Highly and Broad-Spectrum In Vitro Antitumor Active cis-Dichloridoplatinum(II) Complexes with 7-Azaindoles
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{"title"=>"Highly and broad-spectrum in vitro antitumor active cis-dichloridoplatinum(II) complexes with 7-azaindoles", "type"=>"journal", "authors"=>[{"first_name"=>"Pavel", "last_name"=>"Štarha", "scopus_author_id"=>"24077542900"}, {"first_name"=>"Zdeněk", "last_name"=>"Dvořák", "scopus_author_id"=>"44861288800"}, {"first_name"=>"Zdeněk", "last_name"=>"Trávníček", "scopus_author_id"=>"7006550955"}], "year"=>2015, "source"=>"PLoS ONE", "identifiers"=>{"issn"=>"19326203", "pui"=>"606225711", "sgr"=>"84943303321", "scopus"=>"2-s2.0-84943303321", "doi"=>"10.1371/journal.pone.0136338"}, "id"=>"9fff0610-7ffe-33d8-9d41-27318f5ba106", "abstract"=>"© 2015 Štarha et al. The cis-[PtCl 2 (naza) 2 ] complexes (1-3) containing monosubstituted 7-azaindole halogenoderivatives (naza), showed significantly higher activity than cisplatin towards ovarian carcinoma A2780, its cisplatin-resistant variant A2780R, osteosarcoma HOS, breast carcinoma MCF7 and cervix carcinoma HeLa cell lines, with the IC 50 values of 3.8, 3.5, 4.5, 2.7, and 9.2 μM, respectively, obtained for the most active complex 3. As for 4 and 5 having disubstituted 7-azaindoles in their molecule, the significant cytotoxicity was detected only for 4 against A2780 (IC 50 = 4.8 μM), A2780R (IC 50 = 3.8 μM) and HOS (IC 50 = 4.3 μM), while 5 was evaluated as having only moderate antiproliferative effect against the mentioned cancer cell lines with IC 50 = 33.4, 24.7 and 46.7 μM, respectively. All the studied complexes 1-5 effectively avoided the acquired resistance of ovarian carcinoma cell line. On the other hand, the complexes did not reveal any inhibition activity on the purified 20S proteasome from the A2780 cells. The representative complexes 3 and 5 showed low ability to be hydrolysed, but their stability was markedly lowered in the presence of physiological sulphur-containing biomolecule glutathione (GSH), as proved by the 1 H NMR spectroscopy and mass spectrometry studies. A rate of interaction of the studied complexes with GSH was affected by an addition of another mechanistically relevant biomolecule guanosine monophosphate. The differences in interactions of 3 and 5 with GSH correlate well with their different cytotoxicity profiles.", "link"=>"http://www.mendeley.com/research/highly-broadspectrum-vitro-antitumor-active-cisdichloridoplatinumii-complexes-7azaindoles", "reader_count"=>2, "reader_count_by_academic_status"=>{"Unspecified"=>1, "Student > Master"=>1}, "reader_count_by_user_role"=>{"Unspecified"=>1, "Student > Master"=>1}, "reader_count_by_subject_area"=>{"Unspecified"=>1, "Chemistry"=>1}, "reader_count_by_subdiscipline"=>{"Chemistry"=>{"Chemistry"=>1}, "Unspecified"=>{"Unspecified"=>1}}, "group_count"=>0}

Scopus | Further Information

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Figshare

  • {"files"=>["https://ndownloader.figshare.com/files/2227939"], "description"=>"<p><sup>1</sup>H NMR spectra of <i>cis</i>-[PtCl<sub>2</sub>(<i>3Cl5Br</i>aza)<sub>2</sub>] (<b>5</b>) dissolved in the DMF-<i>d</i><sub><i>7</i></sub>/H<sub>2</sub>O mixture (1:1, <i>v/</i>v) without or with glutathione (GSH) measured at different time points (0, 24 and 48 h). ○ = N1–H, <b>5</b>; ● = N1–H, GSH adduct of <b>5</b>; □ = C6–H, <b>5</b>; ■ = C6–H, GSH adduct of <b>5</b>; Δ = C4–H, <b>5</b>; ▲ = C4–H, GSH adduct of <b>5</b>; ◊ = C2–H, <b>5</b>; ♦ = C2–H, GSH adduct of <b>5</b>; # = N–H of glycine and cysteine of GSH.