BIOMAT Database Logo BIOMAT Database Logo

Synthesis and Telomeric G-Quadruplex-Stabilizing Ability of Macrocyclic Hexaoxazoles Bearing Three Side Chains. 2019

Yue Ma, and Keisuke Iida, and Shogo Sasaki, and Takatsugu Hirokawa, and Brahim Heddi, and Anh Tuân Phan, and Kazuo Nagasawa
Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan. yue-ma@m2.tuat.ac.jp.

G-quadruplexes (G4s), which are structures formed in guanine-rich regions of DNA, are involved in a variety of significant biological functions, and therefore "sequence-dependent" selective G4-stabilizing agents are required as tools to investigate and modulate these functions. Here, we describe the synthesis of a new series of macrocyclic hexaoxazole-type G4 ligand (6OTD) bearing three side chains. One of these ligands, 5b, stabilizes telomeric G4 preferentially over the G4-forming DNA sequences of c-kit and K-ras, due to the interaction of its piperazinylalkyl side chain with the groove of telomeric G4.

UI MeSH Term Description Entries
D008024 Ligands A molecule that binds to another molecule, used especially to refer to a small molecule that binds specifically to a larger molecule, e.g., an antigen binding to an antibody, a hormone or neurotransmitter binding to a receptor, or a substrate or allosteric effector binding to an enzyme. Ligands are also molecules that donate or accept a pair of electrons to form a coordinate covalent bond with the central metal atom of a coordination complex. (From Dorland, 27th ed) Ligand
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D010080 Oxazoles Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions. Oxazole,1,3-Oxazolium-5-Oxides,Munchnones,1,3 Oxazolium 5 Oxides
D002942 Circular Dichroism A change from planar to elliptic polarization when an initially plane-polarized light wave traverses an optically active medium. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Circular Dichroism, Vibrational,Dichroism, Circular,Vibrational Circular Dichroism
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D016615 Telomere A terminal section of a chromosome which has a specialized structure and which is involved in chromosomal replication and stability. Its length is believed to be a few hundred base pairs. Telomeres
D054856 G-Quadruplexes Higher-order DNA and RNA structures formed from guanine-rich sequences. They are formed around a core of at least 2 stacked tetrads of hydrogen-bonded GUANINE bases. They can be formed from one two or four separate strands of DNA (or RNA) and can display a wide variety of topologies, which are a consequence of various combinations of strand direction, length, and sequence. (From Nucleic Acids Res. 2006;34(19):5402-15) DNA G-Quadruplexes,DNA, Quadruplex,G-Quadruplexes, DNA,G-Quadruplexes, RNA,Guanine-Quadruplexes,Guanine-Quartets,Guanine-Tetrads,Quadruplex DNA,RNA, G-Quadruplexes,Tetraplex DNA,DNA G Quadruplexes,DNA, Tetraplex,G Quadruplexes,G Quadruplexes, DNA,G Quadruplexes, RNA,G-Quadruplexes RNA,G-Quadruplexes RNAs,Guanine Quadruplexes,Guanine Quartets,Guanine Tetrads,Guanine-Quartet,Guanine-Tetrad,RNA G-Quadruplexes,RNA, G Quadruplexes,RNAs, G-Quadruplexes
D060326 Chemistry Techniques, Synthetic Methods used for the chemical synthesis of compounds. Included under this heading are laboratory methods used to synthesize a variety of chemicals and drugs. Inorganic Synthesis,Inorganic Synthesis Methods,Inorganic Synthesis Techniques,Methods of Inorganic Synthesis,Methods of Organic Synthesis,Methods of Peptide Synthesis,Organic Synthesis,Organic Synthesis Methods,Organic Synthesis Techniques,Peptide Synthesis Methods,Peptide Synthesis Techniques,Peptide Synthesis, Synthetic,Synthetic Chemistry Techniques,Synthetic Peptide Synthesis,Chemistry Technique, Synthetic,Inorganic Syntheses,Inorganic Synthesis Method,Inorganic Synthesis Technique,Method, Inorganic Synthesis,Method, Organic Synthesis,Method, Peptide Synthesis,Methods, Inorganic Synthesis,Methods, Organic Synthesis,Methods, Peptide Synthesis,Organic Syntheses,Organic Synthesis Technique,Peptide Syntheses, Synthetic,Peptide Synthesis Method,Peptide Synthesis Technique,Syntheses, Inorganic,Syntheses, Organic,Syntheses, Synthetic Peptide,Synthesis Method, Inorganic,Synthesis Method, Peptide,Synthesis Methods, Inorganic,Synthesis Methods, Peptide,Synthesis Technique, Inorganic,Synthesis Technique, Organic,Synthesis Technique, Peptide,Synthesis Techniques, Inorganic,Synthesis Techniques, Organic,Synthesis Techniques, Peptide,Synthesis, Inorganic,Synthesis, Organic,Synthesis, Synthetic Peptide,Synthetic Chemistry Technique,Synthetic Peptide Syntheses,Technique, Inorganic Synthesis,Technique, Organic Synthesis,Technique, Peptide Synthesis,Technique, Synthetic Chemistry,Techniques, Inorganic Synthesis,Techniques, Organic Synthesis,Techniques, Peptide Synthesis,Techniques, Synthetic Chemistry
D062105 Molecular Docking Simulation A computer simulation technique that is used to model the interaction between two molecules. Typically the docking simulation measures the interactions of a small molecule or ligand with a part of a larger molecule such as a protein. Molecular Docking,Molecular Docking Simulations,Molecular Docking Analysis,Analysis, Molecular Docking,Docking Analysis, Molecular,Docking Simulation, Molecular,Docking, Molecular,Molecular Docking Analyses,Molecular Dockings,Simulation, Molecular Docking

