Literature DB >> 27529700

Fulvestrant-3 Boronic Acid (ZB716): An Orally Bioavailable Selective Estrogen Receptor Downregulator (SERD).

Jiawang Liu1, Shilong Zheng1, Victoria L Akerstrom2, Chester Yuan3, Youning Ma3, Qiu Zhong1, Changde Zhang1, Qiang Zhang1, Shanchun Guo1, Peng Ma4, Elena V Skripnikova4, Melyssa R Bratton4, Antonio Pannuti2, Lucio Miele2, Thomas E Wiese4, Guangdi Wang1.   

Abstract

Orally bioavailable SERDs may offer greater systemic drug exposure, improved clinical efficacy, and more durable treatment outcome for patients with ER-positive endocrine-resistant breast cancer. We report the design and synthesis of a boronic acid modified fulvestrant (5, ZB716), which binds to ERα competitively (IC50 = 4.1 nM) and effectively downregulates ERα in both tamoxifen-sensitive and tamoxifen-resistant breast cancer cells. Furthermore, It has superior oral bioavailability (AUC = 2547.1 ng·h/mL) in mice, indicating its promising clinical utility as an oral SERD.

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Year:  2016        PMID： 27529700      PMCID： PMC5499704          DOI： 10.1021/acs.jmedchem.6b00753

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


  36 in total

Review 1.  Preclinical and clinical experience with fulvestrant (Faslodex) in postmenopausal women with hormone receptor-positive advanced breast cancer.

Authors:  Nigel Bundred
Journal:  Cancer Invest       Date:  2005       Impact factor: 2.176

Review 2.  First-pass metabolism via UDP-glucuronosyltransferase: a barrier to oral bioavailability of phenolics.

Authors:  Baojian Wu; Kaustubh Kulkarni; Sumit Basu; Shuxing Zhang; Ming Hu
Journal:  J Pharm Sci       Date:  2011-04-11       Impact factor: 3.534

3.  Boronic prodrug of endoxifen as an effective hormone therapy for breast cancer.

Authors:  Changde Zhang; Qiu Zhong; Qiang Zhang; Shilong Zheng; Lucio Miele; Guangdi Wang
Journal:  Breast Cancer Res Treat       Date:  2015-06-14       Impact factor: 4.872

4.  Sulfation of afimoxifene, endoxifen, raloxifene, and fulvestrant by the human cytosolic sulfotransferases (SULTs): A systematic analysis.

Authors:  Ying Hui; Lijun Luo; Lingtian Zhang; Katsuhisa Kurogi; Chunyang Zhou; Yoichi Sakakibara; Masahito Suiko; Ming-Cheh Liu
Journal:  J Pharmacol Sci       Date:  2015-06-25       Impact factor: 3.337

5.  Three dose regimens of fulvestrant in postmenopausal Japanese women with advanced breast cancer: results from a double-blind, phase II comparative study (FINDER1).

Authors:  S Ohno; Y Rai; H Iwata; N Yamamoto; M Yoshida; H Iwase; N Masuda; S Nakamura; H Taniguchi; S Kamigaki; S Noguchi
Journal:  Ann Oncol       Date:  2010-05-21       Impact factor: 32.976

6.  Effects of CH4893237, a new orally active estrogen receptor downregulator, on breast cancer xenograft models with low serum estrogen levels.

Authors:  Takaaki Yoneya; Toshiaki Tsunenari; Kenji Taniguchi; Yoshitake Kanbe; Kazumi Morikawa; Hisafumi Yamada-Okabe; Yeon-Ho Lee; Mee-Hyun Lee; Lae-Sung Kwon
Journal:  Oncol Rep       Date:  2009-03       Impact factor: 3.906

7.  Transcription factor EGR3 is involved in the estrogen-signaling pathway in breast cancer cells.

Authors:  A Inoue; Y Omoto; Y Yamaguchi; R Kiyama; S-I Hayashi
Journal:  J Mol Endocrinol       Date:  2004-06       Impact factor: 5.098

8.  Proteomic analysis of acquired tamoxifen resistance in MCF-7 cells reveals expression signatures associated with enhanced migration.

Authors:  Changhua Zhou; Qiu Zhong; Lyndsay V Rhodes; Ian Townley; Melyssa R Bratton; Qiang Zhang; Elizabeth C Martin; Steven Elliott; Bridgette M Collins-Burow; Matthew E Burow; Guangdi Wang
Journal:  Breast Cancer Res       Date:  2012-03-14       Impact factor: 6.466

9.  Stable transfection of protein kinase C alpha cDNA in hormone-dependent breast cancer cell lines.

Authors:  D A Tonetti; M J Chisamore; W Grdina; H Schurz; V C Jordan
Journal:  Br J Cancer       Date:  2000-09       Impact factor: 7.640

Review 10.  Fulvestrant is an effective and well-tolerated endocrine therapy for postmenopausal women with advanced breast cancer: results from clinical trials.

