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ORGANIC CHEMISTRY

         Selections
1. Brief Description 6. Thesis
2. Research Interests 7. Photos
3. Personnel 8. Useful links
4. Funded Research Projects 9. Contact
5. Publications    

1. 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.

2. 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.

3. Personnel:

  •  Professor of Bio-Organic Chemistry  Dimitris Komiotis
  • Senior Researcher,  Dr. S. Manta

 

PhD Candidates

  •  Nikolaos Kollatos
  • Αthanasios Karastergiou

4. Funded Research Programs:

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.

   5.  Publications:

  • New short route to unsaturated fluoroketonucleosides: Case of 5-fluoro-1-(6-O-acetyl-3,4-dideoxy-3-fluoro-β-D-glycero-hex-3-eno-pyranos-2-ulosyl)uracil. Marie Jose Egron, Dimitri Komiotis, Ismet Dorange, Jean Herscovici and Kostas Antonakis. Nucleosides Nucleotides and Nucleic Acids, 24, (2005), 243-246.
  • A facile, one step, conversion of O-Trityl and O-TBDMS sugars into corresponding formate esters. Dimitri Komiotis, George Agelis, Stella Manta, Niki Tzioumaki, Evangelia Tsoukala and Kostas Antonakis. J. Carbohydr. Chem., 25, (2006), 441-450.
  • Detection of unusual mutation within the VP1 region of different re-isolates of poliovirus Sabin vaccine. Evaggelos Dedepsidis, Ioannis Karakasiliotis, Eleni Paximadi, Zaharoula Kyriakopoulou, Dimitri Komiotis and Panayotis Markoulatos. Virus Genes, 33, (2006), 183-191.
  • Fluoro-ketopyranosyl nucleosides: Synthesis and biological evaluation of 3-fluoro-2-keto-β-D-glucopyranosyl derivatives of N4-benzoyl cytosine. Stella Manta, George Agelis, Tanja Botić, Avrelija Cencič and Dimitri Komiotis. Bioorg. Med. Chem., 15, (2007), 980 – 987.
  • An efficient synthesis of 3-fluoro-5-thio-β-D-xylofuranosyl nucleosides of thymine, uracil and 5-fluorouracil as Potential Antitumor or/and Antiviral Agents. Evangelia Tsoukala, George Agelis, Jan Dolinšek, Tanja Botić, Avrelija Cencič and Dimitri Komiotis. Bioorg. Med. Chem., 15, (2007), 3241 – 3247.
  • Synthesis and structural characterization of neutral “3+2” οxorhenium and οxotechnetium complexes of the 2-mercaptoethyl-N-glycine (SNO) / 2,2΄-bipyridine (NN) mixed ligand system. Dionysia Papagiannopoulou, Ioannis Pirmettis, Maria Pelecanou, Dimitri Komiotis, Catherine P. Raptopoulou, Aris Terzis, Minas S. Papadopoulos. Inorg. Chim. Acta., 360, (2007), 3597-3602.
  • Exomethylene pyranonucleosides: Efficient synthesis and biological evaluation of 1-(2,3,4-trideoxy-2-methylene-β-D-glycero-hex-3-enopyranosyl)thymine. George Agelis, Niki Tzioumaki, Jan Dolinšek, Tanja Botić, Avrelija Cencič and Dimitri Komiotis. Bioorg. Med. Chem., 15, (2007), 5448 - 5456.
  • Antioxidant activity of a series of fluorinated pyrano-nucleoside analogues of N4-benzoyl cytosine and N6-benzoyl adenine. Chrysoula Spanou, Stella Manta, Dimitri Komiotis and Demetrios Kouretas. Int. J. Mol. Sci., 8, (2007), 695 - 704.
  • A Retrospective characterization of a Vaccine derived Poliovirus type 1 isolated from sewages in Greece. Evaggelos Dedepsidis, Zaharoula Kyriakopoulou, Vaia Pliaka, Christine Kottaridi, Eugenia Bolanaki, Stamatina Levidiotou-Stefanou, Dimitri Komiotis and Panayotis Markoulatos. Appl. Environ. Microbiol., 73, (2007), 6697 - 6704.
  • Unsaturated fluoro-ketopyranosyl nucleosides: Synthesis and biological evaluation of 3-fluoro-4-keto-β-D-glucopyranosyl derivatives of N4-benjoyl cytosine and N6-benzoyl adenine. Stella Manta, George Agelis, Tanja Botić, Avrelija Cencič and Dimitri Komiotis. Eur. J. Med. Chem., 43, (2008), 420 – 428.
