Literature DB >> 16826403

Mode of interaction between butyroyloxymethyl-diethyl phosphate (AN-7) and doxorubicin in MCF-7 and resistant MCF-7/Dx cell lines.

Dikla Engel1, Abraham Nudelman, Inesa Levovich, Tal Gruss-Fischer, Michal Entin-Meer, Don R Phillips, Suzanne M Cutts, Ada Rephaeli.   

Abstract

PURPOSE: To investigate the anticancer activity and mode of action of butyroyloxymethyl-diethyl phosphate (AN-7), a prodrug of butyric acid and formaldehyde, as a single agent and in combination with doxorubicin in human carcinoma MCF-7 and the multidrug resistant MCF-7 Dx cell lines.
METHODS: The anti-cancer activity of AN-7 as a single agent or in combination with doxorubicin was measured by the Hoechst cell viability and colony forming assays as well as by FACS analyses of cells stained with propidium iodide and annexin V-FITC. Modulations of protein expression and acetylation were measured by Western blot analyses. The number of doxorubicin-DNA adducts formed was evaluated using (14)C-labeled doxorubicin.
RESULTS: The AN-7 and homologous prodrugs exhibited similar growth inhibition effects against drug resistant and sensitive cells, and elicited their anticancer effect partially by inhibition of HDAC. The AN-7 transiently augmented histone acetylation and increase of p21 expression. Synergy between AN-7 and doxorubicin was demonstrated in the sensitive and the resistant cell lines by viability and colony formation assays and was further confirmed by FACS analysis showing an increase in cell mortality. The number of doxorubicin-DNA adducts in total genomic DNA isolated from cells treated with (14)C-labeled doxorubicin and AN-7 increased substantially compared to treatment with doxorubicin only. Treatment with AN-7 or doxorubicin increased p53 acetylation that was further potentiated by their combination.
CONCLUSION: The AN-7 combined with doxorubicin overcame drug resistance; at least in part by the intracellularly releasable formaldehyde that augmented formation of doxorubicin-DNA adducts and butyric acid that induced histone and p53 acetylation. Since the use of doxorubicin is limited by toxicity, the combination could offer an effective treatment modality with lower toxicity for breast cancer.

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Year:  2006        PMID: 16826403     DOI: 10.1007/s00432-006-0116-6

Source DB:  PubMed          Journal:  J Cancer Res Clin Oncol        ISSN: 0171-5216            Impact factor:   4.553


  34 in total

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Authors:  E Appella; C W Anderson
Journal:  Eur J Biochem       Date:  2001-05

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3.  Phase I study of an oral histone deacetylase inhibitor, suberoylanilide hydroxamic acid, in patients with advanced cancer.

Authors:  William Kevin Kelly; Owen A O'Connor; Lee M Krug; Judy H Chiao; Mark Heaney; Tracy Curley; Barbara MacGregore-Cortelli; William Tong; J Paul Secrist; Lawrence Schwartz; Stacy Richardson; Elaina Chu; Semra Olgac; Paul A Marks; Howard Scher; Victoria M Richon
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4.  Phase I trial of the histone deacetylase inhibitor, depsipeptide (FR901228, NSC 630176), in patients with refractory neoplasms.

Authors:  Victor Sandor; Susan Bakke; Robert W Robey; Min H Kang; Mikhail V Blagosklonny; Jonathon Bender; Rebecca Brooks; Richard L Piekarz; Eben Tucker; William D Figg; Kenneth K Chan; Barry Goldspiel; Antonio Tito Fojo; Stanley P Balcerzak; Susan E Bates
Journal:  Clin Cancer Res       Date:  2002-03       Impact factor: 12.531

5.  Formaldehyde-releasing prodrugs in combination with adriamycin can overcome cellular drug resistance.

Authors:  Suzanne M Cutts; Abraham Nudelman; Vinochani Pillay; Damian M S Spencer; Inesa Levovich; Ada Rephaeli; Don R Phillips
Journal:  Oncol Res       Date:  2005       Impact factor: 5.574

6.  Phase I clinical trial of histone deacetylase inhibitor: suberoylanilide hydroxamic acid administered intravenously.

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Journal:  Clin Cancer Res       Date:  2003-09-01       Impact factor: 12.531

7.  Histone deacetylase inhibitors activate p21(WAF1) expression via ATM.

Authors:  Rong Ju; Mark T Muller
Journal:  Cancer Res       Date:  2003-06-01       Impact factor: 12.701

Review 8.  The follow-up of breast cancer.

Authors:  Leisha A Emens; Nancy E Davidson
Journal:  Semin Oncol       Date:  2003-06       Impact factor: 4.929

Review 9.  A phase I study of pivaloyloxymethyl butyrate, a prodrug of the differentiating agent butyric acid, in patients with advanced solid malignancies.

