Pablications

Recent publications
From 2000 to present
  1. Kakiuchi, M.; Ito, S.; Kiyama, M.; Goto, F.; Matsuhashi, T.; Yamaji, M.; Maki, S.; Hirano, T., “Electronic and steric effects of cyclic amino substituents of luciferin analogues on a firefly luciferin−luciferase reaction,” Chem. Lett. 46 (8), 1090–1092 (2017).
  2. Kakiuchi, M.; Ito, S.; Yamaji, M.; Viviani, V. R.; Maki, S.; Hirano, T., “Spectroscopic properties of amine-substituted analogues of firefly luciferin and oxyluciferin,” Photochem. Photobiol., 93, 486–494 (2017).
  3. Fukuchi, M.; Izumi, H.; Mori, H.; Kiyama, M.; Otsuka, S.; Maki, A.; Maehata, Y.; Tabuchi, A.; Tsuda, M., “Visualizing changes in brain-derived neurotrophic factor (BDNF) expression using bioluminescence imaging in living mice”, Sci. Rep., 7, 4949 (2017).
  4. Viviani, V. R.; Simoes, A. F.; Bevilaqua, V. R.; de Mello Gabriel, G. V.; Arnoldi, F. G. C.; Hirano, T., “Glu311 and Arg337 stabilize a closed conformation and provide a critical catalytic base and countercation for green bioluminescence in beetle luciferases,” Biochemistry, 55, 4764–4776 (2016).
  5. Hachiya, S.; Hashizume, D.; Ikeda, H.; Yamaji, M.; Maki, S.; Niwa, H.; Hirano, T., “Spectroscopic properties of BF2 complexes of N-(5-phenyl-2-pyrazinyl)pivalamides exhibiting fluorescence in solution and solid state,” J. Photochem. Photobiol. A, 331, 206–214 (2016).
  6. Suzuki, Y.; Yamaji, M.; Maki, S.; Hirano, T., “Enhanced brightness of 2,6-diphenylthiazolo[4,5-b]pyrazines by introducing double electron donating groups,” J. Photochem. Photobiol. A, 314, 93–95 (2016).
  7. Ioka, S.; Saitoh, T.; Iwano, S.; Suzuki, K.; Maki, S. A.; Miyawaki, A.; Imoto, M.; Nishiyama, S., “Synthesis of firefly luciferin analogues and evaluation of the luminescent properties”, Chem. Eur. J., 22, 9330–9337 (2016).
  8. Kuchimaru, T.; Iwano, S.; Kiyama, M.; Mitsumata, S.; Kadonosono, T.; Niwa, H.; Maki, S.; Kizaka-Kondoh, S., “A luciferin analog generating near-infrared bioluminescence achieves highly sensitive deep-tissue imaging”, Nature Commun., 7, 11856 (2016).
  9. Kiyama, M.; Saito, R.; Iwano, S.; Obata, R.; Niwa, H.; Maki, S., “Multicolor bioluminescence obtained using firefly luciferin”, Curr. Top. Med. Chem., 16, 2648-2655 (2016).
  10. Hirano, T., “Molecular origin of color variation in firefly (beetle) bioluminescence: a chemical basis for biological imaging,” Curr. Top. Med. Chem., 16, 2638–2647 (2016).
  11. Ioka, S.; Saitoh, T.; Iwano, S.; Suzuki, K.; Maki, S.; Niwa, H.; Miyawaki, A.; Imoto, M.; Nishiyama, S., “Synthesis and evaluation of the luminescent properties of firefly luciferin analogues” Chem. Eur. J., 22, 1-9 (2016).
  12. Nakagawa, T.; Yamaji, M.; Maki, S.; Niwa, H.; Hirano, T., “Fluorescence properties of diphenylthiazolo[4,5-b]pyrazines tuned by donor-acceptor substituent effects,” Photochem. Photobiol., 91, 807–813 (2015).
  13. Nakagawa, T.; Yamaji, M.; Maki, S.; Niwa, H.; Hirano, T., “Substituent effects on fluorescence properties of thiazolo[4,5-b]pyrazine derivatives,” Photochem. Photobiol. Sci., 13, 1765–1772 (2014).
