Article
Materials Science, Multidisciplinary
Rongsheng Gao, Lingxiao Li, Xueyan Liu, Chengyou Kan
Summary: A novel fluorescent molecule DADENA with disulfide bond and amino was synthesized and its spectral properties were studied. The PU-DADENA nanoparticles showed good transparency, uniformity, and high stability, with almost 100% reduction conversion of disulfide bonds. DADENA and PU-DADENA nanoparticles have potential applications in fluorescent cell marking, cancer detection, and drug delivery.
Article
Chemistry, Multidisciplinary
Yogajivan Rout, Rajneesh Misra
Summary: A series of multi-acceptor push-pull derivatives were designed and synthesized with different acceptor units to improve their photophysical and electrochemical properties, showing multiple redox waves in cyclic voltammetry.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Physical
Liu Hu, Huayu Han, Zihan Xu, Kaili Song, Fu Wang
Summary: Designing a novel molecular skeleton with a bi-chromophore, this study introduced four 4-substituted 1,8-naphthalimide fluorophores as energy pumps for the zinc(II) phthalocyanine photosensitive group. Four symmetrical 4-NH-substituted-1,8-naphthalimide functionalized zinc(II) phthalocyanine molecules were synthesized and characterized, showing dual-channel absorption and emission features of both chromophores. The fluorescence resonance energy transfer (FRET) process from 1,8-naphthalimide to zinc(II) phthalocyanine was confirmed, and the singlet oxygen quantum yields of the molecules were measured. The introduction of four 1,8-naphthalimide energy pumps significantly improved the photophysical and photochemical properties of zinc(II) phthalocyanine, showing promise for developing high-performance photosensitizers.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Biotechnology & Applied Microbiology
Zhong-jie Xu, Ying-jie Zhou, Jia-hao Wang, Long-fei Mao, Wei Li, Gui-qing Xu
Summary: In this study, acenaphthylene was used as the raw material to synthesize a series of novel 1,8-naphthalimide-1,2,3-triazole derivatives, which were then tested for their anti-tumor activities. Compound 5e exhibited good activity against H1975 lung cancer cells, with an IC50 of 16.56 mu M.
FRONTIERS IN BIOENGINEERING AND BIOTECHNOLOGY
(2021)
Article
Chemistry, Medicinal
Gui-Bin Liang, Jian-Hua Wei, Hong Jiang, Ri-Zhen Huang, Jing-Ting Qin, Hui-Ling Wang, Heng-Shan Wang, Ye Zhang
Summary: The newly synthesized antitumor agents compounds 6b and 7b demonstrated effective antiproliferative activity in vitro and in vivo by targeting DNA, inducing DNA damage, inhibiting Topo I, causing cell cycle arrest at the S phase, and inducing apoptosis.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Marianna Pioli, Cecilia Loffi, Paolo Pio Mazzeo, Alessia Bacchi, Paolo Pelagatti
Summary: Two different N-substituted naphthalimide ligands have been synthesized and reacted with a cationic organometallic fragment, showing different coordination behaviors. One ligand forms a sandwich complex with six coordination sites, while the other forms two isomeric complexes with different stabilities.
INORGANICA CHIMICA ACTA
(2021)
Article
Chemistry, Organic
Tomas Beranek, Martin Jakubec, Jan Sykora, Ivana Cisarova, Jaroslav Zadny, Jan Storch
Summary: A synthetic strategy for phosphahelicenes with a terminal phosphinine ring was explored. The 4-phenyl-6-methyl-2-phospha[7]helicene was synthesized in 12 steps from 2-bromobenzo[c]phenanthrene with an overall yield of 12%. The synthetic approach involved introducing the phosphorus function before photocyclization to form the helicene skeleton, followed by the formation of a phosphorus hexacycle. The structure of the first phosphahelicene with a terminal phosphinine ring was confirmed by X-ray crystallography.
