Development of DDS-carrier for BBB based onsialic acid

• Project/Area Number: 22658038
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Single-year Grants
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Gifu University
• Principal Investigator: KISO Makoto 岐阜大学, 応用生物科学部, 教授 (90092931)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥3,700,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥600,000); Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2011: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2010: ¥1,100,000 (Direct Cost: ¥1,100,000)
• Keywords: 生物活性物質 / シアル酸 / 血液脳幹門 / 薬剤送達システム

Research Abstract

The DDS in which the medicine are included in the liposome and delivered to the diseased region has already been partially used in practice. However, restriction of drug distribution in to the brain by the blood-brain barrier (BBS) is one of the serious issue for DDS. Based onthe molecular basis for breast cancer metastasis to the brain, the liposome modified with the sialoglycan uniquely found on breast cancer was prepared and applied for the DDS to brain.

Research Products

• [Journal Article] Role of Binding in Mycoplasma mobile and Mycoplasma pneumoniae Gliding Analyzed through Inhibition by Synthesized Sialylated Compounds (2013)
  • Author(s): Kasai, T., Nakane, D., Ishida, H., Ando, H., Kiso, M.and Miyata, M
  • Journal Title: J. Bacteriol Volume: 195 Pages: 429-435
  • Peer Reviewed
• [Journal Article] Binding in Mycoplasma mobile and Mycoplasma pneumoniae gliding analyzed through inhibition by synthesized sialylated compounds (2013)
  • Author(s): Kasai T, Nakane D, Ishida H, Ando H, Kiso M, Miyata M
  • Journal Title: Journal of Bacteriology Volume: 195 Issue: 3 Pages: 429-435
  • DOI: 10.1128/jb.01141-12
  • Peer Reviewed
• [Journal Article] First synthesis of a pentasaccharide moiety of ganglioside GAA-7 containing unusually modified sialic acids through the use of N-Troc-sialic acid derivative as a key unit (2012)
  • Author(s): Tamai, H., Ando, H., Ishida, H. and Kiso, M
  • Journal Title: Organic Lett Volume: 14 Pages: 6342-6345
  • Peer Reviewed
• [Journal Article] Design and synthesis of a novel ganglioside ligand for influenza A viruses (2012)
  • Author(s): Nohara, T., Imamura, A., Yamaguchi, M., Hidari, K.I.P.J., Suzuki, T., Komori, T., Ando, H., Ishida, H. and Kiso, M
  • Journal Title: Molecules Volume: 17 Pages: 9590-9620
  • Peer Reviewed
• [Journal Article] Efficiently synthesizing lacto-ganglio-series gangliosides by using a glucosyl ceramide cassette approach: the total synthesis of ganglioside X2 (2012)
  • Author(s): Nakashima, S., Ando, H., Saito, R., Tamai, H., Ishida, H. and Kiso, M
  • Journal Title: Chemistry-An Asian J Volume: 7 Pages: 1041-1051
  • Peer Reviewed
• [Journal Article] First synthesis of a pentasaccharide moiety of ganglioside GAA-7 containing unusually modified sialic acids through the use of N-Troc-sialic acid derivative as a key unit (2012)
  • Author(s): Tamai, H., Ando, H., Ishida, H. and Kiso, M.
  • Journal Title: Organic Lett. Volume: 14 Issue: 24 Pages: 6342-6345
  • DOI: 10.1021/ol303122w
  • Peer Reviewed
• [Journal Article] Efficiently synthesizing lacto-ganglio-series gangliosides by using a glucosyl ceramide cassette approach: the total synthesis of ganglioside X2 (2012)
  • Author(s): Nakashima, S., Ando, H., Saito, R., Tamai, H., Ishida, H. and Kiso, M.
  • Journal Title: Chemistry An Asian J. Volume: 7 Issue: 5 Pages: 1041-1051
  • DOI: 10.1002/asia.201100928
  • Peer Reviewed
• [Journal Article] Identification of rare 6-deoxy-D-altrose from an edible mushroom (Lactarius lividatus) (2012)
  • Author(s): Tako, M., Dobashi, Y., Tamaki, T., Konishi, T., Yamada, M., Ishida, H., Kiso, M.
