Literature DB >> 17112722

Solid phase-assisted synthesis and screening of a small library of N-(4-hydroxyphenyl)retinamide (4-HPR) analogs.

Serena M Mershon1, Allyson L Anding, Jason S Chapman, Margaret Clagett-Dame, Laura A Stonerock, Robert W Curley.   

Abstract

Using solid phase-assisted synthesis and purification, a 49 member library of analogs of the mammary tumor chemopreventive retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) has been prepared. After prescreening for growth inhibitory activity in human mammary tumor cells (MCF-7) in culture, most of those analogs which showed activity (12 of them) were assayed for apoptosis-inducing activity in the MCF-7 cells. At least 3 of the analogs (13, 24, and 28) showed activity approaching that of 4-HPR.

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Year:  2006        PMID： 17112722      PMCID： PMC1885232          DOI： 10.1016/j.bmcl.2006.10.050

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  20 in total

Review 1.  Solid-phase extraction for combinatorial libraries.

Authors:  U J Nilsson
Journal:  J Chromatogr A       Date:  2000-07-14       Impact factor: 4.759

2.  N-(4-hydroxyphenyl) retinamide induces cell cycle specific growth inhibition in PC3 cells.

Authors:  M Igawa; T Tanabe; G W Chodak; D B Rukstalis
Journal:  Prostate       Date:  1994-06       Impact factor: 4.104

3.  Chemopreventive activity of a C-glucuronide analog of N-(4-hydroxyphenyl) retinamide-O-glucuronide against mammary tumor development and growth.

Authors:  H M Abou-Issa; G A Alshafie; R W Curley; M F Wong; M Clagett-Dame; J J Repa; V Sikri
Journal:  Anticancer Res       Date:  1999 Mar-Apr       Impact factor: 2.480

Review 4.  Annexin V-affinity assay: a review on an apoptosis detection system based on phosphatidylserine exposure.

Authors:  M van Engeland; L J Nieland; F C Ramaekers; B Schutte; C P Reutelingsperger
Journal:  Cytometry       Date:  1998-01-01

5.  N-(4-Hydroxyphenyl)retinamide, a new retinoid for prevention of breast cancer in the rat.

Authors:  R C Moon; H J Thompson; P J Becci; C J Grubbs; R J Gander; D L Newton; J M Smith; S L Phillips; W R Henderson; L T Mullen; C C Brown; M B Sporn
Journal:  Cancer Res       Date:  1979-04       Impact factor: 12.701

6.  N-(4-hydroxyphenyl)retinamide (4-HPR)-mediated biological actions involve retinoid receptor-independent pathways in human breast carcinoma.

Authors:  M S Sheikh; Z M Shao; X S Li; J V Ordonez; B A Conley; S Wu; M I Dawson; Q X Han; W R Chao; T Quick
Journal:  Carcinogenesis       Date:  1995-10       Impact factor: 4.944

7.  N-(4-hydroxyphenyl)retinamide: interactions with retinoid-binding proteins/receptors.

Authors:  B P Sani; Y F Shealy; D L Hill
Journal:  Carcinogenesis       Date:  1995-10       Impact factor: 4.944

8.  N-(4-hydroxyphenyl)retinamide induces apoptosis of malignant hemopoietic cell lines including those unresponsive to retinoic acid.

Authors:  D Delia; A Aiello; L Lombardi; P G Pelicci; F Grignani; F Grignani; F Formelli; S Menard; A Costa; U Veronesi
Journal:  Cancer Res       Date:  1993-12-15       Impact factor: 12.701

9.  Teratogenicity of N-(4-hydroxyphenyl)-all-trans-retinamide in rats and rabbits.

Authors:  M F Kenel; J H Krayer; E A Merz; J F Pritchard
Journal:  Teratog Carcinog Mutagen       Date:  1988

10.  4-Hydroxyphenyl retinamide is a highly selective activator of retinoid receptors.

Authors:  A N Fanjul; D Delia; M A Pierotti; D Rideout; J Q Yu; M Pfahl; J Qiu
Journal:  J Biol Chem       Date:  1996-09-13       Impact factor: 5.157
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  4 in total

1.  Identification of dihydroceramide desaturase as a direct in vitro target for fenretinide.

Authors:  Mehrdad Rahmaniyan; Robert W Curley; Lina M Obeid; Yusuf A Hannun; Jacqueline M Kraveka
Journal:  J Biol Chem       Date:  2011-05-04       Impact factor: 5.157

2.  One-Step, Low-Cost, Operator-Friendly, and Scalable Procedure to Synthetize Highly Pure N-(4-ethoxyphenyl)-retinamide in Quantitative Yield without Purification Work-Up.

Authors:  Silvana Alfei; Guendalina Zuccari
Journal:  Molecules       Date:  2022-06-06       Impact factor: 4.927

3.  Inhibitory effects of fenretinide metabolites N-[4-methoxyphenyl]retinamide (MPR) and 4-oxo-N-(4-hydroxyphenyl)retinamide (3-keto-HPR) on fenretinide molecular targets β-carotene oxygenase 1, stearoyl-CoA desaturase 1 and dihydroceramide Δ4-desaturase 1.

Authors:  Eugenia Poliakov; William Samuel; Todd Duncan; Danielle B Gutierrez; Nathan L Mata; T Michael Redmond
Journal:  PLoS One       Date:  2017-04-27       Impact factor: 3.240

4.  Fenretinide treatment prevents diet-induced obesity in association with major alterations in retinoid homeostatic gene expression in adipose, liver, and hypothalamus.

Authors:  George D Mcilroy; Mirela Delibegovic; Carl Owen; Patrick N Stoney; Kirsty D Shearer; Peter J McCaffery; Nimesh Mody
Journal:  Diabetes       Date:  2012-11-27       Impact factor: 9.461
  4 in total

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