  14. Viviani, V. R.; Rodrigues, D.; Amaral, D.; Prado, R. A.; Matsuhashi, T.; Hirano, T., “Bioluminescence of beetle luciferases with 6’-amino-D-luciferin analogues reveals excited keto-oxyluciferin as the emitter and phenolate/luciferin binding site interactions modulate bioluminescence colors,” Biochemistry, 53, 5208–5220 (2014).
  15. Saito, R.; Hirano, T.; Maki, S.; Niwa, H., “Synthesis and chemiluminescent properties of 6,8-diaryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones: systematic investigation of substituent effect at para-position of phenyl group at 8-position,” J. Photochem. Photobiol. A, 293, 12–25 (2014).
  16. Ishii, Y.; Hayashi, C.; Suzuki, Y.; Hirano, T., “Chemiluminescent 2,6-diphenylimidazo[1,2-a]pyrazin-3(7H)-ones: a new entry to Cypridina luciferin analogues,” Photochem. Photobiol. Sci., 13, 182–189 (2014).
  17. Miura, C.; Kiyama, M.; Iwano, S.; Ito, K.; Obata, R.; Hirano, T.; Maki, S.; Niwa, H., “Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore,” Tetrahedron, 69, 9726–9734 (2013).
  18. Iwano, S.; Obata, R.; Miura, C.; Kiyama, M.; Hama, K.; Nakamura, M.; Amano, Y.; Kojima, S.; Hirano, T.; Maki, S.; Niwa, H., “Development of simple firefly luciferin analogs emitting blue, green, red, and near-infrared biological window light,” Tetrahedron, 69, 3847–3856 (2013).
  19. Hirano, T.; Nakagawa, T.; Kodaka, A.; Maki, S.; Niwa, H.; Yamaji, M., “5-[4-(Dimethylamino)phenyl]-2-benzamidopyrazines: Fluorescent dyes based on Cypridina oxyluciferin,” Res. Chem. Intermed., 39, 233–245 (2013).
  20. Hirano, T.; Nagai, H.; Matsuhashi, T.; Hasumi, Y.; Iwano, S.; Ito, K.; Maki, S.; Niwa, H.; Viviani, V. R., "Spectroscopic studies of the color modulation mechanism of firefly (beetle) bioluminescence with amino-analogs of luciferin and oxyluciferin," Photochem. Photobiol. Sci., 11. 1281-1284 (2012).
  21. Hirano, T.; Nakagawa, T.; Kodaka, A.; Maki, S.; Niwa, H.; Yamaji, M., "5-[4-(Dimethylamino)phenyl]-2-benzamidopyrazines: Fluorescent dyes based on Cypridina oxyluciferin," Res. Chem. Intermed., in press.
  22. Hirano, T., "The reaction mechanism of calcium-activated photoprotein bioluminescence," Curr. Pharm. Biotech., in press.
  23. Ohashi, Y.; Kubota, M.; Hatase, H.; Hirano, T.; Maki, S.; Niwa, H., "Studies on (-) ESI-MS/MS of a glycosaminoglycan disaccharide N-acetyllactosamine-6, 6'-disulfate disodium salt-Charge-localization isomers," Int. J. Mass Spectrom., 312, 179-184 (2012).
  24. Mori, K.; Kojima, S.; Maki, S.; Hirano, T.; Niwa, H., "Bioluminescence characteristics of the fruiting body of Mycena chlorophos," Luminescence, 26, 604-610 (2011).
  25. Saito, R.; Hirano, T.; Maki, S.; Niwa, H.; M. Ohashi, M. "Influence of Electron-Donating and Electron-Withdrawing Substituents on the Chemiluminescence Behavior of Coelenterazine Analogs," Bull. Chem. Soc. Jpn., 84, 90-99 (2011).
  26. Hirano, T.; Sekiguchi, T.; Hashizume, D.; Ikeda, H.; Maki, S.; Niwa, H. "Colorimetric and fluorometric sensing of the Lewis acidity of a metal ion by metal-ion complexation of imidazo[1,2-a]pyrazin-3(7H)-ones," Tetrahedron, 66, 3842-3848 (2010).
  27. Hachiya, S.; Inagaki, T.; Hashizume, D.; Maki, S.; Niwa, H.; Hirano T. "Synthesis and fluorescence properties of difluoro[amidopyrazinato-O, N]boron derivatives: a new boron-containing fluorophore," Tetrahedron Lett., 51, 1613-1615 (2010).
