群馬大学理工学府分子科学部門　吉原研究室

Reference

【業績】

-2020年-

Spontaneously blinking fluorophore based on nucleophilic addition/dissociation of intracellular glutathione for lice-cell super-resolution imaging
A. Morozumi, M. Kamiya, S. Uno, K. Umezawa, R. Kojima, T. Yoshihara, S. Tobita and Y. Urano
J. Am. Chem. Soc., 142, 9625-9633 (2020)

Chemical transformation of push-pull fluorenones: push-pull dibenzodicyanofulvenes as well as fluorenone- and dibenzodicyanofulvene-tetracyanobutadiene conjugates
S. Kato, T. Kijima, Y. Shiota, T. Abe, S. Kuwako, H. Miyauchi, N. Yoshikawa, K. Yamamoto, K. Yoshizawa, T. Yoshihara, S. Tobita and Y. Nakamura
Org. Bio. Chem., 18, 4198-4209 (2020)

Visualization of Lipid Droplets in Living Cells and Fatty Livers of Mice Based on the Fluorescence of -Extended Coumarin Using Fluorescence Lifetime Imaging Microscopy
T. Yoshihara, R. Maruyama, S. Shiozaki, K.Yamamoto, S. Kato, Y. Nakamura and S.Tobita
Anal. Chem., 92, 4996-5003 (2020).

Synthesis, structures and properties of neutral and radical cationic S,C,C-bridged triphenylamines
S. Kato, T. Matsuoka, S. Suzuki, M. Asano, T. Yoshihara, S. Tobita, T. Matsumoto and C. Kitamura
Org. Lett., 22, 734-738 (2020)

Absolute Quantum Yield Measurements of Near-Infrared Emission with Correction for Solvent Absorption
R. Hoshi, K. Suzuki, N. Hasebe, T. Yoshihara and S. Tobita
Anal. Chem.,92, 607-611 (2020).



-2019年-

Ratiometric oxygen probes with a cell-penetrating peptide for imaging oxygen levels in living cells
M. Yasukagawa, K. Yamada, S. Tobita and T. Yoshihara
J. Photochem. Photobiol. A: Chem., 383, 111983 (2019).

Fluorescence quenching-based assay for measuring golgi endo-α-mannosidase
K. Sano, T. Kuribara, N. Ishii, A. Kuroiwa, T. Yoshihara, S. Tobita, K. Totani and I. Matsuo
Chem. Asian J., 14, 1965-1969 (2019).

Structure-efficiency relationship of photoinduced electron transfer-triggered nitric oxide releasers
N. Ieda, Y. Oka, T. Yoshihara, S. Tobita, T. Sasamori, M. Kawaguchi and H. Nakagawa
Sci. Rep., 9, 1430-1-8 (2019).

-2018年-

Ir(III) complex-based oxygen imaging of living cells and ocular fundus with a gated ICCD camera
H. Akiyama, I. Takahashi, Y. Shimoda, R. Mukai, T. Yoshihara S. Tobita
Photochem. Photobiol. Sci., 17, 846-853 (2018).

Intravital phosphorescence lifetime imaging of the renal cortex accurately measures renal hypoxia
Y. Hirakawa, K. Muzukami, T. Yoshihara, I. Takahashi, P. Khulan, T. Honda, I. Mimura, T. Tanaka, S. Tobita and
M. Nangaku
Kidney Int., 93, 1483-1489 (2018).



-2017年-

Extension of p-system of silylated porphyrin derivative for photodynamic therapy.
H. Horiuchi, A. Sasaki, S. Akiyama, R. Ikeda, S. Ito, M. Furuya, Y. Gomibuchi, M. Ichikawa, T. Yoshihara, S. Tobita and
T. Okutsu.
J. Photochem. Photobiol. A: Chem., 339, 19-24 (2017).