Article
Biochemistry & Molecular Biology
Sebastian Rykowski, Dorota Gurda-Wozna, Marta Orlicka-Plocka, Agnieszka Fedoruk-Wyszomirska, Malgorzata Giel-Pietraszuk, Eliza Wyszko, Aleksandra Kowalczyk, Pawel Staczek, Andrzej Bak, Agnieszka Kiliszek, Wojciech Rypniewski, Agnieszka B. Olejniczak
Summary: A series of novel 3-carboranyl-1,8-naphthalimide derivatives were synthesized and their effects on cytotoxicity, cell cycle arrest, and apoptosis in a HepG2 cancer cell line were investigated. The compounds were found to induce various cellular responses, with conjugate 35 showing strong apoptosis induction and ROS production.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Multidisciplinary
Toshiyuki Uesaka, Tomoyuki Ishitani, Takahito Shimeno, Naoya Suzuki, Shigeyuki Yagi, Takeshi Maeda
Summary: This article presents a method to retard the photodegradation of fluorophores by covalently attaching benzotriazole units. The results show that the dyes with covalently linked benzotriazole units have a higher resistance against degradation, mainly due to the preferential absorption of harmful UV light and involvement in nonradiative deactivation by benzotriazole units.
Article
Chemistry, Physical
O. A. Fedorova, A. N. Arkhipova, P. A. Panchenko, J. Berthet, S. Delbaere, S. Minkovska, Yu. V. Fedorov
Summary: The study introduces a photochromic supramolecular complex with benzopyran and a fluorescent compound, demonstrating that the presence of the fluorophore can significantly increase the bleaching rate compared to free benzopyran at room temperature. Varying the components in the supramolecular complex is preferable for obtaining desired characteristics in the system.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2021)
Article
Chemistry, Physical
Michela Cangiotti, Desislava Staneva, M. Francesca Ottaviani, Evgenia Vasileva-Tonkova, Ivo Grabchev
Summary: A new fluorescent dendrimer was obtained by modifying the periphery of a PAMAM dendrimer. The modified dendrimer showed good fluorescence properties and antimicrobial activity, making it a promising candidate for anticancer and antimicrobial drugs.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2021)
Article
Chemistry, Analytical
Fang Zhang, Fan Chen, Ruipeng Shen, Ya-xiong Chen, Zhengjia Zhao, Baoxin Zhang, Jianguo Fang
Summary: This study reports the construction of a probe library based on the naphthalimide skeleton to detect glutathione (GSH). Compound R13 was identified as a highly efficient GSH fluorescent probe and could be used to quantify GSH in cells and tissues. The probe was applied to study the alteration of GSH level in mouse livers after X-ray irradiation and Parkinson's mouse brains, providing valuable insights into the fluctuation of GSH/GSSG ratio in diseases.
ANALYTICAL CHEMISTRY
(2023)
Article
Chemistry, Applied
Jing-Yang Ni, Xiao-Feng Weng, Ru Sun, Yu-Jie Xu, Jian-Feng Ge
Summary: This study successfully synthesized fluorescent dyes with high fluorescence quantum yields and excellent photostability by modifying 1,8-naphthalimide, which can effectively label lipid droplets with low toxicity.
Article
Polymer Science
Periyan Durairaju, Chinnasamy Umarani, Govindasami Periyasami, Perumberkandigai Adikesavan Vivekanand, Mostafizur Rahaman
Summary: This study reports a novel method for synthesizing multiblock chalcone conjugate phthalimide and naphthalimide functionalized copolymers with a unique topology, and investigates their structure, solubility, photophysical properties, and antimicrobial activities against various pathogens.
