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Development of selective nuclear receptor modulators with a 2,25-modified seco-steroidal skeleton

Research Project

Project/Area Number 17590012
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionTeikyo University

Principal Investigator

KITTAKA Atsushi  Teikyo University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (00214833)

Co-Investigator(Kenkyū-buntansha) SAITO Nozomi  Hokkaido University, Graduate School of Pharmaceutical Sciences, Associate Professor, 大学院・薬学研究院, 助教授 (80349258)
TAKANO Masashi  Teikyo University, Faculty of Pharmaceutical Sciences, Research Associate, 薬学部, 助手 (50386611)
SUGIYAMA Toru  The University of Tokyo, Department of Life Sciences, Research Associate, 大学院・総合文化研究科, 助手 (40242036)
本澤 忍  帝京大学, 薬学部, 助手 (90311547)
荒井 緑  帝京大学, 薬学部, 助手 (40373261)
Project Period (FY) 2005 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2006: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2005: ¥2,100,000 (Direct Cost: ¥2,100,000)
Keywordsactive vitamin D_3 / vitamin D receptor / agonist / 19-norvitamin D_3 / modulator / osteoporosis / structure-activity relationship / bone formation / 核内受容体 / 転写共役因子 / ハイスループット評価
Research Abstract

1α,25-Dihydroxyvitamin D_3 (1α,25(OH)_2D_3) is known to inhibit the proliferation and invasiveness of prostate cancer cells. However, 1α,25(OH)_2D_3 can cause hypercalcemia and is not suitable as a therapeutic agent. 19-Norvitamin D derivatives are known to be less calcemic when administered systemically. In order to develop more potent anti-cancer agents with less calcemic side effect, we therefore utilized ^3H-thymidine incorporation as an index for cell proliferation and examined the antiproliferative activities of fifteen C-2-substituted 19-nor-1α,25(OH)_2D_3 analogs including 14-epi analogs in the immortalized PZ-HPV-7 normal prostate cell line. Among the fifteen analogs we observed that the substitution with the 2α- or 2β-hydroxypropyl group produced two analogs having antiproliferative potency that is approximately 500- to 1000-fold higher than the natural 1α,25(OH)_2D_3. The ^3H-thymidine incorporation data were supported by the cell counting data after cells were treated with … More 1α,25(OH)_2D_3, 19-nor-2α-(3-hydroxypropyl)-1α,25(OH)_2D_3 or 19-nor-2β-(3-hydroxypropyp-1α,25(OH)_2D_3 for 7days. 19-Nor-2α-(3-hydroxypropyl)-1α,25(OH)_2D_3 and 19-nor-2β-(3-hydroxypropy1)-1α,25(OH)_2D_3 were also shown to be about 10-fold more active than 1α,25(OH)_2D_3 in cell invasion studies using prostate cancer cells.
We also found that one of the 14-epi-19-nor-1α,25(OH)_2D_3 analogs with a 2-substituent showed bone formation effect on the OVX model rats, which was 18% increase in bone density after 0.1 μg/kg treatment a day in one week. This analog has no effect for hypercalcemia with that dose. We have more than eleven million patients of osteoporosis in Japan, today, therefore, it is very important to develop effective anti-osteoporosis drugs.
In conclusion, a substitution at the C-2 position of 19-nor-1α,25(OH)_2D_3 molecule with a 3-hydroxypropyl group greatly increased the antiproliferative and anti-invasion potencies. Thus, these two analogs could be developed to be effective therapeutic agents for treating early and late stages of prostate cancer. We also found the 14-epi-19-nor-1α,25(OH)_2D_3 analog which has strong bone formation activity without calcemic effect. Less

Report

(3 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • Research Products

    (90 results)

All 2007 2006 2005 Other

All Journal Article (80 results) Book (7 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] Synthesis and Biological Evaluation of Several Structural Analogs of 2-Arachidonoylglycerol, an Endogenous Cannabinoid Receptor Ligand2007

    • Author(s)
      Yoshitomo Suhara, et al.
    • Journal Title

      Bioorganic and Medicinal Chemistry 15・2

      Pages: 854-867

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Creative Synthesis of Novel Vitamin D Analogs for Health and Disease2007