  • Journal Title: Carbohydr.Res. Volume: 350 Pages: 25-30
  • DOI: 10.1016/j.carres.2011.12.016
  • Peer Reviewed
• [Journal Article] The first total synthesis of ganglioside GalNAc-GD1a, a target molecule for autoantibodies in Guillain-Barre syndrome (2011)
  • Author(s): Fujikawa, K., Nakashima, S., Konishi, M., Fuse, T., Komura, N., Ando, T., Ando, H., Yuki, N., Ishida, H. and Kiso, M.
  • Journal Title: Chem. Eur. J Volume: 17 Pages: 5641-5651
  • Peer Reviewed
• [Journal Article] A first total synthesis of a hybrid-type ganglioside associated with amyotrophic lateral sclerosis-like disorder (2011)
  • Author(s): Nakashima, S., Ando, H., Imamura, A., Yuki, N., Ishida, H. and Kiso, M
  • Journal Title: Chem. Eur. J Volume: 17 Pages: 588-597
  • Peer Reviewed
• [Journal Article] Synthesis of the Disialic Acid-Embedded Glycan Part of Ganglioside HPG-1 (2011)
  • Author(s): Shimizu, H., Iwayama, Y., Imamura, A., Ando, H., Ishida, H., Kiso, M.
  • Journal Title: Bioscience, Biotechnology, and Biochemistry Volume: 75 Issue: 10 Pages: 2079-2082
  • DOI: 10.1271/bbb.110619
  • NAID: 10029873464
  • ISSN: 0916-8451, 1347-6947
  • Peer Reviewed
• [Journal Article] Design and synthesis of a multivalent heterobifunctional CD22 ligand as apotential immunomodulator (2011)
  • Author(s): Abdu-Allah, H.H.M., Watanabe, K., Daikoku, S., Kanie, O., Tsubata, T., Ando, H., Ishida, H., Kiso, M.
  • Journal Title: Synthesis Volume: 18 Issue: 18 Pages: 2968-2974
  • DOI: 10.1055/s-0030-1260151
  • Peer Reviewed
• [Journal Article] High-affinity ligands of siglec receptors and their therapeutic potentials (2011)
  • Author(s): Sadagopan, M., Ando, H., Tsubata, T., Ishida, H., Kiso, M.
  • Journal Title: Current Medicinal Chemistry Volume: 18 Pages: 3537-3550
  • Peer Reviewed
• [Journal Article] Synthesis of the glycan moiety of ganglioside HPG-7 with an unusualtrimer of sialic acid as the inner sugar residue (2011)
  • Author(s): Iwayama, Y., Ando, H., Tanaka, H., Ishida, H., Kiso, M.
  • Journal Title: Chem.Comm. Volume: 47 Issue: 34 Pages: 9726-9728
  • DOI: 10.1039/c1cc13200h
  • Peer Reviewed
• [Journal Article] Evaluation of a set of C9 N-acyl Neu5Ac2en mimetics as viral sialidase selective inhibitors (2011)
  • Author(s): S. Magesh, N. Sriwilaijaroen, M. Setsuko, H. Ando, M. Taeko, Y. Suzuki, H. Ishida and M. Kiso
  • Journal Title: International J. Medicinal Chemistry Volume: Vol.2011 Pages: 7-7
  • DOI: 10.1155/2011/539245
  • Peer Reviewed
• [Journal Article] Synthesis of 6-deoxy-D-altrose used as an authentic sample to identify an unknown monosaccharide isolated from the fruiting body of an edible mushroom (2011)
  • Author(s): Yamada, M., Yoshida, F., Ando, H., Ishida, H., Kiso, M., Tako, M.
  • Journal Title: HETEROCYCLES Volume: 82 Pages: 1699-1704
  • Peer Reviewed
• [Journal Article] The first total synthesis of ganglioside Ga1NAc-GD1a, a target molecule for autoantibodies in Guillain-Barre syndrome (2011)
  • Author(s): Fujikawa, K., Nakashima, S., Konishi, M., Fuse, T., Komura, N., Ando, T., Ando, H., Yuki, N., Ishida, H., Kiso, M.