</p>", "links"=>[], "tags"=>["gsh", "1 H NMR spectroscopy", "IC 50 values", "carcinoma cell line", "20 S proteasome", "biomolecule guanosine monophosphate", "interaction", "mass spectrometry studies", "cancer cell lines", "IC 50", "representative complexes 3", "2780R osteosarcoma HOS", "cervix carcinoma HeLa cell lines", "cytotoxicity", "azaindole", "breast carcinoma MCF 7"], "article_id"=>1523188, "categories"=>["Uncategorised"], "users"=>["Pavel Štarha", "Zdenek Dvorak", "Zdeněk Trávníček"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0136338.g005", "stats"=>{"downloads"=>0, "page_views"=>15, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Time_dependent_1_H_NMR_studies_of_5_and_its_interaction_with_GSH_/1523188", "title"=>"Time-dependent <sup>1</sup>H NMR studies of 5 and its interaction with GSH.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-08-26 03:32:25"}
  • {"files"=>["https://ndownloader.figshare.com/files/2227936"], "description"=>"<p>Graphically depicted comparison of <i>in vitro</i> cytotoxicity of the studied complexes against ovarian carcinoma (A2780), <i>cisplatin</i>-resistant ovarian carcinoma (A2780R), osteosarcoma (HOS), breast carcinoma (MCF7) and cervix carcinoma (HeLa), where the significant differences (<i>p</i> < 0.05; assigned with the asterisks) between the obtained IC<sub>50</sub> values (μM) of <b>1</b>–<b>5</b> were observed.</p>", "links"=>[], "tags"=>["gsh", "1 H NMR spectroscopy", "IC 50 values", "carcinoma cell line", "20 S proteasome", "biomolecule guanosine monophosphate", "interaction", "mass spectrometry studies", "cancer cell lines", "IC 50", "representative complexes 3", "2780R osteosarcoma HOS", "cervix carcinoma HeLa cell lines", "cytotoxicity", "azaindole", "breast carcinoma MCF 7"], "article_id"=>1523185, "categories"=>["Uncategorised"], "users"=>["Pavel Štarha", "Zdenek Dvorak", "Zdeněk Trávníček"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0136338.g003", "stats"=>{"downloads"=>0, "page_views"=>5, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_In_vitro_cytotoxicity_of_1_5_/1523185", "title"=>"<i>In vitro</i> cytotoxicity of 1–5.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-08-26 03:32:25"}
  • {"files"=>["https://ndownloader.figshare.com/files/2227935"], "description"=>"<p>The spectra show the signals of the corresponding atoms and point to chemical and isomeric purity of <b>3</b>.</p>", "links"=>[], "tags"=>["gsh", "1 H NMR spectroscopy", "IC 50 values", "carcinoma cell line", "20 S proteasome", "biomolecule guanosine monophosphate", "interaction", "mass spectrometry studies", "cancer cell lines", "IC 50", "representative complexes 3", "2780R osteosarcoma HOS", "cervix carcinoma HeLa cell lines", "cytotoxicity", "azaindole", "breast carcinoma MCF 7"], "article_id"=>1523184, "categories"=>["Uncategorised"], "users"=>["Pavel Štarha", "Zdenek Dvorak", "Zdeněk Trávníček"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0136338.g002", "stats"=>{"downloads"=>3, "page_views"=>65, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_The_1_H_NMR_and_195_Pt_NMR_inset_spectra_of_3_in_DMF_d_7_/1523184", "title"=>"The <sup>1</sup>H NMR and <sup>195</sup>Pt NMR (inset) spectra of 3 in DMF-<i>d</i><sub><i>7</i></sub>.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-08-26 03:32:25"}