Oxygen Imaging of Living Cells and Tissues Using Luminescent Molecular Probes
T. Yoshihara, Y. Hirakawa, M. Hosaka, M. Nangaku and S. Tobita
J. Photochem. Photobiol. C: Photochem. Rev., 30, 71-95 (2017).

Interrogation of Metabolic and Oxygen States of Tumors with Fiber-Based Luminescence Lifetime Spectroscopy
M. Lukina, A. Orlova, M. Shirmanova, D. Shirokov, A. Pavlikov, A. Neubauer, H. Studier, W. Becker, E. Zagaynova, T. Yoshihara, S. Tobita and V. Shcheslavskiy
Opt. Lett., 42, 731-734 (2017).



-2016年-

Intracellular and in vivo oxygen sensing using phosphorescent iridium(III) complexes
S. Tobita and T. Yoshihara
Curr. Opin. Chem. Biol., 33, 39-45 (2016).

Biological oxygen sensing via two-photon absorption by an Ir(III) complex using a femtosecond fiber laser
H. Morimoto, A. Fujii, Y. Suzuki, T. Yoshihara, S. Tobita and J. Kawamata
Jpn. J. Appl. Phys., 55, 092401-1-4 (2016).


Push-pull fluorenones and benzazulenequinones: regioselective [4+2] and [2+2] cycloadditions of benzopentalenequinone derivative and alkynes bearing an aniline moiety
S. Kato, T. Kijima, Y. Shiota, T.Yoshihara, S. Tobita, K. Yoshizawa, Y. Nakamura
Tetrahedron Lett., 57, 4604-4607 (2016)

Phosphorescence quenching of neutral and cationic iridium(III) complexes by molecular oxygen and aromatic electron acceptors
H. Hasebe, Y. Deguchi, S. Murayama, T. Yoshihara, H. Horiuchi, T. Okutsu and S. Tobita
J. Photochem. Photobiol. A: Chem., 324, 134-144 (2016).

The effect of central metal on the photodynamic properties of silylated tetraphenylporphyrin Derivative
H. Horiuchi, K. Terashima, A. Sakai, D. Suda, T. Yoshihara, A. Kobayashi, S. Tobita, and T. Okutsu
J. Photochem. Photobiol. A: Chem., 321, 72-78 (2016). 

-2015年-

Quantitating intracellular oxygen tension in vivo by phosphorescence lifetime measurement
Y. Hirakawa, T. Yoshihara, M. Kamiya, I. Mimura, D. Fujikura, T. Masuda, R. Kikuchi, I. Takahashi, Y. Urano,
S. Tobita, and M. Nangaku
Sci. Rep., 5, 17838-1-10 (2015).

Ratiometric molecular probes based on dual emission of a blue fluorescent coumarin and a red phosphorescent cationic iridium(III) complex for intramolecular oxygen sensing
T. Yoshihara, S. Murayama, and S. Tobita
Sensors, 15, 13503-13521 (2015).

Intracellular and in vivo oxygen sensing using phosphorescent Ir(III) complexes with a modified acetylacetonato ligand
T. Yoshihara, M. Hosaka, M. Terata, K. Ichikara, S. Murayama, A. Tanaka, M. Mori, H. Itabashi, T. Takeuchi, and
S. Tobita
Anal. Chem., 87, 2710-2717 (2015).

Absolute phosphorescence quantum yields of singlet molecular oxygen in solution determined using an integrating sphere instrument
N. Hasebe, K. Suzuki, H. Horiuchi, H. Suzuki, T. Yoshihara, T. Okutsu, and S. Tobita
Anal. Chem., 87, 2360-2366 (2015).

A series of p-​extended thiadiazoles fused with electron-​donating heteroaromatic moieties: Synthesis, properties, and polymorphic crystals
S. Katoh, T. Furuya, M. Nitani, N. Hasebe, Y. Ie, Y. Aso, T. Yoshihara, S. Tobita, and Y. Nakamura
Chem. Eur. J., 21, 3115-3128 (2015).