Related Publications

Yue Ma, and Keisuke Iida, and Shogo Sasaki, and Takatsugu Hirokawa, and Brahim Heddi, and Anh Tuân Phan, and Kazuo Nagasawa
Lysinyl macrocyclic hexaoxazoles: synthesis and selective G-quadruplex stabilizing properties.
February 2008, Bioorganic & medicinal chemistry letters,
Yue Ma, and Keisuke Iida, and Shogo Sasaki, and Takatsugu Hirokawa, and Brahim Heddi, and Anh Tuân Phan, and Kazuo Nagasawa
Macrocyclic hexaoxazoles as sequence- and mode-selective G-quadruplex binders.
January 2008, Angewandte Chemie (International ed. in English),
Yue Ma, and Keisuke Iida, and Shogo Sasaki, and Takatsugu Hirokawa, and Brahim Heddi, and Anh Tuân Phan, and Kazuo Nagasawa
Macrocyclic hexaoxazoles: Influence of aminoalkyl substituents on RNA and DNA G-quadruplex stabilization and cytotoxicity.
May 2010, Bioorganic & medicinal chemistry letters,
Yue Ma, and Keisuke Iida, and Shogo Sasaki, and Takatsugu Hirokawa, and Brahim Heddi, and Anh Tuân Phan, and Kazuo Nagasawa
Synthesis of Macrocyclic Hexaoxazole (6OTD) Dimers, Containing Guanidine and Amine Functionalized Side Chains, and an Evaluation of Their Telomeric G4 Stabilizing Properties.
January 2010, Journal of nucleic acids,
Yue Ma, and Keisuke Iida, and Shogo Sasaki, and Takatsugu Hirokawa, and Brahim Heddi, and Anh Tuân Phan, and Kazuo Nagasawa
Linear consecutive hexaoxazoles as G4 ligands inducing chair-type anti-parallel topology of a telomeric G-quadruplex.
November 2020, RSC advances,
Yue Ma, and Keisuke Iida, and Shogo Sasaki, and Takatsugu Hirokawa, and Brahim Heddi, and Anh Tuân Phan, and Kazuo Nagasawa
Targeting human telomeric G-quadruplex DNA with oxazole-containing macrocyclic compounds.
August 2008, Biochimie,
Yue Ma, and Keisuke Iida, and Shogo Sasaki, and Takatsugu Hirokawa, and Brahim Heddi, and Anh Tuân Phan, and Kazuo Nagasawa
Human telomeric G-quadruplex.
March 2010, The FEBS journal,
Yue Ma, and Keisuke Iida, and Shogo Sasaki, and Takatsugu Hirokawa, and Brahim Heddi, and Anh Tuân Phan, and Kazuo Nagasawa
Stability of the Na+ Form of the Human Telomeric G-Quadruplex: Role of Adenines in Stabilizing G-Quadruplex Structure.
January 2018, ACS omega,
Yue Ma, and Keisuke Iida, and Shogo Sasaki, and Takatsugu Hirokawa, and Brahim Heddi, and Anh Tuân Phan, and Kazuo Nagasawa
9-Substituted berberine derivatives as G-quadruplex stabilizing ligands in telomeric DNA.
August 2007, Bioorganic & medicinal chemistry,
Yue Ma, and Keisuke Iida, and Shogo Sasaki, and Takatsugu Hirokawa, and Brahim Heddi, and Anh Tuân Phan, and Kazuo Nagasawa
Macrocyclic G-quadruplex ligands.
January 2010, Current medicinal chemistry,
Copied contents to your clipboard!