Authors:  I Vergote; J F R Robertson
Journal:  Br J Cancer       Date:  2004-03       Impact factor: 7.640
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  15 in total

1.  Discovery of GNE-149 as a Full Antagonist and Efficient Degrader of Estrogen Receptor alpha for ER+ Breast Cancer.

Authors:  Jun Liang; Robert Blake; Jae Chang; Lori S Friedman; Simon Goodacre; Steven Hartman; Ellen Rei Ingalla; James R Kiefer; Tracy Kleinheinz; Sharada Labadie; Jun Li; Kwong Wah Lai; Jiangpeng Liao; Vidhi Mody; Neville McLean; Ciara Metcalfe; Michelle Nannini; Daniel Otwine; Yingqing Ran; Nick Ray; Fabien Roussel; Amy Sambrone; Deepak Sampath; Maia Vinogradova; John Wai; Tao Wang; Kuen Yeap; Amy Young; Jason Zbieg; Birong Zhang; Xiaoping Zheng; Yu Zhong; Xiaojing Wang
Journal:  ACS Med Chem Lett       Date:  2020-05-26       Impact factor: 4.345

Review 2.  Prodrug strategies for targeted therapy triggered by reactive oxygen species.

Authors:  Jorge Peiró Cadahía; Viola Previtali; Nikolaj S Troelsen; Mads H Clausen
Journal:  Medchemcomm       Date:  2019-05-08       Impact factor: 3.597

3.  Rational Design of a Boron-Modified Triphenylethylene (GLL398) as an Oral Selective Estrogen Receptor Downregulator.

Authors:  Jiawang Liu; Shilong Zheng; Shanchun Guo; Changde Zhang; Qiu Zhong; Qiang Zhang; Peng Ma; Elena V Skripnikova; Melyssa R Bratton; Thomas E Wiese; Guangdi Wang
Journal:  ACS Med Chem Lett       Date:  2016-11-29       Impact factor: 4.345

Review 4.  Structural underpinnings of oestrogen receptor mutations in endocrine therapy resistance.

Authors:  John A Katzenellenbogen; Christopher G Mayne; Benita S Katzenellenbogen; Geoffrey L Greene; Sarat Chandarlapaty
Journal:  Nat Rev Cancer       Date:  2018-06       Impact factor: 60.716

5.  Adamantyl Antiestrogens with Novel Side Chains Reveal a Spectrum of Activities in Suppressing Estrogen Receptor Mediated Activities in Breast Cancer Cells.

Authors:  Jian Min; Valeria Sanabria Guillen; Abhishek Sharma; Yuechao Zhao; Yvonne Ziegler; Ping Gong; Christopher G Mayne; Sathish Srinivasan; Sung Hoon Kim; Kathryn E Carlson; Kendall W Nettles; Benita S Katzenellenbogen; John A Katzenellenbogen
Journal:  J Med Chem       Date:  2017-07-14       Impact factor: 7.446

Review 6.  ERα-targeted endocrine therapy, resistance and the role of GPER.

Authors:  Richard A Pepermans; Eric R Prossnitz
Journal:  Steroids       Date:  2019-09-10       Impact factor: 2.668

Review 7.  Recent progress in selective estrogen receptor downregulators (SERDs) for the treatment of breast cancer.

Authors:  Irshad Ahmad; Shimy Mathew; Sofia Rahman
Journal:  RSC Med Chem       Date:  2020-03-06

8.  Structurally Novel Antiestrogens Elicit Differential Responses from Constitutively Active Mutant Estrogen Receptors in Breast Cancer Cells and Tumors.

Authors:  Yuechao Zhao; Mary J Laws; Valeria Sanabria Guillen; Yvonne Ziegler; Jian Min; Abhishek Sharma; Sung Hoon Kim; David Chu; Ben Ho Park; Steffi Oesterreich; Chengjian Mao; David J Shapiro; Kendall W Nettles; John A Katzenellenbogen; Benita S Katzenellenbogen
Journal:  Cancer Res       Date:  2017-09-13       Impact factor: 12.701

9.  Biocompatible Boron-Containing Prodrugs of Belinostat for the Potential Treatment of Solid Tumors.

Authors:  Shilong Zheng; Shanchun Guo; Qiu Zhong; Changde Zhang; Jiawang Liu; Lin Yang; Qiang Zhang; Guangdi Wang
Journal:  ACS Med Chem Lett       Date:  2018-01-08       Impact factor: 4.345

10.  SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization.

Authors:  Zilei Liu; Jie Li; Suhua Li; Gencheng Li; K Barry Sharpless; Peng Wu
Journal:  J Am Chem Soc       Date:  2018-02-16       Impact factor: 15.419
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