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  1. AU="Iwao Ojima"
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  1. Article ; Online: Great Challenges in Organic Chemistry

    Iwao Ojima

    Frontiers in Chemistry, Vol

    2017  Volume 5

    Keywords grand challenges ; interface of organic chemistry ; new frontiers ; interdisciplinary ; multidisciplinary ; Chemistry ; QD1-999
    Language English
    Publishing date 2017-07-01T00:00:00Z
    Publisher Frontiers Media S.A.
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  2. Article ; Online: Fatty acid binding protein 5 regulates docetaxel sensitivity in taxane-resistant prostate cancer cells.

    Andrew Hillowe / Chris Gordon / Liqun Wang / Robert C Rizzo / Lloyd C Trotman / Iwao Ojima / Agnieszka Bialkowska / Martin Kaczocha

    PLoS ONE, Vol 18, Iss 10, p e

    2023  Volume 0292483

    Abstract: Prostate cancer is a leading cause of cancer-related deaths in men in the United States. Although treatable when detected early, prostate cancer commonly transitions to an aggressive castration-resistant metastatic state. While taxane chemotherapeutics ... ...

    Abstract Prostate cancer is a leading cause of cancer-related deaths in men in the United States. Although treatable when detected early, prostate cancer commonly transitions to an aggressive castration-resistant metastatic state. While taxane chemotherapeutics such as docetaxel are mainstay treatment options for prostate cancer, taxane resistance often develops. Fatty acid binding protein 5 (FABP5) is an intracellular lipid chaperone that is upregulated in advanced prostate cancer and is implicated as a key driver of its progression. The recent demonstration that FABP5 inhibitors produce synergistic inhibition of tumor growth when combined with taxane chemotherapeutics highlights the possibility that FABP5 may regulate other features of taxane function, including resistance. Employing taxane-resistant DU145-TXR cells and a combination of cytotoxicity, apoptosis, and cell cycle assays, our findings demonstrate that FABP5 knockdown sensitizes the cells to docetaxel. In contrast, docetaxel potency was unaffected by FABP5 knockdown in taxane-sensitive DU145 cells. Taxane-resistance in DU145-TXR cells stems from upregulation of the P-glycoprotein ATP binding cassette subfamily B member 1 (ABCB1). Expression analyses and functional assays confirmed that FABP5 knockdown in DU145-TXR cells markedly reduced ABCB1 expression and activity, respectively. Our study demonstrates a potential new function for FABP5 in regulating taxane sensitivity and the expression of a major P-glycoprotein efflux pump in prostate cancer cells.
    Keywords Medicine ; R ; Science ; Q
    Subject code 570
    Language English
    Publishing date 2023-01-01T00:00:00Z
    Publisher Public Library of Science (PLoS)
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  3. Article: Pd-catalyzed asymmetric allylic amination with BOP ligands and its applications to the synthesis of fused polycyclic alkaloids

    Zang, Yang / Iwao Ojima

    Tetrahedron letters. 2015 June 03, v. 56

    2015  

    Abstract: Pd-catalyzed asymmetric allylic amination reaction of piperonylamides and a 2-siloxymethylcyclohexenyl carbonate, using chiral biphenol-based diphosphinite (BOP) ligands gave the corresponding cyclohexenylpiperonylamides in excellent yield and ... ...

    Abstract Pd-catalyzed asymmetric allylic amination reaction of piperonylamides and a 2-siloxymethylcyclohexenyl carbonate, using chiral biphenol-based diphosphinite (BOP) ligands gave the corresponding cyclohexenylpiperonylamides in excellent yield and enantiopurity (93–95% ee). These amides were applied to the synthesis of fused polycyclic alkaloids in a short sequence of steps.
    Keywords alkaloids ; amides ; chemical reactions ; chemical structure ; ligands
    Language English
    Dates of publication 2015-0603
    Size p. 3288-3292.
    Publishing place Elsevier Ltd
    Document type Article
    ZDB-ID 204287-3
    ISSN 1873-3581 ; 0040-4039
    ISSN (online) 1873-3581
    ISSN 0040-4039
    DOI 10.1016/j.tetlet.2015.01.047
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  4. Article ; Online: Catalytic Asymmetric Synthesis, 2nd Edition

    Iwao Ojima

    Molecules, Vol 6, Iss 12, Pp 1013-

    2001  Volume 1014

    Abstract: ... n/ ... ...

    Abstract n/a
    Keywords n/a ; Organic chemistry ; QD241-441
    Language English
    Publishing date 2001-12-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
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  5. Article ; Online: Design, Synthesis, and Biological Evaluations of Asymmetric Bow-Tie PAMAM Dendrimer-Based Conjugates for Tumor-Targeted Drug Delivery

    Tao Wang / Yaozhong Zhang / Longfei Wei / Yuhan G. Teng / Tadashi Honda / Iwao Ojima

    ACS Omega, Vol 3, Iss 4, Pp 3717-

    2018  Volume 3736

    Keywords Chemistry ; QD1-999
    Language English
    Publishing date 2018-04-01T00:00:00Z
    Publisher American Chemical Society
    Document type Article ; Online
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  6. Article ; Online: Construction of Fused Tropone Systems Through Intramolecular Rh(I)-Catalyzed Carbonylative [2+2+2+1] Cycloadditon of Triynes

    Yu-Han G. Teng / Chih-Wei Chien / Wen-Hua Chiou / Tadashi Honda / Iwao Ojima

    Frontiers in Chemistry, Vol

    2018  Volume 6

    Abstract: Tropone” is a non-benzenoid aromatic skeleton that can be found in a variety of natural products. This cyclohepta-2,4,6-trien-1-one skeleton appears simple, but there have been no straightforward ways to construct this molecular architecture. It is ... ...

