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Bioorganic Chemistry

Brief Description

The Laboratory of Organic Chemistry (LBC) was established in 2003 and mainly focuses on the synthesis of modified nucleosides and glucosides with interesting anticancer, antiviral, antioxidant and antidiabetic properties. Recently, the research interest also includes the synthesis of modified pyrrolo and quinoxaline analogs possessing interesting pharmaceutical applications.

Research Interests

The research interests of the LBC mainly focus on the synthesis of novel modified nucleoside analogues with interesting properties and biological activities.

Modified nucleosides play an important role in antiviral and anticancer chemotherapy. It is noteworthy that 15% of anticancer agents and 55% of antiviral agents are related to nucleoside analogues. The last decades nucleosides with five-membered and six-membered carbohydrate moieties have been evaluated for their potential antiviral and anticancer properties and as building blocks in nucleic acid chemistry. Lately, considerable interest in, exomethylene, fluoro and fluorothionucleosides has been generated in order to find new antitumor, antiviral, or anti-HIV drugs with better selectivity and less immunosuppressive effects compared with known clinically used compounds. It is also noteworthy that unsaturated ketonucleosides have been established for their antineoplastic activity and immunosuppressive effects. Based on these considerations the research interest of the LBC mainly focuses on the synthesis and biological evaluation of novel nucleoside analogues with specific structural features in the sugar and base moieties, such as unsaturation, exomethylene, fluorine, sulfur, cyano and ethynyl functions.

Pyrrole ring has found a wide number of applications and is present in many natural products. It is used as an important skeleton in organic synthesis and is also utilized in other important fields, such as materials science, medicinal chemistry, and pharmacology. Especially, 2-oxopyrroles show versatility and they are important substructures in a variety of drugs, including products active against viral infections (HIV , influenza, cytomegalovirus), anticancer agents, and products active against microbiological diseases (bacterial or fungal). Pyrroles fused to other heterocyclic systems, such as quinoxalines, have been of particular interest, since quinoxaline derivatives constitute the basis of many insecticides, fungicides, herbicides, as well as being important in human health and as receptor antagonists. Based on these data, the research in the LBC also includes the synthesis of halogenated pyrroles and their corresponding quinoxaline analogues.

Personnel

  1. Teaching & Research Staff
  2. Academic Fellows
    • Dr Christos Kyriazis
    • Dr Kollatos Nikolaos

Research Projects-Funding

  1. Research of Chemical Compounds against AIDS Title: ‘Μodified Ιsoniazids Αgainst AIDS’. Funding Body: American Institute of Health. Duration: 1990 – 1993. Coordinator: D.L. Venton.
  2. oint Research Program Greece – Slovenia, Title: ‘Synthesis and biological evaluation of a new class of amino-fluoronucleosides with potential antiviral and anticancer activity’. Funding Body: General Secretariat for Research and Technology. Duration: 2004 – 2006. Coordinator: D. Komiotis.
  3. Research Program Pythagoras ΙΙ, Title: ‘Molecular Detection of enteroviruses in clinical samples and environment. Consequences in public health. Funding Body: European Union, European Committee, European Social Fund. Duration: 2005 – 2008. Coordinator: P. Markoulatos.
  4. Joint Research Program Greece – France Title: ‘Human Angiogenine as molecular target of developing anticancer agents΄. Funding Body: General Secretariat for Research and Technology. Duration: 2010 – 2012. Coordinator: D. Leonidas.
  5. Research Program Aristeia I. Title: ‘Structure-assisted Design, Synthesis, and Evaluation of Bioactive compounds for type 2 Diabetes mellitus’. Funding Body: General Secretariat for Research and Technology. Duration: 2012 – 2015. Coordinator: D. Komiotis.
  6. Focused Research Action. Title: ‘Pyranosyl-amide as novel therapeutic agents for the treatment of type 2 Diabetes mellitus’ Funding Body: Research Committee University of Thessaly. Duration: 2012 – 2013.
  7. Education and Lifelong Learning – Updating Graduate Knowledge. Title: “Medicine, Pharmacy, Biotechnology”: “Modern Bio-Analysis Techniques in Health, Environment and Nutrition”. Duration: 2014 –2016.

