3rcd › Citations

Design and synthesis of novel human epidermal growth factor receptor 2 (HER2)/epidermal growth factor receptor (EGFR) dual inhibitors bearing a pyrrolo[3,2-d]pyrimidine scaffold.

Ishikawa T, Seto M, Banno H, Kawakita Y, Oorui M, Taniguchi T, Ohta Y, Tamura T, Nakayama A, Miki H, Kamiguchi H, Tanaka T, Habuka N, Sogabe S, Yano J, Aertgeerts K, Kamiyama K
J Med Chem 54 8030-50 (2011)
Cited: 97 times
EuropePMC logo PMID: 22003817

Abstract

Dual inhibitors of human epidermal growth factor receptor 2 (HER2) and epidermal growth factor receptor (EGFR) have been investigated for breast, lung, gastric, prostate, and other cancers; one, lapatinib, is currently approved for breast cancer. To develop novel HER2/EGFR dual kinase inhibitors, we designed and synthesized pyrrolo[3,2-d]pyrimidine derivatives capable of fitting into the receptors' ATP binding site. Among the prepared compounds, 34e showed potent HER2 and EGFR (HER1) inhibitory activities as well as tumor growth inhibitory activity. The X-ray cocrystal structures of 34e with both HER2 and EGFR demonstrated that 34e interacts with the expected residues in their respective ATP pockets. Furthermore, reflecting its good oral bioavailability, 34e exhibited potent in vivo efficacy in HER2-overexpressing tumor xenograft models. On the basis of these findings, we report 34e (TAK-285) as a promising candidate for clinical development as a novel HER2/EGFR dual kinase inhibitor.

Reviews - 3rcd mentioned but not cited (1)

  1. Exploring the chemotherapeutic potential of currently used kinase inhibitors: An update. Naik RR, Shakya AK. Front Pharmacol 13 1064472 (2022)

Articles - 3rcd mentioned but not cited (51)

