| Mitsuru Shindo | Last modified date：2024.04.03 |
Professor /
Interdisciplinary Graduate School of Engineering Sciences /
Department of Fundamental Organic Chemistry /
Institute for Materials Chemistry and Engineering
Papers
| 1. | Yamaoka Yousuke; Imahori Hidetaka; Namioka Motoki; Nishina Ryo; Kobori Yukiko; Ueda Motoki; Shindo Mitsuru; Takasu Kiyosei , Entry into Lithium Ynolates from α,α,α-Tribromomethyl ketones: Synthesis of Cyclobutenes via the [2 + 2] Cycloaddition with α,β-Unsaturated Carbonyls, , Organic Letters, https://doi.org/10.1021/acs.orglett.4c00202, 26, 1896-1901 , 2024.03. |
| 2. | Iwata Takayuki; ＃Funatsu Shingo; Shindo Mitsuru, , Nazarov Reaction Triggered by Active Lithium Salts in Cyclopentyl Methyl Ether, Chem Lett, https://doi.org/10.1093/chemle/upad046, in press, 2024.03. |
| 3. | Takayuki Iwata, Mizuki Hyodo, Ryusei Kawano, Mitsuru Shindo, A Strategy based on “Ambident Anthracene” for the Synthesis of Higher-Order Iptycenes e202303687 (2023). https://doi.org/10.1002/chem.202303687【hot paper】, Chem. Eur. J. , https://doi.org/10.1002/chem.202303687, e202303687, 2024.03, アラインと求アラインの両者の性質を併せ持つアンビデントアントラセンを用いたイプチセンの一般的構築法を見出した。これを用いて史上最長の直鎖型イプチセンの合成に成功した。. |
| 4. | Iwata Takayuki; ＃Funatsu Shingo; ＃Kajiwara Kohei; Shiota Yoshihito; Yoshizawa Kazunari; Shindo Mitsuru, , Neutral Nazarov Reaction Using Protic Solvents as Activators, , Bull Chem Soc Jpn, https://doi.org/10.1093/bulcsj/uoad014, in press, 2024.01. |
| 5. | Takayuki Iwata, Masato Hanada, Satoru Kumagai, Tatsuro Yoshinaga, Yoshihito Shiota, Kazunari Yoshizawa, Mitsuru Shindo, Intramolecular Hiyama Coupling: Synthesis of 1,8,13-Trisubstituted Chiral Triptycenes with Three Different Substituents by Intramolecular Substituent Transfer, Chemistry European Journal, doi.org/10.1002/chem.202300988, 29, e202300988, 2023.04, トリプチセン上で分子内檜山カップリングに成功した。この手法によりキラルトリプチセンの合成に成功した。. |
| 6. | Takeshi Nishimura, Saki Makigawa, Jun Sun, Kozue Kodama, Hiromi Sugiyama, Kenji Matsumoto, Takayuki Iwata, Naoya Wasano, Arihiro Kano, Miyo Terao Morita, Yoshiharu Fujii, Mitsuru Shindo,, Design and synthesis of strong root gravitropism inhibitors with no concomitant growth inhibition, Scientific Reports, https://doi.org/10.1038/s41598-023-32063-z, 13, 5173, 2023.03, 植物根に対する強力な重力屈性阻害剤BMAを開発した。成長抑制や毒性を示さない選択的な阻害剤で、従来品の中でももっとも強力な阻害剤である。植物生理学実験で、植物ホルモンのオーキシンの極性輸送に関わることが判明し、それも従来の阻害剤とは異なる機構であることも判明した。今後、環境に優しい緑化調節剤や抑草剤としての応用が期待される。. |
| 7. | Kazuto Takegawa, Takeshi Ito, Atsushi Yamamoto, Naoshi Yamazaki, Mitsuru Shindo, Yasuo Shinohara, KH-17, a simplified derivative of bongkrekic acid, weakly inhibits the mitochondrial ADP/ATP carrier from both sides of the inner mitochondrial membrane,, Chemical Biology & Drug Design,, 10.1111/cbdd.14194, 101, 865-872, 2023.01. |
| 8. | ＠Takeda Shuso, Hirao-Suzuki Masayo, Shindo Mitsuru, Aramaki, Hironori, (-)-Xanthatin as a Killer of Human Breast Cancer MCF-7 Mammosphere Cells: A Comparative Study with Salinomycin, CURRENT ISSUES IN MOLECULAR BIOLOGY, 10.3390/cimb44090264, 44, 9, 3849-3858, 2022.09. |
| 9. | Takayuki Iwata; Mizuki Hyodo, Takumi Fujiwara, Leah Kuhn, Igor V. Alabugin, Mitsuru Shindo,, 3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes, Synthesis, 10.1055/a-1818-0576, 54, 22, 4971-4978, 2022.04. |
| 10. | Takayuki Iwata, Ryusei Kawano, Takuto Fukami, Mitsuru Shindo, Retro-Friedel–Crafts-type Acidic Ring-Opening of Triptycenes: A New Synthetic Approach to Acenes, Chemistry-A Europian Journal, doi.org/10.1002/chem.202200416, 2022.01, トリプチセンの酸による新規開環反応を見出した。本反応を応用して、有機電子材料として重要なアセンの合成に成功した。. |
| 11. | Takayuki Iwata, Satoru Kumagai, Tatsuro Yoshinaga, Masato Hanada, Yoshihito Shiota, Kazunari Yoshizawa, Mitsuru Shindo,, Quadruple Role of Pd Catalyst in Domino Reaction Involving Aryl to Alkyl 1,5-Pd Migration to Access 1,9-Bridged Triptycenes, CHEMISTRY-A EUROPEAN JOURNAL, 10.1002/chem.202101728, 27, 45, 11548-11553, 2021.08, パラジウム触媒による新規４連続反応を見出し、キラルトリプチセンの合成に成功した。本反応では一つのパラジウム触媒が酸化的付加に引き続く炭素水素結合切断反応による還元反応、環化反応、鈴木カップリング、アリルホウ酸のホモカップリングという4種の異種反応を触媒していることを理論計算により明らかにした。。. |
| 12. | Masayo Hirao-Suzuki, Shuso Takeda, Mitsuru Shindo, Exposure to (–)-Xanthatin during the Haploid Formation of Mouse Spermatocyte GC-2spd(ts) Cells, an in vitro Male Germ Cell Model, BPB Reports,, https://doi.org/10.1248/bpbreports.4.6_202, 4, 202-205, 2021.06. |
| 13. | Yoshinobu Fujiwara , Takeshi Ito , Atsumi Toiyama , Takenori Yamamoto , Naoshi Yamazaki , Mitsuru Shindo , Yasuo Shinohara,, Suramin Inhibits Mitochondrial ADP/ATP Carrier, Not Only from the Cytosolic Side But Also from the Matrix Side, of the Mitochondrial Inner Membrane,, BPB Reports, https://doi.org/10.1248/bpbreports.4.3_92, 4, 92-97, 2021.05. |