Authors:  Amita Patnaik; Eric K Rowinsky; Miguel A Villalona; Lisa A Hammond; Carolyn D Britten; Lillian L Siu; Andrew Goetz; Sally A Felton; Susan Burton; Frank H Valone; S Gail Eckhardt
Journal:  Clin Cancer Res       Date:  2002-07       Impact factor: 12.531

10.  Phase II trial of the histone deacetylase inhibitor pivaloyloxymethyl butyrate (Pivanex, AN-9) in advanced non-small cell lung cancer.

Authors:  Tony Reid; Frank Valone; William Lipera; David Irwin; Warren Paroly; Ron Natale; Sunil Sreedharan; Harold Keer; Bert Lum; Frank Scappaticci; Anish Bhatnagar
Journal:  Lung Cancer       Date:  2004-09       Impact factor: 5.705

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  9 in total

1.  Effects of histone deacetylase inhibitory prodrugs on epigenetic changes and DNA damage response in tumor and heart of glioblastoma xenograft.

Authors:  Nataly Tarasenko; Abraham Nudelman; Gabriela Rozic; Suzanne M Cutts; Ada Rephaeli
Journal:  Invest New Drugs       Date:  2017-03-17       Impact factor: 3.850

2.  Accuracy of density functionals in the description of dispersion interactions and IR spectra of phosphates and phosphorylated compounds.

Authors:  Ashwani Sharma; Gilles Ohanessian; Carine Clavaguéra
Journal:  J Mol Model       Date:  2014-08-22       Impact factor: 1.810

3.  The histone deacetylase inhibitor butyroyloxymethyl diethylphosphate (AN-7) protects normal cells against toxicity of anticancer agents while augmenting their anticancer activity.

Authors:  Nataly Tarasenko; Gania Kessler-Icekson; Pnina Boer; Aida Inbal; Hadassa Schlesinger; Don R Phillips; Suzanne M Cutts; Abraham Nudelman; Ada Rephaeli
Journal:  Invest New Drugs       Date:  2010-09-23       Impact factor: 3.850

Review 4.  Doxorubicin, DNA torsion, and chromatin dynamics.

Authors:  Fan Yang; Sheila S Teves; Christopher J Kemp; Steven Henikoff
Journal:  Biochim Biophys Acta       Date:  2013-12-19

5.  Histone deacetylase inhibitors: the anticancer, antimetastatic and antiangiogenic activities of AN-7 are superior to those of the clinically tested AN-9 (Pivanex).

Authors:  Nataly Tarasenko; Abraham Nudelman; Igor Tarasenko; Michal Entin-Meer; Daphne Hass-Kogan; Aida Inbal; Ada Rephaeli
Journal:  Clin Exp Metastasis       Date:  2008-05-28       Impact factor: 5.150

6.  AN-7, a butyric acid prodrug, sensitizes cutaneous T-cell lymphoma cell lines to doxorubicin via inhibition of DNA double strand breaks repair.

Authors:  Lilach Moyal; Neta Goldfeiz; Batia Gorovitz; Ada Rephaeli; Efrat Tal; Nataly Tarasenko; Abraham Nudelman; Yael Ziv; Emmilia Hodak
Journal:  Invest New Drugs       Date:  2017-09-08       Impact factor: 3.850

7.  The Therapeutic Potential of AN-7, a Novel Histone Deacetylase Inhibitor, for Treatment of Mycosis Fungoides/Sezary Syndrome Alone or with Doxorubicin.

Authors:  Lilach Moyal; Nataly Feldbaum; Neta Goldfeiz; Ada Rephaeli; Abraham Nudelman; Michal Weitman; Nataly Tarasenko; Batia Gorovitz; Leah Maron; Shiran Yehezkel; Iris Amitay-Laish; Ido Lubin; Emmilia Hodak
Journal:  PLoS One       Date:  2016-01-11       Impact factor: 3.240

8.  Anticancer prodrugs of butyric acid and formaldehyde protect against doxorubicin-induced cardiotoxicity.

Authors:  A Rephaeli; S Waks-Yona; A Nudelman; I Tarasenko; N Tarasenko; D R Phillips; S M Cutts; G Kessler-Icekson
Journal:  Br J Cancer       Date:  2007-05-01       Impact factor: 7.640

9.  Antitumor effects of a sirtuin inhibitor, tenovin-6, against gastric cancer cells via death receptor 5 up-regulation.

Authors:  Sachiko Hirai; Shinji Endo; Rie Saito; Mitsuaki Hirose; Takunori Ueno; Hideo Suzuki; Kenji Yamato; Masato Abei; Ichinosuke Hyodo
Journal:  PLoS One       Date:  2014-07-17       Impact factor: 3.240

  9 in total

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