  • Journal Title: Chem.Eur.J. Volume: 17 Issue: 20 Pages: 5461-5651
  • DOI: 10.1002/chem.201003357
  • Peer Reviewed
• [Journal Article] The total synthesis of the neurogenic ganglioside LLG-3 isolated from the starfish Linckia laevigata (2011)
  • Author(s): Tamai, H., Ando, H., Tanaka, H., Hosoda-Yabe, R., Yabe, T., Ishida, H., Kiso, M.
  • Journal Title: Angew.Chem.Int.Ed.Engl. Volume: 50 Issue: 10 Pages: 2330-2333
  • DOI: 10.1002/anie.201006035
  • Peer Reviewed
• [Journal Article] CD22-Antagonists with nanomolar potency : The synergistic effect of hydrophobic groups at C-2 and C-9 of sialic acid scaffold (2011)
  • Author(s): Abdu-Allah, H.H.M., Watanabe, K., Completo, G.C., Sadagopan, M., Hayashizaki, K., Takaku, C., Tamanaka, T., Takematsu, H., Kozutsumi, Y., Paulson, J.C., Tsubata, T., Ando, H., Ishida, H., Kiso, M.
  • Journal Title: Bioorg.Med.Chem Volume: 19 Issue: 6 Pages: 1966-1971
  • DOI: 10.1016/j.bmc.2011.01.060
  • Peer Reviewed
• [Journal Article] A first total synthesis of a hybrid-type ganglioside associated with amyotrophic lateral sclerosis-like disorder (2011)
  • Author(s): Nakashima, S., Ando, H., Imamura, A., Yuki, N., Ishida, H., Kiso, M.
  • Journal Title: Chem.Eur.J. Volume: 17 Issue: 2 Pages: 588-597
  • DOI: 10.1002/chem.201002184
  • Peer Reviewed
• [Journal Article] A first total synthesis of a hybrid-type ganglioside associated with amyotrophic lateral sclerosis like disorder (2011)
  • Author(s): Nakashima, S., Ando, H., Imamura, A., Yuki, N., Ishida, H., Kiso, M.
  • Journal Title: Chem. Eur. J. Volume: 17 Pages: 588-597
  • Peer Reviewed
• [Journal Article] A cyclic glucosyl ceramide acceptor as a versatile building block for complex ganglioside synthesis (2010)
  • Author(s): Fujikawa, K., Nohara, T., Imamura, A., Ando, H., Ishida, H. and Kiso, M
  • Journal Title: Tetrahedron Lett Volume: 51 Pages: 1126-1130
  • Peer Reviewed
• [Journal Article] A cyclic glucosyl ceramide acceptor as a versatile building block for complex ganglioside synthesis (2010)
  • Author(s): Fujikawa, K., Nohara, T., Imamura, A., Ando, H., Ishida, H., Kiso, M.
  • Journal Title: Tetrahedron Lett. Volume: 51 Pages: 1126-1130
  • Peer Reviewed
• [Presentation] Siglec-2阻害剤としてのシスリガンドミミックの合成とその生物学的評価 (2013)
  • Author(s): 菅沼勇輝, 松原直子, 岩山祐己, 植木章晴, 今村彰宏, 安藤弘宗, 鍔田武志, 石田秀治, 木曽真
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 仙台市（宮城県）
• [Presentation] N-Trocシアル酸誘導体を鍵化合物とする修飾シアル酸含有ガングリオシドGAA-7の全合成 (2013)
  • Author(s): 玉井秀樹, 安藤弘宗, 石田秀治, 木曽真
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 仙台市（宮城県）
• [Presentation] 硫酸化スフィンゴ糖脂質SM1a、SB1aの合成研究 (2013)
  • Author(s): 廣瀬遥, 玉井秀樹, 安藤弘宗, 石田秀治, 木曽真
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 仙台市（宮城県）
• [Presentation] ジシアリルガラクトースユニットの実用的合成法の開発研究 (2013)
  • Author(s): 廣瀨裕哉, 安藤弘宗, 石田秀治, 木曽真
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 仙台市（宮城県）
• [Presentation] ヘキソピラノース供与体の反応性に4位水酸基保護基がもたらす効果の検証 (2013)
  • Author(s): 松本佳央梨, 中島慎也, 安藤弘宗, 石田秀治, 木曽真
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 仙台市（宮城県）