  1. Antitumor effect of afatinib, as a human epidermal growth factor receptor 2-targeted therapy, in lung cancers harboring HER2 oncogene alterations. Suzawa K, Toyooka S, Sakaguchi M, Morita M, Yamamoto H, Tomida S, Ohtsuka T, Watanabe M, Hashida S, Maki Y, Soh J, Asano H, Tsukuda K, Miyoshi S. Cancer Sci 107 45-52 (2016)
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  3. Oncogenic Receptor Tyrosine Kinases Directly Phosphorylate Focal Adhesion Kinase (FAK) as a Resistance Mechanism to FAK-Kinase Inhibitors. Marlowe TA, Lenzo FL, Figel SA, Grapes AT, Cance WG. Mol Cancer Ther 15 3028-3039 (2016)
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  7. Novel sulphonamide benzoquinazolinones as dual EGFR/HER2 inhibitors, apoptosis inducers and radiosensitizers. Soliman AM, Alqahtani AS, Ghorab M. J Enzyme Inhib Med Chem 34 1030-1040 (2019)
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  17. Navigating into the binding pockets of the HER family protein kinases: discovery of novel EGFR inhibitor as antitumor agent. Liu W, Ning JF, Meng QW, Hu J, Zhao YB, Liu C, Cai L. Drug Des Devel Ther 9 3837-3851 (2015)
  18. Scaffold Repurposing of In-House Small Molecule Candidates Leads to Discovery of First-in-Class CDK-1/HER-2 Dual Inhibitors: In Vitro and In Silico Screening. Elkamhawy A, Ammar UM, Paik S, Abdellattif MH, Elsherbeny MH, Lee K, Roh EJ. Molecules 26 5324 (2021)
  19. Design, Synthesis, Biological Evaluation, and Molecular Dynamics Studies of Novel Lapatinib Derivatives. Elkamhawy A, Son S, Lee HY, El-Maghrabey MH, Hamd MAE, Alshammari SO, Abdelhameed AA, Alshammari QA, Abdeen A, Ibrahim SF, Mahdi WA, Alshehri S, Alnajjar R, Choi WJ, Al-Karmalawy AA, Lee K. Pharmaceuticals (Basel) 16 43 (2022)
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  21. Design, Synthesis, and Biological Evaluation of 2-Mercaptobenzoxazole Derivatives as Potential Multi-Kinase Inhibitors. Alanazi MM, Aldawas S, Alsaif NA. Pharmaceuticals (Basel) 16 97 (2023)
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  26. HER2 transmembrane domain mutation: comprehensive characteristics and real-world evidence of treatment response in Chinese lung adenocarcinoma. Jia Z, Xing J, Li J, Wang W, Wang Y, Song Y, Yang X, Xue J, Ye J, Li B, Han-Zhang H, Zhao J, Zhang X, Peng F, Chen F, Chen X, Lu Y, Ying S, Wu D, Zhang X, Ma C, Lai L, Ma S, Liang D, Liu P, Li X, Liang N, Li S. Transl Lung Cancer Res 10 1383-1396 (2021)
  27. Antiproliferative Activity, Multikinase Inhibition, Apoptosis- Inducing Effects and Molecular Docking of Novel Isatin-Purine Hybrids. Alanazi AS, Mirgany TO, Alsfouk AA, Alsaif NA, Alanazi MM. Medicina (Kaunas) 59 610 (2023)
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  30. Diosgenin and Monohydroxy Spirostanol from Prunus amygdalus var amara Seeds as Potential Suppressors of EGFR and HER2 Tyrosine Kinases: A Computational Approach. Shalayel MHF, Al-Mazaideh GM, Alanezi AA, Almuqati AF, Alotaibi M. Pharmaceuticals (Basel) 16 704 (2023)
  31. Discovery of new symmetrical and asymmetrical nitrile-containing 1,4-dihydropyridine derivatives as dual kinases and P-glycoprotein inhibitors: synthesis, in vitro assays, and in silico studies. Saad MH, El-Moselhy TF, S El-Din N, Mehany ABM, Belal A, Abourehab MAS, Tawfik HO, El-Hamamsy MH. J Enzyme Inhib Med Chem 37 2489-2511 (2022)
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  37. CHMFL-26 is a highly potent irreversible HER2 inhibitor for use in the treatment of HER2-positive and HER2-mutant cancers. Cao JY, Qi S, Wu H, Wang AL, Liu QW, Li XX, Wang BL, Ge J, Zou FM, Chen C, Wang JJ, Hu C, Liu J, Wang WC, Liu QS. Acta Pharmacol Sin 43 2678-2686 (2022)
  38. Design, synthesis, HER2 inhibition and anticancer evaluation of new substituted 1,5-dihydro-4,1-benzoxazepines. Cruz-López O, Ner M, Nerín-Fonz F, Jiménez-Martínez Y, Araripe D, Marchal JA, Boulaiz H, Gutiérrez-de-Terán H, Campos JM, Conejo-García A. J Enzyme Inhib Med Chem 36 1553-1563 (2021)
  39. Design, synthesis, antitumor evaluation, and molecular docking of novel pyrrolo[2,3-d]pyrimidine as multi-kinase inhibitors. Alanazi AS, Mirgany TO, Alsaif NA, Alsfouk AA, Alanazi MM. Saudi Pharm J 31 989-997 (2023)
  40. Development of new TAK-285 derivatives as potent EGFR/HER2 inhibitors possessing antiproliferative effects against 22RV1 and PC3 prostate carcinoma cell lines. Son S, Elkamhawy A, Gul AR, Al-Karmalawy AA, Alnajjar R, Abdeen A, Ibrahim SF, Alshammari SO, Alshammari QA, Choi WJ, Park TJ, Lee K. J Enzyme Inhib Med Chem 38 2202358 (2023)
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  42. High-throughput computational screening and in vitro evaluation identifies 5-(4-oxo-4H-3,1-benzoxazin-2-yl)-2-[3-(4-oxo-4H-3,1-benzoxazin-2-yl) phenyl]-1H-isoindole-1,3(2H)-dione (C3), as a novel EGFR-HER2 dual inhibitor in gastric tumors. Shahrani MA, Gahtani R, Abohassan M, Alshahrani M, Alraey Y, Dera A, Asiri MR, Rajagopalan P. Oncol Res 32 251-259 (2023)
  43. Identification of New Mono/Dihydroxynaphthoquinone as Lead Agents That Inhibit the Growth of Refractive and Triple-Negative Breast Cancer Cell Lines. Schroeder R, Sfondouris M, Goyal N, Komati R, Weerathunga A, Gettridge C, Stevens CLK, Jones FE, Sridhar J. ACS Omega 4 10610-10619 (2019)
  44. Indocyanine Green-based Glow Nanoparticles Probe for Cancer Imaging. Chauhan N, Cabrera M, Chowdhury P, Nagesh PKB, Dhasmana A, Pranav, Jaggi M, Chauhan SC, Yallapu MM. Nanotheranostics 7 353-367 (2023)
  45. New Thiazolyl-Pyrazoline Derivatives as Potential Dual EGFR/HER2 Inhibitors: Design, Synthesis, Anticancer Activity Evaluation and In Silico Study. Fakhry MM, Mattar AA, Alsulaimany M, Al-Olayan EM, Al-Rashood ST, Abdel-Aziz HA. Molecules 28 7455 (2023)
  46. Novel Approaches for the Solid-Phase Synthesis of Dihydroquinazoline-2(1H)-One Derivatives and Biological Evaluation as Potential Anticancer Agents. Wang Q, Pan Y, Luo H, Zhang Y, Gao F, Wang J, Zheng J. Molecules 27 8577 (2022)
  47. Preclinical and clinical activity of DZD1516, a full blood-brain barrier-penetrant, highly selective HER2 inhibitor. Zhang J, McAndrew NP, Wang X, Du Y, DiCarlo B, Wang M, Chen K, Yu W, Hu X. Breast Cancer Res 25 81 (2023)
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  49. Ribociclib Hybrid Lipid-Polymer Nanoparticle Preparation and Characterization for Cancer Treatment. Al-Shdefat R, Hailat M, Alshogran OY, Abu Dayyih W, Gardouh A, Al Meanazel O. Polymers (Basel) 15 2844 (2023)
  50. The integrative bioinformatics approaches to predict the xanthohumol as anti-breast cancer molecule: Targeting cancer cells signaling PI3K and AKT kinase pathway. Gupta KK, Sharma KK, Chandra H, Panwar H, Bhardwaj N, Altwaijry NA, Alsfouk AA, Dlamini Z, Afzal O, Altamimi ASA, Khan S, Mishra AP. Front Oncol 12 950835 (2022)
  51. The protein kinase promiscuities in the cancer-preventive mechanisms of NSAIDs. Norvaisas P, Chan D, Yokoi K, Dave B, Ziemys A. Eur J Cancer Prev 25 77-84 (2016)