Article
Chemistry, Multidisciplinary
Sabiha A. Shaikh, Satish S. Bhat, Pooja L. Hegde, Vidyanand K. Revankar, Anup Kate, Deepti Kirtani, Anupa A. Kumbhar, Vijay Kumbar, Kishore Bhat
Summary: The two novel fluorophore labelled copper(II) complexes exhibit high fluorescence, efficient DNA cleavage, interactions with proteins, and significant anticancer activity, inducing apoptotic cell death.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Takahiro Moriyama, Daiki Mizukami, Makoto Yoritate, Kazuteru Usui, Daisuke Takahashi, Eisuke Ota, Mikiko Sodeoka, Tadashi Ueda, Satoru Karasawa, Go Hirai
Summary: Minimalist photo-reactive probes, consisting of a photo-reactive group and a tag for detection of target proteins, are valuable tools in chemical biology. In this study, minimalist probes based on a 2-thienyl-substituted alpha-ketoamide with an alkyne group on the thiophene ring were developed. The 3-alkyne probe showed the highest photo-affinity labeling efficiency.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Plant Sciences
Akihiro Ochi, Makoto Yoritate, Tomofumi Miyamoto, Kazuteru Usui, Gorawit Yusakul, Waraporn Putalun, Hiroyuki Tanaka, Go Hirai, Satoshi Morimoto, Seiichi Sakamoto
Summary: Harringtonine (HT), derived from Cephalotaxus species, displays potent antiproliferative activity against myeloid leukemia cells. By replacing the C-5' methyl group with different hydrocarbon chains, the derivative 1f showed the highest cytotoxicity among the HT ester derivatives produced, exhibiting strong antiproliferative activity against HL-60 and HeLa cells.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Chemistry, Organic
Kosuke Yamamoto, Yu Suganomata, Takumi Inoue, Masami Kuriyama, Yosuke Demizu, Osamu Onomura
Summary: In this study, asymmetric oxidative desymmetrization of 2-substituted glycerols was achieved using a new chiral bisoxazoline ligand/copper catalyst system. The reaction smoothly proceeds with readily accessible 2-(hetero)aryl- and alkyl-substituted glycerols, providing various glycerate derivatives in good to high yields and high enantioselectivities. The synthetic utility of this protocol was demonstrated by transforming the optically active glycerol into a glyceraldehyde derivative.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Yuya Kaieda, Kosuke Yamamoto, Masami Kuriyama, Osamu Onomura
Summary: A rhodium-catalyzed reaction has been developed to convert N-sulfonyl-1,2,3-triazoles and carboxylic esters into 2,5-disubstituted oxazole derivatives under mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Kazuteru Usui, Nozomi Narita, Ryosuke Eto, Seika Suzuki, Atsushi Yokoo, Kosuke Yamamoto, Kazunobu Igawa, Naoko Iizuka, Yuki Mimura, Tomohiro Umeno, Shota Matsumoto, Masashi Hasegawa, Katsuhiko Tomooka, Yoshitane Imai, Satoru Karasawa
Summary: A study investigated the chiral properties of a compound with organic molecules and enantiomeric structures, revealing that the oxidation of a phosphino group to a phosphine oxide induces a circularly polarized luminescence (CPL) response. The phosphine oxide showed a better CPL response, possibly due to structural changes in the interior of the helicene helix.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Applied
Masami Kuriyama, Genki Maeda, Kazuya Kamata, Yusuke Kodama, Kosuke Yamamoto, Osamu Onomura
Summary: The nickel-catalyzed cross-coupling of bromodifluoromethylphosphonates with arylboron reagents was achieved using a 1,10-phenanthroline-type ligand. Functionalized and heterocycle-containing boroxines were suitable partners for this reaction, and the catalytic modification of biologically active molecules, such as fenofibrate and indomethacin, was successfully accomplished. Moreover, the gram-scale reaction proceeded smoothly with a high yield of desired product.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Editorial Material
Chemistry, Multidisciplinary
K. Usui, N. Narita, R. Eto, S. Suzuki, A. Yokoo, K. Yamamoto, K. Igawa, N. Iizuka, Y. Mimura, T. Umeno, S. Matsumoto, M. Hasegawa, K. Tomooka, Y. Imai, S. Karasawa
Summary: This study reveals a system in which the oxidation of a phosphino group to the corresponding phosphine oxide induces CPL response in helicene derivatives. The helical structures of pi-extended helicenes with phosphine and phosphine oxide groups on their inner helical rims were determined by X-ray crystallography. The results show that phosphine oxide exhibits a significantly better CPL response compared to phosphine.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Yuya Kaieda, Kosuke Yamamoto, Hiroyuki Toguchi, Natsumi Hanazawa, Masami Kuriyama, Osamu Onomura
Summary: A metal-free oxidative C-N bond cleavage of cyclic amines has been developed to provide N-Cl-?-amino acids in moderate to excellent yields. The reactions can proceed even on a gram scale using tetramethylammonium hypochlorite (TMAOCl) as an oxidant. Furthermore, the Hofmann-Loffler-Freytag-type reaction of N-Cl-?-amino acids to form cyclic amino acids has been demonstrated.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Analytical
Tomohiro Umeno, Moeka Fujihara, Shota Matsumoto, Naoko Iizuka, Kazuteru Usui, Satoru Karasawa
Summary: In this study, a quantitative and nondestructive colorimetric amine detection method based on an acid-base reaction was developed for monitoring coupling reactions during solid-phase peptide synthesis (SPPS). The method showed a good linear relationship and a small relative standard deviation for quantitative colorimetric analysis of proteinogenic and nonproteinogenic amino acids. Moreover, it allowed for detailed monitoring of the coupling reaction in the synthesis of peptides, resulting in significantly purer products compared to the traditional Kaiser test.