| 14. | Carbonnel, Samy; Torabi, Salar; Griesmann, Maximilian; Bleek, Elias; Tang, Yuhong; Buchka, Stefan; Basso, Veronica; Shindo, Mitsuru; Boyer, Francois-Didier; Wang, Trevor L.; Udvardi, Michael; Waters, Mark T.; Gutjahr, Caroline, Lotus japonicus karrikin receptors display divergent ligand-binding specificities and organ-dependent redundancy, PLOS GENETICS, 10.1371/journal.pgen.1009249, 16, 12, e1009249, 2020.12, [URL]. |
| 15. | Iwata, Takayuki; Yoshinaga, Tatsuro; Shindo, Mitsuru, Flow Synthesis of Triptycene via Triple Cycloaddition of Ynolate to Benzyne, SYNLETT, 10.1055/s-0040-1706417, 31, 19, 1903-1906, 2020.12.  |
| 16. | Matsumoto, Kenji; Toubaru, Yasunori; Tachikawa, Shohei; Miki, Ayaka; Sakai, Kentaro; Koroki, Syota; Hirokane, Tsukasa; Shindo, Mitsuru; Yoshida, Masahiro, Catalytic and Aerobic Oxidative Biaryl Coupling of Anilines Using a Recyclable Heterogeneous Catalyst for Synthesis of Benzidines and Bicarbazoles, JOURNAL OF ORGANIC CHEMISTRY, 10.1021/acs.joc.0c02020, 85, 23, 15154-15166, 2020.12. |
| 17. | Shindo, Mitsuru; Makigawa, Saki; Kodama, Kozue; Sugiyama, Hiromi; Matsumoto, Kenji; Iwata, Takayuki; Wasano, Naoya; Kano, Arihiro; Morita, Miyo Terao; Fujii, Yoshiharu, Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity, PHYTOCHEMISTRY, 10.1016/j.phytochem.2020.112508, 179, 112508, 2020.11. |
| 18. | Jun Sun, Takayuki Iwata, Mitsuru Shindo, Synthesis of 9-hydroxytriptycenes bearing a functionalized substituent at the C-10 position through a triple cycloaddition reaction of ynolates derived from 2,6-di-tert-butylphenyl esters., Chemistry Letters, https://doi.org/10.1246/cl.200412, 49, in press, 2020.07. |
| 19. | Iwata, Takayuki; Hyodo, Mizuki; Fukami, Takuto; Shiota, Yoshihito; Yoshizawa, Kazunari; Shindo, Mitsuru, Anthranoxides as Highly Reactive Arynophiles for the Synthesis of Triptycenes, CHEMISTRY-A EUROPEAN JOURNAL, 10.1002/chem.202002065, 26, 39, 8506-8510, 2020.07, We report herein an efficient method to synthesize triptycenes by the reaction of benzynes and anthranoxides, which are electron-rich and readily prepared from the corresponding anthrones. Using this method, 1,9-syn-substituted triptycenes were regioselectively obtained employing 3-methoxybenzynes. This method was also applied to synthesize pentiptycenes. A DFT study revealed that the cycloaddition of lithium anthranoxide and benzyne proceeds stepwise.. |
| 20. | Mitsuru Shindo, Saki Makigawa, Kenji Matsumoto, Takayuki Iwata, Naoya Wasano, Arihiro Kano, Miyo Terao Morita, Yoshiharu Fujii, Essential structural features of (2Z,4E)-5-phenylpenta-2,4-dienoic acid for inhibition of root gravitropism, Phytochemistry, 10.1016/j.phytochem.2020.112287, 172, 2020.04, Previously, we found (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) to be a selective inhibitor of root gravitropic bending of lettuce radicles at 5 μM, with no concomitant growth inhibition. Here, we describe a structure-activity relationship study of ku-76 to determine the essential structural features for the inhibitory activity. A series of ku-76 analogues was synthesized and the key features of ku-76 that are necessary for inhibition of lettuce root gravitropic bending were determined. The (2E,4E)-, (2Z,4Z)- (2E,4Z)- analogues were inactive, and 4,5-saturated and 4,5-alkynyl analogues also did not show inhibitory activity, demonstrating the importance of the (2Z,4E) diene unit. The aromatic ring was also crucial and could not be replaced with an alkyl chain. Derivatives in which the carboxylic acid was replaced with amides, alcohols, or esters were much less potent. These results suggest that the (2Z,4E)-diene, the carboxylic acid moiety, and the aromatic ring are essential for potent inhibitory activity against gravitropic bending.. |
| 21. | Tatsuro Yoshinaga, Takayuki Iwata, Mitsuru Shindo, Mild environment-friendly oxidative debenzylation of N-benzylanilines using DMSO as an oxidant, Chemistry Letters, 10.1246/cl.190854, 49, 2, 191-194, 2020.01, Oxidative debenzylation of N-benzyl aromatic amines using DMSO as a non-toxic oxidant and catalyzed by TsOH gave Nphenylimines, which were spontaneously hydrolyzed to form anilines and benzaldehydes in good yields. This reaction employs mild, metal-free conditions. The conditions are also suitable for the debenzylation of benzylphenylethers.. |
| 22. | Masayo Hirao-Suzuki, Shuso Takeda, Takayuki Iwata, Satoshi Fujita, Taishi Tomiyama, Masufumi Takiguchi, Akihisa Toda, Mitsuru Shindo, (–)-Isostemonamine can enhance the anti-proliferative activity of trichostatin A against human breast cancer MDA-MB-231 cells, , BPB Reports, 3, 56-59, 2020.01. |