Reviews citing this publication (7)

  1. αC helix displacement as a general approach for allosteric modulation of protein kinases. Palmieri L, Rastelli G. Drug Discov Today 18 407-414 (2013)
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Articles citing this publication (38)

  1. Activating HER2 mutations in HER2 gene amplification negative breast cancer. Bose R, Kavuri SM, Searleman AC, Shen W, Shen D, Koboldt DC, Monsey J, Goel N, Aronson AB, Li S, Ma CX, Ding L, Mardis ER, Ellis MJ. Cancer Discov 3 224-237 (2013)
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  11. Design, synthesis and biological evaluation of novel 4-anilinoquinazolines with C-6 urea-linked side chains as inhibitors of the epidermal growth factor receptor. Zhang X, Peng T, Ji X, Li J, Tong L, Li Z, Yang W, Xu Y, Li M, Ding J, Jiang H, Xie H, Liu H. Bioorg Med Chem 21 7988-7998 (2013)
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  15. Synthesis, potential antitumor activity, cell cycle analysis, and multitarget mechanisms of novel hydrazones incorporating a 4-methylsulfonylbenzene scaffold: a molecular docking study. Abdel-Aziz AA, El-Azab AS, AlSaif NA, Obaidullah AJ, Al-Obaid AM, Al-Suwaidan IA. J Enzyme Inhib Med Chem 36 1521-1539 (2021)
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  21. Gene Signature-Based Approach Identified MEK1/2 as a Potential Target Associated With Relapse After Anti-TNFα Treatment for Crohn's Disease. Gamo K, Okuzono Y, Yabuki M, Ochi T, Sugimura K, Sato Y, Sagara M, Hayashi H, Ishimura Y, Nishimoto Y, Murakawa Y, Shiokawa Z, Gotoh M, Miyazaki T, Ebisuno Y. Inflamm Bowel Dis 24 1251-1265 (2018)
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  26. Discovery of WS-157 as a highly potent, selective and orally active EGFR inhibitor. He P, Niu S, Wang S, Shi X, Feng S, Du L, Zhang X, Ma Z, Yu B, Liu H. Acta Pharm Sin B 9 1193-1203 (2019)
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  30. Carotenoid-Enriched Fractions From Spondias mombin Demonstrate HER2 ATP Kinase Domain Inhibition: Computational and In Vivo Animal Model of Breast Carcinoma Studies. Metibemu DS, Akinloye OA, Omotuyi IO, Okoye JO, Popoola MA, Akamo AJ. Front Oncol 11 687190 (2021)
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  32. Design and Synthesis of 4-Anilinothieno[2,3-d]pyrimidine-Based Compounds as Dual EGFR/HER-2 Inhibitors. Abd El Hadi SR, Lasheen DS, Hassan MA, Abouzid KA. Arch Pharm (Weinheim) 349 827-847 (2016)
  33. Effect of double mutations T790M/L858R on conformation and drug-resistant mechanism of epidermal growth factor receptor explored by molecular dynamics simulations. Yan F, Liu X, Zhang S, Su J, Zhang Q, Chen J. RSC Adv 8 39797-39810 (2018)
  34. Identification of Novel Aryl Carboxamide Derivatives as Death-Associated Protein Kinase 1 (DAPK1) Inhibitors with Anti-Proliferative Activities: Design, Synthesis, In Vitro, and In Silico Biological Studies. Elkamhawy A, Paik S, Ali EMH, Hassan AHE, Kang SJ, Lee K, Roh EJ. Pharmaceuticals (Basel) 15 1050 (2022)
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