Cisplatin binding to human serum albumin: a structural study.

The reaction between cisplatin and human serum albumin (HSA) was investigated by X-ray crystallography and crystal structures of the cisplatin/HSA adduct were eventually solved for the first time. Structural data unambiguously prove that cisplatin mainly binds to His105 and Met329 side chains; additional binding sites are detected at His288, Met298, and Met548 and at His535, His67 and His247.

[1]  M. Yamamoto,et al.  In vitro cytotoxicities and in vivo distribution of transferrin-platinum(II) complex. , 1995, Journal of pharmaceutical sciences.

[2]  G. Murshudov,et al.  Refinement of macromolecular structures by the maximum-likelihood method. , 1997, Acta crystallographica. Section D, Biological crystallography.

[3]  D. Bowdler,et al.  Disposition and tumour concentrations of platinum in hypoalbuminaemic patients after treatment with cisplatin for cancer of the head and neck. , 1991, British journal of clinical pharmacology.

[4]  S. Curry,et al.  Binding of the General Anesthetics Propofol and Halothane to Human Serum Albumin , 2000, The Journal of Biological Chemistry.

[5]  H. Tajmir-Riahi,et al.  Interaction of cisplatin with human serum albumin. Drug binding mode and protein secondary structure. , 1998, Biochimica et biophysica acta.

[6]  S. Pizzo,et al.  Selectivity and stereospecificity of the reactions of dichlorodiammineplatinum(II) with three purified plasma proteins. , 1988, Journal of inorganic biochemistry.

[7]  P. Sadler,et al.  Arene control over thiolate to sulfinate oxidation in albumin by organometallic ruthenium anticancer complexes. , 2009, Chemistry.

[8]  Randy J. Read,et al.  Phaser crystallographic software , 2007, Journal of applied crystallography.

[9]  T. Ueno,et al.  Elucidation of metal-ion accumulation induced by hydrogen bonds on protein surfaces by using porous lysozyme crystals containing Rh(III) ions as the model surfaces. , 2010, Chemistry.

[10]  C. Pabo,et al.  Basis for recognition of cisplatin-modified DNA by high-mobility-group proteins , 1999, Nature.

[11]  U. Bornscheuer,et al.  Protein Engineering , 2018, Methods in Molecular Biology.

[12]  M. Panzner,et al.  Silver metallation of hen egg white lysozyme: X-ray crystal structure and NMR studies. , 2011, Chemical communications.

[13]  P. Nissen,et al.  Crystals of Na(+)/K(+)-ATPase with bound cisplatin. , 2014, Biochemical pharmacology.

[14]  G. Fountzilas,et al.  Factors influencing complete response and survival in patients with head and neck cancer treated with platinum-based induction chemotherapy. A Hellenic Co-operative Oncology Group Study. , 1992, Annals of oncology : official journal of the European Society for Medical Oncology.

[15]  W. Denny,et al.  Mutagenic and carcinogenic properties of platinum-based anticancer drugs. , 1996, Mutation research.

[16]  Dong Wang,et al.  Cellular processing of platinum anticancer drugs , 2005, Nature Reviews Drug Discovery.

[17]  E. Espinosa,et al.  Serum albumin and other prognostic factors related to response and survival in patients with advanced non-small cell lung cancer. , 1995, Lung cancer.

[18]  J. Essigmann,et al.  Cisplatin-DNA adducts inhibit ribosomal RNA synthesis by hijacking the transcription factor human upstream binding factor. , 1998, Biochemistry.

[19]  K. Paull,et al.  Oxaliplatin, tetraplatin, cisplatin, and carboplatin: spectrum of activity in drug-resistant cell lines and in the cell lines of the National Cancer Institute's Anticancer Drug Screen panel. , 1996, Biochemical pharmacology.

[20]  R. Lange,et al.  Clinical and pharmacological studies with cis-diamminedichloroplatinum (II). , 1973, Cancer research.

[21]  M. L. Mena,et al.  A shotgun approach for the identification of platinum–protein complexes , 2015, Analytical and Bioanalytical Chemistry.

