Nanoscale Reaction Vessels Designed for Synthesis of Copper-Drug Complexes Suitable for Preclinical Development
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{"title"=>"Nanoscale reaction vessels designed for synthesis of copper-drug complexes suitable for preclinical development", "type"=>"journal", "authors"=>[{"first_name"=>"Mohamed", "last_name"=>"Wehbe", "scopus_author_id"=>"56281778400"}, {"first_name"=>"Malathi", "last_name"=>"Anantha", "scopus_author_id"=>"8235314500"}, {"first_name"=>"Ian", "last_name"=>"Backstrom", "scopus_author_id"=>"56950816600"}, {"first_name"=>"Ada", "last_name"=>"Leung", "scopus_author_id"=>"56742717100"}, {"first_name"=>"Kent", "last_name"=>"Chen", "scopus_author_id"=>"57188843463"}, {"first_name"=>"Armaan", "last_name"=>"Malhotra", "scopus_author_id"=>"57188834326"}, {"first_name"=>"Katarina", "last_name"=>"Edwards", "scopus_author_id"=>"7402956250"}, {"first_name"=>"Marcel B.", "last_name"=>"Bally", "scopus_author_id"=>"7006109241"}], "year"=>2016, "source"=>"PLoS ONE", "identifiers"=>{"pui"=>"609703269", "sgr"=>"84963783428", "issn"=>"19326203", "pmid"=>"27055237", "scopus"=>"2-s2.0-84963783428", "doi"=>"10.1371/journal.pone.0153416"}, "id"=>"58b83c06-fd81-3eec-b836-1d7021fd4f9c", "abstract"=>"The development of copper-drug complexes (CDCs) is hindered due to their very poor aqueous solubility. Diethyldithiocarbamate (DDC) is the primary metabolite of disulfiram, an approved drug for alcoholism that is being repurposed for cancer. The anticancer activity of DDC is dependent on complexation with copper to form copper bis-diethyldithiocarbamate (Cu(DDC)2), a highly insoluble complex that has not been possible to develop for indications requiring parenteral administration. We have resolved this issue by synthesizing Cu(DDC)2 inside liposomes. DDC crosses the liposomal lipid bilayer, reacting with the entrapped copper; a reaction that can be observed through a colour change as the solution goes from a light blue to dark brown. This method is successfully applied to other CDCs including the anti-parasitic drug clioquinol, the natural product quercetin and the novel targeted agent CX-5461. Our method provides a simple, transformative solution enabling, for the first time, the development of CDCs as viable candidate anticancer drugs; drugs that would represent a brand new class of therapeutics for cancer patients.", "link"=>"http://www.mendeley.com/research/nanoscale-reaction-vessels-designed-synthesis-copperdrug-complexes-suitable-preclinical-development", "reader_count"=>12, "reader_count_by_academic_status"=>{"Unspecified"=>1, "Student > Doctoral Student"=>2, "Researcher"=>2, "Student > Ph. D. Student"=>2, "Student > Master"=>1, "Student > Bachelor"=>3, "Professor"=>1}, "reader_count_by_user_role"=>{"Unspecified"=>1, "Student > Doctoral Student"=>2, "Researcher"=>2, "Student > Ph. D. Student"=>2, "Student > Master"=>1, "Student > Bachelor"=>3, "Professor"=>1}, "reader_count_by_subject_area"=>{"Unspecified"=>3, "Biochemistry, Genetics and Molecular Biology"=>1, "Agricultural and Biological Sciences"=>2, "Medicine and Dentistry"=>3, "Pharmacology, Toxicology and Pharmaceutical Science"=>3}, "reader_count_by_subdiscipline"=>{"Medicine and Dentistry"=>{"Medicine and Dentistry"=>3}, "Agricultural and Biological Sciences"=>{"Agricultural and Biological Sciences"=>2}, "Biochemistry, Genetics and Molecular Biology"=>{"Biochemistry, Genetics and Molecular Biology"=>1}, "Unspecified"=>{"Unspecified"=>3}, "Pharmacology, Toxicology and Pharmaceutical Science"=>{"Pharmacology, Toxicology and Pharmaceutical Science"=>3}}, "group_count"=>0}

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Figshare