    • Author(s)
      Atsushi Kittaka, et al.
    • Journal Title

      The Journal of Steroid Biochemistry and Molecular Biology (in press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Evaluation of C-2-substituted 19-nor-1α, 25-dihydroxyvitamin D_3 analogs as therapeutic agents for prostate cancer2007

    • Author(s)
      T.C.Chen et al.
    • Journal Title

      The Journal of Steroid Biochemistry and Molecular Biology (in press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and Biological Evaluation of Several Structural Analogs of 2-Arachidonoylglycerol, an Endogenous Cannabinoid Receptor Ligand2007

    • Author(s)
      Yoshitomo Suhara, Saori Oka, Atsushi Kittaka, Hiroaki Takayama, Keizo Waku, Takayuki Sugiura
    • Journal Title

      Bioorg. Med. Chem. 15(2)

      Pages: 854-867

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Creative Synthesis of Novel Vitamin D Analogs for Health and Disease2007

    • Author(s)
      Atsushi Kittaka, Nozomi Saito, Sinobu Honzawa, Kazuya Takenouchi, Seiichi Ishizuka, Tai C. Chen, Sara Peleg, Sigeaki Kato, Midori A. Arai
    • Journal Title

      J. Steroid Biochem. Mol. Biol. doi:10.1016/j.jsbmb.2006.12.002

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Evaluation of C-2-Substituted 19-Nor-1α, 25-dihydroxy- vitamin D_3 Analogs as Therapeutic Agents for Prostate Cancer2007

    • Author(s)
      Tai C.Chen, K.S.Persons, S.Zheng, J.Mathieu, M.F.Holick, Y.F.Lee, B.Bao, Midori A.Arai, Atsushi Kittaka
    • Journal Title

      J. Steroid Biochem. Mol. Biol. doi:10.1016/j.jsbmb.2006.12.009

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] High-Throughput System for Analyzing Ligand-Induced Cofactor Recruitment by Vitamin D Receptor2007

    • Author(s)
      Midori A.Arai, Ken-ichi Takeyama, Saya Ito, Shigeaki Kato, Tai C.Chen, Atsushi Kittaka
    • Journal Title

      Bioconjugate Chem

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and Biological Evaluation of Several Structural Analogs of 2-Arachidonoylglycerol, an Endogenous Cannabinoid Receptor Ligand2007

    • Author(s)
      Yoshitomo Suhara, et al.
    • Journal Title

      Bioorganic and Medicinal Chemistry 15.2

      Pages: 854-867

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Recent Results on A-Ring Modification of 1α, 25-Dihydroxyvitamin D_3 : Design and Synthesis of VDR-Agonists and Antagonists with High Biological Activity2006

    • Author(s)
      Nozomi Saito, et al.
    • Journal Title

      Current Topics in Medicinal Chemistry 6・12

      Pages: 1273-1288

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Novel 2-Alkyl-1α, 25-dihydroxy-19-norvitamin D_3 : Efficient Synthesis with Julia Olefination, Evaluation of Biological Activity, and Development of New Analyzing System for Co-activator Recruitment2006

    • Author(s)
      Midori A.Arai, et al.
    • Journal Title

      Anticancer Research 26・4

      Pages: 2621-2632

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Methyl-introduced A-ring Analogues of 1α, 25-Dihydroxyvitamin D_3 : Synthesis and Biological Evaluation2006

    • Author(s)
      Toshie Fujishima, et al.
    • Journal Title

      Anticancer Research 26・4

      Pages: 2633-2636

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Highly Potent Vitamin D Antagonists : Design, Synthesis and Biological Evaluation2006

    • Author(s)
      Nozomi Saito, et al.
    • Journal Title

      ChemBioChem 7・10

      Pages: 1478-1490

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Efficient Synthesis of Carbopeptoid Oligomers : Insight into Mimicry of β-Peptide2006

    • Author(s)
      Yoshitomo Suhara, et al.
    • Journal Title

      Tetrahedron 62・34

      Pages: 8207-8217

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Probing a Water Channel near the A-Ring of Receptor-Bound 1α, 25-Dihydroxyvitamin D3 with Selected 2α-Sunstituted Analogues2006

    • Author(s)
      Shinji Hourai, et al.
    • Journal Title

      Journal of Medicinal Chemistry 49・17

      Pages: 5199-5205

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Biological Activities of 2α-Substituted Analogues of 1α, 25-Dihydroxyvitamin D_3 in Transcriptional Regulation and Human Promyelocytic Leukemia (HL-60) Cell Proliferation and Differentiation2006

