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And Tellurium Containing Surfactants and Their Biological Activity Against Cancer Cells

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And Tellurium Containing Surfactants and Their Biological Activity Against Cancer Cells Development of selenium- and tellurium containing surfactants and their biological activity against cancer cells Dissertation zur Erlangung des Grades des Doktors der Naturwissenschaften der Naturwissenschaftlich-Technischen Fakultät III Chemie, Pharmazie, Bio- und Werkstoffwissenschaften der Universität des Saarlandes von Diplom Apotheker Peng Du Saarbrücken 2014 Tag des Kolloquiums: 28. Oktober. 2014 Dekan: Prof. Dr. Volkhard Helms Berichterstatter: Prof. Dr. Claus Jacob Prof. Dr. Ingolf Bernhardt Vorsitz: Prof. Dr. Christian Ducho Akad. Mitarbeiterin: Dr. Sonja Keßler Diese Dissertation entstand unter der Anleitung von Prof. Dr. Claus Jacob in der Arbeitsgruppe für Bioorganische Chemie, Fachrichtung 8.2 Pharmazie der Naturwissenschaftlich-Technischen Fakultät III der Universität des Saarlandes im Zeitraum von August 2010 bis Juni 2013. Dedicated to my parents and my family Acknowledgement/Danksagung Acknowledgement/Danksagung Ich bedanke mich herzlich bei Herrn Prof. Dr. Claus Jacob für die Möglichkeit, diese Dissertation mit den sehr interessanten Themen im Fachbereich Pharmazie, Fachrichtung Bioorganische Chemie anzufertigen. Ebenso bedanke ich mich herzlich bei Herrn Prof. Dr. Ingolf Bernhardt für die Übernahme des Koreferates sowie Herrn Prof. Dr. Christian Ducho für die Übernahme des Prüfungsvorsitzes. Ich bedanke mich herzlich bei Frau Dr. Sonja Keßler für die Teilnahme am Prüfungsausschuss als akademische Mitarbeiterin. Ein weiterer großer Dank gilt Herrn Prof. Dr. Gilbert Kirsch und dem gesamten Team für die schöne Zeit im Labor und die hilfreiche Unterstützung bei Fragen jeder Art. Desweiteren bedanke ich mich herzlich bei Herrn Prof. Dr. Mathias Montenarh sowie dem gesamten Team für die ausgezeichnete Betreuung und jedes hilfreiche Gespräch bei Fragen. Ferner bekanke ich mich bei Herrn Dr. Torsten Burkholz, Herrn Dr. Zhanjie Xu, Herrn Dr. Nathaniel Saidu, Herrn Hadi Ebrahimnejad, Herrn Benjamin Hanf, Herrn Dr. Khairan Khairan und Frau Uma M. Viswanathan für die gute Zusammenarbeit im Labor. Ein weiterer Dank gilt allen internen und externen Kooperationspartnern im Rahmen meiner Veröffentlichungen. Ein besonderer Dank gilt meinen Eltern, die mich bei meinem Pharmazie-Studium sowie der Promotion in jeder Hinsicht unterstützt haben. Zum Schluss bedanke ich mich bei meiner Ehefrau Taotao Kuang für ihr aufgebrachtes Verständnis und ihre große Unterstützung in den letzten Jahren. I Overview of The Attached Publications The publications attached to this thesis Pulication 1 Synthesis of amphiphilic, chalcogen-based redox modulators with in vitro cytotoxic activity against cancer cells, macrophages and microbes Peng Du, Uma M. Viswanathan, Khairan Khairan, Tomislav Buric, Nathaniel E. B. Saidu, Zhanjie Xu, Benjamin Hanf, Inga Bazukyan, Armen Trchounian, Frank Hannemann, Ingolf Bernhardt, Torsten Burkholz, Britta Diesel, Alexandra K. Kiemer, Karl-Herbert Schäfer, Mathias Montenarh, Gilbert Kirsch and Claus Jacob This manuscript was published as an article in the following journal: Medicinal Chemistry Communications, 2014, 5, 25-31 Publication 2 A new tellurium-containing amphiphilic molecule induces apoptosis in HCT116 colon cancer cells Peng Du, Nathaniel Edward Bennett Saidu, Johanna Intemann, Claus Jacob, Mathias Montenarh This manuscript was published as an article in the following journal: Biochimica et Biophysica Acta 1840 (2014) 1808–1816 Publication 3 Synthesis of amphiphilic seleninic acid derivatives with considerable activity against cellular membranes and certain pathogenic microbes Peng Du, Uma M. Viswanathan, Zhanjie Xu, Hadi Ebrahimnejad, Benjamin Hanf, Torsten Burkholz, Marc Schneider, Ingolf Bernhardt, Gilbert Kirsch, Claus Jacob This manuscript was published as an article in the following journal: Journal of Hazardous Materials 269 (2014) 74–82 II Declaration of Author Contributions Declaration of author contributions for publications 1-3 Publication 1 The first author, Peng Du (Division of Bioorganic Chemistry, Saarland University, Saarbruecken, Germany), hereby declares that under the guidance of Prof. Dr. Gilbert Kirsch (Laboratoire d’Ing´enierie Mol´eculaire et Biochimie Pharmacologique, SRSMC UMR, Universit´e de Lorraine, Metz, France) and Prof. Dr. Claus Jacob (Division of Bioorganic Chemistry, Saarland University,Saarbruecken, Germany), Peng Du designed, synthesized, purified and chemically characterized the amphiphilic selenium- and tellurium-containing compounds mentioned in this paper with some technical assistance from Dr. Zhanjie Xu (Laboratoire d’Ing´enierie Mol´eculaire et Biochimie Pharmacologique, SRSMC UMR, Universit´e de Lorraine, Metz, France). With the essential guidance from Prof. Dr. Claus Jacob, I personally characterized the biological activities of the compounds with the haemolysis assay, circular dichroism measurements, REM and EDX measurements, MTT assay, ROS assay and mitochondria potential measurements. The biological investigations were supervised by the following collaborators as listed below: 1. Prof. Dr. Ingolf Bernhardt and Mr. Benjamin Hanf (Division of Biophysics, Saarland University, Saarbruecken, Germany) provided necessary technical assistance with the haemolysis assay used for the compounds synthesized. 