  • A concise synthesis of 3-fluoro-5-thio-xylo- and glucopyranoses, useful precursors towards their corresponding pyranonucleoside derivatives. Evangelia Tsoukala, Stella Manta, Niki Tzioumaki, George Agelis and Dimitri Komiotis. Carbohydr. Res., 343, (2008), 1099 – 1103.
  • Exomethylene pyranonucleosides: Synthesis, conformational analysis and biological evaluation of 1-(2,3,4-trideoxy-4-methylene-α-D-glycero-hex-2-enopyranosyl)uracile. George Agelis, Niki Tzioumaki, Theodore Tselios, Jan Dolinšek, Tanja Botić, Avrelija Cencič and Dimitri Komiotis. Eur. J.  Med. Chem., 43, (2008), 1366 – 1375.
  • Antioxidant and chemopreventive properties of Polyphenolic compound derived from Greek legume plant extracts. Chrisoula Spanou, Georgia Bourou, Albiona Dervishi, Nektarios Aligiannis, Apostolos Angelis, Dimitri Komiotis, Alexios-Leandros Skaltsounis and Demetrios Kouretas. J. Agric. Food Chem., 56, (2008), 6967 – 6976.
  • Antiviral Unsaturated Nucleosides. Dimitri Komiotis, Stella Manta, Evangelia Tsoukala, and Niki Tzioumaki. Curr. Med. Chem., 7, (2008), 219 - 244.
  • Competitive Inhibition of Human Poly(A)-Specific Ribonuclease (PARN) by Synthetic Fluoro-Pyranosyl Nucleosides. Nikolaos Balatsos, Dimitrios Vlachakis, Panagiotis Maragozidis, Stella Manta, Dimitrios Anastasakis, Athanasios Kyritsis, Metaxia Vlassi, Dimitri Komiotis and Constantinos Stathopoulos. Biochemistry, 48, (2009), 6044-6051.
  • Synthesis, Antiviral and Cytostatic Evaluation of Unsaturated Exomethylene & Keto D-Lyxopyranonucleoside Analogues. Niki Tzioumaki, Evangelia Tsoukala, Stella Manta, George Agelis, Jan Balzarini and Dimitri Komiotis. Archiv der Pharmazie, 342, (2009), 353-360.
  • Dideoxy fluoro-ketopyranosyl nucleosides as potent antiviral agents: Synthesis and biological evaluation of 2,3- and 3,4-dideoxy-3-fluoro 4- and -2-keto-β-D-glucopyranosyl derivatives of N4-benzoyl cytosine. Stella Manta, Evangelia Tsoukala, Ales Goropevšek, Ravi Teja Pamulapati, Avrelija Cencič, Jan Balzarini and Dimitri Komiotis. Eur. J. Med. Chem. 44, (2009), 2696-2704.
  • Unsaturated dideoxy fluoro-ketopyranosyl nucleosides as potent antitumor agents: A convenient synthesis of 2,6-dideoxy-3-fluoro-4-keto-β-D-glucopyranosyl analogues of uracil, 5-fluorouracil, thymine, N4-benzoyl cytosine and N6-benzoyl adenine. Stella Manta, Niki Tzioumaki, Evangelia Tsoukala, Aggeliki Panagiotopoulou, Maria Pelecanou, Jan Balzarini and Dimitri Komiotis. Eur. J. Med. Chem. 44, (2009), 4764–4771.
  • Fluoro-glucopyranosyl derivatives of Ketonucleosides, potent inhibitors of DNA virus replication in infected cells. Tanja Botic, Stella Manta, Dimitri Komiotis, Avrelija Cencič and Francois Lefevre. Acta Medico-Biotechnica 2, (2009), 41-47.
  • Synthesis of 4,6-dideoxy-3-fluoro-2-keto-β-D-glucopyranosyl analogues of 5-fluorouracil, N6-benzoyl adenine, uracil, thymine and N4-benzoyl cytosine and evaluation of their antitumor activities. Stella Manta, Evangelia Tsoukala, Niki Tzioumaki, Christos Kiritsis, Jan Balzarini and Dimitri Komiotis. Bioorg. Chem. 38, (2010), 48-55.
  • 1-(3-Deoxy-3-fluoro-β-D-glucopyranosyl) pyrimidine derivatives as inhibitors of glycogen phosphorylase b: kinetic, crystallographic and modelling studies. Vicky G. Tsirkone, Evangelia Tsoukala, Christos Lamprakis, Stella Manta, Joseph M. Hayes, Vicky T. Skamnaki, Christina Drakou, Spyros E. Zographos, Dimitri Komiotis and Demetres D. Leonidas. Bioorg. Med. Chem. 18, (2010) 3413-3425.
  • Synthesis of 3-fluoro-6-S-(2-S-pyridyl) nucleosides as potential lead cytostatic agents. Evangelia Tsoukala, Niki Tzioumaki, Stella Manta, Alexandra Riga, Jan Balzarini and Dimitri Komiotis. Bioorg Chem. (2010, in press).