Amphiphilic benzothiadiazole-​triphenylamine-​based aggregates that emit red light in water
T. Ishi-i, I. Kitahara, S. Yamada, Y. Sanada, K. Sakurai, A. Tanaka, N. Hasebe, T. Yoshihara, and S. Tobita
Org. Biomol. Chem., 13, 1818-1828 (2015).

Mitochondria-​targeted oxygen probes based on cationic iridium complexes with a 5-​amino-​1, 10-​phenanthroline ligand
T. Yoshihara, S. Murayama, T. Masuda, T. Kikuchi, K. Yoshida, M. Hosaka, and S. Tobita
J. Photochem. Photobiol. A: Chem., 299, 172-182 (2015).

-2014年-

Minimal thioflavin T modifications improve visual discrimination of guanine-​quadruplex topologies and alter compound-​induced topological structures
Y. Kataoka, H. Fujita, Y. Kasahara, T. Yoshihara, S. Tobita, and M. Kuwahara
Anal. Chem., 86, 12078-12084 (2014).

A spontaneously blinking fluorophore based on intramolecular spirocyclization for live-cell super-resolution imaging
S. Uno, K. Kamiya, T. Yoshihara, K. Sugawara, K. Okabe, M. C. Tarhan, H. Fujita, T. Funatsu, Y. Okada, S. Tobita, and Y. Urano
Nat. Chem., 8, 681-689 (2014).

Mitochondrial respiratory function induces endogenous hypoxia
S. Prior, A. Kim, T. Yoshihara, S. Tobita, T. Takeuchi, and M. Higuchi
PLoS One, 9, e88911-1-e88991-13 (2014).

Systematic structure-​property investigations on a series of alternating carbazole-​thiophene oligomers
S. Katoh, S. Simizu, A. Kobayashi, T. Yoshihara, S. Tobita, and Y. Nakamura
J. Org. Chem. 79, 618-619 (2014).

-2013年-

Tetraalkoxyphenanthrene-fused dehydroannulenes: Synthesis, self-Assembly, and electronic, optical, and electrochemical properties
S. Katoh, N. Takahashi, H. Tanaka, A. Kobayashi, T. Yoshihara, S. Tobita, T. Yamanobe, H. Uehara, and Y. Nakamura
Chem. Eur. J., 19, 12138-12151 (2013).

Fluorescent peptides labeled with environment-sensitive 7-aminocoumarins and their interactions with lipid bilayer membranes and living cells
T. Murase, T. Yoshihara, K. Yamada, and S. Tobita
Bull. Chem. Soc. Jpn., 86, 510-519 (2013).

-2012年-

Bicarbazoles: Systematic structure-property investigation on a series of conjugated carbazole dimers
S. Katoh H. Noguchi, A. Kobayashi, T. Yoshihara, S. Tobita, and Y. Nakamura
J. Org. Chem., 77, 9120-9133 (2012).

p-Extended thiadiazoles fused with thienopyrrole or indole moieties: Synthesis, structures, and properties
S. Katoh, T. Furuya, A. Kobayashi, M. Nitani, Y. Ie, Y. Aso, T. Yoshihara, S. Tobita, and Y. Nakamura
J. Org. Chem., 77, 7595-7606 (2012).

Remarkable fluorescent enhancement of benzo[g]chromen-2-ones induced by hydrogen-bonding interactions with protic solvents
A. Kobayashi, K. Takehira, T. Yoshihara, S. Uchiyama, and S. Tobita
Photochem. Photobiol. Sci., 11, 1368-1376 (2012).

Environment-sensitive fluorophores with benzothiadiazole and benzoselenadiazole structures as candidate components of a fluorescent polymeric thermometer
S. Uchiyama, K. Kimura, C. Gota, K. Okabe, K. Kawamoto, N. Inada, T. Yoshihara, and S. Tobita
Chem. Eur. J., 18, 9552-9563 (2012).