  28. Hachiya, S.; Hashizume, D.; Maki, S.; Niwa, H.; Hirano T. "Synthesis and properties of bis(pyrazino[2',3':4,5]imidazole)-fused 1,2,5,6-tetrahydro-1,4,5,8,9,10-hexaazaanthracenes: a new fluorescent nitrogen-rich heterocycle," Tetrahedron Lett., 51, 1401-1403 (2010).
  29. Ohashi, Y.; Kubota, M.; Hatase, H.; Nakamura, M.; Hirano, T.; Niwa, H.; Nagai, Y. "Distinction of Sialyl Anomers on ESI- and FAB-MS/MS: Stereo-Specific Fragmentations," J. Am. Soc. Mass Spectrom., 20, 394-397 (2009).
  30. Hirano, T.; Hasumi, Y.; Ohtsuka, K.; Maki, S.; Niwa, H.; Yamaji, M.; Hashizume, D. "Spectroscopic Studies of the Light-Color Modulation Mechanism of Firefly (Beetle) Bioluminescence," J. Am. Chem. Soc., 131, 2385-2396 (2009).
  31. Hirano, T.; Takahashi, Y.; Kondo, H.; Maki, S.; Kojima, S.; Ikeda, H.; Niwa, H. "The reaction mechanism for the high quantum yield of the Cypridina (Vargula) bioluminescence supported by chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues)," Photochem. Photobiol. Sci., 7, 197-207 (2008).
  32. Namai, H.; Ikeda, H.; Hirano, T.; Ishii, H.; Mizuno, K. "Spectroscopic and Density Functional Theory Studies of the Molecular Geometry and Electronic Structure of Classical and Nonclassical Radical Ions Derived from 7-Benzhydrylidenenorbornene Analogues," J. Phys. Chem. A, 111, 7898-7905 (2007).
  33. Takahashi, Y.; Kondo, H.; Maki, S.; Niwa, H.; Ikeda, H.; Hirano, T. "Chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones in DMSO/TMG and in diglyme/acetate buffer: support for the chemiexcitation process to generate the singlet-excited state of neutral oxyluciferin in high quantum yield in the Cypridina (Vargula) bioluminescence mechanism," Tetrahedron Lett., 47, 6057-6061 (2006).
  34. Mori, K.; Maki, S.; Niwa, H.; Ikeda, H.; Hirano, T. "Real light emitter in the bioluminescence of the calcium-activated photoproteins aequorin and obelin: light emission from the singlet-excited state of coelenteramide phenolate anion in a contact ion pair," Tetrahedron, 62, 6272-6288 (2006).
  35. Suzuki, M.; Fujii, T.; Nogami, T.; Hirano, T.; Ishida, T. "Bio-inspired Materials for Electron Donors and Charge-transfer Complex Formation Based on the Imidazopyrazinone Luciferin Core," Chem. Lett., 35, 250-251 (2006).
  36. Nakamura, M.; Niwa, K.; Maki, S.; Hirano, T.; Ohmiya, Y.; Niwa, H. "Construction of a new firefly bioluminescence system using L-luciferin as substrate," Tetrahedron Lett., 47, 1197-1200 (2006).
  37. Ohashi, Y.; Hatase, H.; Nakamura, M.; Hirano, T.; Maki, S.; Niwa, H. "Characterization of [1-13C]- Specifically Labeled Amino Acids Using ESIMS/MS in the Selected Reaction Monitoring Mode," J. Mass Spectrom. Soc. Jpn., 53, 309-314 (2005).
  38. Kondo, H.; Igarashi, T.; Maki, S.; Niwa, H.; Ikeda, H.; Hirano, T. "Substituent effects on the kinetics for the chemiluminescence reaction of 6-arylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues): support for the SET-oxygenation mechanism with triplet molecular oxygen," Tetrahedron Lett., 46, 7701-7704 (2005).
  39. Ikeda, H.; Namai, H.; Hirano, T. "Spectroscopic and DFT studies of nonclassical and classical radical cations of 7-benzhydrylidenenorbornene analogues: contrasting molecular geometry and electronic structures originating from the different patterns of electronic coupling," Tetrahedron Lett., 46, 7631-7635 (2005).
  40. Takamuki, Y.; Maki, S.; Niwa, H.; Ikeda, H.; Hirano, T. "Substituent effects on the spectroscopic properties of solvatochromic 2-phenylimidazo[1,2-a]pyrazin-3(7H)-ones: an effective control for the colorimetric sensor properties," Tetrahedron, 61, 10073-10080 (2005).