6. Thesis:

BSc Thesis
  • Karantana Stella (2004) Studies in crystalisation of inulin during gel formation – Applications in Food Industry (Supervisor: D. Komiotis)
  • Manoli Christina (2005) Synthesis of a new class of fluoronucleosides with potential antiviral and anticancer activity (Supervisor: D. Komiotis)
  • Ξενιτίδης Παναγιώτης (2006) Παραγοντοποίηση στη θέση ένα της γλυκόζης για την εν δυνάμει συμπλοκοποίηση με μέταλλα μετάπτωσης (Supervisor: D. Komiotis)
  • Tsoukala Evangelia (2006) Synthesis of 1-(3-deoxy-3-fluoro-5-S-acetyl-5-thio-β-D-xylofuranosyl) nucleoside of thymine with potential antiviral and anticancer activity (Supervisor: D. Komiotis)
  • Svirinaki Pelagia (2007) Unsaturated fluoro-ketopyranonucleosides: Synthesis and biological evaluation of  3-fluoro-4-keto-β-D-glucopyranosyl derivatives of N4–benzoylcytosine and of Ν6–benzoyl adenine (Supervisor: D. Komiotis)
  • Tsiggiavouridou Despoina (2007)Synthesis and  biological evaluation of 2΄-keto and 2΄-exomethylene pyranonucleosides of thymine (Supervisor: D. Komiotis)
  • Symeonidi Despoina (2007) Synthesis and  biological evaluation of 3΄-fluoro-6΄-thio-nucleosides of thymine, uracil and 5-fluorouracil (Supervisor: D. Komiotis)
  • Patista Eleonora-Iris (2009) Fluoro-thio-xylo and glucopyranoses: precursors for  the synthesis of new antiviral and anticancer nucleosides (Supervisor: D. Komiotis)
  • Zingou Lenitsa (2009) 4΄,6΄-Dideoxy-2΄-ketounsaturated-3΄-fluoro-β-D-glucopyranonucleosides of Ν6-benzoyl adenine and of Ν4-benzoyl cytosine: Synthesis and  biological evaluation (Supervisor: D. Komiotis)
  • Petrakis Tsampikos (2010) Synthesis of unsaturated dideoxy fluoro-ketopyranonucleosides of cytosine and of adenine as new anticancer agents (Supervisor: D. Komiotis)
MSc Thesis
  • Portesis Nikos (2009) Synthesis of nucleoside analogues of galactose and mannose and study of their antioxidant activity (Supervisor: D. Komiotis)
  • Margaris Panagiotis (2009) Synthesis of nucleoside analogues of lyxose and arabinose and study of their  antioxidant activity (Supervisor: D. Komiotis)
  • Riga Alexandra (2010) Synthesis of fluorinated thiopyridinylo nucleoside analogues as potential cytostatic agents (Supervisor: D. Komiotis)
  • Kiritsis Christos (2010) Synthesis of new ethynyl and cyano nucleosides as potential antiviral and anticancer agents (Supervisor: D. Komiotis)
  • Fountarlis Dimitris (2010) Synthesis and potential antioxidant activity of novel keto-exomethylene nucleosides of thymine  (Supervisor: D. Komiotis)
  • Vavilis Theofanis(2010) Synthesis and biological evaluation of ketounsaturated nucleoside of trifluoromethyluracil (Supervisor: D. Komiotis)
  • Kapetanidou Triantafilia (2010) HACCP system application in a hospital unit (Supervisor: D. Komiotis)
PhD Thesis  
  • Bioactive unsaturated ketonucleosides. Synthesis and biological evaluation of fluoroketonucleosides of adenine and cytosine. (Stella Manta 2004-2008)
  • Synthesis of novel keto and exomethylene pyranonucleosides with antiviral and cytostatic activity. (Niki Tzioumaki 2006-2010)
  • Synthesis of a novel class of fluoro-sulfur nucleosides with potential antiviral and anticancer activity.(Evangelia Tsoukala 2006-2010)
  • Cyano and ethynyl- pyranonucleosides: Synthesis and evaluation of antiviral and anticancer activity. (Christos Kyritsis 2009-2013)
  • Synthesis and biochemical evaluation of novel modified nucleosides and glucopyranosyl amides. (Vanessa Parmenopoulou, in progress)
  • Synthesis of modified on the heterocyclic base pyranonoucleosides as potential antiviral, anticancer and antidiabetic agents. (Athina Dimopoulou in progress)
  • Synthesis of novel trifluoromethyl and difluoromethyl pyranonucleosides with antiviral and cytotoxic activity. (Nikolaos Kollatos in progress)
  • Halogenophenyl-pyrroles as novel antiviral, anticancer and antioxidant agents. (Dimitra-Niki Gkaragkouni in progress)

 

7. Photos:

bioximeia_1 bio_ximeia_5 bioximeia_3

 

8. Useful Links:

 

9. Contact:

Professor D. Komiotis
University of Thessaly
Department of Biochemistry and Biotechnology
Viopolis
41500 Larisa
GREECE
Tel +30-2410-565299
Fax. +30-2410-565290Email: This e-mail address is being protected from spambots. You need JavaScript enabled to view it

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