  • {"files"=>["https://ndownloader.figshare.com/files/2227948", "https://ndownloader.figshare.com/files/2227949", "https://ndownloader.figshare.com/files/2227950", "https://ndownloader.figshare.com/files/2227951", "https://ndownloader.figshare.com/files/2227952", "https://ndownloader.figshare.com/files/2227953", "https://ndownloader.figshare.com/files/2227954", "https://ndownloader.figshare.com/files/2227955"], "description"=>"<div><p>The <i>cis</i>-[PtCl<sub>2</sub>(<i>n</i>aza)<sub>2</sub>] complexes (<b>1</b>–<b>3</b>) containing monosubstituted 7-azaindole halogeno-derivatives (<i>n</i>aza), showed significantly higher activity than <i>cisplatin</i> towards ovarian carcinoma A2780, its <i>cisplatin</i>-resistant variant A2780R, osteosarcoma HOS, breast carcinoma MCF7 and cervix carcinoma HeLa cell lines, with the IC<sub>50</sub> values of 3.8, 3.5, 4.5, 2.7, and 9.2 μM, respectively, obtained for the most active complex <b>3</b>. As for <b>4</b> and <b>5</b> having disubstituted 7-azaindoles in their molecule, the significant cytotoxicity was detected only for <b>4</b> against A2780 (IC<sub>50</sub> = 4.8 μM), A2780R (IC<sub>50</sub> = 3.8 μM) and HOS (IC<sub>50</sub> = 4.3 μM), while <b>5</b> was evaluated as having only moderate antiproliferative effect against the mentioned cancer cell lines with IC<sub>50</sub> = 33.4, 24.7 and 46.7 μM, respectively. All the studied complexes <b>1</b>–<b>5</b> effectively avoided the acquired resistance of ovarian carcinoma cell line. On the other hand, the complexes did not reveal any inhibition activity on the purified 20S proteasome from the A2780 cells. The representative complexes <b>3</b> and <b>5</b> showed low ability to be hydrolysed, but their stability was markedly lowered in the presence of physiological sulphur-containing biomolecule glutathione (GSH), as proved by the <sup>1</sup>H NMR spectroscopy and mass spectrometry studies. A rate of interaction of the studied complexes with GSH was affected by an addition of another mechanistically relevant biomolecule guanosine monophosphate. The differences in interactions of <b>3</b> and <b>5</b> with GSH correlate well with their different cytotoxicity profiles.</p></div>", "links"=>[], "tags"=>["gsh", "1 H NMR spectroscopy", "IC 50 values", "carcinoma cell line", "20 S proteasome", "biomolecule guanosine monophosphate", "interaction", "mass spectrometry studies", "cancer cell lines", "IC 50", "representative complexes 3", "2780R osteosarcoma HOS", "cervix carcinoma HeLa cell lines", "cytotoxicity", "azaindole", "breast carcinoma MCF 7"], "article_id"=>1523197, "categories"=>["Uncategorised"], "users"=>["Pavel Štarha", "Zdenek Dvorak", "Zdeněk Trávníček"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0136338.s001", "https://dx.doi.org/10.1371/journal.pone.0136338.s002", "https://dx.doi.org/10.1371/journal.pone.0136338.s003", "https://dx.doi.org/10.1371/journal.pone.0136338.s004", "https://dx.doi.org/10.1371/journal.pone.0136338.s005", "https://dx.doi.org/10.1371/journal.pone.0136338.s006", "https://dx.doi.org/10.1371/journal.pone.0136338.s007", "https://dx.doi.org/10.1371/journal.pone.0136338.s008"], "stats"=>{"downloads"=>0, "page_views"=>7, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/Highly_and_Broad_Spectrum_In_Vitro_Antitumor_Active_cis_Dichloridoplatinum_II_Complexes_with_7_Azaindoles/1523197", "title"=>"Highly and Broad-Spectrum <i>In Vitro</i> Antitumor Active <i>cis</i>-Dichloridoplatinum(II) Complexes with 7-Azaindoles", "pos_in_sequence"=>0, "defined_type"=>4, "published_date"=>"2015-08-26 03:32:25"}