[22]  C. Briand,et al.  Influence of time and chloride ions on the interaction of cisplatin with human albumin in‐vitro , 1987, The Journal of pharmacy and pharmacology.

[23]  Phase I trial of a cisplatin-albumin complex for the treatment of cancer of the head and neck. , 1992, British journal of clinical pharmacology.

[24]  M. Greene,et al.  Is cisplatin a human carcinogen? , 1992, Journal of the National Cancer Institute.

[25]  A. Casini,et al.  Structural investigation of cisplatin-protein interactions: selective platination of His19 in a cuprozinc superoxide dismutase. , 2006, Angewandte Chemie.

[26]  L. Kèlland,et al.  The resurgence of platinum-based cancer chemotherapy , 2007, Nature Reviews Cancer.

[27]  B. Keppler.  Metal complexes in cancer chemotherapy , 1993 .

[28]  Enzo Terreno,et al.  The extraordinary ligand binding properties of human serum albumin , 2005, IUBMB life.

[29]  Jan Reedijk,et al.  Interactions of anticancer Pt compounds with proteins: an overlooked topic in medicinal inorganic chemistry? , 2012 .

[30]  C. Supuran,et al.  ESI mass spectrometry and X-ray diffraction studies of adducts between anticancer platinum drugs and hen egg white lysozyme. , 2007, Chemical communications.

[31]  A. Merlino,et al.  The X-ray structure of the complex formed in the reaction between oxaliplatin and lysozyme. , 2014, Chemical communications.

[32]  Peter J Sadler,et al.  Half-sandwich arene ruthenium(II)-enzyme complex. , 2004, Chemical communications.

[33]  W. Bal,et al.  Binding of transition metal ions to albumin: sites, affinities and rates. , 2013, Biochimica et biophysica acta.

[34]  D C Carter,et al.  Structure of serum albumin. , 1994, Advances in protein chemistry.

[35]  E. Raymond,et al.  Cellular and molecular pharmacology of oxaliplatin. , 2002, Molecular cancer therapeutics.

[36]  W Wolf,et al.  Preparation and metabolism of a cisplatin/serum protein complex. , 1980, Chemico-biological interactions.

[37]  Chemical conversion of cisplatin and carboplatin with histidine in a model protein crystallized under sodium iodide conditions , 2014, Acta crystallographica. Section F, Structural biology communications.

[38]  S. Ito,et al.  Disulfide bond cleavage of human serum albumin and alterations of its secondary structure by cis-diamminedichloroplatinum(II) , 1992 .

[39]  B. Sikic,et al.  Pharmacokinetics and protein binding of cis-dichlorodiammine platinum (II) administered as a one hour or as a twenty hour infusion , 2004, Cancer Chemotherapy and Pharmacology.

[40]  W. Delano.  The PyMOL Molecular Graphics System , 2002 .

[41]  Christian G Hartinger,et al.  Interactions of antitumor metallodrugs with serum proteins: advances in characterization using modern analytical methodology. , 2006, Chemical reviews.

[42]  N. Bhagavan,et al.  Site-directed mutagenesis study of the role of histidine residues in the neutral-to-basic transition of human serum albumin. , 2005, Biochimica et biophysica acta.

[43]  Stephen B. Howell.  Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy , 1991, Springer US.

[44]  D. Wolters,et al.  Characterisation of Cisplatin Binding Sites in Human Serum Proteins Using Hyphenated Multidimensional Liquid Chromatography and ESI Tandem Mass Spectrometry , 2008, ChemMedChem.

[45]  S. Kitagawa,et al.  Porous protein crystals as reaction vessels for controlling magnetic properties of nanoparticles. , 2012, Small.

[46]  P. Sadler,et al.  The anticancer drug cisplatin can cross-link the interdomain zinc site on human albumin. , 2011, Chemical communications.

[47]  Chung-Eun Ha,et al.  Structural basis of albumin–thyroxine interactions and familial dysalbuminemic hyperthyroxinemia , 2003, Proceedings of the National Academy of Sciences of the United States of America.

