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MOLECULAR DESIGN OF BIOACTIVE HYBRID COMPLEXES

Research Project

Project/Area Number 11694083
Research Category

Grant-in-Aid for Scientific Research (B).

Allocation TypeSingle-year Grants
Section一般
Research Field Inorganic chemistry
Research InstitutionNARA WOMEN'S UNIVERSITY

Principal Investigator

YANO Shigenobu  NARA WOMEN'S UNIV., PROF.Graduate Scholl of Human Culture, 大学院・人間文化研究科, 教授 (60011186)

Co-Investigator(Kenkyū-buntansha) KINOSHITA Isamu  OSAKA CITY UNIV., ASSOCIATED PROF.Fac.of Science, 理学部, 助教授 (80128735)
TANASE Tomoaki  NARA WOMEN'S, PROF.Fac.of Science, 理学部, 教授 (50207156)
KAKUCHI Toyoji  HOKKAIDO UNIV., ASSOCIATED PROF.Graduate School of Environmental Earth Science, 大学院・地球環境科学研究科, 助教授 (80113538)
三方 裕司  奈良女子大学, 理学部, 助手 (10252826)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥6,100,000 (Direct Cost: ¥6,100,000)
Fiscal Year 2000: ¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1999: ¥3,200,000 (Direct Cost: ¥3,200,000)
KeywordsENVIRONMENT / SUGAR-PENDANT / BIOACTIBITY / GLYCOSIDE COMPLEX / ANTI TUMOR ACTIVITY / ELECTRODE / PHOTOTOXITY / FULLERENE / PORPHYIRIN
Research Abstract

Human activity has serious and adverse effects on the Earth's ecosystems. To keep the beautiful natural environment, chemists should play an important role in much respect. From this viewpoint, we have hold a great interest in green chemistry (=we call green earth chemistry) over the past years and studied the following topics on the basis of coordination chemistry. A set of 1,3-propanediamine derivatives connected to carbohydrates has been prepared. D-Glucose, D-mannose, D-galactose, D-xylose, D-ribose, and D-maltose are utilized as sugar molecules in this work. The diamine moiety was connected to the Cl carbon of the glycopyranose ring via an O-glycoside bond. All the anomeric configurations and sugar puckering conformations, except in the D-maltose derivative, were determined by X-ray crystallography of the diazido or dibromo precursors. This method has been used to synthesize a library of sugar-pendant diamines including an OH-protected derivative, and an N,N'-diisopropyl-substituted derivative. Acidty constants of these sugar-pendant diamines have been examined, as have the stability constants of these ligands with the divalent metal ions in solution. The effective antitumor cisplatin type complexes of these sugar-pendant dimaines were developed. Sugar-dependent photocytotoxic property of tetra- and octa-glycoconjugated tetraphenylporphyrin and fullarene derivatives has been examined. Effective phototoxic property of newly prepared these glycoconjugated compounds was observed. Functional modification of surface of gold electrodes by utilizing Fe and Ru clusters relevant to non-heme diiron Active Centers has been carried out.

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (42 results)

All Other

All Publications (42 results)