| 23. | Arihiro Kano, Takuma Iwasaki, Mitsuru Shindo, Bongkrekic acid facilitates glycolysis in cultured cells and induces cell death under low glucose conditions, Biochemistry and Biophysics Reports, 10.1016/j.bbrep.2019.100683, 20, 2019.12, Bongkrekic acid (BKA) inhibits adenine nucleotide translocator (ANT) and suppresses ADP/ATP exchange in the mitochondrial inner membrane. Previously, we demonstrated that BKA exhibited cytotoxic effects on 4T1 tumor cells, depending on the cell number in the culture, but not on NIH3T3 cells. However, the cause of this differential sensitivity was unelucidated. Here we demonstrate that BKA reduced the O2 consumption in both cell lines and increased the mitochondrial membrane potential, thereby facilitating glucose consumption. BKA reduced cellular ATP in 4T1 cells in a dose-dependent manner but not in NIH3T3 cells. The cellular ATP of 4T1 cells was decreased with a reduced glucose concentration in the media, but that of NIH3T3 cells remained constant. We also demonstrated that BKA-induced cell death in both cell lines in low glucose media; however, the susceptibility to the reduced glucose concentration was slightly higher in 4T1 cells, which may be attributed to the difference in the dependency on glycolysis as their energy source. These results indicate that 4T1 tumor cells rely heavily on glucose for energy production. Our data demonstrate that BKA disturbs ATP production in mitochondria and increases the susceptibility to a low glucose condition.. |
| 24. | Tatsuro Yoshinaga, Takumi Fujiwara, Takayuki Iwata, Mitsuru Shindo, Synthesis of Distorted 1,8,13-Trisilyl-9-hydroxytriptycenes by Triple Cycloaddition of Ynolates to 3-Silylbenzynes, Chemistry - A European Journal, 10.1002/chem.201903024, 25, 61, 13855-13859, 2019.11, 1,8,13-Trialkyl(aryl)silyl-9-hydroxytriptycenes (trisilyltriptycenes) were synthesized by the triple addition of ynolates and 3-silylbenzynes with high regioselectivity. Benzene rings in the resulting triptycenes were highly distorted where the dihedral angles between the substituents were as high as 35°. The distortion energy induced step-by-step halogenation reactions to yield halogenated triptycenes, including chiral triptycenes. The 1,8,13-trihalogenated triptycenes were then converted to 1,8,13-functionalized triptycenes.. |
| 25. | Jun Sun, Toshiya Yoshiiwa, Takayuki Iwata, Mitsuru Shindo, Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters, Organic Letters, 10.1021/acs.orglett.9b02069, 21, 17, 6585-6588, 2019.09, Herein, we report a double deprotonation method used for the preparation of ynolates starting from nonbrominated 2,6-di-tert-butylphenyl esters. The current method is superior to the previously described double lithium/halogen exchange approach because easily accessible starting materials are used. This method will be especially useful for preparation of ynolates bearing functional groups in organic synthesis.. |
| 26. | Masayo Hirao-Suzuki, Shuso Takeda, Takayuki Iwata, Satoshi Fujita, Taishi Tomiyama, Masufumi Takiguchi, Mitsuru Shindo, Anti-proliferative effects of (–) -isostemonamine on highly aggressive human breast cancer MDA-MB-231 cells, BPB Reports, 1, 2, 32-34, 2018.11. |
| 27. | Takayuki Iwata, Taishi Tomiyama, Satoshi Fujita, Mitsuru Shindo, First Asymmetric Total Synthesis Of (−)-Isostemonamine And Kinetic Analysis Of Its Isomerizations, Heterocycles, 10.3987/COM-18-S(T)71, 97, 2, 712-718, 2018.04. |
| 28. | Satoshi Fujita, Masaki Suyama, Kenji Matsumoto, Atsushi Yamamoto, Takenori Yamamoto, Yuka Hiroshima, Takayuki Iwata, Arihiro Kano, Yasuo Shinohara, Mitsuru Shindo, Synthesis and evaluation of simplified functionalized bongkrekic acid analogs, Tetrahedron, 10.1016/j.tet.2018.01.018, 74, 9, 962-969, 2018.03, Bongkrekic acid (BKA) is a strong inhibitor of adenine nucleotide translocase (ANT), inducing inhibition of adenosine triphosphate synthesis. We designed and synthesized simplified benzene-ring-containing BKA analogs. The key reaction is the one-pot double Sonogashira reaction, which forms the main skeleton. The analogs were efficiently synthesized in 8–10 longest linear sequence steps. This synthetic method can be applied for the preparation of other analogs having different combinations of carbon chain lengths. Furthermore, the allyloxy group on the benzene ring can be easily replaced by other functional groups. Our preliminary biological evaluation based on mitochondrial inhibitory effects revealed the high potency of the analogs bearing the same carbon chain length as that of BKA. In particular, the prefunctionalized analogs are potential ANT inhibitors.. |
| 29. | Satoshi Fujita, Keisuke Nishikawa, Takayuki Iwata, Taishi Tomiyama, Hiroshi Ikenaga, Kenji Matsumoto, Mitsuru Shindo, Asymmetric Total Synthesis of (−)-Stemonamine and Its Stereochemical Stability, Chemistry - A European Journal, 10.1002/chem.201706057, 24, 7, 1539-1543, 2018.02, The first asymmetric total synthesis of (−)-stemonamine is described. The key reactions included intramolecular acylation to construct the seven-membered ring and a tandem [2+2] cycloaddition-Dieckmann condensation reaction using an ynolate to form the fully substituted cyclopentenone moiety. Racemization and epimerization of the natural product were first experimentally demonstrated.. |