[48]  S. Pizzo,et al.  Complexes of serum albumin and cis-dichlorodiammineplatinum (II). The role of cysteine 34 as a nucleophilic entering group and evidence for reaction between bound platinum and a second macromolecule. , 1983, The Journal of biological chemistry.

[49]  A. Eastman.  The formation, isolation and characterization of DNA adducts produced by anticancer platinum complexes. , 1987, Pharmacology & therapeutics.

[50]  S. Lippard,et al.  Inhibition of transcription by platinum antitumor compounds. , 2009, Metallomics : integrated biometal science.

[51]  A. Merlino,et al.  Interactions between anticancer trans-platinum compounds and proteins: crystal structures and ESI-MS spectra of two protein adducts of trans-(dimethylamino)(methylamino)dichloridoplatinum(II). , 2014, Inorganic chemistry.

[52]  D. Carter,et al.  Atomic structure and chemistry of human serum albumin , 1992, Nature.

[53]  P. A. Lay,et al.  Characterization of a ruthenium(III)/NAMI-A adduct with bovine serum albumin that exhibits a high anti-metastatic activity. , 2010, Angewandte Chemie.

[54]  A. Trapananti,et al.  Interaction of cisplatin with human superoxide dismutase. , 2012, Journal of the American Chemical Society.

[55]  良二 上田.  J. Appl. Cryst.の発刊に際して , 1970 .

[56]  J. Verweij,et al.  Pharmacokinetic-dynamic relationship of cisplatin in vitro: simulation of an i.v. bolus and 3 h and 20 h infusion. , 1994, British Journal of Cancer.

[57]  M. Aapro.  Radiotherapy and drugs: 'setrons' once again. , 1996, Annals of oncology : official journal of the European Society for Medical Oncology.

[58]  M. Dolan,et al.  Molecular mechanisms of resistance and toxicity associated with platinating agents. , 2007, Cancer treatment reviews.

[59]  F. Guissard,et al.  Biochemical Pharmacology , 1960, Nature.

[60]  K. Diederichs,et al.  Carboplatin binding to histidine , 2014, Acta crystallographica. Section F, Structural biology communications.

[61]  S. Lippard,et al.  Structure, Recognition, and Processing of Cisplatin-DNA Adducts. , 1999, Chemical reviews.

[62]  S. Ito,et al.  Multiple and irreversible binding of cis-diamminedichloroplatinum(II) to human serum albumin and its effect on warfarin binding. , 1991, Chemical & pharmaceutical bulletin.

[63]  A. Sanz-Medel,et al.  Atomic (HPLC-ICP-MS) and molecular mass spectrometry (ESI-Q-TOF) to study cis-platin interactions with serum proteins , 2008 .

[64]  G. Ferraro,et al.  The X-ray structure of the primary adducts formed in the reaction between cisplatin and cytochrome c. , 2015, Chemical communications.

[65]  Yi Lu,et al.  Time-dependent, protein-directed growth of gold nanoparticles within a single crystal of lysozyme. , 2011, Nature nanotechnology.

[66]  Z. Siddik,et al.  Cisplatin: mode of cytotoxic action and molecular basis of resistance , 2003, Oncogene.

[67]  O. Pinato,et al.  Pt-based drugs: the spotlight will be on proteins. , 2014, Metallomics : integrated biometal science.

[68]  A. Merlino,et al.  Cisplatin binding to proteins: molecular structure of the ribonuclease a adduct. , 2014, Inorganic chemistry.

[69]  J. Helliwell,et al.  The crystal structure analysis of the relative binding of cisplatin and carboplatin in a mixture with histidine in a protein studied at 100 and 300 K with repeated X-ray irradiation. , 2013, Acta crystallographica. Section D, Biological crystallography.

[70]  Gonçalo J. L. Bernardes,et al.  CORM-3 reactivity toward proteins: the crystal structure of a Ru(II) dicarbonyl-lysozyme complex. , 2011, Journal of the American Chemical Society.

[71]  J Christodoulou,et al.  Cisplatin Binding Sites on Human Albumin* , 1998, The Journal of Biological Chemistry.