Platination of Cysteine by an Epidermal Growth Factor Receptor Kinase-targeted Hybrid Agent

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2018 Jun 20

PMID 29915817

Citations 2

Authors

Mu Yang

Hanzhi Wu

Julie Chu

Lucas A Gabriel

Y Kim

Karen S Anderson

Cristina M Furdui

Ulrich Bierbach

Affiliations

Soon will be listed here.

Abstract

Hybrid molecules have been developed which are comprised of a tyrosine kinase-targeted, quinazoline-based scaffold and a flexibly linked dia(m)minechloridoPt(ii) moiety. The target compounds maintain high affinity and selectivity for ErbB family kinase proteins and one of the derivatives induces platinum adducts with a pharmacologically important cysteine residue.

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References

Fabian M, Biggs 3rd W, Treiber D, Atteridge C, Azimioara M, Benedetti M . A small molecule-kinase interaction map for clinical kinase inhibitors. Nat Biotechnol. 2005; 23(3):329-36. DOI: 10.1038/nbt1068. View

Zhao Z, Bourne P . Progress with covalent small-molecule kinase inhibitors. Drug Discov Today. 2018; 23(3):727-735. DOI: 10.1016/j.drudis.2018.01.035. View

Ma Z, Rao L, Bierbach U . Replacement of a thiourea-S with an amidine-NH donor group in a platinum-acridine antitumor compound reduces the metal's reactivity with cysteine sulfur. J Med Chem. 2009; 52(10):3424-7. PMC: 2693338. DOI: 10.1021/jm900451y. View

Wei Y, Poon D, Fei R, Lam A, Au-Yeung S, To K . A platinum-based hybrid drug design approach to circumvent acquired resistance to molecular targeted tyrosine kinase inhibitors. Sci Rep. 2016; 6:25363. PMC: 4858680. DOI: 10.1038/srep25363. View

Chaikuad A, Koch P, Laufer S, Knapp S . The Cysteinome of Protein Kinases as a Target in Drug Development. Angew Chem Int Ed Engl. 2017; 57(16):4372-4385. DOI: 10.1002/anie.201707875. View

Kuwano M, Sonoda K, Murakami Y, Watari K, Ono M . Overcoming drug resistance to receptor tyrosine kinase inhibitors: Learning from lung cancer. Pharmacol Ther. 2016; 161:97-110. DOI: 10.1016/j.pharmthera.2016.03.002. View

Roskoski Jr R . The ErbB/HER family of protein-tyrosine kinases and cancer. Pharmacol Res. 2013; 79:34-74. DOI: 10.1016/j.phrs.2013.11.002. View

Truong T, Ung P, Palde P, Paulsen C, Schlessinger A, Carroll K . Molecular Basis for Redox Activation of Epidermal Growth Factor Receptor Kinase. Cell Chem Biol. 2016; 23(7):837-848. PMC: 4958504. DOI: 10.1016/j.chembiol.2016.05.017. View

Sharma S, Bell D, Settleman J, Haber D . Epidermal growth factor receptor mutations in lung cancer. Nat Rev Cancer. 2007; 7(3):169-81. DOI: 10.1038/nrc2088. View

10.

Liu Q, Sabnis Y, Zhao Z, Zhang T, Buhrlage S, Jones L . Developing irreversible inhibitors of the protein kinase cysteinome. Chem Biol. 2013; 20(2):146-59. PMC: 3583020. DOI: 10.1016/j.chembiol.2012.12.006. View

11.

Zhang J, Yang P, Gray N . Targeting cancer with small molecule kinase inhibitors. Nat Rev Cancer. 2008; 9(1):28-39. DOI: 10.1038/nrc2559. View

12.

Boal A, Rosenzweig A . Crystal structures of cisplatin bound to a human copper chaperone. J Am Chem Soc. 2009; 131(40):14196-7. PMC: 2760026. DOI: 10.1021/ja906363t. View

13.

Park J, Liu Y, Lemmon M, Radhakrishnan R . Erlotinib binds both inactive and active conformations of the EGFR tyrosine kinase domain. Biochem J. 2012; 448(3):417-23. PMC: 3507260. DOI: 10.1042/BJ20121513. View

14.

Zhang Y, Zhang D, Tian H, Jiao Y, Shi Z, Ran T . Identification of Covalent Binding Sites Targeting Cysteines Based on Computational Approaches. Mol Pharm. 2016; 13(9):3106-18. DOI: 10.1021/acs.molpharmaceut.6b00302. View

15.

Herbst R, Morgensztern D, Boshoff C . The biology and management of non-small cell lung cancer. Nature. 2018; 553(7689):446-454. DOI: 10.1038/nature25183. View

16.

Pao W, Miller V, Zakowski M, Doherty J, Politi K, Sarkaria I . EGF receptor gene mutations are common in lung cancers from "never smokers" and are associated with sensitivity of tumors to gefitinib and erlotinib. Proc Natl Acad Sci U S A. 2004; 101(36):13306-11. PMC: 516528. DOI: 10.1073/pnas.0405220101. View

17.

Yang M, Pickard A, Qiao X, Gueble M, Day C, Kucera G . Synthesis, reactivity, and biological activity of gold(I) complexes modified with thiourea-functionalized tyrosine kinase inhibitors. Inorg Chem. 2015; 54(7):3316-24. PMC: 4450862. DOI: 10.1021/ic502998a. View

18.

Kim Y, Li Z, Apetri M, Luo B, Settleman J, Anderson K . Temporal resolution of autophosphorylation for normal and oncogenic forms of EGFR and differential effects of gefitinib. Biochemistry. 2012; 51(25):5212-22. PMC: 3390174. DOI: 10.1021/bi300476v. View

19.

Paez J, Janne P, Lee J, Tracy S, Greulich H, Gabriel S . EGFR mutations in lung cancer: correlation with clinical response to gefitinib therapy. Science. 2004; 304(5676):1497-500. DOI: 10.1126/science.1099314. View

20.

Olow A, Chen Z, Niedner R, Wolf D, Yau C, Pankov A . An Atlas of the Human Kinome Reveals the Mutational Landscape Underlying Dysregulated Phosphorylation Cascades in Cancer. Cancer Res. 2016; 76(7):1733-45. PMC: 4907268. DOI: 10.1158/0008-5472.CAN-15-2325-T. View