    Abstract “Tropone” is a non-benzenoid aromatic skeleton that can be found in a variety of natural products. This cyclohepta-2,4,6-trien-1-one skeleton appears simple, but there have been no straightforward ways to construct this molecular architecture. It is conceivable that this molecule can be constructed via a higher order cycloaddition of three acetylene units and CO, but such process was not known until we have discovered that the carbonylative [2+2+2+1] cycloaddition of triynes can take place in the presence of a Rh complex catalyst and CO. However, this highly challenging process is naturally accompanied by ordinary [2+2+2] cyclotrimization products, i.e., benzenes, as side products. A mechanistic study led to two competing processes wherein the critical CO insertion occurs either to a rhodacyclopentadiene intermediate (Path A) or a rhodacycloheptatriene intermediate (Path B). The DFT analysis of those two pathways disclosed that the Path A should be the one that yields the carbonylative [2+2+2+1] cycloaddition products, i.e., fused tricyclic tropones. A further substrate design, inspired by colchicine structure, led to the almost exclusive formation of a fused tetracyclic tropone from a triyne bearing 1,2-disubstituted benzene moiety in a single step and excellent yield.
    Keywords tropone ; [2+2+2+1] cycloaddition ; Rh complex catalyst ; higher order cycloaddition ; carbonylative cycloaddition ; triynes ; Chemistry ; QD1-999
    Subject code 540
    Language English
    Publishing date 2018-09-01T00:00:00Z
    Publisher Frontiers Media S.A.
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  7. Article: Synthesis of a Next-Generation Taxoid by Rapid Methylation Amenable for 11C-Labeling

    Seitz, Joshua D / Iwao Ojima / Jacob G. Vineberg / Tadashi Honda / Tao Wang

    Journal of organic chemistry. 2018 Mar. 02, v. 83, no. 5

    2018  

    Abstract: Next-generation taxoids, such as SB-T-1214, are highly potent cytotoxic agents that exhibit remarkable efficacy against drug-resistant tumors in vivo, including those that overexpress the P-glycoprotein (Pgp) efflux pump. As SB-T-1214 is not a substrate ... ...

    Abstract Next-generation taxoids, such as SB-T-1214, are highly potent cytotoxic agents that exhibit remarkable efficacy against drug-resistant tumors in vivo, including those that overexpress the P-glycoprotein (Pgp) efflux pump. As SB-T-1214 is not a substrate for Pgp-mediated efflux, it may exhibit a markedly different biodistribution and tumor-accumulation profile than paclitaxel or docetaxel, which are both Pgp substrates. To investigate the biodistribution and tumor-accumulation levels of SB-T-1214 using positron emission tomography (PET), a new synthetic route has been developed to allow the incorporation of 11C, a commonly employed positron-emitting radionucleide, via methyl iodide at the last step of chemical synthesis. This synthetic route features a highly stereoselective chiral ester enolate–imine cyclocondensation, regioselective hydrostannation of the resulting β-lactam, and the Stille coupling of the novel vinylstannyl taxoid intermediate with methyl iodide. Conditions have been established to allow the rapid methylation and HPLC purification of the target compound in a time frame amenable to 11C-labeling for applications to PET studies.
    Keywords beta-lactams ; chemical structure ; cytotoxicity ; drug resistance ; high performance liquid chromatography ; methyl iodide ; methylation ; neoplasms ; organic chemistry ; organoiodine compounds ; paclitaxel ; P-glycoproteins ; positron-emission tomography ; regioselectivity ; stereoselectivity ; Stille reaction ; synthesis
    Language English
    Dates of publication 2018-0302
    Size p. 2847-2857.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.7b03284
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  8. Article: Synthesis of Colchicinoids and Allocolchicinoids through Rh(I)-Catalyzed [2+2+2+1] and [2+2+2] Cycloadditions of o-Phenylenetriynes with and without CO

    Chien, Chih-Wei / Iwao Ojima / Tadashi Honda / Yu-Han Gary Teng

    Journal of organic chemistry. 2018 Aug. 21, v. 83, no. 19

    2018  

    Abstract: The nonbenzenoid aromatics, tropones and tropolones, are found in various natural products such as colchicine and hinokitol, which possess significant biological activities. The traditional methods to construct the tropone skeletons include oxidation of ... ...