    • Author(s)
      Eiji Takahashi, et al.
    • Journal Title

      Biological and Pharmaceutical Bulletin 29・11

      Pages: 2246-2250

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Further Synthetic and Biological Studies on Vitamin D Hormone Antagonists Based on C24-Alkylation and C2α-Functionalization of 25-Dehydro-1α-hydroxyvitamin D_3-26, 23-lactones2006

    • Author(s)
      Nozomi Saito, et al.
    • Journal Title

      Journal of Medicinal Chemistry 49・24

      Pages: 7063-7075

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Sequence-specific Recognition of Double-Stranded DNA by Cooperative Strand Invasion2006

    • Author(s)
      Toru Sugiyama, et al.
    • Journal Title

      Nucleic Acids Symposium Series 50

      Pages: 157-158

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Recent Progress of Study on Vitamin D Analogs2006

    • Author(s)
      Atsushi Kittaka, et al.
    • Journal Title

      Clinical Calcium 16・7

      Pages: 1154-1165

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] 14-epi-25-hydroxy-19-norvitamin D_3誘導体の分子設計と合成2006

    • Author(s)
      荒井 緑 ら
    • Journal Title

      ビタミン 80・4

      Pages: 226-226

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] シトクロムP450による25(OH)-19-ノルおよび1α, 25(OH)_2-19-ノルビタミンD_3の代謝2006

    • Author(s)
      漆野菜穂子 ら
    • Journal Title

      ビタミン 80・4

      Pages: 224-224

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] フルオロメチル基を有する新規2α位置換活性型ビタミンD_3の合成とその生理作用2006

    • Author(s)
      藤井晋也 ら
    • Journal Title

      ビタミン 80・4

      Pages: 226-226

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] ビタミンD受容体アンタゴニストTEI-9647とTEI-9648の2位、及び24位同時化学修飾による活性強化2006

    • Author(s)
      齋藤 望 ら
    • Journal Title

      ビタミン 80・11

      Pages: 564-565

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] ビタミンD受容体(VDR)モジュレーターと新たな評価系の開発2006

    • Author(s)
      橘高敦史
    • Journal Title

      上原記念生命科学財団研究報告集 20

      Pages: 16-19

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and 2α-Modification of 24-Phenylvitamin D_3 Lactones : Effects on VDR Antagonistic Activity2006

    • Author(s)
      Nozomi Saito, Toshihiro Matsunaga, Hiroshi Saito, Miyuki Anzai, Kazuya Takenouchi, Daishiro Miura, Seiichi Ishizuka, Hiroaki Takayama, Atsushi Kittaka
    • Journal Title

      Heterocycles 67(1)

      Pages: 311-336

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Recent Results on A-Ring Modification of 1α, 25- Dihydroxyvitamin D_3 : Design and Synthesis of VDR-Agonists and Antagonists with High Biological Activity2006

    • Author(s)
      Nozomi Saito, Shinobu Honzawa, Atsushi Kittaka
    • Journal Title

      Current Topics in Medicinal Chemistry 6(12)

      Pages: 1273-1288

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Novel 2-Alkyl-1α, 25-dihydroxy-19-norvitamin D_3 : Efficient Synthesis with Julia Olefination, Evaluation of Biological Activity, and Development of New Analyzing System for Co-activator Recruitment2006

    • Author(s)
      Midori A.Arai, Atsushi Kittaka
    • Journal Title

      Anticancer Research 26 (4)

      Pages: 2621-2632

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Methyl-introduced A-ring Analogues of 1α,25- Dihydroxyvitamin D_3 : Synthesis and Biological Evaluation2006

    • Author(s)
      Toshie Fujishima, Ryuji Tsutsumi, Yoichi Negishi, Shinya Fujii, Hiroaki Takayama, Atsushi Kittaka, Masaaki Kurihara
    • Journal Title

      Anticancer Research 26 (4)

      Pages: 2633-2636

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Highly Potent Vitamin D Antagonists : Design, Synthesis and Biological Evaluation"2006

    • Author(s)
      Nozomi Saito, Atsushi Kittaka
    • Journal Title

      Chem Bio Chem 7(10)

      Pages: 1478-1490

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Efficient Synthesis of Carbopeptoid Oligomers : Insight into Mimicry of β-Peptide2006