• [Presentation] 神経突起伸展活性をもつガングリオシドLLG-3の構造活性相関研究 (2013)
  • Author(s): 山岸愛実, 矢部（細田）律子, 玉井秀樹, 小西美紅, 今村彰宏, 矢部富雄, 安藤弘宗, 石田秀治, 木曽真
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 仙台市（宮城県）
• [Presentation] マンノース結合タンパク質の認識機構解明に向けたルイスAタンデムリピートの効率的合成研究 (2013)
  • Author(s): 山路智也, 植木章晴, 安藤弘宗, 石田秀治, 木曽真
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 仙台市（宮城県）
• [Presentation] Synthetic gangliosides and analogs: Versatile tools to elucidate the cell functions of sialoglycans (2012)
  • Author(s): Makoto Kiso
  • Organizer: Commemorative Symposium on the 20th Anniversary of the Mizutani Foundation for Glycoscience Glycoscience : diversity and integration～生命多様性の統合的理解に向けた糖質科学～
  • Place of Presentation: 東京コンファレンスセンター・品川(東京)
• [Presentation] Synthesis and Evaluation of Glyco-coated Liposomes as DDS Carriers (2012)
  • Author(s): Ueki, A., Mino, Y., Un, K., Yoshida, M., Kawakami, S., Ando, H., Ishida, H., Yamashita, F., Hashida, M. and Kiso, M.
  • Organizer: The 4th Asian Communication for Glycobiology and Glycotechnology (ACGG)
  • Place of Presentation: 済州島（韓国）
• [Presentation] Synthesis and biological evaluation of the mimics of cis ligand for CD22 (2012)
  • Author(s): Suganuma, Y., Matsubara, N., Iwayama, Y., Ueki, A., Imamura, A., Ando, H., Tsubata, T., Ishida, H. and Kiso, M.
  • Organizer: The 4th Asian Communication for Glycobiology and Glycotechnology (ACGG)
  • Place of Presentation: 済州島（韓国）
• [Presentation] DDSを目的とした糖修飾コレステロールの合成と機能評価 (2012)
  • Author(s): 植木章晴, 美濃由佳, 運敬太, 吉田允, 川上茂, 安藤弘宗, 石田秀治, 山下富義, 橋田充, 木曽真
  • Organizer: FCCAセミナー/FCCAグライコサイエンス若手 フォーラム2012
  • Place of Presentation: 鹿児島市民文化ホール（鹿児島県）
• [Presentation] 糖鎖 -タンパク質複合体の X線結晶構造解析用のセレン標識糖鎖プローブの開発 (2012)
  • Author(s): 鈴木達哉, 安藤弘宗, 牧尾尚能, 山田悠介, 加藤龍一, 若槻壮市, 石田秀治, 木曽真
  • Organizer: FCCAセミナー/FCCAグライコサイエンス若手 フォーラム2012
  • Place of Presentation: 鹿児島市民文化ホール（鹿児島県）
• [Presentation] ガングリオシドGAA-7 の合成 (2012)
  • Author(s): 玉井秀樹, 安藤弘宗, 石田秀治, 木曽真
  • Organizer: FCCAセミナー/FCCAグライコサイエンス若手 フォーラム2012
  • Place of Presentation: 鹿児島市民文化ホール（鹿児島県）
• [Presentation] トラフナマコ由来ガングリオシドHPG-7の全合成 (2012)
  • Author(s): 岩山祐己, 安藤弘宗, 石田秀治, 木曽真
  • Organizer: FCCAセミナー/FCCAグライコサイエンス若手 フォーラム2012
  • Place of Presentation: 鹿児島市民文化ホール（鹿児島県）
• [Presentation] 棘皮動物に由来する修飾シアル酸含有ガングリオシドの合成研究 (2012)
  • Author(s): 玉井秀樹, 水野孝星, 安藤弘宗, 石田秀治, 木曽真
  • Organizer: 第31回日本糖質学会年会
  • Place of Presentation: 鹿児島市民文化ホール（鹿児島県）
• [Presentation] DDSを指向した糖修飾コレス テロールの合成と糖修飾リポソームの機能評価 (2012)
  • Author(s): 植木章晴, 美濃由佳, 運敬太, 吉田允, 川上茂, 安藤弘宗, 石田秀治, 山下富義, 橋田充, 木曽真
  • Organizer: 第31回日本糖質学会年会
  • Place of Presentation: 鹿児島市民文化ホール（鹿児島県）
• [Presentation] 修飾シアル酸合成法の開発とガングリオシドGAA-7の合成 (2012)
  • Author(s): 玉井秀樹, 安藤弘宗, 石田秀治, 木曽真
  • Organizer: 第10回糖鎖科学名古屋拠点「若手の力」フォーラム
  • Place of Presentation: 静岡県立大学（静岡県）
• [Presentation] Synthesis and evaluation of 6-phospho-mannosylated liposomes for positive targeting in DDS (2012)
  • Author(s): Ueki, A., Un, K., Yoshida, M., Kawakami, S., Ando, H., Ishida, H., Yamashita, F., Hashida, M., Kiso, M.