2. Dr. Frank Hannemann (Division of Biochemistry, Saarland University, Saarbruecken, Germany) provided necessary technical assistance in the circular dichroism measurements with the compounds. 3. Prof. Dr. Karl-Herbert Schäfer (Department of Biotechnology, University of Applied Sciences Kaiserslautern, Zweibruecken, Germany) and Dr. Khairan Khairan (Division of Bioorganic Chemistry, Saarland University, Saarbruecken, Germany) provided necessary technical assistance with the REM and EDX measurements. III Declaration of Author Contributions 4. Prof. Dr. Alexandra K. Kiemer and Dr. Britta Diesel (Department of Pharmacy, Saarland University, Saarbruecken, Germany) supervised the MTT assay on RAW 264.7 cells. 5. Prof. Dr. Mathias Montenarh and Dr. Nathaniel E. B. Saidu (Division of Medical Biochemistry and Molecular Biology, Saarland University, Homburg, Germany) provided necessary technical assistance with the MTT assay with HCT116 and ARPE-19 cells, and the ROS measurements and the mitochondria potential assay with HCT116 cells. Ms. Uma M. Viswanathan (Division of Bioorganic Chemistry, Saarland University, Saarbruecken, Germany) carried out the CMC determination and Cyclic Voltammetry studies. Ms. Uma M. Viswanathan also performed the bacterium-inhibition assay under the supervision of Dr. Inga Bazukyan and Prof. Dr. Armen Trchounian (Division of Microbiology, Plants and Microbes Biotechnology, Yerevan State University, Yerevan, Armenia). Dr. Khairan Khairan performed the nematode assay. Prof. Dr. Claus Jacob wrote and submitted the manuscript, Mr. Tomislav Buric (Division of Bioorganic Chemistry, Saarland University, Saarbruecken, Germany) and Dr. Torsten Burkholz (Division of Bioorganic Chemistry, Saarland University, Saarbruecken, Germany) kindly reviewed the manuscript and provided necessary supervision during the laboratory based studies and as a part of the submission of the manuscript. Publication 2 The first author, Peng Du (Division of Bioorganic Chemistry, Saarland University, Saarbruecken, Germany), declares that under the principle guidance of Prof. Dr. Claus Jacob (Division of Bioorganic Chemistry, Saarland University, Saarbruecken, Germany), Peng Du designed, synthesized, purified and chemically characterized the new amphiphilic selenium- and tellurium-containing compounds for all the biological tests mentioned in this paper. IV Declaration of Author Contributions With appropriate guidance from Prof. Dr. Mathias Montenarh (Division of Medical Biochemistry and Molecular Biology, Saarland University, Homburg, Germany), Peng Du performed the ROS assay, tubulin immunofluorescence analysis, cell cycle analysis and analysis of apoptosis. Dr. Nathaniel Edward Bennett Saidu (Division of Medical Biochemistry and Molecular Biology, Saarland University, Homburg, Germany) carried out the Western Blot analysis involving HCT 116 cells. Ms Johanna Intemann (Division of Medical Biochemistry and Molecular Biology, Saarland University, Homburg, Germany) carried out Western Blot analysis involving ARPE-19 cells. Prof. Dr. Mathias Montenarh wrote and submitted the manuscript; Prof. Dr. Claus Jacob and Dr. Nathaniel Edward Bennett Saidu revised the manuscript and provided necessary assistance during the submission Publication 3 The first author, Peng Du (Division of Bioorganic Chemistry, Saarland University, Saarbruecken, Germany), hereby declares that under the principle guidance of Prof. Dr. Gilbert Kirsch (Laboratoire d’Ing´enierie Mol´eculaire et Biochimie Pharmacologique, SRSMC UMR, Universit´e de Lorraine, Metz, France) and Prof. Dr. Claus Jacob (Division of Bioorganic Chemistry, Saarland University, Saarbruecken, Germany), Peng Du designed, synthesized, purified and chemically characterized novel amphiphilic seleninic acid derivatives mentioned in this publication with some technical assistance from Dr. Zhanjie Xu (Laboratoire d’Ing´enierie Mol´eculaire et Biochimie Pharmacologique, SRSMC UMR, Universit´e de Lorraine, Metz, France). With the essential guidance from Prof. Dr. Claus Jacob, Peng Du characterized the synthesized compounds biologically with the haemolysis assay and Ca2+-uptake assay with technical assistance of Mr. Benjamin Hanf under supervision of Prof. Dr. Ingolf Bernhardt (Division of Biophysics, Saarland University, Saarbruecken, Germany). Under
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