    • Author(s)
      Yoshitomo Suhara, Masaaki Kurihara, Atsushi Kittaka, Yoshitaka Ichikawa
    • Journal Title

      Tetrahedron 62(34)

      Pages: 8207-8217

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Probing a Water Channel near the A-Ring of Receptor- Bound 1α, 25-Dihydroxyvitamin D_3 with Selected 2α- Substituted Analogues2006

    • Author(s)
      Shinji Hourai, Toshie Fujishima, Atsushi Kittaka, Yoshitomo Suhara, Hiroaki Takayama, Natacha Rochel, Dino Moras
    • Journal Title

      J. Med. Chem 49 (17)

      Pages: 5199-5205

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Biological Activities of 2α-Substituted Analogues of 1α, 25-Dihydroxyvitamin D_3 in Transcriptional Regulation and Human Promyelocytic Leukemia (HL-60) Cell Proliferation and Differentiation2006

    • Author(s)
      Eiji Takahashi, Kimie Nakagawa, Yoshitomo Suhara, Atsushi Kittaka, Ken-ichi Nihei, Katsuhiro Konno, Hiroaki Takayama, Keiichi Ozono, Toshio Okano
    • Journal Title

      Biol. Pharm. Bull. 29(11)

      Pages: 2246-2250

    • NAID

      110004840399

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Further Synthetic and Biological Studies on Vitamin D Hormone Antagonists Based on C24-Alkylation and C2α-Functionalization of 25-Dehydro-1α-hydroxyvitamin D_3-26, 23-lactones2006

    • Author(s)
      Nozomi Saito, Toshihiro Matsunaga, Hiroshi Saito, Miyuki Anzai, Kazuya Takenouchi, Daishiro Miura, Jun-ichi Namekawa, Seiichi Ishizuka, Atsushi Kittaka
    • Journal Title

      J. Med. Chem. 49 (24)

      Pages: 7063-7075

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Sequence-specific Recognition of Double-Stranded DNA by Cooperative Strand Invasion2006

    • Author(s)
      Toru Sugiyama, Yasutada Imamura, Wataru Hakamata, Masaaki Kurihara, Atsushi Kittaka
    • Journal Title

      Nucleic Acids Symp. Ser. (No. 50)

      Pages: 157-158

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Recent Progress of Study on Vitamin D Analogs2006

    • Author(s)
      Atsushi Kittaka, Nozomi Saito, Masashi Takano
    • Journal Title

      Clinical Calcium 16 (7)

      Pages: 1154-1165

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Recent Results on A-Ring Modification of 1α,25-Dihydroxyvitamin D_3 : Design and Synthesis of VDR-Agonists and Antagonists with High Biological Activity2006

    • Author(s)
      Nozomi Saito, et al.
    • Journal Title

      Current Topics in Medicinal Chemistry 6・12

      Pages: 1273-1288

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Novel 2-Alkyl-1α,25-dihydroxy-19-norvitamin D_3 : Efficient Synthesis with Julia Olefination, Evaluation of Biological Activity, and Development of New Analyzing System for Co-activator Recruitment2006

    • Author(s)
      Midori A., Arai, et al.
    • Journal Title

      Anticancer Research 26・4

      Pages: 2621-2632

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Methyl-introduced A-ring Analogues of 1α,25-Dihydroxyvitamin D_3 : Synthesis and Biological Evaluation2006

    • Author(s)
      Toshie Fujishima, et al.
    • Journal Title

      Anticancer Research 26・4

      Pages: 2633-2636

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Efficient Synthesis of Carbopeptoid Oligomers : Insight into Mimicry of β一Peptide2006

    • Author(s)
      Yoshitomo Suhara, et al.
    • Journal Title

      Tetrahedron 62・34

      Pages: 8207-8217

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Probing a Water Channel near the A-Ring of Receptor-Bound 1α,25-Dihydroxyvitamin D3 with Selected 2α-Sunstituted Analogues2006

    • Author(s)
      Shinji Hourai, et al.
    • Journal Title

      Journal of Medicinal Chemistry 49・17

      Pages: 5199-5205

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Biological Activities of 2α-Substituted Analogues of lα,25-Dihydroxyvitamin D_3 in Transcriptional Regulation and Human Promyelocytic Leukemia (HL-60) Cell Proliferation and Differentiation2006

