| 1. |
Takeru Araki , Yasufumi Fuchi , Shuhei Murayama, Ryoma Shiraishi, Tokimi Oyama, Mariko Aso, Ichio Aoki, Shigeki Kobayashi, Ken-ichi Yamada, Satoru Karasawa, Fluorescence Tumor-Imaging Using a Thermo-Responsive Molecule with an Emissive Aminoquinoline Derivative, Nanomaterials, 8, 782-792, 2018.10, 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. |
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.. |
| 3. |
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.. |
| 4. |
Manami Kurita, Yoshitaka Higuchi, JW Mirc,Shintaro Matsumoto, Kazuteru Usui, Hiroshi Suemune, Mariko Aso, Synthesis and Electron Paramagnetic Resonance Studies of Oligodeoxynucleotides Containing 2-N-tert-Butylaminoxyl-2'-deoxyadenosines, ChemBioChem, DOI: 10.1002/cbic.201600465, 17, 24, 2346-2352, 2016.12, Oligodeoxynucleotides (ODNs) containing 2-N-tert-butylaminoxyladenosine (A*) were synthesized to accurately monitor of adenine motion by electron paramagnetic resonance (EPR) spectroscopy via the agency of direct linkage of the acyclic aminoxyl group to the nucleobase and EPR studies of the ODNs in single- and double-stranded forms were performed. Upon duplex formation, peak broadening and decrease in peak height were observed in EPR spectra and synthesized ODNs were shown to be excellent monitors of hybridization. Comparison of peak height and the h1/ho signal ratio provided information on the relative mobility of A* in duplexes with different stability. A second set of ODNs containing two A*s at different intervals and four adenines were also synthesized. In the case of these ODNs, correlations were observed between EPR signal intensities of duplexes and adenine numbers between A*s, demonstrating the potential of A* to allow for the assessment of distances between spin labels by EPR.. |
| 5. |
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.. |
| 6. |
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.. |
| 7. |
Mariko Aso, Yasuhiro Matsui, Bo Yang, Midori Sasagaki, Daiki Okado, Kazuteru Usui, Noboru Koga, Hiroshi Suemune, Synthesis of 5-N-tert-butylaminoxylcytidine and EPR studies on its base pairing properties, Tetrahedron, doi:10.1016/j.tet.2015.05.080, 71, 33, 5414-5419, 2015.06. |
| 8. |
Seiichi Sakamoto, M. Yurino, Y.Yayoi, Y. Tsuneura, Mariko Aso, Hitoshi Kurose, Hiroyuki Tanaka, Satoshi Morimoto, Production and Characterization of Highly Specific MonoclonalAntibodies to D-glutamic Acid, Monoclon. Antib. Immunodiagn. Immunother., 33, 6, 414-419, 2014.12. |
| 9. |
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. |
| 10. |
H. Nakatake, H. Ekimoto, M. Aso, A. Ogawa, A. Yamaguchi, H. Suemune, Dialkyl Bisphosphonate Platinum (II) Complex as a Potential Drug for Metastatic Bone Tumor, Chem. Pharm. Bull., 59, 6, 710-713, 2011.06. |
| 11. |
E. Tomi, M. Aso, S. Inoue, Y. Toguchi, K. Usui, M. Hamdy, A. Jinnouchi, H. Suemune, Photochemical generation and reaction of 2’-substituted analogues of C4’-oxidized abasic lesion, Nucleic Acids Symposium Series, 53, 151-153, 2009.10. |
| 12. |
Y. Higuchi, M. Aso, R. Harada, N. Koga, H. Suemume, Evaluation of mobility of 2-N-tert-butylaminoxyladenosine incorporated into oligodeoxy- nucleotide, Nucleic Acids Symposium Series, 53, 185-186, 2009.10. |
| 13. |
Y. Sato, H. Hayashi, M. Okazaki, M. Aso, S. Karasawa, S. Ueki, H. Suemune, N. Koga, Water-proton relaxivities of DNA oligomers carrying TEMPO radicals, Magn. Reson. Chem., 46, 1055-1058, 2008.09. |
| 14. |
K. Yamada, Y. Kinoshita, T. Yamasaki, H. Sadasue, F. Mito, M. Nagai, S. Matsumoto, M. Aso, H. Suemune, K. Sakai, and H. Utsumi, Synthesis of nitroxyl radicals for Overhauser-enhanced magnetic resonance imaging, Arch. Pharm., 341(9), 548-553, 2008.09. |
| 15. |
M. Aso, M. Kurita, J. W. Mirc, T. Kaneko, Y. Higuchi, N. Koga, H. Suemune, Dynamics of 2-N-tert-butylaminoxyladenosine Incorporated into Oligodeoxynucleotides, Nucleic Acids Symposium Series, 52 , 151-152, 2008.09. |
| 16. |
K. Usui, M. Aso, M. Fukuda, H. Suemune, Photochemical generation of oligodeoxynucleotide containing C4’-oxidized abasic site and its efficient amine modification: Dependence on Structure and Microenvironment, J. Org. Chem., 73 (1), 241-248, 2008.01. |
| 17. |
M. Aso, K. Usui, M. Fukuda, Y. Kakihara, T. Goromaru, H. Suemune, Photochemical generation of C4’-oxidized abasic site containing oligodeoxynucleotide and its efficient amine modification, Org. Lett., 8(15), 3183-3186, 2006.07. |
| 18. |
T. Kaneko, M. Aso, N. Koga, H. Suemune, Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine Derivatives, Org. Lett., 10.1021/ol047668t, 7, 2, 303-306, 2, 303-306, 2005.01. |
| 19. |
M. Aso, T. Kaneko, M. Nakamura, N. Koga, H. Suemune, A simple and efficient method for synthesis of 5-substituted 2’-deoxyuridine nucleosides using metal-halogen exchange reaction of 5-iodo-2’-deoxyuridine sodium salt, J. Chem. Soc., Chem. Commun., 10.1039/b301425h, 9, 1094-1095, 2, 1094 - 1095, 2003.01. |
| 20. |
M. Aso, K. Ryuo, M. Kondo, H.Suemune, A novel method of preparing amine-modyfying C-4' oxidized nucleotide, Chem. Pharm. Bull., 48, 9, 1384-1386, 48(9), 1384-1386, 2000.01. |
| 21. |
M. Aso, K. Norihisa, M. Tanaka, N. Koga, H.Suemune, Synthesis of a new class of spin-labeled purine ribonucleosides and development of a novel nucleophilic reaction to form 2,6,8-trifunctionalized purine derivatives, J. Chem. Soc., Perkin Trans. 2, 10.1039/b004445h, 8, 1637-1638, 8. 1637-1638, 2000.01. |
| 22. |
M. Aso, M. Kondo, H. Suemune, S. M. Hecht, Chemistry of the Bleomycin-induced alkali-labile DNA lesion, J. Am. Chem. Soc., 10.1021/ja991574a, 121, 39, 9023-9033, 121(39), 9023-9033, 1999.01. |