Mitochondria-specific oxygen probe based on iridium complexes bearing triphenylphosphonium cation
T. Murase, T. Yoshihara, and S. Tobita
Chem. Lett., 41, 262-263 (2012).

Ratiometric molecular sensor for monitoring oxygen levels in living cells
T. Yoshihara, Y. Yamaguchi, and S. Tobita
Angew. Chem. Int. Ed., 51, 4148-4151 (2012).

Iridium complex probes for monitoring of cellular oxygen levels and imaging of hypoxic tissues
T. Yoshihara, A. Kobayashi, S. Oda, M. Hosaka, T. Takeuchi, and S. Tobita
Proc. of SPIE, 8233, 82330A-1-82330A-8 (2012). 

-2011年-

Control of photophysical properties of 1,8-naphthalimides by electron-withdrawing substituents introduced into N-alkyl side chains
M. Matsubayashi, C. Kagimura, Y. Kubo, T. Yoshihara, and S. Tobita
Bull. Chem. Soc. Jpn., 84, 520-525 (2011).

-2010年-

Kinetic analysis for the effect of intramolecular hydrogen bonding on photophysical properties of N-hydroxyalkyl-1,8-naphthalimides
M. Matsubayashi, C. Kajimura, H. Shiratori, Y. Kubo, T. Yoshihara, and S. Tobita
Bull. Chem. Soc. Jpn., 83, 1067-1073, (2010).

Phosphorescent light-emitting iridium complexes serve as a hypoxia-sensing probe for tumor imaging in living animals
S. Zhang, M. Hosaka, T. Yoshihara, K. Negishi, Y. Ida, S. Tobita, and T. Takeuchi
Cancer Res., 70, 4490-4498 (2010).

Absolute measurements of photoluminescence quantum yields of 1-halonaphthalenes in 77 K rigid solution using an integrating sphere instrument
A. Kobayashi, K. Suzuki, T. Yoshihara, and S. Tobita
Chem. Lett., 39, 282-283 (2010).

-2009年-

In-vivo phosphorescence imaging of cancer using iridium complexes
T. Yoshihara, Y. Karasawa, S. Zhang, M. Hosaka, T. Takeuchi, Y. Ida, K. Endo, T. Imamura, and S. Tobita
Proc. of SPIE, 7190, 71900X-1-71900X-8 (2009).

Reevaluation of absolute luminescence quantum yields of standard solutions using a spectrometer with an integrating sphere and a back-thinned CCD detector
K. Suzuki, A. Kobayashi, S. Kaneko, K. Takehira, T. Yoshihara, H. Ishida, Y. Shiina, S. Oishi, and S. Tobita
Phys. Chem. Chem. Phys., 11, 9850-9860 (2009).

Synthesis and photophysical properties of N-arylcarbazolophanes
H.Shimizu, Y. Kakinoya, K. Takehira, T. Yoshihara, S. Tobita, Y. Nakamura, and J. Nishimura
Bull. Chem. Soc. Jpn., 82, 860-869 (2009).

Substituent effects on photophysical properties of N-thienylcarbazoles
H. Shimizu, A. Kobayashi, S. Itoi, T. Yoshihara, S. Tobita, Y. Nakamura, and J. Nishimura
Heterocycles, 785, 1265-1269 (2009).

The rate of excited-state proton transfer to solvent from trifluoromethylphenols in water
S. Kaneko, T. Yoshihara, and S. Tobita
Chem. Lett., 38, 312 (2009).

-2008年-

Measurement of photoluminesence efficiency of Ir(III) phenylpyridine derivatives in solution and solid-state films
A. Endo, K. Suzuki, T. Yoshihara, S. Tobita, M. Yahiro, and C. Adachi
Chem. Phys. Lett., 460, 155-157 (2008).

Temperature-dependent fluorescence lifetime of a fluorescent polymetric thermometer poly(N-isopropylacrylamide), labeled by polarity and hydrogen bonding sensitive 4-sulfamoyl-7-aminobenzofurazan
C. Gota, S. Uchiyama, T. Yoshihara, S. Tobita, and T. Ohwada
J. Phys. Chem. B, 112, 2829-2836 (2008).