    • Author(s)
      Eiji Takahashi, et al.
    • Journal Title

      Biological and Pharmaceutical Bulletin 29・11

      Pages: 2246-2250

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Further Synthetic and Biological Studies on Vitamin D Hormone Antagonists Based on C24-Alkylation and C2α-Functionalization of 25-Dehydro-lα-hydroxyvitamin D_3,23-lactones2006

    • Author(s)
      Nozomi Saito, et al.
    • Journal Title

      Journal of Medicinal Chemistry 49・24

      Pages: 7063-7075

    • Related Report
      2006 Annual Research Report
  • [Journal Article] シトクロムP450による25(OH)-19-ノルおよび1α,25(OH),-19-ノルビタミン3の代謝2006

    • Author(s)
      漆野 菜穂子 ら
    • Journal Title

      ビタミン 80・4

      Pages: 224-224

    • Related Report
      2006 Annual Research Report
  • [Journal Article] フルオロメチル基を有する新規2α位置換活性型ビタミンD_3の合成とその生理作用2006

    • Author(s)
      藤井晋也ら
    • Journal Title

      ビタミン 80・4

      Pages: 226-226

    • Related Report
      2006 Annual Research Report
  • [Journal Article] ビタミンD受容体アンタゴニストTEI-9647とTEI-9648の2位,及び24位同時化学修飾による活性強化2006

    • Author(s)
      齋藤 望 ら
    • Journal Title

      ビタミン 80・11

      Pages: 564-565

    • Related Report
      2006 Annual Research Report
  • [Journal Article] ビタミンD受容体(VDR)モジュレ-タ-と新たな評価系の開発2006

    • Author(s)
      橘高 敦史
    • Journal Title

      上原記念生命科学財団研究報告集 20

      Pages: 16-19

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Metabolism of 2α-Propoxy-1α, 25-dihydroxyvitamin D_3 and 2α-(3-Hydroxypropoxy)-1α, 25-dihydroxyvitamin D_3 by Human CYP27A1 and CYP24A12005

    • Author(s)
      Daisuke Abe, et al.
    • Journal Title

      Drug Metabolism and Disposition 33・6

      Pages: 778-784

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] The Antagonism between 2-Methyl-1, 25-dihydroxyvitamin D_3 and 2-Methyl-20-epi-1, 25-dihydroxyvitamin D, in Non-genomic Pathway-mediated Biological Responses Induced by 1α, 25-Dihydroxyvitamin D_3 Assessed by NB4 Cell Differentiation2005

    • Author(s)
      Daishiro Miura, et al.
    • Journal Title

      The Journal of Steroid Biochemistry and Holecular Biology 94・5

      Pages: 469-479

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of 24, 24-Ethanovitamin D_3 Lactones Using Ruthenium-Catalyzed Intermolecular Enyne Metathesis : Potent Vitamin D Receptor Antagonists2005

    • Author(s)
      Nozomi Saito, et al.
    • Journal Title

      Synthesis 15

      Pages: 2533-2543

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Design, Synthesis and Biological Evaluation of Novel 1α, 25-Dihydroxyvitamin D_3 Analogues Possessing Aromatic Ring on 2α-Position2005

    • Author(s)
      Shinobu Honzawa, et al.
    • Journal Title

      Tetrahedron 61・47

      Pages: 11253-11263

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Cooperative Strand Invasion of Double-Stranded DNA by Peptide Nucleic Acid2005

    • Author(s)
      Toru Sugiyama, et al.
    • Journal Title

      Nucleic Acids Symposium Series 49

      Pages: 167-168

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of 25-Hydoxy-19-norvitamin D_3 Analogs and Their Antiproliferative Activities on Prostate Cells2005

    • Author(s)
      Midori A.Arai, et al.
    • Journal Title

      Heterocycles 66・1

      Pages: 469-479

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] Synthesis and 2α-Modification of 24-Phenylvitamin D_3 Lactones : Effects on VDR Antagonistic Activity2005

    • Author(s)
      Nozomi Saito, et al.
    • Journal Title

      Heterocycles 67・1

      Pages: 311-336

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] Efficient Synthesis of 2-Alkylated 1α, 25-Dihydroxy-19-norvitamin D_3 with Julia Olefination and Its Biological Activity2005