    Abstract The nonbenzenoid aromatics, tropones and tropolones, are found in various natural products such as colchicine and hinokitol, which possess significant biological activities. The traditional methods to construct the tropone skeletons include oxidation of cycloheptatriene and [4+3] cycloadditions. In addition, the total synthesis of colchicine and its analogues requires laborious organic transformations in the formations of 6–7–7 fused-ring systems. Transition metal-catalyzed carbocyclization and cycloaddition reactions have proven to be among the most efficient methods for constructing complex polycyclic systems. On the basis of our recent discovery of the Rh-catalyzed carbonylative [2+2+2+1] cycloaddition of triynes to the formation of a fused tropone system, we report here the application of this methodology to the one-step formation of the 6–7–7–5 fused tetracyclic scaffold of colchicinoids based on the [2+2+2+1] cycloaddition of o-phenylenetriynes with CO. In addition, the one-step formation of allocolchicinoids bearing the 6–7–6–5 fused tetracyclic system through the Rh-catalyzed [2+2+2] cycloaddition of o-phenylenetriynes is also described.
    Keywords aromatic compounds ; bioactive properties ; chemical structure ; colchicine ; cycloaddition reactions ; organic chemistry ; oxidation
    Language English
    Dates of publication 2018-0821
    Size p. 11623-11644.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.8b01608
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  9. Article ; Online: The Role of TRIP6, ABCC3 and CPS1 Expression in Resistance of Ovarian Cancer to Taxanes

    Karolina Seborova / Alzbeta Kloudova-Spalenkova / Kamila Koucka / Petr Holy / Marie Ehrlichova / Changwei Wang / Iwao Ojima / Iveta Voleska / Petr Daniel / Kamila Balusikova / Michael Jelinek / Jan Kovar / Lukas Rob / Martin Hruda / Marcela Mrhalova / Pavel Soucek / Radka Vaclavikova

    International Journal of Molecular Sciences, Vol 23, Iss 73, p

    2022  Volume 73

    Abstract: The main problem precluding successful therapy with conventional taxanes is de novo or acquired resistance to taxanes. Therefore, novel experimental taxane derivatives (Stony Brook taxanes; SB-Ts) are synthesized and tested as potential drugs against ... ...

    Abstract The main problem precluding successful therapy with conventional taxanes is de novo or acquired resistance to taxanes. Therefore, novel experimental taxane derivatives (Stony Brook taxanes; SB-Ts) are synthesized and tested as potential drugs against resistant solid tumors. Recently, we reported alterations in ABCC3 , CPS1 , and TRIP6 gene expression in a breast cancer cell line resistant to paclitaxel. The present study aimed to investigate gene expression changes of these three candidate molecules in the highly resistant ovarian carcinoma cells in vitro and corresponding in vivo models treated with paclitaxel and new experimental Stony Brook taxanes of the third generation (SB-T-121605 and SB-T-121606). We also addressed their prognostic meaning in ovarian carcinoma patients treated with taxanes. We estimated and observed changes in mRNA and protein profiles of ABCC3, CPS1, and TRIP6 in resistant and sensitive ovarian cancer cells and after the treatment of resistant ovarian cancer models with paclitaxel and Stony Brook taxanes in vitro and in vivo. Combining Stony Brook taxanes with paclitaxel caused downregulation of CPS1 in the paclitaxel-resistant mouse xenograft tumor model in vivo. Moreover, CPS1 overexpression seems to play a role of a prognostic biomarker of epithelial ovarian carcinoma patients’ poor survival. ABCC3 was overexpressed in EOC tumors, but after the treatment with taxanes, its up-regulation disappeared. Based on our results, we can suggest ABCC3 and CPS1 for further investigations as potential therapeutic targets in human cancers.
    Keywords ovarian carcinoma ; multidrug resistance ; taxanes ; Stony Brook taxanes ; TRIP6 ; CPS1 ; Biology (General) ; QH301-705.5 ; Chemistry ; QD1-999
    Subject code 616
    Language English
    Publishing date 2022-12-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  10. Article ; Online: Structure and inhibition of Cryptococcus neoformans sterylglucosidase to develop antifungal agents

    Nivea Pereira de Sa / Adam Taouil / Jinwoo Kim / Timothy Clement / Reece M. Hoffmann / John E. Burke / Robert C. Rizzo / Iwao Ojima / Maurizio Del Poeta / Michael V. Airola

    Nature Communications, Vol 12, Iss 1, Pp 1-

    2021  Volume 12

    Abstract: Sterylglucosidase 1 (Sgl1) is a virulence factor in Cryptococcus neoformans that modulates fungal pathogenesis and host response. Here, the authors characterize Sgl1 structurally, identify Sgl1 inhibitors, and demonstrate Sgl1 inhibition has efficacy in ... ...

    Abstract Sterylglucosidase 1 (Sgl1) is a virulence factor in Cryptococcus neoformans that modulates fungal pathogenesis and host response. Here, the authors characterize Sgl1 structurally, identify Sgl1 inhibitors, and demonstrate Sgl1 inhibition has efficacy in mouse models of infection.
    Keywords Science ; Q
    Language English
    Publishing date 2021-10-01T00:00:00Z
    Publisher Nature Portfolio
    Document type Article ; Online
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