ANALYTICAL CHEMISTRY
(2023)
Article
Biochemical Research Methods
Tomohiro Umeno, Lisa Muroi, Yuto Kayama, Kazuteru Usui, Koichi Hamada, Akihiro Mizutani, Satoru Karasawa
Summary: In bioengineering, fluorescent amine-reactive probes are essential for detecting amine species, especially for lysine protein detection. However, the existing probes require improvements.
BIOCONJUGATE CHEMISTRY
(2023)
Article
Chemistry, Organic
Masashi Hasegawa, Yuki Nojima, Yuya Nagata, Kazuteru Usui, Ken-ichi Sugiura, Yasuhiro Mazaki
Summary: This study reports the synthesis, structure, and circularly polarized luminescence (CPL) of two types of shape-persistent [5]helicenes. The effective Wittig ring-closure reaction was facilitated by the binaphthyl tethering system, which resulted in the synthesis of a macrocyclic precursor that could be easily converted to the title compound via successive photocyclization. The tethered groups were replaced with untethered -OCH3 groups, and both compounds exhibited similar spectra and exhibited CPL with higher dissymmetry factors g(lum) values than unlocked helicenes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Kosuke Yamamoto, Masami Kuriyama, Osamu Onomura
Summary: The development of efficient and environmentally benign methods for the oxidation of alcohols is an important research field due to the high importance of carbonyl compounds in organic synthesis and fine chemical industries. Electrochemistry is an ideal strategy to achieve green redox processes without the use of chemical oxidants/reductants. This review summarizes the electrogenerated active halogen-mediated transformations of primary, secondary, and tertiary alcohols, as well as recent advances in the direct oxidation of alcohols.
ISRAEL JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shota Matsumoto, Tomohiro Umeno, Noriko Suzuki, Kazuteru Usui, Masatoshi Kawahata, Satoru Karasawa
Summary: Fluorescence is the gold standard for detecting trivalent metal ions. This study presents a new chelate-free approach using Bronsted base-type probes for the selective detection of trivalent metal ions, and also discovers the X-ray structure of an outer-sphere aluminum(III) aqua complex coordinated by fluorescent probes via hydrogen bonds.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Yuri Fukumoto, Tomohiro Umeno, Hina Kuramochi, Koichi Hamada, Shota Matsumoto, Noriko Suzuki, Kazuteru Usui, Akihiro Mizutani, Satoru Karasawa
Summary: In this study, emissive aminoquinoline derivatives (TFMAQ) containing alkylmorpholine and arylmorpholine groups were investigated for their photophysical properties, acid-responsiveness, and organelle targeting. Surprisingly, the TFMAQ derivatives with ethylmorpholine groups showed limited accumulation in lysosomes, which are known to favor alkylmorpholine group accumulation, and instead preferred accumulation in lipid droplets. These findings have significant implications for the development of organelle/tissue specific dyes for cell imaging and diagnosis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