  • {"files"=>["https://ndownloader.figshare.com/files/2227933"], "description"=>"<p>The general structural formulas of used 4-chloro-7-azaindole (<i>4Cl</i>aza; complex <b>1</b>), 3-bromo-7-azaindole (<i>3Br</i>aza; <b>2</b>), 4-bromo-7-azaindole (<i>4Br</i>aza; <b>3</b>), 3-iodo-5-bromo-7-azaindole (<i>3I5Br</i>aza; <b>4</b>) and 3-chloro-5-bromo-7-azaindole (<i>3Cl5Br</i>aza; <b>5</b>) are given together with their atom numbering scheme.</p>", "links"=>[], "tags"=>["gsh", "1 H NMR spectroscopy", "IC 50 values", "carcinoma cell line", "20 S proteasome", "biomolecule guanosine monophosphate", "interaction", "mass spectrometry studies", "cancer cell lines", "IC 50", "representative complexes 3", "2780R osteosarcoma HOS", "cervix carcinoma HeLa cell lines", "cytotoxicity", "azaindole", "breast carcinoma MCF 7"], "article_id"=>1523182, "categories"=>["Uncategorised"], "users"=>["Pavel Štarha", "Zdenek Dvorak", "Zdeněk Trávníček"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0136338.g001", "stats"=>{"downloads"=>0, "page_views"=>11, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Structural_formula_of_the_studied_complexes_cis_PtCl_2_n_aza_2_1_8211_5_and_7_azaindole_derivatives_used_for_their_preparation_/1523182", "title"=>"Structural formula of the studied complexes <i>cis</i>-[PtCl<sub>2</sub>(<i>n</i>aza)<sub>2</sub>] (1–5) and 7-azaindole derivatives used for their preparation.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-08-26 03:32:25"}
  • {"files"=>["https://ndownloader.figshare.com/files/2227942"], "description"=>"<p>asterisks (*), significantly different values (<i>p</i> < 0.05) between <b>1</b>–<b>5</b> and <i>cisplatin</i></p><p><sup>a</sup>) IC<sub>50</sub> were not reached up to the given concentration</p><p><sup>b</sup>) RF = resistance factor calculated as IC<sub>50</sub>(A2780R)/IC<sub>50</sub>(A2780)</p><p>Cells were treated with tested compounds for 24 h, measurements were performed in triplicate, and cytotoxicity experiment was repeated in three different cell passages. Data are expressed as IC<sub>50</sub> ± SD (μM).</p>", "links"=>[], "tags"=>["gsh", "1 H NMR spectroscopy", "IC 50 values", "carcinoma cell line", "20 S proteasome", "biomolecule guanosine monophosphate", "interaction", "mass spectrometry studies", "cancer cell lines", "IC 50", "representative complexes 3", "2780R osteosarcoma HOS", "cervix carcinoma HeLa cell lines", "cytotoxicity", "azaindole", "breast carcinoma MCF 7"], "article_id"=>1523191, "categories"=>["Uncategorised"], "users"=>["Pavel Štarha", "Zdenek Dvorak", "Zdeněk Trávníček"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0136338.t001", "stats"=>{"downloads"=>2, "page_views"=>9, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_The_results_of_in_vitro_cytotoxicity_of_1_5_and_cisplatin_CDDP_against_eight_human_cancer_cell_lines_/1523191", "title"=>"The results of <i>in vitro</i> cytotoxicity of 1–5 and <i>cisplatin</i> (CDDP) against eight human cancer cell lines.", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2015-08-26 03:32:25"}
  • {"files"=>["https://ndownloader.figshare.com/files/2227941"], "description"=>"<p>The results (CT-like activity (%±SD) of the studies of the ability of the complexes 1–4 to inhibit 20S proteasome activity assayed in purified proteasome obtained from A2780 cancer cell line</p>", "links"=>[], "tags"=>["gsh", "1 H NMR spectroscopy", "IC 50 values", "carcinoma cell line", "20 S proteasome", "biomolecule guanosine monophosphate", "interaction", "mass spectrometry studies", "cancer cell lines", "IC 50", "representative complexes 3", "2780R osteosarcoma HOS", "cervix carcinoma HeLa cell lines", "cytotoxicity", "azaindole", "breast carcinoma MCF 7"], "article_id"=>1523190, "categories"=>["Uncategorised"], "users"=>["Pavel Štarha", "Zdenek Dvorak", "Zdeněk Trávníček"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0136338.g006", "stats"=>{"downloads"=>0, "page_views"=>12, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_The_results_CT_like_activity_177_SD_of_the_studies_of_the_ability_of_the_complexes_1_8211_4_to_inhibit_20S_proteasome_activity_assayed_in_purified_proteasome_obtained_from_A2780_cancer_cell_line_/1523190", "title"=>"The results (CT-like activity (%±SD) of the studies of the ability of the complexes 1–4 to inhibit 20S proteasome activity assayed in purified proteasome obtained from A2780 cancer cell line", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-08-26 03:32:25"}