Publications

Indicative recent publications of the group for the period 2015-2020 are presented

  1. Branched-chain sugar nucleosides: Stereocontrolled synthesis and bioevaluation of novel 3΄-C-trifluoromethyl and 3΄-C-methyl pyranonucleosides. Nikolaos Kollatos, Stella Manta, Athina Dimopoulou, Vanessa Parmenopoulou, Virginia V. Triantakonstanti,Tahsin Kellici, Thomas Mavromoustakosc, Dominique Schols, Dimitri Komiotis. Carbohydr. Res. 407 (2015), 170-178.
  2. An easy microwave-assisted synthesis of C8-alkynyl adenine pyranonucleosides as novel cytotoxic antitumor agents. Athina Dimopoulou, Stella Manta, Vanessa Parmenopoulou, Nikolaos Kollatos, Ourania Christidou, VirginiaTriantakonstanti, Dominique Schols and Dimitri Komiotis. Frontiers in Chemistry, Medicinal and Pharmaceutical Chemistry section, 3 (2015), 1-7.
  3. Dissipation, metabolism and sorption of pesticides used in fruit-packaging plants: Towards an optimized depuration of their pesticide-contaminated agro-industrial effluents. Panagiotis Karas, Aria Metsoviti, Vasileios Zisis, Constantinos Ehaliotis, Michalis Omirou, Evangelia S. Papadopoulou, Urania Menkissoglou-Spiroudi, Stella Manta, Dimitri Komiotis, Dimitrios G. Karpouzas. Science of The Total Environment, 530-31 (2015), 129-139.
  4. Glycogen Phosphorylase as a Target for Type 2 Diabetes: Synthetic, Biochemical, Structural and Computational Evaluation of Novel N-acyl-N´-(β-D-glucopyranosyl) Urea Inhibitors. Anastassia L. Kantsadi, Vanessa Parmenopoulou, Dimitar N. Bakalov, Laura Snelgrove, George A. Stravodimos, Demetra S.M. Chatzileontiadou, Stella Manta, Angeliki Panagiotopoulou, Joseph M. Hayes, Dimitri Komiotis, Demetres D. Leonidas. Curr. Topics Med. Chem. 15 (2015), 2373-2389.
  5. Triazole double-headed ribonucleosides as inhibitors of eosinophil derived neurotoxin. Demetra S.M Chatzileontiadou, Vanessa Parmenopoulou, Stella Manta, Anastassia L. Kantsadi, Paroula Kylindri, Marianna Griniezaki, Filitsa Kontopoulou, Aikaterini Telopoulou, Helena Prokova, Dimitrios Panagopoulos, Ester Boix, Nikolaos A.A Balatsos, Dimitri Komiotis, Demetres D. Leonidas. Bioorg. Chem. 63 (2015), 152-165.
  6. Synthesis of novel N-acyl-β-D-glucopyranosylamines and ureas as potential lead cytostatic agents. Vanessa Parmenopoulou, Stella Manta, Athina Dimopoulou, Nikolaos Kollatos, Dominique Schols, Dimitri Komiotis. Med, Chem. Res. 25 (2016), 932-940.
  7. Novel feed including bioactive compounds from winery wastes improved broilers’ redox status in blood and tissues of vital organs. Sotiria Makri, Ioannis Kafantaris, Dimitrios Stagos, Theodora Chamokeridou, Konstantinos Petrotos , Konstantinos Gerasopoulos, Anastasios Mpesios, Nikolaos Goutzourelas, Stylianos Kokkas, Panagiotis Goulas, Dimitrios Komiotis, Dimitrios Kouretas. Food Chem. Toxicol. 102 (2017), 24-31.
  8. Rapid Microwave-Assisted Synthesis of Modified Pyrimidine and Purine Pyranonucleosides as Novel Cytotoxic, Antiviral Agents and Glycogen Phosphorylase B Inhibitors. Manta Stella, Dimopoulou Athina, Kollatos Nikolaos, Kyrkou Georgia, Spanos Stylianos and Komiotis Dimitri. Med. Chem. 7(5) (2017), 865-868.
  9. Facile microwave-assisted synthesis of various C5-modified pyrimidine pyranonucleosides as potential cytotoxic antitumor agents. Athina Dimopoulou, Nikolaos Kollatos, Stella Manta, Aggeliki Panagiotopoulou, Athanasios Karastergiou, Filitsa Kontopoulou, Dominique Schols and Dimitri Komiotis. Curr. Microwave Chem. 4(4) (2017), 324-338.
  10. Evidence for Novel Action at the Cell‐Binding Site of Human Angiogenin Revealed by Heteronuclear NMR Spectroscopy, in silico and in vivo Studies. Demetra Chatzileontiadou, Aikaterini Tsika, Zoi Diamantopoulou, Jean Delbé, Josette Badet, Jose Courty, Vassiliki Skamnaki, Vanessa Parmenopoulou, Dimitri Komiotis, Joseph Hayes, Georgios Spyroulias, Demetres Leonidas. Chem. Med. Chem. 13(3) (2018), 259-269.
  11. Polyfunctionalized Pyrrole Derivatives: Easy Three-component Microwave-assisted Synthesis, Cytostatic and Antiviral Evaluation. Stella Manta, Niki Tzioumaki, Nikolaos Kollatos Pelagia Andrea, Marili Margaritouli, Aggeliki Panagiotopoulou, Ioannis Papanastasiou, Christos Mitsos, Andrew Tsotinis, Dominique Schols and Dimitri Komiotis. Curr. Microwave Chem. 5(1) (2018), 23-31.
  12. Novel Feed Including Olive Oil Mill Wastewater Bioactive Compounds Enhanced the Redox Status of Lambs. Sotiria Makri, Ioannis Kafantaris, Salomi Savva, Polyxeni Ntanou, Dimitrios Stagos, Ioannis Argyroulis, Basiliki Kotsampasi, Vladimiros Christodoulou, Konstantinos Gerasopoulos, Konstantinos Petrotos, Dimitrios Komiotis and Demetrios Kouretas. in vivo, 32 (2018), 291-302.
  13. Synthesis of diphenoxyadamantane alkylamines with pharmacological interest. Markos-Orestis Georgiadis, Violeta Kourbeli, Vaya Ioannidou, Evangelos Karakitsios, Ioannis Papanastasiou, Andrew Tsotinis, Dimitri Komiotis, Anthony Vocat, Stewart T.Cole, Martin C.Taylor, John M.Kelly. Bioorg. Med. Chem, Lett. 29(11) (2019), 1278-1281.
  14. Design, Synthesis, and Biological Evaluation of Novel C5-Modified Pyrimidine Ribofuranonucleosides as Potential Antitumor or/and Antiviral Agents. Nikolaos Kollatos, Christos Mitsos, Stella Manta, Niki Tzioumaki, Christos Giannakas, Tania Alexouli, Aggeliki Panagiotopoulou, Dominique Schols, Graciela Andrei, Dimitri Komiotis. Med Chem. 2019 Feb 24. doi: 10.2174/1573406415666190225112950.
  15. Design, Synthesis, and Biological Evaluation of Novel C5-Modified Pyrimidine Acyclic Nucleosides. Nikolaos Kollatos, Christos Mitsos, Roula Karetsou, Styliani Danai Antonaki, Aggeliki Panagiotopoulou, Niki Tzioumaki, Stella Manta, Dominique Schols and Dimitri Komiotis. Journal of Pharmaceutics and Drug Research, J Pharm Drug Res, 3(1): 257-267.