  • [Publications] S.Yano: "General Synthesis of Useful Chelating Reagents having a Sugar Unit, 1, 3-Diamino-2-propyl β-D-Glucopyranoside and 1, 3-Diamino-2-propyl α-D-Manno pyranoside"Chem.Lett.. 255-256 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Yano: "First synthesis and characterization of zinc (II) complexes containing N-glycosides derived from ethylenediamine and D-glucosamine"J.Chem.Soc.DALTON Trans.. 1851-1855 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Takagi: "Feasible attachment of a dinuclear ruthenlum complex to gold electrode surfaces, -A screening method to find functional electrodes"Electrochemistry. 67. 1192-1193 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Kato: "Luminescence Properties and Crystal Structures of Dicyano (diimine) platinum (II) Complexes Controlled by Pt…Pt and π-π Interactions"Inorg.Chem.. 38. 1638-16〓 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Tanase: "Peroxo-Bridged Dinuclear Cobalt (III) Complex Containing N-Glycoside Ligands from Tris (2-aminoethyl) amine and D-Glucose or Maltose (α, D-Glucopyranosyl- (1->4)-D-Glucose)"Inorg.Chem.. 38. 3150-3159 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Mikata: "Formation of 8-Hydroxydeoxyguanosine under Anaerobic Conditions by Reductively Acivated Nitro-5-Deazaflavin Derivatives"Bioorg.Med.Chem.Lett.. 9. 2141-2144 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Tanase: "Tetranuclear Iron (III) Complexes with a Planar (μ-oxo)(μ-hydroxo) bis (μ-alkoxo) bis (μ-carboxylato) tetrairon Core Derived from Hydrolysis of Carboxylic Acid Amides by Diiron (III) Center"Inorg.Chim.Acta.. 297. 18-26 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Tanase: "Substrate-dependent Chemoselective Aldose-Aldose and Aldose-Ketose Isomerizations of Carbohydrates Promoted by Combinations of Calcium Ion and Monoamine"Carbohydr.Res.. 39. 692-704 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Tanase: "Novel MnIIMnIIIMnII Trinuclear Complexes with Carbohydrates Bridged Derived from Seven-Coordinate Mn (II) Complexes with N-Glycoside"Inorg.Chem.. 39. 692-704 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] B.Song: ""Acid-base and metal ion-binding properties of diaminopropyl D-glucopyranoside and diaminopropyl D-mannopyranoside compounds in aqueous solution,"J.Chem.Soc.Dalton Trans.. 1325-1333 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Mikata: "Effect of Linking Position of Side Chain in Bis (quinolylmethyl) ethylenediamine as a DNA Binding Agent"Chem.Pharm.Bull. 48. 477-479 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Mikata: "Highly Reactive and Stereospecific Reaction of Quinoline-type NADH Model Compounds with Methyl Benzoylformate"Tetrahedron Lett.. 41. 1035-1038 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Ikeuchi: "Synthesis and Antitumor Activities of Novel 5-Deazaflavin-Sialic Acid Conjugate Molecules"Bioorg.Med.Chem.. 8. 2027-2035 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Mikata: "NAD Models with Axial Chirality at the Carbamoyal Moiety : Superiority of the Quinolinium Ring System"J.Org.Chem. 66(in press.). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Mikata: "Sugar-Pendant Diamines"J.Org.Chem.. 66(in press.). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 矢野重信: "X線構造解析"朝倉書店. 174 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Yano, Y,Shinohara, K,Mogami, M,Yokoyama, T.Tanase, T.Sakakibara, F.Nishida, K.Mochida, I.Kinoshita, M.Doe, I.Kanako, Y.Naruta, P.Mehrkhodavandi, P.Bugly, B.Song, C.Orvig and Y.Mikata: "General Synthesis of Useful Chelating Reagents having a Sugar Unit, 1, 3-Diamino-2-propyl β-D-Glucopyranoside and 1, 3-Diamino-2-propyl α-D-Manno pyranoside"Chem.Lett.. 255-256 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Kato, C.Kosuge, K.Morii, J.S.Ahn, H.Kitagawa, T.Mitani, M.Matsushita, T.Kato, S.Yano and M.Kimura: "Luminescence Properties and Crystal Structures of Dicyano (diimine) platinum (II) Complexes Controlled by Pt Pt and π-π Interactions"Inorg.Chem.. 38. 1638-1641 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Tanase, T.Onaka, M.Nakagoshi, I.Kinoshita, K.Shibata, M.Doe, J.Fujii and S.Yano: "Peroxo-Bridged Dinuclear Cobalt (III) Complex Containing N-Glycoside Ligands from Tris (2-aminoethyl) amine and D-Glucose or Maltose (α, D-Glucopyranosyl-(1->4)-D-Glucose)"Inorg.Chem.. 38. 3150-3159 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Yano, S.Inoue, Y.Yasuda, T.Tanase, Y.Mikata, T.Kakuchi, T.Tsubomura, M.Yamasaki, I.Kinoshita and M.Doe: "First synthesis and characterization of zinc (II) complexes containing N-glycosides derived from ethylenediamine and D-glucosamine"J.Chem.Soc.DALTON Trans.. 1851-1855 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Mikata, M.Kishigami, M.Nishida, S.Yano, T.Kawamoto, Y.Ikeuchi and F.Yoneda: "Formation of 8-Hydroxydeoxyguanosine under Anaerobic Conditions by Reductively Acivated Nitro-5-Deazaflavin Derivatives"Bioorg.Med.Chem.Lett.. 9. (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Takagi, A.Ichimura, T.Yano, I.Kinoshita, K.Isobe, M.Abe, Y.Sasaki, Y.Mikata, T.Tanase, N.Takeshita, C.Inoue, Y.Kimura, S.Endo, K.Tamura and S.Yano: "Feasible attachment of a dinuclear ruthenium complex to gold electrode surfaces. -A screening method to find functional electrodes"Electrochemistry. 