| 30. | Kenji Matsumoto, Naoyuki Mizushina, Masahiro Yoshida, Mitsuru Shindo, Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene-Claisen Rearrangement, Synlett, 10.1055/s-0036-1590970, 28, 17, 2340-2344, 2017.10, We herein developed a stereoselective synthetic method for the preparation of multisubstituted 1,3-dienes via an allene-Claisen rearrangement. The Claisen rearrangement of anti -allenyl alcohols provided (1 E,3 Z)-1,3-dienes, which are essential components of bongkrekic acid, in high stereoselectivities. To demonstrate the synthetic utility of the resulting 1,3-dienes, further functional transformations and Diels-Alder reactions are described.. |
| 31. | Hee Jin Jeong, Kenji Matsumoto, Shuya Itayama, Kozue Kodama, Ryoji Abe, Jinhua Dong, Mitsuru Shindo, Hiroshi Ueda, Construction of dye-stapled Quenchbodies by photochemical crosslinking to antibody nucleotide-binding sites, Chemical Communications, 10.1039/c7cc03043f, 53, 73, 10200-10203, 2017.10, We successfully converted an antibody single-chain variable fragment and a full-sized antibody to Quenchbodies, which are a type of powerful fluorescent immunosensor, through ultraviolet-based photochemical crosslinking of an indole-3-butyric acid-conjugated fluorescent dye to the nucleotide-binding sites near the antigen-binding sites.. |
| 32. | Arihiro Kano, Moses Kibunja Kamita, Takuma Iwasaki, Mitsuru Shindo, Bongkrekic acid induces selective cytotoxicity in tumor cells, revealed by CCK-8, Evergreen, 4, 2-3, 23-27, 2017.09, Bongkrekic acid (BKA) is shown to inhibit adenine nucleotide translocator in the mitochondrial inner membrane, which is bifunctional and facilitates ATP/ADP exchange and permeability transition pore opening in mitochondria. We demonstrate that BKA reduces the viability of tumor cells depending on the cell number in the culture. This reduction was first demonstrated by Cell Counting Kit-8 (CCK-8), which indicates cellular viabilities based on the reduction of a formazan dye by cellular NADH. Reduced viability was not seen in normal cells. The glycolysis inhibitor 2-deoxyglucose enhanced the effect of BKA. BKA is thought to work as a mitochondrial inhibitor; however, its action is different from mitochondrial uncouplers. We further demonstrate that BKA suppresses autophagy induction, directing cells to death in nutrient-depleted conditions. Together these data indicate that BKA is a new type of mitochondrial inhibitor that does not disrupt the mitochondrial membrane and that is thus used together with a glycolysis inhibitor as an anticancer agent.. |
| 33. | Moses Kamita, Mitsuru Shindo, Arihiro Kano, Macrophage colony-stimulating factor mediates its immunosuppressive activity through the emerging myeloid cells during tumor progression, Evergreen, 4, 2-3, 18-22, 2017.09, Mechanisms by which tumors evade immune surveillance remain to be addressed. In our previous study, we reported that murine mammary tumor (4T1) cells secrete immunosuppressive soluble factor(s), which was identified to be a 10-100 kDa protein. In the current study, we report that analysis of the proteins in the active fractions revealed the presence of macrophage colony-stimulating factor (M-CSF) as one of the suppressive factors secreted by 4T1 tumor cells. Although previously identified as a cytokine that regulates survival, proliferation, and differentiation of macrophages and monocytes, M-CSF has also been associated with tumor progression and metastasis. To date, the immunosuppressive activity of M-CSF is not well understood. To better understand the immunosuppressive activity of M-CSF, we studied the activity of recombinant murine M-CSF in splenocytes isolated from 4T1 tumor-bearing mice. Reduced levels of interferon-gamma (IFN-γ) by M-CSF were observed in a dose-dependent manner indicating suppressive activities of M-CSF on the T-cell activation. M-CSF reduces the secretion of IFN-γ without affecting its intracellular protein expression. The suppressive activity of M-CSF is dependent on the length of days after tumor inoculation as no activity was observed in splenocytes from one-week tumor-bearing mice. This phenomenon correlates with an increase in the number of myeloid cells in the spleen during tumor progression. The suppressive activity of M-CSF is thus thought to be mediated by the myeloid cells emerging during tumor growth.. |
| 34. | Kenji Matsumoto, Shohei Tachikawa, Noriko Hashimoto, Rina Nakano, Masahiro Yoshida, Mitsuru Shindo, Aerobic C-H Oxidation of Arenes Using a Recyclable, Heterogeneous Rhodium Catalyst, Journal of Organic Chemistry, 10.1021/acs.joc.7b00300, 82, 8, 4305-4316, 2017.04, A novel, practical protocol for the aerobic direct C-H acetoxylation of arenes, employing a recyclable heterogeneous rhodium catalyst, is reported herein. The trifluoroacetoxylation of 2-amido-substituted anthracenes proceeded at the 9-position with exclusive regioselectivity. The oxidation of variously substituted anthracenes and other polycyclic aromatics with molecular oxygen as a terminal oxidant proceeded under mild conditions, providing products in good to excellent yields.. |