    • Author(s)
      Atsushi Kittaka, et al.
    • Journal Title

      Anticancer Research 25

      Pages: 2288-2288

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Design and Synthesis of 19-Norvitamin D_3 Analogs as Prostate Cancer Chemoprevention Agents : Less Calcemic and Prohormone Like Activity2005

    • Author(s)
      Midori A.Arai, et al.
    • Journal Title

      Anticancer Research 25

      Pages: 2278-2278

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] Novel 2,2-Functionalized Analogues of 1α, 25-Dihydroxyvitamin D_3 : Synthesis, Biological Evaluation and Their Possible Binding Modes to Vitamin D Receptor2005

    • Author(s)
      Toshie Fujishima, et al.
    • Journal Title

      Anticancer Research 25

      Pages: 2285-2285

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Design, Synthesis and Biological Activity of Less Calcemic, Prohormone- and Hormone-like 19-Norvitamin D_3 Analogs for Prostate Cancer Treatment2005

    • Author(s)
      Atsushi Kittaka, et al.
    • Journal Title

      Journal of Bone and Mineral Research. Suppl. 1 20

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 1-アルキル置換活性型ビタミンD_3誘導体の合成と生物活性2005

    • Author(s)
      本澤 忍 ら
    • Journal Title

      ビタミン 79・4

      Pages: 258-258

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] 前立腺がんを標的としたプロホルモン型25(OH)-19-nor-vitamin D_3誘導体2005

    • Author(s)
      荒井 緑 ら
    • Journal Title

      ビタミン 79・4

      Pages: 258-258

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] ヒトCYP24A1によるビタミンDアナログの代謝2005

    • Author(s)
      榊 利之 ら
    • Journal Title

      ビタミン 79・4

      Pages: 259-259

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] Metabolism of 2α-Propoxy-lα, 25-dihydroxyvitamin D_3 and 2a-(3-Hydroxypropoxy)-1α, 25-dihydroxyvitamin D_3 by Human CYP27A1 and CYP24A12005

    • Author(s)
      Daisuke Abe, Toshiyuki Sakaki, Tatsuya Kusudo, Atsushi Kittaka, Nozomi Saito, Yoshitomo Suhara, Toshie Fujishima, Hiroaki Takayama, Hiromi Hamamoto, Masaki Kamakura, Miho Ohta, Kuniyo Inouye
    • Journal Title

      Drug Metabolism and Disposition 33 (6)

      Pages: 778-784

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] The Antagonizm between 2-Methyl-1, 25-dihydroxyvitamin D_3 and 2-Methyl-20-epi-1, 25-dihydroxyvitamin D_3 in Non-genomic Pathway-mediated Biological Responses Induced by lα, 25-Dihydroxyvitamin D_3 Assessed by NB4 Cell Differentiation2005

    • Author(s)
      Daishiro Miura, Anthony W.Norman, Mathew T.Mizwicky, Toshie Fujishima, Katsuhiro Konno, Atsushi Kittaka, Hiroaki Takayama, Seiichi Ishizuka
    • Journal Title

      J Steroid Biochem. Ma. Biol. 94 (5)

      Pages: 469-479

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of 24, 24-Ethanovitamin D_3 Lactones Using Ruthenium-Catalyzed Intermolecular Enyne Metathesis : Potent Vitamin D Receptor Antagonists2005

    • Author(s)
      Nozomi Saito, Manami Masuda, Hiroshi Saito, Kazuya Takenouchi, Ishizuka Seiichi, Jun-ichi Namekawa, Midori Takimoto-Kamimura, Atsushi Kittaka
    • Journal Title

      Synthesis (15)

      Pages: 2533-2543

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Design, Synthesis and Biological Evaluation of Novel lα, 25-Dihydroxyvitamin D_3 Analogues Possessing Aromatic Ring on 2α-Position2005

    • Author(s)
      Shinobu Honzawa, Koshiro Hirasaka, Yasuhiro Yamamoto, Salα Peleg, Toshie Fujishima, Masaaki Kurihara, Nozomi Saito, Seishi Kishimoto, Takayuki Sugiura, Keizo Waku, Hiroaki Takayama, Atsushi Kittaka
    • Journal Title

      Tetrahedron 61 (47)

      Pages: 11253-11263

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Cooperative Strand Invasion of Double-Stranded DNA by Peptide Nucleic Acid2005