  • {"files"=>["https://ndownloader.figshare.com/files/4927315"], "description"=>"<p><b>(A)</b> Disulfiram is metabolized to diethyldithiocarbamate (DDC) and DDC complexes with Copper (Cu) (II). <b>(B)</b> Cytotoxicity curves for DSF (●) and DSF + CuSO<sub>4</sub> (■) were obtained with the IN CELL Analyzer using U87 glioblastoma cells where cell viability was assessed based on loss of plasma membrane integrity 72 hours following treatment; i.e. total cell count and dead cell count were determined using Hoechst 33342 and ethidium homodimer staining, respectively. <b>(C)</b> Cytotoxicity curves for DDC (●) and DDC + CuSO<sub>4</sub> (■); where cytotoxicity was measured as described above. <b>(D)</b> DDC and Cu(DDC)<sub>2</sub> IC<sub>50</sub> for U251, MDA-231-BR, and A549 cancer cell lines as well as HBEcP a normal cell line; averages (±SEM) are reported from three separate experiments each done in triplicate. <b>(E)</b> Photograph of DDC, CuSO<sub>4</sub> and Cu(DDC)<sub>2</sub> solutions in water.</p>", "links"=>[], "tags"=>["candidate anticancer drugs", "transformative solution", "cancer patients", "liposomal lipid bilayer", "entrapped copper", "method", "Nanoscale Reaction Vessels", "parenteral administration", "Preclinical Development", "product quercetin", "DDC", "CDC", "CX", "anticancer activity", "colour change", "Cu"], "article_id"=>3164056, "categories"=>["Biophysics", "Biochemistry", "Genetics", "Molecular Biology", "Pharmacology", "Biotechnology", "Chemical Sciences not elsewhere classified", "Biological Sciences not elsewhere classified", "Developmental Biology", "Cancer"], "users"=>["Mohamed Wehbe", "Malathi Anantha", "Ian Backstrom", "Ada Leung", "Kent Chen", "Armaan Malhotra", "Katarina Edwards", "Marcel B. Bally"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0153416.g001", "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/The_anticancer_activity_of_diethyldithiocarbmamate_DDC_is_dependent_on_copper_/3164056", "title"=>"The anticancer activity of diethyldithiocarbmamate (DDC) is dependent on copper.", "pos_in_sequence"=>1, "defined_type"=>1, "published_date"=>"2016-04-07 05:13:07"}
  • {"files"=>["https://ndownloader.figshare.com/files/4927339"], "description"=>"<p><b>(A)</b> Measured (AAS) copper to liposomal lipid ratio (black bars) compared to measured Cu(DDC)<sub>2</sub> (UV-Vis spectrophotometer) to liposomal lipid ratio (grey bars) after DDC was added to CuSO<sub>4</sub>-containing DSPC/Chol liposomes prepared with different amounts of DSPE-PEG<sub>2000</sub> (ranging from 0 to 5 mole%). <b>(B)</b> Formation of Cu(DDC)<sub>2</sub> inside CuSO<sub>4</sub>-containing DSPC/Chol liposomes as a function of the CuSO<sub>4</sub> concentration used to prepare the liposomes (ranging from 0 to 300 mM); where the measured copper (AAS) to liposomal lipid ratio (black bar) is compared to the measured Cu(DDC)<sub>2</sub> (UV-Vis spectrophotometer) to liposomal lipid ratio (grey bar). <b>(C)</b> Linear regression analysis comparing measured (AAS) copper concentration (assuming encapsulated copper was free in solution) to measured Cu(DDC)<sub>2</sub> (UV-Vis spectrophotometer) concentration (assuming encapsulated Cu(DDC)<sub>2</sub> was free in solution); R<sup>2</sup> = 0.9754; each data point represents a mean ± SEM determined from at least three separate experiments done in duplicate.