.514

Review 3.  The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.

Authors:  Lukas Wanka; Khalid Iqbal; Peter R Schreiner
Journal:  Chem Rev       Date:  2013-02-25       Impact factor: 60.622

4.  Structure-Activity Relationship and Anticancer Profile of Second-Generation Anti-MRSA Synthetic Retinoids.

Authors:  Ana V Cheng; Wooseong Kim; Iliana E Escobar; Eleftherios Mylonakis; William M Wuest
Journal:  ACS Med Chem Lett       Date:  2019-07-17       Impact factor: 4.345

5.  Insights into the binding mode and mechanism of action of some atypical retinoids as ligands of the small heterodimer partner (SHP).

Authors:  Marco Cellanetti; Viswanath Gunda; Li Wang; Antonio Macchiarulo; Roberto Pellicciari
Journal:  J Comput Aided Mol Des       Date:  2010-09-30       Impact factor: 3.686

6.  Identification of a novel non-retinoid pan inverse agonist of the retinoic acid receptors.

Authors:  Scott A Busby; Naresh Kumar; Dana S Kuruvilla; Monica A Istrate; Juliana J Conkright; Yongjun Wang; Theodore M Kamenecka; Michael D Cameron; William R Roush; Thomas P Burris; Patrick R Griffin
Journal:  ACS Chem Biol       Date:  2011-03-17       Impact factor: 5.100

7.  Development of resistance to the atypical retinoid, ST1926, in the lung carcinoma cell line H460 is associated with reduced formation of DNA strand breaks and a defective DNA damage response.

Authors:  Valentina Zuco; Chiara Zanchi; Cinzia Lanzi; Giovanni L Beretta; Rosanna Supino; Claudio Pisano; Marcella Barbarino; Romina Zanier; Federica Bucci; Concetta Aulicino; Paolo Carminati; Franco Zunino
Journal:  Neoplasia       Date:  2005-07       Impact factor: 5.715

8.  Mechanism of action of the atypical retinoid ST1926 in colorectal cancer: DNA damage and DNA polymerase α.

Authors:  Rana Abdel-Samad; Patrick Aouad; Hala Gali-Muhtasib; Zeinab Sweidan; Raed Hmadi; Humam Kadara; Egildo Luca D'Andrea; Alessandra Fucci; Claudio Pisano; Nadine Darwiche
Journal:  Am J Cancer Res       Date:  2018-01-01       Impact factor: 6.166

9.  Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and inhibition of SRC homology 2 domain-containing protein tyrosine phosphatase-2 activity.

Authors:  Marcia I Dawson; Zebin Xia; Tao Jiang; Mao Ye; Joseph A Fontana; Lulu Farhana; Bhaumik Patel; Li Ping Xue; Mohammad Bhuiyan; Roberto Pellicciari; Antonio Macchiarulo; Roberto Nuti; Xiao-Kun Zhang; Young-Hoon Han; Lutz Tautz; Peter D Hobbs; Ling Jong; Nahid Waleh; Wan-Ru Chao; Gen-Sheng Feng; Yuhong Pang; Ying Su
Journal:  J Med Chem       Date:  2008-08-30       Impact factor: 7.446

10.  Ion-exchange-resin-catalyzed adamantylation of phenol derivatives with adamantanols: Developing a clean process for synthesis of 2-(1-adamantyl)-4-bromophenol, a key intermediate of adapalene.

Authors:  Nan Wang; Ronghua Wang; Xia Shi; Gang Zou
Journal:  Beilstein J Org Chem       Date:  2012-02-08       Impact factor: 2.883

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