PhD thesis

Stella Manta: Bioactive unsaturated ketonucleosides. Synthesis and biological evaluation of fluoroketonucleosides of adenine and cytosine. (2004-2008)

Niki Tzioumaki: Synthesis of novel keto and exomethylene pyranonucleosides with antiviral and cytostatic activity. (2006-2010)

Evangelia Tsoukala: Synthesis of a novel class of fluoro-sulfur nucleosides with potential antiviral and anticancer activity.(2006-2010)

Christos Kyritsis: Cyano and ethynyl- pyranonucleosides: Synthesis and evaluation of antiviral and anticancer activity. (2009-2013)

Vanessa Parmenopoulou: Synthesis and biochemical evaluation of novel modified nucleosides and glucopyranosyl amides. (2011-2016)

Athina Dimopoulou: Synthesis of modified on the heterocyclic base pyranonoucleosides as potential antiviral, anticancer and antidiabetic agents. (2012-2017)

Nikolaos Kollatos: Synthesis of novel trifluoromethyl and methyl pyranonucleosides with antiviral and cytotoxic activity. (2013-2020)

Laboratory of Bioorganic Chemistry

Department of Biochemistry and Biotechnology (2nd Floor)
University of Thessaly
Viopolis, 41500 – Larissa

Contact

2410-565299
orgchem-at-bio.uth.gr