  • {"files"=>["https://ndownloader.figshare.com/files/2227938"], "description"=>"<p>(A) <sup>1</sup>H NMR spectra of <i>cis</i>-[PtCl<sub>2</sub>(<i>4Br</i>aza)<sub>2</sub>] (<b>3</b>) dissolved in DMF-<i>d</i><sub><i>7</i></sub> or DMF-<i>d</i><sub><i>7</i></sub>/H<sub>2</sub>O mixture (1:1, <i>v/</i>v) without or with glutathione (GSH) measured at different time points (0, 24 and 48 h). ○ = N1–H, <i>cis</i>-[PtCl<sub>2</sub>(<i>4Br</i>aza)<sub>2</sub>]; * = N1–H, <i>trans</i>-[PtCl<sub>2</sub>(<i>4Br</i>aza)<sub>2</sub>]; ● = N1–H, hydrolysis product, <i>cis</i>-[Pt(<i>4Br</i>aza)<sub>2</sub>(H<sub>2</sub>O)Cl]<sup>+</sup>; ♦ = N1–H, GSH adduct of <b>3</b>; ^ = C6–H, <i>cis</i>-[PtCl<sub>2</sub>(<i>4Br</i>aza)<sub>2</sub>]; # = C6–H, <i>trans</i>-[PtCl<sub>2</sub>(<i>4Br</i>aza)<sub>2</sub>]; ◊ = N–H of glycine and cysteine of GSH. (B) ESI–mass spectra (200–1050 <i>m/z</i> range) of the mixture of <b>3</b> with GSH (dissolved in the methanol/H<sub>2</sub>O, 1:1, <i>v/v</i>) as detected at different time points (0, 1 and 24 h). The region of the {[Pt(<i>4Br</i>aza)<sub>2</sub>Cl(GSH)]–2H}<sup>−</sup>species is highlighted by red colour. The detail of the experimental peak of {[Pt(<i>4Br</i>aza)<sub>2</sub>Cl(GSH)]–2H}<sup>–</sup>, as observed after 24 h, is given below (bottom left, given in black) together with the simulated isotope distribution (bottom right, given in grey).</p>", "links"=>[], "tags"=>["gsh", "1 H NMR spectroscopy", "IC 50 values", "carcinoma cell line", "20 S proteasome", "biomolecule guanosine monophosphate", "interaction", "mass spectrometry studies", "cancer cell lines", "IC 50", "representative complexes 3", "2780R osteosarcoma HOS", "cervix carcinoma HeLa cell lines", "cytotoxicity", "azaindole", "breast carcinoma MCF 7"], "article_id"=>1523187, "categories"=>["Uncategorised"], "users"=>["Pavel Štarha", "Zdenek Dvorak", "Zdeněk Trávníček"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0136338.g004", "stats"=>{"downloads"=>0, "page_views"=>49, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Time_dependent_studies_of_stability_of_3_1_H_NMR_and_its_interaction_with_GSH_1_H_NMR_and_ESI_MS_/1523187", "title"=>"Time-dependent studies of stability of 3 (<sup>1</sup>H NMR) and its interaction with GSH (<sup>1</sup>H NMR and ESI-MS).", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2015-08-26 03:32:25"}

PMC Usage Stats | Further Information

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  • {"unique-ip"=>"4", "full-text"=>"2", "pdf"=>"0", "scanned-summary"=>"0", "scanned-page-browse"=>"0", "figure"=>"2", "supp-data"=>"10", "cited-by"=>"0", "year"=>"2019", "month"=>"3"}
  • {"unique-ip"=>"6", "full-text"=>"8", "pdf"=>"0", "scanned-summary"=>"0", "scanned-page-browse"=>"0", "figure"=>"0", "supp-data"=>"0", "cited-by"=>"0", "year"=>"2019", "month"=>"4"}
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  • {"unique-ip"=>"8", "full-text"=>"9", "pdf"=>"0", "scanned-summary"=>"0", "scanned-page-browse"=>"0", "figure"=>"6", "supp-data"=>"0", "cited-by"=>"0", "year"=>"2019", "month"=>"8"}

Relative Metric

{"start_date"=>"2015-01-01T00:00:00Z", "end_date"=>"2015-12-31T00:00:00Z", "subject_areas"=>[]}
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