</p>", "links"=>[], "tags"=>["candidate anticancer drugs", "transformative solution", "cancer patients", "liposomal lipid bilayer", "entrapped copper", "method", "Nanoscale Reaction Vessels", "parenteral administration", "Preclinical Development", "product quercetin", "DDC", "CDC", "CX", "anticancer activity", "colour change", "Cu"], "article_id"=>3164080, "categories"=>["Biophysics", "Biochemistry", "Genetics", "Molecular Biology", "Pharmacology", "Biotechnology", "Chemical Sciences not elsewhere classified", "Biological Sciences not elsewhere classified", "Developmental Biology", "Cancer"], "users"=>["Mohamed Wehbe", "Malathi Anantha", "Ian Backstrom", "Ada Leung", "Kent Chen", "Armaan Malhotra", "Katarina Edwards", "Marcel B. Bally"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0153416.g003", "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/Characterization_of_copper_complex_loading_method_/3164080", "title"=>"Characterization of copper-complex loading method.", "pos_in_sequence"=>3, "defined_type"=>1, "published_date"=>"2016-04-07 05:13:07"}
  • {"files"=>["https://ndownloader.figshare.com/files/4927327"], "description"=>"<p><b>(A)</b> Photograph of solutions consisting of DDC (5mg/mL) and added to CuSO<sub>4</sub>-containing DSPC/Chol (55:45) liposomes (20 mM liposomal lipid) over a 1 hour at 25°C. <b>(B)</b> Formation of Cu(DDC)<sub>2</sub> inside DSPC/Chol liposomes (20 mM) as a function of time over 1 hour at 4(●), 25(■) and 40(▲)°C following addition of DDC at a final DDC concentration of (5 mM); Cu(DDC)<sub>2</sub> was measured using a UV-Vis spectrophotometer and lipid was measured using scintillation counting. <b>(C)</b> Cu(DDC)<sub>2</sub> formation inside DSPC/Chol (55:45) liposomes over time where the external pH was 7.4 (▲) and 3.5 (▼). <b>(D)</b> Measured Cu(DDC)<sub>2</sub> as a function of increasing DDC added, represented as the theoretical Cu(DDC)<sub>2</sub> to total liposomal lipid ratio; where the lipid concentration was fixed at 20 mM and final DDC concentration was varied. <b>(E)</b> Cryo-electron microscopy photomicrograph of CuSO<sub>4</sub>- containing DSPC/Chol (55:45) liposomes and the same liposomes after formation of encapsulated Cu(DDC)<sub>2</sub>. <b>(F)</b> Size of the CuSO<sub>4</sub>- containing liposomes and liposomes with encapsulated Cu(DDC)<sub>2</sub> as determined by quasi-electric light scattering and cryo-electron microscopy; data points are given as mean ± SD.</p>", "links"=>[], "tags"=>["candidate anticancer drugs", "transformative solution", "cancer patients", "liposomal lipid bilayer", "entrapped copper", "method", "Nanoscale Reaction Vessels", "parenteral administration", "Preclinical Development", "product quercetin", "DDC", "CDC", "CX", "anticancer activity", "colour change", "Cu"], "article_id"=>3164068, "categories"=>["Biophysics", "Biochemistry", "Genetics", "Molecular Biology", "Pharmacology", "Biotechnology", "Chemical Sciences not elsewhere classified", "Biological Sciences not elsewhere classified", "Developmental Biology", "Cancer"], "users"=>["Mohamed Wehbe", "Malathi Anantha", "Ian Backstrom", "Ada Leung", "Kent Chen", "Armaan Malhotra", "Katarina Edwards", "Marcel B. Bally"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0153416.g002", "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/Diethyldithiocarbamate_DDC_loading_into_DSPC_Chol_55_45_liposomes_prepared_with_encapsulated_300_mM_CuSO_sub_4_sub_/3164068", "title"=>"Diethyldithiocarbamate (DDC) loading into DSPC/Chol (55:45) liposomes prepared with encapsulated 300 mM CuSO<sub>4</sub>.", "pos_in_sequence"=>2, "defined_type"=>1, "published_date"=>"2016-04-07 05:13:07"}