Photoinduced intramolecular electron transfer of carbazole trimer-[60]fullerene studied by laser flash photolysis techniques
T. Konno, M. E. El-Khouly, Y. Nakamura, K. Kinoshita, Y. Araki, O. Ito, T. Yoshihara, S. Tobita, and J. Nishimura
J. Phys. Chem. C, 112, 1244-1249 (2008).

-2007年-

Extremely low-threshold amplified spontaneous emission of 9,9’-spirobifluorene derivatives and electroluminescence from field-effect transistor structure
H. Nakanotani, S. Akiyama, D. Ohnishi, M. Moriwake, M. Yahiro, T. Yoshihara, S. Tobita, and C. Adachi
Adv. Funct. Mater., 17, 2328-2335 (2007).

Effect of pH on absorption spectra of photogenerated holes in nanocrystalline TiO₂ films
T. Yoshihara, Y. Tamaki, A. Furube, M. Murai, K. Hara, and R. Katoh
Chem. Phys. Lett., 438, 268-273 (2007).

Synthesis and photophysical properties of [60]fullerene adducts carryning oligocarbazole dendrons
Y. Nakamura, T. Konno, S. Watanabe, M. Suzuki, T. Yoshihara, S. Tobita, and J. Nishimura
Chem. Lett., 36, 264-265 (2007).

-2006年-

Environment-sensitive fluorophore emitting in protic environments
S. Uchiyama, K. Takehira, T. Yoshihara, S. Tobita, and T. Ohwada
Org. Lett., 8, 5869-5872 (2006).

Intramolecular charge transfer and dielectric solvent relaxation in n-propyl cyanide. N-phenylpyrrole and 4-dimethylamino-4’-cyanostilbene
S. I. Druzhinin, V. A. Galievsky, T. Yoshihara, and K. A. Zachariasse
J. Phys. Chem. A, 110, 12760-12768 (2006).

Water-induced fluorescence quenching of mono- and dicyanoanilines
J. Oshima, T. Yoshihara, and S. Tobita
Chem. Phys. Lett., 423, 306-311 (2006).

Photophysics properties of 3-[2-Cyano-4-(dimethylamino)phenyl]alanine: A highly fluorescent and environment-sensitive amino acid with small molecular size
J. Oshima, H. Tsujimoto, T. Yoshihara, K. Yamada, R. Katakai, and S, Tobita
Chem. Lett., 35, 620-621 (2006).

Extreme fluorescence sensitivity of some aniline derivatives to aqueous and nonaqueous environments: Mechanistic study and its implication as a fluorescent probe
J. Oshima, S. Shiobara, H. Naoumi, S. Kaneko, T. Yoshihara, A. K. Mishra, and S. Tobita
J. Phys. Chem. A, 110, 4629-4637 (2006).

An efficient energy transfer found in triphenylene/hexaazatriphenylene system with electric complimentarity and structural similarity
T. Ishi-I, H. Tashiro, R. Kuwahara, S. Mataka, T. Yoshihara, and S. Tobita
Chem. Lett., 35, 158-159 (2006). 

-2005年-

The exo-outstretching effect governing the exclusive stereoselectivity of the intramolecular [2+2] photocycloaddition of vinylarenes
J. Nishimura, T. Funaki, N. Saito, S. Inokuma, Y. Nakamura, S. Tajima, T. Yoshihara, and S. Tobita
Helv. Chim. Acta, 88, 1226-1239 (2005).

Intramolecular and intermolecular hydrogen-bonding effects on photophysics properties of 2’-aminoacetophenone and its derivatives in solution
H. Shimada, A. Nakamura, T. Yoshihara, and S. Tobita
Photochem. Photobiol. Sci., 4, 367-375 (2005).