    • Author(s)
      Toru Sugiyama, Yasutada Imamura, Wataru Hakamata, Masaaki Kurihara, Atsushi Kittaka
    • Journal Title

      Nucleic Acids Symp. Ser. (No. 49)

      Pages: 167-168

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of 25-Hydoxy-19-norvitamin D_3 Analogs and Their Antiproliferative Activities on Prostate Cells2005

    • Author(s)
      Midori A.Arai, Ryuji Tsutsumi, Hideki Hara, Tai C.Chen, Toshiyuki Sakaki, Naoko Urushino, Kuniyo Inouye, Atsushi Kittaka
    • Journal Title

      Heterocycles 66 (1)

      Pages: 469-479

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Efficient Synthesis of 2-Alkylated 1α, 25-Dihydroxy- 19-norvitamin D_3 with Julia Olefination and Its Biological Activity2005

    • Author(s)
      Atsushi Kittaka, Keiichiro Ono, Nozomi Saito, Akihiro Yoshida, Shinobu Honzawa, Toshie Fujishima, Hiroaki Takayama, Midori A. Arai, Tai C. Chen
    • Journal Title

      Anticancer Research 25

      Pages: 2288-2288

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Design and Synthesis of 19-Norvitamin D_3 Analogs as Prostate Cancer Chemoprevention Agents : Less Calcemic and Prohormone Like Activity2005

    • Author(s)
      Midori A.Arai, Ryuji Tsutsumi, Tai C.Chen, Michael F.Holick, Toshiyuki Sakaki, Naoko Urushino, Kuniyo Inoue, Atsushi Kittaka
    • Journal Title

      Anticancer Research 25

      Pages: 2278-2278

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Novel 2, 2-Functionalized Analogues of 1α, 25- Dihydroxyvitamin D_3 : Synthesis, Biological Evaluation and Their Possible Binding Modes to Vitamin D Receptor2005

    • Author(s)
      Toshie Fujishima, Ryuji Tsutsumi, Yoichi Negishi, Hiroaki Takayama, Atsushi Kittaka, Masaaki Kurihara
    • Journal Title

      Anticancer Research 25

      Pages: 2285-2285

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Metabolism of 2α-Propoxy-1α,25-dihydroxyvitamin D_3 and 2α-(3-Hydroxypropoxy)-1α,25-dihydroxyvitamin D_3 by Human CYP27A1 and CYP24A12005

    • Author(s)
      Daisuke Abe, et al.
    • Journal Title

      Drug Metabolism and Disposition 33・6

      Pages: 778-784

    • Related Report
      2005 Annual Research Report
  • [Journal Article] The Antagonizm between 2-Methyl-1,25-dihydroxyvitamin D_3 and 2-Methyl-20-epr1,25-dihydroxyvitamin D_3 in Non-genomic Pathway- mediated Biological Responses Induced by 1α,25-Dihydroxyvitamin D_3 Assessed by NB4 Cell Differentiation2005

    • Author(s)
      Daishiro Miura, et al.
    • Journal Title

      J.Steroid Biochem.Mol.Biol. 94・5

      Pages: 469-479

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of 24,24-Ethanovitamin D_3 Lactones Using RutheniumCatalyzed Intermolecular Enyne Metathesis : Potent Vitamin D Receptor Antagonists2005

    • Author(s)
      Nozomi Saito, et al.
    • Journal Title

      Synthesis 15

      Pages: 2533-2543

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Design, Synthesis and Biological Evaluation of Novel 1α,25-Dihydroxy-vitamin D_3 Analogues Possessing Aromatic Ring on 2α-Position2005

    • Author(s)
      Shinobu Honzawa, et al.
    • Journal Title

      Tetrahedron 61・47

      Pages: 11253-11263

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Cooperative Strand Invasion of Double-Stranded DNA by Peptide Nucleic Acid2005

    • Author(s)
      Toru Sugiyama, et al.
    • Journal Title

      Nucleic Acids Symp.Ser. 49

      Pages: 167-168

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Efficient Synthesis of 2-Alkylated 1α,25-Dihydroxy-19-norvitamin D_3 with Julia Olefination and Its Biological Activity2005

