Kyushu University Academic Staff Educational and Research Activities Database
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Mariko Aso Last modified date:2023.11.28

Associate Professor / Department of Chemo-Pharmaceutical Sciences
Department of Chemo-Pharmaceutical Sciences
Faculty of Pharmaceutical Sciences

Graduate School
Undergraduate School

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Field of Specialization
Pharmaceutical Synthetic Chemistry, Nucleic Acid Chemistry, Biomoles function related chemistry
Total Priod of education and research career in the foreign country
Outline Activities
Introduction of useful functions and artificial functions into biomolecules, such as nucleic acids, peptides, and proteins, provides new biomolecules, which find a wide range of applications; studying biomolecules, biomaterials, and therapeutics. In our group, several research projects on development of chemically modified biomolecules with useful functions are in progress:
(1) Design of nucleic acids with useful functions,
(2) Site-specific protein modification for development of Biodrugs; We design and prepare artificial nucleic acids which modify proteins at specific lysine residue to introduce useful functions such as fluorescence, and to yield protein-conjugate. Obtained modified proteins can be useful for protein-studies and as biodrugs.
(3) Development of bone-targeting therapeutic molecules; Bones provide structure for bodies and other important functions. We work on development of molecules with high bone affinity and its conjugation with therapeutic proteins for treatment of bone diseases.
Research Interests
  • Chemical modification of protein for medical use
    keyword : protein modification
    2015.04Studies on oxidatively damaged DNA.
  • Design of amine reactive artificial nucleic acids
    keyword : nucleic acid, amine, lysine residue, site-specific modification, protein
    2008.04Synthesis of nucleosides with stable radical and studies on their properties..
  • Design of novel spin-labeled nucleosides and studies on DNA dynamics
    keyword : nucleic acid, spin label, stable radical, EPR
    2000.04~2018.03Synthesis of nucleosides with stable radical and studies on their properties..
  • Reactivity of Oxidatively Damaged DNA Lesion
    keyword : DNA, oxidative damage, protein modification
    1994.10Studies on oxidatively damaged DNA.
  • Synthesis of Bisphosphonate derivatives and studies on their function
    keyword : bisphosphonate
Academic Activities
1. Kazuma Shimoda, Takahiro Mitsuoka, Kenta Ueda, Hiroshi Suemune, Go Hirai, Mariko Aso, Synthesis of dendritic bisphosphonates as bone targeting ligands, Tetrahedron Lett., 59, 4528-4531, 2018.11, A dendritic bisphosphonate carrying three bisphosphonate (BP) units in close proximity was designed as a ligand to conjugate large therapeutic molecules for their bone selective delivery. The Bu3P-catalyzed conjugate addition of nitromethane to vinylidene bisphosphonate was effective to construct a quaternary carbon center carrying BP units. Owing to multivalent interactions, the dendritic bisphosphonate showed considerable affinity for the bone mineral hydroxyapatite even in the presence of a competitor, demonstrating potential as a bone targeting ligand..
2. Yusuke Kimuro, Kazuteru Usui, Satoru Karasawa, Go Hirai, Mariko Aso, 7-Hydroxy-3-methyleneisoindolin-1-one as a new ESIPT-fluorescent probe to monitor aqueous environments, Chemical and Pharmaceutical Bulletin, 65, 8, 796-800, 2017.08, A 7-hydroxy derivative of 3-methyleneisoindolin-1-one 1 was synthesized and its properties as a new fluorophore undergoing excited-state intramolecular proton transfer (ESIPT) were investigated. In alcohols and dimethylsulfoxide, 1 exhibited dual emission at ~380 and ~525−541 nm when excited at ~336 nm, which agreed well with the density functional theory (DFT) and time-dependent (TD)-DFT-calculated emission predictions of 1 and its ESIPT tautomer. In aqueous solutions at near neutral pH, 1 exhibited a broad emission band at ~497 nm, presumably caused by the overlap of emissions from 1 and the excited state phenolate species of 1. In binary mixtures of H2O and EtOH, the wavelength and intensity of fluorescence maxima were dependent on the dielectric constant of the solvent, suggesting that 1 could be applied as a fluorescent probe to monitor aqueous environments..