  • {"files"=>["https://ndownloader.figshare.com/files/4927363"], "description"=>"<p>Mice were injected with a single dose of 15 mg/kg Cu(DDC)<sub>2</sub> (-●-), 30mg/kg Cu(CQ)<sub>2</sub> (-■-), 70mg/kg CuQu (-▲-) and 50 mg/kg Cu-CX-5461 (-▼-). <b>(A)</b> Changes in body weight following administration of the indicated liposomal formulation where body weights were measured over 14 days after injection (n = 3). <b>(B)</b> Preliminary plasma elimination profiles of the indicated liposomal formulations where the copper-complexed compound was measured at 1, 4, 8 and 24 hrs after administration (n = 4); concentrations were measured using HPLC or AAS as described in the Methods.</p>", "links"=>[], "tags"=>["candidate anticancer drugs", "transformative solution", "cancer patients", "liposomal lipid bilayer", "entrapped copper", "method", "Nanoscale Reaction Vessels", "parenteral administration", "Preclinical Development", "product quercetin", "DDC", "CDC", "CX", "anticancer activity", "colour change", "Cu"], "article_id"=>3164104, "categories"=>["Biophysics", "Biochemistry", "Genetics", "Molecular Biology", "Pharmacology", "Biotechnology", "Chemical Sciences not elsewhere classified", "Biological Sciences not elsewhere classified", "Developmental Biology", "Cancer"], "users"=>["Mohamed Wehbe", "Malathi Anantha", "Ian Backstrom", "Ada Leung", "Kent Chen", "Armaan Malhotra", "Katarina Edwards", "Marcel B. Bally"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0153416.g005", "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/Preliminary_tolerability_and_plasma_elimination_profiles_for_liposomal_formulations_of_Cu_DDC_sub_2_sub_Cu_CQ_sub_2_sub_CuQu_and_CuCX_5461_after_intravenous_injection_into_CD_1_mice_/3164104", "title"=>"Preliminary tolerability and plasma elimination profiles for liposomal formulations of Cu(DDC)<sub>2</sub>, Cu(CQ)<sub>2</sub>, CuQu and CuCX-5461 after intravenous injection into CD-1 mice.", "pos_in_sequence"=>5, "defined_type"=>1, "published_date"=>"2016-04-07 05:13:07"}
  • {"files"=>["https://ndownloader.figshare.com/files/4927354"], "description"=>"<p>Copper is able to form complexes with compounds containing S-Donor, O-Donor and N,O-Donor systems as well as other mixed donor systems. Examples of drugs that are described here, in addition to DDC (an S-Donor), include Quercetin (Qu) (an O-Donor), Clioquinol (CQ) (an N,O donor) as well as CX-5461, previously not identified as a copper complexing agent. Each was loaded into DSPC/Chol (55:45 mol ratio) liposomes prepared with 300 mM CuSO<sub>4</sub>. The loading temperature used in these examples was 25, 50, 40 and 60°C, respectively.</p>", "links"=>[], "tags"=>["candidate anticancer drugs", "transformative solution", "cancer patients", "liposomal lipid bilayer", "entrapped copper", "method", "Nanoscale Reaction Vessels", "parenteral administration", "Preclinical Development", "product quercetin", "DDC", "CDC", "CX", "anticancer activity", "colour change", "Cu"], "article_id"=>3164095, "categories"=>["Biophysics", "Biochemistry", "Genetics", "Molecular Biology", "Pharmacology", "Biotechnology", "Chemical Sciences not elsewhere classified", "Biological Sciences not elsewhere classified", "Developmental Biology", "Cancer"], "users"=>["Mohamed Wehbe", "Malathi Anantha", "Ian Backstrom", "Ada Leung", "Kent Chen", "Armaan Malhotra", "Katarina Edwards", "Marcel B. Bally"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0153416.g004", "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/Donor_systems_that_can_be_used_in_Copper_II_complex_loading_/3164095", "title"=>"Donor systems that can be used in Copper(II)-complex loading.", "pos_in_sequence"=>4, "defined_type"=>1, "published_date"=>"2016-04-07 05:13:07"}

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Relative Metric

{"start_date"=>"2016-01-01T00:00:00Z", "end_date"=>"2016-12-31T00:00:00Z", "subject_areas"=>[]}
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