    • Author(s)
      Atsushi Kittaka, et al.
    • Journal Title

      Anticancer Research 25

      Pages: 2288-2288

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Novel 2,2-Functionalized Analogues of 1α,25-Dihydroxyvitamin D_3 : Synthesis, Biological Evaluation and Their Possible Binding Modes to Vitamin D Receptor2005

    • Author(s)
      Toshie Fujishima, et al.
    • Journal Title

      Anticancer Research 25

      Pages: 2285-2285

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Design, Synthesis and Biological Activity of Less Calcemic, Prohormone- and Hormone-like 19-Norvitamin D_3 Analogs for Prostate Cancer Treatment2005

    • Author(s)
      Atsushi Kittaka, et al.
    • Journal Title

      J.Bone Miner.Res.Suppl.1 20

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Design, Synthesis and Biological Activity of Less Calcemic, Prohormone-and Hormone-like 19-Norvitamin D_3 Analogs for Prostate Cancer Treatment

    • Author(s)
      Atsushi Kittaka, Midori A.Arai, Ryuji Tsutsumi, Toshiyuki Sakaki, Naoko Urushino, Kuniyo Inouye, Saya Ito, Ken-ichi Takeyama, Shigeaki Kato, Michael F.Holick, Tai C.Chen
    • Journal Title

      J Bone Miner. Res. Suppl 12005

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Creative Synthesis of Novel Vitamin D Analogs for Health and Disease

    • Author(s)
      Atsushi Kittaka, et al.
    • Journal Title

      The Journal of Steroid Biochemistry and Molecular Biology in press

    • Related Report
      2006 Annual Research Report
  • [Journal Article] 14-epi-25-hydroxy-19-norvitaminD_3誘導体の分子設計と合成

    • Author(s)
      荒井 緑 ら
    • Journal Title

      ビタミン 80・4

      Pages: 226-226

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Evaluation of C-2-substituted 19-nor-1α,25-dihydroxyvitamin D3 analogs as therapeutic agents for prostate cancer

    • Author(s)
      T.C.Chen, et al.
    • Journal Title

      The Journal of Steroid Biochemistry and Molecular Biology in press

    • Related Report
      2006 Annual Research Report
  • [Book] 知っておきたい有機反応1002006

    • Author(s)
      橘高 敦史
    • Publisher
      東京化学同人
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Book] スタンダード薬学シリーズ3 化学系薬学II. ターゲット分子の合成と生体分子・医薬品の化学 SBO 24, 27, 28, 50.2005

    • Author(s)
      橘高 敦史
    • Publisher
      東京化学同人
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Book] スタンダード薬学シリーズ3 化学系薬学II.ターゲット分子の合成と生体分子・医薬品の化学 SBO 24,27,28,50.2005

    • Author(s)
      橘高 敦史
    • Publisher
      東京化学同人
    • Related Report
      2005 Annual Research Report
  • [Book] スタンダード薬学シリーズ化学系薬学 演習編

    • Author(s)
      橘高 敦史
    • Publisher
      東京化学同人(印刷中)
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Book] 創薬科学

    • Author(s)
      橘高 敦史
    • Publisher
      化学同人(印刷中)
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Book] スタンダ-ド薬学シリ-ズ化学系薬学演習編

    • Author(s)
      橘高 敦史
    • Publisher
      東京化学同人(印刷中)
    • Related Report
      2006 Annual Research Report
  • [Book] 創薬科学

    • Author(s)
      橘高 敦史
    • Publisher
      化学同人(印刷中)
    • Related Report
      2006 Annual Research Report
  • [Patent(Industrial Property Rights)] ビタミンD_3ラクタム誘導体2006

    • Inventor(s)
      橘高敦史ら
    • Industrial Property Rights Holder
      帝人フアーマ株式会社
    • Industrial Property Number
      2006-076417
    • Filing Date
      2006-03-20
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 2-置換-14-エピ・プレビタミンD_3誘導体2006

    • Inventor(s)
      橘高敦史ら
    • Industrial Property Rights Holder
      帝人ファーマ株式会社
    • Industrial Property Number
      2006-266863
    • Filing Date
      2006-09-29
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 特許権2006

    • Inventor(s)
      橘高 敦史 ら
    • Industrial Property Rights Holder
      帝人ファーマ株式会社
    • Industrial Property Number
      2006-266863
    • Filing Date
      2006-09-29
    • Related Report
      2006 Annual Research Report

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Published: 2005-04-01   Modified: 2016-04-21  

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