Novel analogs of alloferon: Synthesis, conformational studies, pro-apoptotic and antiviral activity. 2016

Mariola Kuczer, and Elżbieta Czarniewska, and Anna Majewska, and Maria Różanowska, and Grzegorz Rosiński, and Marek Lisowski
Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie Str., 50-383 Wrocław, Poland. Electronic address: mariola.kuczer@chem.uni.wroc.pl.

In this study, we report the structure-activity relationships of novel derivatives of the insect peptide alloferon (H-His-Gly-Val-Ser-Gly-His-Gly-Gln-His-Gly-Val-His-Gly-OH). The peptide structure was modified by exchanging His at position 9 or 12 for natural or non-natural amino acids. Biological properties of these peptides were determined in antiviral in vitro test against Human Herpes Virus 1 McIntrie strain (HHV-1MC) using a Vero cell line. The peptides were also evaluated for the pro-apoptotic action in vivo on hemocytes of the Tenebrio molitor beetle. Additionally, the structural properties of alloferon analogs were examined by the circular dichroism in water and methanol. It was found that most of the evaluated peptides can reduce the HHV-1 titer in Vero cells. [Ala(9)]-alloferon exhibits the strongest antiviral activity among the analyzed compounds. However, no cytotoxic activity against Vero cell line was observed for all the studied peptides. In vivo assays with hemocytes of T. molitor showed that [Lys(9)]-, [Phg(9)]-, [Lys(12)]-, and [Phe(12)]-alloferon exhibit a twofold increase in caspases activity in comparison with the native peptide. The CD conformational studies indicate that the investigated peptides seem to prefer the unordered conformation.

UI MeSH Term Description Entries
D008826 Microbial Sensitivity Tests Any tests that demonstrate the relative efficacy of different chemotherapeutic agents against specific microorganisms (i.e., bacteria, fungi, viruses). Bacterial Sensitivity Tests,Drug Sensitivity Assay, Microbial,Minimum Inhibitory Concentration,Antibacterial Susceptibility Breakpoint Determination,Antibiogram,Antimicrobial Susceptibility Breakpoint Determination,Bacterial Sensitivity Test,Breakpoint Determination, Antibacterial Susceptibility,Breakpoint Determination, Antimicrobial Susceptibility,Fungal Drug Sensitivity Tests,Fungus Drug Sensitivity Tests,Sensitivity Test, Bacterial,Sensitivity Tests, Bacterial,Test, Bacterial Sensitivity,Tests, Bacterial Sensitivity,Viral Drug Sensitivity Tests,Virus Drug Sensitivity Tests,Antibiograms,Concentration, Minimum Inhibitory,Concentrations, Minimum Inhibitory,Inhibitory Concentration, Minimum,Inhibitory Concentrations, Minimum,Microbial Sensitivity Test,Minimum Inhibitory Concentrations,Sensitivity Test, Microbial,Sensitivity Tests, Microbial,Test, Microbial Sensitivity,Tests, Microbial Sensitivity
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D010455 Peptides Members of the class of compounds composed of AMINO ACIDS joined together by peptide bonds between adjacent amino acids into linear, branched or cyclical structures. OLIGOPEPTIDES are composed of approximately 2-12 amino acids. Polypeptides are composed of approximately 13 or more amino acids. PROTEINS are considered to be larger versions of peptides that can form into complex structures such as ENZYMES and RECEPTORS. Peptide,Polypeptide,Polypeptides
D002522 Chlorocebus aethiops A species of CERCOPITHECUS containing three subspecies: C. tantalus, C. pygerythrus, and C. sabeus. They are found in the forests and savannah of Africa. The African green monkey is the natural host of SIMIAN IMMUNODEFICIENCY VIRUS and is used in AIDS research. African Green Monkey,Cercopithecus aethiops,Cercopithecus griseoviridis,Cercopithecus griseus,Cercopithecus pygerythrus,Cercopithecus sabeus,Cercopithecus tantalus,Chlorocebus cynosuros,Chlorocebus cynosurus,Chlorocebus pygerythrus,Green Monkey,Grivet Monkey,Lasiopyga weidholzi,Malbrouck,Malbrouck Monkey,Monkey, African Green,Monkey, Green,Monkey, Grivet,Monkey, Vervet,Savanah Monkey,Vervet Monkey,Savannah Monkey,African Green Monkey,Chlorocebus cynosuro,Green Monkey, African,Green Monkeys,Grivet Monkeys,Malbrouck Monkeys,Malbroucks,Monkey, Malbrouck,Monkey, Savanah,Monkey, Savannah,Savannah Monkeys,Vervet Monkeys
D004305 Dose-Response Relationship, Drug The relationship between the dose of an administered drug and the response of the organism to the drug. Dose Response Relationship, Drug,Dose-Response Relationships, Drug,Drug Dose-Response Relationship,Drug Dose-Response Relationships,Relationship, Drug Dose-Response,Relationships, Drug Dose-Response
D006434 Hemocytes Any blood or formed element especially in invertebrates. Hemocyte
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000998 Antiviral Agents Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. Antiviral,Antiviral Agent,Antiviral Drug,Antivirals,Antiviral Drugs,Agent, Antiviral,Agents, Antiviral,Drug, Antiviral,Drugs, Antiviral
D001517 Coleoptera Order of winged insects also known as beetles comprising over 350,000 species in 150 families. They possess hard bodies with mouthparts adapted for chewing. Beetles,Beetle
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

Related Publications

Mariola Kuczer, and Elżbieta Czarniewska, and Anna Majewska, and Maria Różanowska, and Grzegorz Rosiński, and Marek Lisowski
April 1993, Journal of medicinal chemistry,
Mariola Kuczer, and Elżbieta Czarniewska, and Anna Majewska, and Maria Różanowska, and Grzegorz Rosiński, and Marek Lisowski
November 2011, Journal of peptide science : an official publication of the European Peptide Society,
Mariola Kuczer, and Elżbieta Czarniewska, and Anna Majewska, and Maria Różanowska, and Grzegorz Rosiński, and Marek Lisowski
February 2013, Chemical biology & drug design,
Mariola Kuczer, and Elżbieta Czarniewska, and Anna Majewska, and Maria Różanowska, and Grzegorz Rosiński, and Marek Lisowski
March 2011, Chembiochem : a European journal of chemical biology,
Mariola Kuczer, and Elżbieta Czarniewska, and Anna Majewska, and Maria Różanowska, and Grzegorz Rosiński, and Marek Lisowski
May 1988, Bioorganicheskaia khimiia,
Mariola Kuczer, and Elżbieta Czarniewska, and Anna Majewska, and Maria Różanowska, and Grzegorz Rosiński, and Marek Lisowski
September 1987, International journal of peptide and protein research,
Mariola Kuczer, and Elżbieta Czarniewska, and Anna Majewska, and Maria Różanowska, and Grzegorz Rosiński, and Marek Lisowski
January 2014, Acta poloniae pharmaceutica,
Mariola Kuczer, and Elżbieta Czarniewska, and Anna Majewska, and Maria Różanowska, and Grzegorz Rosiński, and Marek Lisowski
January 2003, Nucleosides, nucleotides & nucleic acids,
Mariola Kuczer, and Elżbieta Czarniewska, and Anna Majewska, and Maria Różanowska, and Grzegorz Rosiński, and Marek Lisowski
January 1978, Acta poloniae pharmaceutica,
Mariola Kuczer, and Elżbieta Czarniewska, and Anna Majewska, and Maria Różanowska, and Grzegorz Rosiński, and Marek Lisowski
September 2016, Bioorganic & medicinal chemistry,
Copied contents to your clipboard!