Synthsis and complexing properties of [2.n](2,6)pyridinocrownophanes
S. Inokuma, H. Ide, T. Yonekura, T. Funaki, S. Kondo, S. Shiobara, T. Yoshihara, S. Tobita, and J. Nishimura
J. Org. Chem., 70, 1698-1703 (2005).

Novel conjugated organic dyes for efficient dye-sensitized solar cells
K. Hara, T. Sato, R. Katoh, A. Furube, T. Yoshihara, M. Murai, M. Kurashige, S. Ito, A. Shinpo, S. Suga, and H. Arakawa
Adv. Funct. Mater., 15, 246-252 (2005).

Kinetics of intramolecular charge transfer with N-phenylpyrrole in alkyl cyanides
T. Yoshihara, S. I. Druzhinin, A. Demeter, N. Kocher, D. Stalke, and K. A. Zachariasse
J. Phys. Chem. A, 109, 1497-1509 (2005).

【著書】

Toshitada Yoshihara, Yosuke Hirakawa, Masaomi Nangaku, Seiji Tobita（分担執筆），Chapter 4. Hydrophilic Ir(iii) Complexes for
In vitro and In vivo Oxygen Imaging, Royal Society of Chemistry, p71-90 (2018).

吉原利忠（分担執筆）1-4 りん光を用いた生体内酸素レベル計測，丸善出版，p50-68 (2017).

吉原利忠，飛田成史（分担執筆），Chapter14. 低酸素応答ルミネッセンスに基づくin vivoがんイメージング，DO JIN BIOSCIENCE SERIES，化学同人，p129-136 (2015).

吉原利忠，飛田成史（分担執筆），第25章 分子内エネルギー移動を利用したサンスクリーン，光老化科学の最前線，シーエムシー出版，p220-228 (2015).

吉原利忠（分担執筆），6.2.4 光線過敏症，光化学の事典，光化学協会光化学の事典編集委員会，朝倉出版，p262-263 (2014).

吉原利忠（分担執筆），1.8 イリジウム錯体のりん光を利用した細胞・組織イメージング，炭素とケイ素の元素化学，エレメント・イノベーションプロジェクト，群馬大学，p100-111 (2014).

飛田成史，吉原利忠，穂坂正博，竹内利行（分担執筆），第2章4. りん光プローブの設計・開発に基づくin vivo低酸素環境イメージング，実験医学，羊土社，第30巻，p1100-1106 (2012).

【総説・解説】

吉原利忠，水上輝市，塩崎秀一，平川陽介，南学正臣，飛田成史，りん光寿命計測に基づく組織内酸素分圧イメージング，JSMI Report, 12(2), 3-8 (2019).

田村拓人，吉原利忠，水上輝市，塩崎秀一，片野彩花，松村菜生，六代範，西山正彦，飛田成史，共焦点りん光イメージング顕微鏡を用いた腫瘍の酸素化状態の高分解能イメージング，JSMI Report, 12(1), 32-36 (2018).

吉原利忠，飛田成史，りん光寿命計測による細胞・組織内酸素濃度定量，ファルマシア，53，220-224 (2017).

飛田正史，吉原利忠，光学的方法による細胞・組織内酸素濃度計測，細胞，45，592-595 (2013).

吉原利忠，村瀬秋子，飛田成史，りん光性分子プローブによる低酸素細胞イメージング，細胞，45，431-434 (2013).

吉原利忠，飛田成史，イリジウム錯体のりん光を用いた低酸素細胞・組織イメージング，光化学協会誌，44，86-89 (2013).

飛田成史，吉原利忠，穂坂正博，竹内利行，イリジウム錯体のりん光を利用した酸素濃度センサー，ケミカルエンジニヤリング，55，584-588 (2010).

飛田成史，吉原利忠，穂坂正博，竹内利行，りん光性分子プローブを用いた癌環境イメージング-低酸素の可視化-，Medical Science Digest，35，538-541 (2009).