| 35. | 新藤 充, Shigenobu Fujimoto, kenji matsumoto, Aerobic oxidative homocoupling reaction of anilides using heterogeneous metal catalysts, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2017.01.075, 58, 10, 973-976, 2017.03. |
| 36. | Hisashi Wauke, Kazumasa Matsuo, kenji matsumoto, 新藤 充, Synthesis of Dissymmetric Malonic Acid Monoamides from Symmetric Dithiomalonates,, ChemistrySelect , 1, 21, 6830-6833, 2017.01. |
| 37. | Satoshi Umezu, Gomes, Gabriel dos Passos, Tatsuro Yoshinaga, Mikei Sakae, kenji matsumoto, Takayuki IWATA, Igor Alabugin, 新藤 充, Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 10.1002/anie.201609111, 56, 5, 1298-1302, 2017.01, We developed the novel one-pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four-step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucleophiles (ynolate, enolate and anthracenolate) reacts with o-benzyne in the same predictable manner controlled by chelation and negative hyperconjugation. The resulting functionalized C3-symmetrical triptycenes hold promise in the design of functional materials.. |
| 38. | Hiroyuki Okazaki, Shuso Takeda, Hiroyuki Ishii, Yukimi Takemoto, Satoshi Fujita, Masaki Suyama, Kenji Matsumoto, Mitsuru Shindo, Hironori Aramaki, A Novel Bongkrekic Acid Analog-Mediated Modulation of the Size of Lipid Droplets Evidence for the Appearance of Smaller Adipocytes, Biological and Pharmaceutical Bulletin, 40, 8, 1192-1198, 2017.01, Thiazolidinediones (TZDs) are known as peroxisome proliferator-activated receptor γ (PPARγ) activators, and are used in the treatment of diabetes. Although the usefulness of TZDs has been demonstrated, some of their side effects are becoming an obstacle to their clinical applicability; edema is known to be evoked by the “structural characteristics” of TZD, but not by the PPAR? activation. Thus, novel therapeutic modalities (i.e., non-TZD-type PPAR? activators) having different structures to those of TZDs are desired. We previously identified bongkrekic acid (BKA) as a PPAR? activator using the human breast cancer MCF-7 cell line as a model system. In the present study, we newly synthesized BKA analogs and examined the usefulness of BKA and its analogs as PPAR? activators in differentiated adipocyte cells. Among the chemicals investigated, one of the BKA analogs (BKA-#2) strongly stimulated PPAR? and the differentiation of 3T3-L1 cells similar to pioglitazone, a positive control. Furthermore, BKA-#2 reduced the size of lipid droplets in the mature adipocyte cells. The possible modulation mechanism by BKA-#2 is discussed.. |
| 39. | 新藤 充, Shuso Takeda, 松本 健司, Hironori Aramaki, Bongkrekic acid as a Warburg effect modulator in long-term estradiol deprived MCF-7 breast cancer cells, Anticancer Res., 36, 5171-5128, 2016.10. |
| 40. | 福田洋, 西川 慶祐, 福永 幸裕, 児玉梢, kenji matsumoto, 奥田 勝博, Arihiro Kano, 新藤 充, Synthesis of Fluorescent Molecular Probes Based on cis-Cinnamic acid and Molecular Imaging of Lettuce Roots, Tetrahedron, 印刷中, 2016.09. |
| 41. | 藤本茂伸, kenji matsumoto, 新藤 充, Aerobic Oxidative Intramolecular Aromatic Coupling via Heterogeneous Metal Catalysts,, Advanced Synthesis & Catalysis, 印刷中, 2016.07. |
| 42. | 新藤 充, Shusho Takeda, Kuniyoshi Koyachi, kenji matsumoto, Arihiro Kano, Hironori Aramaki, Possible involvement of FosB in (–)-xanthatin-mediated anti-proliferative effects in human cancer MDA-MB-231 cells, Fundam. Toxicol. Sci., 3, 115-119, 2016.04. |
| 43. | 松本 健司, 吉田まさひろ, 新藤 充, Heterogeneous Rhodium−Catalyzed Aerobic Oxidative Dehydrogenative Cross−Coupling Affording Nonsymmetrical Biaryl Amines, Angew. Chem. Int. Ed., 55, 17, 5272-5276, 2016.02, The first heterogeneously catalyzed oxidative C–H/C–H cross-coupling of aryl amines is reported herein. 2-Naphthyl amine analogs were reacted with various electron-rich arenes using a heterogeneous Rh/C catalyst under aerobic conditions, affording nonsymmetrical biaryl amines in excellent yields with high selectivities. This reaction provides a mild, operationally simple, and efficient approaches for the synthesis of biaryls that important to pharmaceutical and materials chemistry.. |
| 44. | たけだしゅうそう, おかじましゅんすけ, みよしひろこ, 小谷内くによし, 松本 健司, 新藤 充, 荒牧弘範, (-)-Xanthatin-mediated marked up-regulation of RhoB, a sonsor for damaged DNA, , Fundamental Toxicological Sciences, 2, 6, 233-238, 2015.12. |
| 45. | Yamamoto, Atsushi, はすいけいすけ, まつろひろし, 奥田 勝博, 安部真人, 松本 健司, はらだかずき, よしむらゆうや, 山本武範, おおくらかずと, 新藤 充, 篠原康雄, Bongkrekic Acid Analogue, Lacking One of the Carboxylic Groups of its Parent Compound, Shows Moderate but pH-insensitive Inhibitory Effects on the Mitochondrial ADP/ATP Carrier, CHEMICAL BIOLOGY & DRUG DESIGN, 10.1111/cbdd.12594, 86, 5, 1304-1322, 2015.11. |