  41. Nakamura, M.; Maki, S.; Amano, Y.; Ohkita, Y.; Niwa, K.; Hirano, T.; Ohmiya, Y.; Niwa, H. "Firefly luciferase exhibits bimodal action depending on the luciferin chirality," Biochem. Biophys. Res. Commun., 331, 471-475 (2005).
  42. Ikeda, H.; Namai, H.; Hirano, T. "Spectroscopic and DFT evidence for a nonclassical radical cation derived from 7-benzhydrylidenenorbornene," Tetrahedron Lett., 46, 3917-3921 (2005).
  43. Nakamura, M.; Mamino, M.; Masaki, M.; Maki, S.; Matsui, R.; Kojima, S.; Hirano, T.; Ohmiya, Y.; Niwa, H., "Bioluminescence activity of Latia luciferin analogues: replacement of the 2,6,6-trimethylcyclohexene ring onto the methyl-substituted phenyl groups," Tetrahedron Lett., 46, 53-56 (2005).
  44. Takamuki, Y.; Maki, S.; Niwa, H.; Ikeda, H.; Hirano, T. "Substituent Effects on the Solvatochromism of 2-Phenylimidazopyrazinones: Effective Control of the Color Variation Range and Sensitivity toward an Indication of the Proton-Donor Ability of Solvents by an Electron-withdrawing Group Substitution," Chem. Lett., 33, 1484-1485 (2004).
  45. Fujio, S.; Hashizume, D.; Takamuki, Y.; Yasui, M.; Iwasaki, F.; Maki, S.; Niwa, H.; Ikeda, H.; Hirano, T. "Regioselective phenyl-substitution effects on the solvatochromism of 2-phenylimidazo[1,2-a]pyrazin-3(7H)-one derivatives: Expansion of the color variation range of a visible indicator for the proton donor ability of solvents," Tetrahedron Lett., 45, 8531-8534 (2004).
  46. Ohashi, Y.; Itoh, Y.; Kubota, M.; Hamada, K.; Ohashi, M.; Hirano, T.; Niwa, H. "Analysis of sugar epimers using mass spectrometry: N-acetyllactosamine-6,6’-disulfate and the 2’-epimer," Eur. J. Mass Spectrom., 10, 269-278 (2004).
  47. Nakamura, M.; Masaki, M.; Maki, S.; Matsui, R.; Hieda, M.; Mamino, M.; Hirano, T.; Ohmiya, Y.; Niwa, H., "Synthesis of Latia luciferin benzoate analogues and their bioluminescent activity," Tetrahedron Lett., 45, 2203-2205 (2004).
  48. Sekiguchi, T.; Maki, S.; Niwa, H.; Ikeda, H.; Hirano, T., "Metal-ion Complexation of Imidazo[1,2-a]pyrazin-3(7H)-ones: Continuous Changes in Absorption Spectra of Complexes Depending on the Lewis Acidity of a Metal Ion," Tetrahedron Lett., 45, 1065-1069 (2004).
  49. Nakai, S.; Yasui, M.; Nakazato, M.; Iwasaki, F.; Maki, S.; Niwa, H.; Ohashi, M.; Hirano, T., "Fundamental Studies on the Structures and Spectroscopic Properties of Imidazo[1,2-a]pyrazin-3(7H)-one Derivatives," Bull. Chem. Soc. Jpn., 76, 2361-2387 (2003).
  50. Maki, S.; Okawa, M.; Makii, T.; Hirano, T.; Niwa, H. "Pd Black Deposited on Polypropylene Sheet as a Selective Catalyst for Hydrogenation of Alkenes," Tetrahedron Lett., 44, 3717-3721 (2003).
  51. Maki, S.; Okawa, M.; Makii, T.; Hirano, T.; Niwa, H. "Hydrogenolysis-free Hydrogenation Using Pd Black Catalyst Deposited on Pd Sheet," ITE Lett., 4, 49-54 (2003).
  52. Obitsu, K.; Maki, S.; Hirano, T.; Niwa, H. "Preparation and Toxic Property of Carbapicrotoxinin, a Cyclopropane-containing Analog of a GABA-antagonistic Sesquiterpenoid Piricrotoxinin," ITE Lett., 3, 72-75 (2002).