67. 1192-1193 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Tanase, C.Inoue, E.Ota, and S.Yano: "Tetranuclear Iron (III) Complexes with a Planar (μ-oxo)(μ-hydroxo) bis (μ-alkoxo) bis (μ-carboxylato) tetrairon Core Derived from Hydrolysis of Carboxylic Acid Amides by Diiron (III) Cente"Inorg.Chim.Acta.. 297. 18-26 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Tanase, T.Takei, M.Hidai, and S.Yano: "Substrate-dependent Chemoselective Aldose-Aldose and Aldose-Ketose Isomerizations of Carbohydrates Promoted by Combinations of Calcium Ion and Monoamine"Carbohydr.Res.. 39. 692-704 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Tanase, S.Tamakoshi, M.Doi, M.Mikuriya, H.Sakurai, and S.Yano: "Novel MnIIMnIIIMnII Trinuclear Complexes with Carbohydrates Bridged Derived from Seven-Coordinate Mn (II) Complexes with N-Glycoside"Inorg.Chem.. 39. 692-704 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Mikata, Y.Onchi, M.Kishigami, and S.Yano: "Effect of Linking Position of Side Chain in Bis (quinolylmethyl) ethylenediamine as a DNA Binding Agent"Chem.Pharm.Bull.. 48(4). 477-479 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Bin Song, Parisa Mehrkhodavandi, Peter Buglyo, Yuji Mikata, Yoshie Shinohara, Kazumi Yoneda, Shigenobu Yano and Chris Orvig: "Acid-base and metal ion-binding properties of diaminopropyl D-glucopyranoside and diaminopropyl D-mannopyranoside compounds in aqueous solution"J.Chem.Soc.Dalton Trans.. 1325-1333 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Mikata, K.Hayashi, K.Mizukami, S.Matsumoto, S.Yano, N.Yamazaki, and A.Ohno: "Highly Reactive and Stereospecific Reaction of Quinoline-type NADH Model Compounds with Methyl Benzoylformate"Tetrahedron Lett.. 41. 1035-1038 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Ikeuchi, M.Sumiya, T.Kawamoto, N.Akimoto, Y.Mikata, M.Kishigami, S.Yano, T.Sasaki, and F.Yoneda: "Synthesis and Antitumor Activities of Novel 5-Deazaflavin-Sialic Acid Conjugate Molecules"Bioorg.Med.Chem.. 8(8). 2027-2035 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Mikata, K.Mizukami, S.Yano, N.Yamasaki, and A.Ohno: "NAD Models with Axial Chirality at the Carbamoyal Moiety : Superiority of the Quinolinium Ring System"J.Org.Chem.. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Mikata, Y.Shinohara, K.Yoneda, Y.Nakamura, K.Esaki, M.Tanahashi, I.Brudzinska, M.Yokoyama, K.Mogami, T.Tanase, T.Kitayama, K.Takashiba, K.Nabeshima, R.Takagi, M.Takatani, T.Okamoto, I.Kinoshita, M.Doe, A.Hamazawa, M.Morita, F.Nishida, T.Sakakibara, C.Orvig, and S.Yano: "Sugar-Pendant Diamines"J.Org.Chem.. 66(in press). (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] B.Song: ""Acid-base and metal ion-binding properties of diaminopropyl D-glucopyranoside and diaminopropyl D-mannopyranoside compounds in aqueous solution."J.Chem.Soc.Dalton Trans.. 1325-1333 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Tanase: "Tetranuclear Iron (III) Complexes with a Planar (μ-oxo)(μ-hydroxo) bis (μ-alkoxo) bis (μ-carboxylato) tetrairon Core Derived from Hydrolysis of Carboxylic Acid Amides by Diiron (III) Center"Inory.Chim.Acta.. 397. 13-26 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Tanase: "Synthesis and Characterization of Gold (I) Complexes with a Triphosphine Ligand Having a Bent Trinuclear Core Interacted with a Halide Anion"Inorg.Chim.Acta.. 399. 91-99 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Inada: "reparations and Characterizations of Novel N, N'-Etylene-Bridged- (S) -Histydyl- (S) -Tyrosine Derivatives and Their Copper (II) Complexes as Models of Galactose Oxidase."Bull.Chem.Soc.Jpn. 73. 903-912 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Tanase: "Mn^<II> Mnl^<III> Mn^<II> Trinuclear Complexes with Carbohydrates Bridged Derived from Seven-Coordinate Mn (II) Complexes with N-Glycoside."Inorg.Chem.. 43. 477-479 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Y.Mikata: "Sgar-Pendant Diamines"J.Org.Chem.,. (in press). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] S.Yano: "General Synthesis of UsefUl Chelating Reagents having a Sugar Unit 1,3-Diamino-2-propyl β-D-Glucopyranoside and 1,3-Diamino-2-propyl α-D-Manno pyranoside"Chem.Lett. 255-256 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] S.Yano: "First synthesis and characterization of zinc(II) complexes containing N-glycosides derived from ethylenediamine and D-glucosamine"J.Chem.Soc.DALTON Trans.. 1851-1855 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Takagi: "Feasible attachment of a dinuclear ruthenium complex to gold electrode surfaces.-A screening method to find functional electrodes"Electrochemistry. 67. 1192-1193 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Tanase: "Peroxo-Bridged Dinuclear Cobalt(III) Complex Containing N-Glycoside Ligands from Tris (2-aminoethyl)amine and D-Glucose or Maltose (α,D-Glucopyranosyl-(1->4)-D-Glucose)"Inorg.Chem.. 38. 3150-3159 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] M.Kato: "Luminescence Properties and Crystal Structures of Dicyano(diimine)platinum(II) Complexes Controlled by Pt ・ ・ ・ Pt and ππ Interactions"Inorg.Chem.. 38. 1638-1641 (1999)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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