3. Chiemi Gatanaga, Bo Yang, Yuka Inadomi, Kazuteru Usui, Chiyoe Ota, Tsutomu Katayama, Hiroshi Suemune, Mariko Aso, Site-Specific Turn-On Fluorescent Labeling of DNA-Interacting Protein Using Oligodeoxynucleotides That Modify Lysines To Produce 5,6-Dimethoxy 3-Methyleneisoindolin-1-one, ACS Chem. Biol., DOI: 10.1021/acschembio.6b00090, 11, 8, 2216-2221, 2016.06, We have developed oligodeoxynucleotides (ODNs) that modify primary amines to produce 5,6-dimethoxy 3-methyleneisoindolin-1-one. Compared to the oxygen isosteric fluorophore, 4,5-dimethoxyphthalimide, this methyleneisoindolinone was more stable and exhibited an 85 nm blue-shifted fluorescent emission (λmax at 425 nm) with an intensity comparable to that of the phthalimide. Reaction of the DNA-binding domain of Escherichia coli DnaA protein with an ODN containing its binding sequence efficiently afforded a
modified fluorescent protein at a specific lysine residue in the proximity of the ODN. A full-length DnaA protein was also successfully fluorescently labeled. These results demonstrate the potential utility of the ODNs developed in this study for the fluorescent labeling of DNA-interacting protein at the lysine residue of interest..
4. Bo Yang, Akiko Jinnouchi, Kazuteru Usui, Tsutomu Katayama, Hiroshi Suemune, Mariko Aso, Bioconjugation of oligodeoxynucleotides carrying 1,4-dicarbonyl groups via reductive amination with lysine residues, Bioconjugate Chemistry, DOI.10.1021/acs.bioconjchem.5b00361, 26, 8, 1830-1838, 2015.07, We evaluated the efficacy of bioconjugation of oligodeoxynucleotides (ODNs) containing 1,4-dicarbonyl groups, a C4′-oxidized abasic site (OAS) and a newly designed 2′-methoxy analog, via reductive aminations with lysine residues. Dicarbonyls, aldehyde and ketone at C1- and C4-positions of deoxyribose in the ring-opened form of OAS, allowed their efficient reaction with amines. Kinetic studies indicated that reductive amination of OAScontaining ODNs with a proximal amine on the complementary strand proceeded 10 times
faster than the corresponding reaction of an ODN containing an abasic site with C1-aldehyde. Efficient reductive amination between the DNA-binding domain of Escherichia coli DnaA protein and ODNs carrying OAS in the DnaA-binding sequence proceeded at the lysine residue in proximity to the phosphate group at the 5′-position of the OAS, in contrast to unsuccessful conjugation with abasic site ODNs, even they have similar aldehydes. Theoretical calculation indicated that the C1-aldehyde of OAS was more accessible to the target lysine than that of the abasic site. These results demonstrate the potential utility of cross-linking strategies that use dicarbonyl-containing ODNs for the study of protein-nucleic acid interactions. Conjugation with a lysine-containing peptide that lacked specific affinity for ODN was also successful, further highlighting the advantages of 1,4-dicarbonyls..
5. B. Yang, A. Jinnouchi, H. Suemune, M. Aso, Difluoro-C4’-oxidized Aabsic Site for Efficient Amine Modification in Biological Systems, Org. Lett., 14, 5852-5855, 2012.12.
1. Mariko Aso, Chiemi Gatanaga, Chiyoe Ota, Go Hirai, Yosuke Taniguchi, Shigeki Sasaki, Synthesis of Oligodeoxynucleotides for Lysine Modifi-cation to Induce Solvatochromic Fluorescent Lactam, The 45rd International Symposium on Nucleic Acids Chemistry, 2019.10.
2. Mariko Aso, Chiemi Gatanaga, Chiyoe Ota, Go Hirai, Yosuke Taniguchi, Shigeki Sasaki, Synthesis of Oligodeoxynucleotides for Lysine Modifi-cation to Induce Solvatochromic Fluorescent Lactam, The 45rd International Symposium on Nucleic Acids Chemistry, 2018.11.
3. Mariko Aso, 潟永 ちえみ, Bo Yang, 太田 千代枝, Hiroshi Suemune, Oligodeoxynucleotides that modify lysines to produce fluorescent lactam for DNA-interacting potein labeling, The 43rd International Symposium on Nucleic Acids Chemistry, 2016.09.
4. Amine modification of target molecules by DNA with activated dicarbonyl groups.
Educational Activities
Chemistry for the 1st year students, English lecture of chemistry for the 2nd and 3rd year students. Safety Education of Chemistry Experiment for the 2nd year students, Bioorganic Chemistry and Medicinal Chemistry for the 3rd year students. Advanced Organic Chemistry, and Presentation Practice I and II in Clinical Pharmaceutics for the students in the master program.