| 46. | Okazaki, Hiroyuki, Takeda, Shuso, Ikeda, Erika, 松本 健司, 新藤 充, 荒牧弘範, Bongkrekic acid as a selective activator of the peroxisome proliferator-activated receptor gamma (PPAR gamma) isoform, JOURNAL OF TOXICOLOGICAL SCIENCES, 40, 2, 223-233, 2015.04. |
| 47. | 岡崎博之, 竹田修三, 池田恵理子, 福西義文, 石井博之, 谷口彩, 徳安美紀, 姫野太一, 垣添和弘, 松本 健司, 新藤 充, Curtis J. Omiecinski, 荒牧弘範, Bongkrekic acid as a selective activator of the peroxisom proliferator-activated receptor gannma (PPARgannma) isoform, , J. Toxicol. Sci. , 40, 2, 223-233, 2015.03. |
| 48. | 松本 健司, 堂籠健斗, 太刀川祥平, 石井孝典, 新藤 充, Aerobic Oxidative Homocoupling of Aryl Amines Using Heterogeneous Rhodium Catalysts, , Org. Lett. 16, 4754-4757 (2014)., 16, 4754-4757, 2014.10. |
| 49. | 吉岩俊也, 梅津智, 渡慶次学, 馬場義信, 新藤 充, Synthesis and Reactions of Ynolates via a Stop-Flow Method with a Flow Microreactor, J. Flow Chemistry, 180-184, ４, 2014.10. |
| 50. | 奥田 勝博, 福田洋, 西川 慶祐, 新藤 充, cis-Cinnamic acid selective suppressors distinct from auxin inhibitors., Chem. Pharm. Bull., in press, 2014.06. |
| 51. | 和佐野直也, 菅野真美, 西川 慶祐, 奥田 勝博, 新藤 充, Yo Young Park, 平館俊太郎, 加茂綱吉, 藤井義晴, Transcriptomic evaluation of the enhanced plant growth-inhibitory activity caused by derivatization of cis-cinnamic acid., Journal of Pesticide Science, 39, 85-90, 2014.04. |
| 52. | 竹田修三, 八道健太郎, 松本 健司, 新藤 充, 荒牧弘範, Xanthocidin Derivatives As Topoisomerase II Enzymatic Inhibitors, Biol. Pharm. Bull. , 37, 331-334, 2014.02. |
| 53. | 三浦 大典, 藤村 由紀, 新藤 充, 割石 博之, MALDI Efficiency of Metabolites Quantitatively Associated with their Structural Properties: A QSPR Approach, Journal of The American Society for Mass Spectrometry, http://dx.doi.org/10.1007/s13361-013-0772-0, 25, 1-5, 2014.01. |
| 54. | 梅津智, 吉岩俊也, 渡慶次学, 新藤 充, Generation of Ynolates via Reductive Lithiation Using Flow Microreactors, Tetrahedron Lett., http://dx.doi.org/10.1016/j.tetlet.2014.01.147, 55, 1822-1825, 2014.01. |
| 55. | 西川 慶祐, 福田洋, 安倍真人, 中西一成, 谷口智也, 野村隆, 平館俊太郎, 藤井義晴, 奥田勝博, 新藤 充, Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors, PHYTOCHEMISTRY, 10.1016/j.phytochem.2013.08.013, 96, 132-147, 2013.12. |
| 56. | 和佐野直哉, 菅野真美, 西川 慶祐, 奥田 勝博, 新藤 充, 平館俊太郎, 加茂綱吉, 藤井義晴, Root-specific induction of early auxin-responsive genes in Arabidopsis thaliana by cis-cinnamic acid, Plant Biotechnology, 30, 465-471, 2013.11. |
| 57. | 梅津智, 新藤 充, alpha-Substituent Effect on Olefination of Ester Carbonyl Groups with Ynolates, Tetrahedron Lett , http://dx.doi.org/10.1016/j.tetlet.2013.10.027, 54, 6871-6873, 2013.11. |
| 58. | 新藤 充, 松本 健司, Synthesis of Xanthanolides Including New Acylations and Their Synthetic Applications, J. Syn. Org. Chem. Japan, 71, 1152-1162, 2013.11. |
| 59. | 西川 慶祐, 福田洋, 安倍真人, 中西一成, 田澤雄太, 平館俊太郎, 藤井義晴, 奥田 勝博, 新藤 充, Design and Synthesis of Conformationally Constrained Analogues of cis-Cinnamic Acid and Evaluation of Their Plant Growth Inhibitory Activity, Phytochemistry, http://dx.doi.org/10.1016/j.phytochem.2013.10.001, 96, 223-234, 2013.10. |
| 60. | 竹田修三, 新藤 充, Hironori Aramaki, (-)-Xanthatin induces the prolonged expression of c-Fos through an N-acetyl-L-cysteine (NAC)-sensitive mechanism in human breast cancer MDA-MB-231 cells, JOURNAL OF TOXICOLOGICAL SCIENCES, 38, 4, 547-557, 2013.08. |
| 61. | Takeda, Shuso, 松尾和真, Mitsuru Shindo, Aramaki, Hironori, (-)-Xanthatin up-regulation of the GADD45 gamma tumor suppressor gene in MDA-MB-231 breast cancer cells: Role of topoisomerase II alpha inhibition and reactive oxygen species, TOXICOLOGY, 10.1016/j.tox.2012.12.019, 305, 1-9, 2013.03. |
| 62. | Yamada, Yuma, 奥田 勝博, kenji matsumoto, Mitsuru Shindo, Harashima, Hideyoshi, Mitochondrial delivery of bongkrekic acid using a MITO-porter prevents the induction of apoptosis in human hela cells, JOURNAL OF PHARMACEUTICAL SCIENCES, 10.1002/jps.23442, 102, 3, 1008-1015, 2013.03. |
| 63. | 松本 健司, 小谷内邦吉, 新藤充, Asymmetric total syntheses of xanthatin and 11,13-dihydroxanthatin using a stereocontrolled conjugate allylation to gamma-butenolide, TETRAHEDRON, 10.1016/j.tet.2012.11.077, 69, 3, 1043-1049, 2013.01. |
| 64. | 安倍真人, 西川 慶祐, 福田洋, 中西一成, 平館俊太郎, 藤井義晴, 奥田 勝博, 新藤 充, Key structural features of cis-cinnamic acid as an allelochemical, PHYTOCHEMISTRY, 10.1016/j.phytochem.2012.08.001, 84, 56-67, 2012.12. |
| 65. | 奥田 勝博, Keisuke Hasui, 松本 健司, Mitsuru Shindo, Molecular Design, Synthesis, and Evaluation of Novel Potent Apoptosis Inhibitors Inspired from Bongkrekic Acid, CHEMICAL RESEARCH IN TOXICOLOGY, 10.1021/tx300315h, 25, 10, 2253-2260, 2012.10. |
| 66. | 松本 健司, 新藤充, Palladium-Catalyzed Fluoride-Free Cross Coupling of Intramolecularly Activated Alkenylsilanes and Alkenylgermanes: Synthesis of Tamoxifen as a Synthetic Application, , Adv. Synth. Catal., 354, 642-650 , 2012.01. |
| 67. | 松尾和真、西川慶介、新藤 充, Stereoselective synthesis of beta-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors, Tetrahedron Letters, in press, 2011.09. |