  53. Kummer, A. D.; Kompa, C.; Niwa, H.; Hirano, T.; Kojima, S.; Michel-Beyerle, M. E. "Viscosity-Dependent Fluorescence Decay of the GFP Chromophore in Solution Due to Fast Internal Conversion," J. Phys. Chem. B, 106, 7554-7559 (2002).
  54. Itoh, Y.; Ohashi, Y.; Shibue, T.; Hayashi, A.; Maki, S.; Hirano, T.; Niwa, H. "Reduction in Desorption Mass Spectrometry: Multiple Protonation on Flavins without Charge Increment," J. Mass Spectrom. Soc. Jpn., 50, 52-57 (2002).
  55. Obitsu, K.; Maki, S.; Hirano, T.; Niwa, H. "Preparation of Deoxygenated Derivatives of Neoanisatin, a Neurotoxic Sesquiterpenoid Having a β-Lactone," Bull. Chem. Soc. Jpn., 75, 347-354 (2002).
  56. Imai, Y.; Shibata, T.; Maki, S.; Niwa, H.; Ohashi, M.; Hirano, T. "Fluorescence Properties of Phenolate Anions of Coelenteramide Analogues: the Light-emitter Structure in Aequorin Bioluminescence," J. Photochem. Photobiol. A, 146, 95-107 (2001).
  57. Maki, S.; Harada, Y.; Matsui, R.; Okawa, M.; Hirano, T.; Niwa, H.; Koizumi, M.; Nishiki, Y.; Furuta, T.; Inoue, H.; Iwakura, C. "Effect of Solvent and Hydrogen during Selective Hydrogenation," Tetrahedron Lett., 42, 8323-8327 (2001).
  58. Maki, S.; Okawa, M.; Matsui, R.; Hirano, T.; Niwa, H. "Hydrogenolysis-free Hydrogenation by Pd Black Powder Catalyst," Synlett, 1590-1592 (2001).
  59. Kojima, S.; Maki, S.; Hirano, T.; Ohashi, M.; Tsuji, F. I.; Niwa, H. "Improved Syntheses of Watasenia Preluciferin (Coelenterazine) and Watasenia Luciferin (Coelenterazine Disulfate), and Site Specific Syntheses of the Coelenterazine Monosulfates," ITE Lett., 2, 393-397 (2001).
  60. Ishii, H.; Imai, Y.; Hirano, T.; Maki, S.; Niwa, H.; Ohashi, M. " Isoquinoline Formation by a Novel Photochemical Intermolecular Cycloaddition of 1,1-Diphenylethene Derivatives to 1,4-Dicyanobenzene," Tetrahedron Lett., 41, 6467-6471 (2000).
  61. Maki, S.; Harada, Y.; Hirano, T.; Niwa, H.; Yoshida, Y.; Ogata, S.; Nakamatsu, S.; Inoue, H.; Iwakura, C. "Selective Alkene Hydrogenation with Atomic Hydrogen Permeating through a Pd Sheet Electrode," Syn. Commun., 30, 3575-3583 (2000).
  62. Kojima, S.; Maki, S.; Hirano, T.; Ohmiya, Y.; Niwa, H. "Bioluminescence Activity of Latia Luciferin Analogs," Tetrahedron Lett., 41, 409-4413 (2000).
  63. Hirano, T.; Li, W.; Abrams, L.; Krusic, P. J.; Ottaviani, M. F.; Turro, N. J. "Supramolecular Steric Effect As The Means of Making Reactive Carbon Radicals Persistent; Quantitative Characterization of The External Surface of MFI Zeolites through A Persistent Radical Probe and A Langmuir Adsorption Isotherm," J. Org. Chem., 65, 1319-1330 (2000).
  64. Jockusch, S.; Hirano, T.; Liu, Z.; Turro, N. J. "A Spectroscopic Study of Diphenylmethyl Radicals and Diphenylmethyl Carbocations Stabilized by Zeolites," J. Phys. Chem. B, 104, 1212-1216 (2000).
  65. Zheng, J. L.; Chen, F. Q.; Hirano, T.; Ohmiya, Y.; Maki, S.; Niwa, H.; Ohashi, M. "Synthesis, Chemi- and Bioluminescence Properties, and Photolysis of a Coelenterazine Analogue Having a Photoactive Azido Group," Bull. Chem. Soc. Jpn., 73, 465--469 (2000).