| 68. | 松尾和真、新藤 充, Efficient Synthesis of Dissymmetric Malonic Acid S,O-Esters via Mono-alcoholysis of Symmetric Dithiomalonates under Neutral Conditions, Organic Letters, 13, 4406-4409, 2011.09. |
| 69. | Takeda, Shuso; Matsuo, Kazumasa; Yaji, Kentaro; Okajima-Miyazaki, Shunsuke; Harada, Mari; Miyoshi, Hiroko; Okamoto, Yoshiko; Amamoto, Toshiaki; Shindo, Mitsuru; Omiecinski, Curtis; Aramaki, Hironori,, (-)-Xanthatin selectively induces GADD45γ and stimulates caspase-independent cell death in human breast cancer MDA-MB-231 cells, Chemical Research in Toxicology, 10.1021/tx200046s, 24, 855-865, 2011.06. |
| 70. | Kazumasa Matsuo, Mitsuru Shindo, Efficient Synthesis of Karrikinolide via Cu(II)-Catalyzed Lactonization, Tetrahedron, 10.1016/j.tet.2010.11.108, 67, 971-975, 2011.01. |
| 71. | Kentaro Yaji, Mitsuru Shindo, Total Synthesis of (±)-Xanthocidin using FeCl3-Mediated Nazarov Reaction, Tetrahedron, 66, 9808-9813, 2010.12. |
| 72. | Kazumasa Matsuo, Mitsuru Shindo, Cu(II)-Catalyzed Acylation by Thiol Esters Under Neutral Conditions: Tandem Acylation-Wittig Reaction Leading to a One-Pot Synthesis of Butenolides, Organic letters, 12, 5346-5349, 2010.11. |
| 73. | Kazumasa Matsuo, Keiko Ohtsuki, Takashi Yoshikawa, Kozo Shishido, Kaori Yokotani-Tomita, Mitsuru Shindo, Total Synthesis of Xanthanolides, Tetrahedron, 10.1016/j.tet.2010.08.061, 66, 8407-8419, 2010.09. |
| 74. | Kentaro Yaji, Mitsuru Shindo, Construction of a fully substituted cyclopentenone as the core skeleton of stemonamide via a Nazarov cyclization, Tetrahedron Letters, 10.1016/j.tetlet.2010.08.032, 51, 5469-5472, 2010.08. |
| 75. | 吉川孝, 新藤充, Stereoselective Synthesis of (E)-2-en-4-ynoic acids with Ynolates. Catalytic Conversion to Tetronic acids and 2-Pyrones, Organic letters, １１, ２３, 5378-5381, 2009.11. |
| 76. | T. Yosikawa, S. Mori, M. Shindo , The Effects of C-S and C-Se bonds on torquoselectivity: stereoselective olefination of alpha-thio- and alpha-selenoketones with ynolates, Tetrahedron, http://dx.doi.org/10.1016/j.tet.2009.08.060, 65, 8832-8838 , 2009.10. |
| 77. | K. Yaji, M. Shindo,, Chiral Acid-Catalyzed Asymmetric Nazarov Reaction. Nucleophilic Construction of a Quaternary Asymmetric Center at the a-Position of the Keto Function, Synlett, 2524-2528, 2009.08. |
| 78. | M. Kanematsu, M. Shindo, M. Yoshida, K. Shishido, Total Synthesis of Bongkrekic Acid via Sequential Suzuki–Miyaura Coupling Reactions, Synthesis, 2893-2904, 2009.08. |
| 79. | 佐藤幸子, 麻生祥文, 新藤充, Efficient synthesis of bongkrekic acid. Three component convergent strategy, Tetrahedron Lett., 50 , 4164-4166, 2009.06. |
| 80. | M. Shindo,Y. Yamamoto, K. Yamada, K. Tomioka, Asymmetric construction of binaphthyl by the chiral diether-mediated conjugate addition of naphthyllithium to naphthalenecarboxylic acid BHA ester, Chem. Pharm. Bull., 57, 752-754, 2009.05. |
| 81. | H. Sasaki, H. Yokoe, M. Shindo, M. Yoshida, K. Shishido, Synthesis of sundiversifolide and diversifolide via a diastereoselective [3 + 2] nitrile oxide cycloaddition reaction., Heterocycles , 77, 2, 773-777, 2009.02. |
| 82. | T. Yoshikawa, S. Mori, M. Shindo, The Effect of Alkynyl Groups on Torquoselectivity. Highly Stereoselective Olefination of Alkynyl Ketones with Ynolates, Journal of the American Chemical Society, 131, 2092–2093, 2009.01. |
| 83. | Kazumasa Matsuo, Hiromasa Yokoe, Kozo Shishido, Mitsuru Shindo, Synthesis of Diversifolide and Structure Revision, Tetrahedron Lett., 49, 4279-4281, 2008.05. |
| 84. | K. Ohtsuki, K. Matsuo, T. Yoshikawa, C. Moriya, K. Yokotani, K. Shishido, M. Shindo, Total Synthesis of (+) and (-)-Sundiversifolide and Determination of the Absolute Cnfiguration, Organic Letters, 10, 1247-1250, 2008.04. |
| 85. | M. Shindo, Y. Yoshimura, M. Hayashi, H. SOejima, T. Yoshikawa, K. Matsumoto, K. Shishido, Synthesis of Multisubstituted Furans, Pyrroles, and Thioophenes via Ynolates, Organic Letters, 9, 1963-1966, 2007.05. |
| 86. | Mitsuru Shindo, Kentaro Yaji, Taisuke Kita, Kozo Shishido, Acid-Catalyzed Nazarov Reaction Controlled by -Alkoxy Groups, Synlett, 1096, 2007.04. |
| 87. | Mitsuru Shindo, Kenji Matsumoto, Kozo Shishido,, Hyperconjugative Effect of C-Ge Bonds: Synthesis of Multisubstituted Alkenylgermanes via Torquoselective Olefination of Acylgermanes with Ynolates, Tetrahedron, 63, 4271-4277, 2007.04. |
| 88. | Hiromasa Yokoe, Hiroyuki Sasaki, Tomoyuki Yoshimura, Mitsuru Shindo, Masahiro Yoshida, Kozo Shishido,, Total Synthesis of (+)-Sundiversifolide, Organic Letters, 9, 969-971, 2007.03. |
| 89. | Mitsuru Shindo, Kenji Matsumoto, Kozo Shishido, Generation of Ynolate and Z-Selective Olefination of Acylsilanes: (Z)-2-Methyl-3-Trimethylsilyl-2-butenoic acid, Organic Synthesis, 84, 11-21, 2007.01. |
| 90. | Sachie Morimoto, Mitsuru Shindo, Masahiro Yoshida, Kozo Shishido, Syntheses of heliannuols G and H; structure revision of the natural products, Tetrahedron Lett., 47, 7353-7356, 2006.09. |
| 91. | Mitsuru Shindo,*† Taisuke Kita, Toshihiro Kumagai, Kenji Matsumoto, Kozo Shishido, Synthesis of Tetrasubstituted and Functionalized Enol Ethers by E-Selective Olefination of Esters with Ynolates, J. Am. Chem. Soc., 128, 1062-1063, 2006.01. |
| 92. | Tomoyuki Yoshimura, Fumika Yakushiji, Shingo Kondo, Xiaofeng Wu, Mitsuru Shindo, Kozo Shishido, Total Synthesis of (+)-Lasonolide A, Org. Lett., 2006.01. |
| 93. | Sachie Morimoto, Mitsuru Shindo, and Kozo Shishido, ENANTIOSELECTIVE SYNTHESES OF HELIANNUOLS G AND H, Heterocycles, 66, 69-73, 2005.12. |
| 94. | Mitsuru Shindo,* Akiko Harada, Kenji Matsumoto, Kozo Shishido, [2 + 2] AND [2 + 4] TYPE CYCLOADDITIONS OF ISOCYANATES WITH YNOLATES, Heterocycles, 66, 39-43, 66, 39-43, 2005.12. |
| 95. | Mitsuru Shindo,* Takashi Yoshikawa, Yasuaki Itou, Seiji Mori, Takeshi Nishii, Kozo Shishido, Heteroatom-Guided Torquoselective Olefination of alpha-Oxy and alpha-Amino Ketones via Ynolates, Chemistry-Europian Journal, 10.1002/chem.200500574, 12, 2, 524-536, 2005.10. |
| 96. | Mitsuru Shindo,* Keiko Ohtsuki, Kozo Shishido,, Asymmetric inverse electron-demand 1,3-dipolar cycloaddition of ynolates with a chiral nitrone derived from L-serine leading to beta-amino acid derivatives,, Tetrahedron: Asymmetry,, 10.1016/j.tetasy.2005.07.023, 16, 16, 2821-2831, 2005.07. |
| 97. | Mitsuru Shindo, Kenji Matsumoto and Kozo Shishido, A synthesis of multisubstituted vinylsilanes via ynolates: stereoselective formation of -silyl--lactones followed by decarboxylation, Chem. Commun., 2477, 2005.05. |
| 98. | Mari Fujita, Mitsuru Shindo, Kozo Shishido, Total synthesis of (+)-kuhistaferone, Tetrahedron Lett, 46, 1269-1271, 2005.01. |
| 99. | Y. Murakami, M. Shindo, K. Shishido, Enantiocontrolled Synthesis of a Chiral Building Block via Diastereoselective Ring-Closing Metathesis, Synlett, 664-666, 2005.01. |
| 100. | M. Shindo, K. Matsumoto, K. Shishido, Intramolecularly Activated Vinylsilanes: Fluoride-free Cross-Coupling of (Z)-β-(Trialkylsilyl)acrylic Acids, Synlett, 176-178, 2005.01. |
| 101. | T. Yoshimura, T. Bando, M. Shindo, K. Shishido,, Diastereoselective Synthesis of the 19-epi-C18-C25 Segment of (+)-Lasonolide A and an Unusual Inversion at C19,, Tetrahedron Letters,, 45, 9241-9244, 2004.10. |
| 102. | Mitsuru Shindo,* Tomoyuki Sugioka, Kozo Shishido,, Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides,, Tetrahedron Lett., 45, 9265-9268, 2004.10. |
| 103. | Mitsuru Shindo,* Tomoyuki Sugioka, Yuko Umaba, Kozo Shishido,*, Total Synthesis of (+)-Bongkrekic Acid,, Tetrahedron Lett.,, 45, 8863-8866, 2004.09. |
| 104. | S. Mori, M. Shindo,, Hyperconjugative Effects in the Stereoselective Ring Opening Reactions of Oxetenoxides, Org. Lett., 22, 3945-3948, 2004.06. |
| 105. | Y. Fukuda, M. Shindo, K. Shishido,, A formal total synthesis of (-)-limaspermine,, Heterocycles, 62, 787-792, 2004.02. |
| 106. | M. Shindo, Y. Sato, T. Yoshikawa, R. Koretsune, K. Shishido,, Stereoselective Olefination of Unfunctionalized Ketones via Ynolates, J. Org. Chem, 69, 3912-3916, 2004.01. |
| 107. | M. Shindo, K. Matsumoto, K. Shishido,, Electrophilic Cleavage of One Silicone-Carbon Bond of Pentacoordinate Tetraorganosilanes. Novel Synthesis of Silalactones,, Angew. Chem. Int. Ed., 43, 104-106, 2004.01. |
| 108. | M. Shindo, Y. Sato, R. Koretsune, T. Yoshikawa, K. Matsumoto, K. Itoh, K. Shishido,, Synthesis of -Dibromo Esters as Precursors of Ynolates, Chem. Pharm. Bull.,, 51, 477-478, 2003.02. |
| 109. | H. Kisyuku, M. Shindo, K. Shishido,, Enantioselective total synthesis of (-)-heliannuol A, Chem. Comm.,, 350-351, 2003.01. |
| 110. | Y. Fukuda, M. Shindo, K. Shishido, Total Synthesis of (-)-Aspidospermine via Diastereoselective Ring-Closing Olefin Metathesis, Org. Lett.,, 5, 749-751, 2003.01. |
| 111. | M. Shindo. K. Itoh, K. Ohtsuki, C. Tsuchiya, K. Shishido,, Diastereoselective 1,3-Dipolar Cycloaddition of Ynolates with Chiral Nitrones, Synthesis, 1441-1445, 2003.01. |
| 112. | T. Deba, F. Yakushiji, M. Shindo, K. Shishido,, Enantioselective Construction of the C1-C16 Segment of Lasonolide A, Synlett,, 1500-1502, 2003.01. |
| 113. | T. Kamei, M. Shindo, K. Shishido,, First Enantioselective Total Synthesis of (-)-Heliannuol C, Tetrahedron Lett.,, 44, 8505-8707, 2003.01. |
| 114. | T. Yoshimura, H. Kisyuku, T. Kamei, K. Takabatake, M. Shindo, K. Shishido,, Enantiocontrolled synthesis of (+)-curcuquinone and (-)-curcuhydroquinone, ARKIVOC,, 247-255, viii, 2003.01. |
| 115. | T. Kamei, M. Shindo, K. Shishido,, An Alternative Total Synthesis of (-)-Heliannuol E, Synlett, 2395-2397, 2003.01. |
| 116. | H. Kishuku, T. Yoshimura, T. Kakehashi, M. Shindo, K. Shishido,, Enantiocontrolled total synthesis of (+)-heliannuol D via palladium-mediated heterocyclization, Heterocycles, 61, 125-131, 2003.01. |
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