  • Organizer: 4th iCeMS Retreat
  • Place of Presentation: 大阪
• [Presentation] The First Total Synthesis of Ganglioside HPG-7 (2012)
  • Author(s): Iwayama, Y., Ando, H., Ishida, H., Kiso, M.
  • Organizer: 26th International Carbohydrate Symposium (ICS2012)
  • Place of Presentation: マドリッド（スペイン）
• [Presentation] The Total Synthesis of Neurogenic Ganglioside GAA-7 from Starfish Asterias amurensis versicolor (2012)
  • Author(s): Tamai, H., Ando, H., Ishida, H., Kiso, M.
  • Organizer: 26th International Carbohydrate Symposium (ICS2012)
  • Place of Presentation: マドリッド（スペイン）
• [Presentation] Synthesis of Novel Glycosylated Cholesterols and Evaluation of Glyco-coated Liposomes for DDS (2012)
  • Author(s): Ueki, A., Mino, Y., Un, K., Yoshida, M., Kawakami, S., Ando, H., Ishida, H., Yamashita, F., Hashida, M., Kiso, M.
  • Organizer: 26th International Carbohydrate Symposium (ICS2012)
  • Place of Presentation: マドリッド（スペイン）
• [Presentation] Synthesis and evaluation of glyco-coated liposomes as drug carrier for positive targeting in DDS (2011)
  • Author(s): Ueki, A., Mino, Y., Un, K., Yoshida, M., Kawakami, S., Ando, H., Ishida, H., Yamashita, F., Hashida, M., Kiso, M.
  • Organizer: 11th iCeMS International Symposium "Chemical Control of Cells"
  • Place of Presentation: 京都
  • Year and Date: 2011-12-06
• [Presentation] DDSを指向した糖修飾リポソームの合成と機能評価 (2011)
  • Author(s): 植木章晴, 美濃由佳, 運敬太, 吉田允, 川上茂, 安藤弘宗, 石田秀治, 山下富義, 橋田充, 木曽真
  • Organizer: 第9回糖鎖科学名古屋拠点「若手の力」フォーラム
  • Place of Presentation: 岐阜
  • Year and Date: 2011-10-22
• [Presentation] PECAM のホモフィリックな相互作用にシアル酸が果たす役割 (2011)
  • Author(s): 今牧理恵, 北爪しのぶ, 小川加寿子, 石田秀治, 安藤弘宗, 木曽真, 谷口直之
  • Organizer: 第30回日本糖質学会
  • Place of Presentation: 長岡リリックホールとハイブ長岡(新潟)
• [Presentation] Synthesis and evaluation of glyco-coated liposomes as drug carrier for positive targeting in DDS (2011)
  • Author(s): Ueki, A., Mino, Y., Un, K., Yoshida, M., Kawakami, S., Ando, H., Ishida, H., Yamashita, F., Hashida, M., Kiso, M.
  • Organizer: 3rd iCeMS Retreat
  • Place of Presentation: 奈良
• [Presentation] Novel gangliosides synthesis toward applications in medicinal chemistry and cell biology (2010)
  • Author(s): Kiso, M., Ishida, H. and Ando, H.
  • Organizer: 13th International Conference on Biology and Chemistry of Sialic Acids - SialoGlyco 2010
  • Place of Presentation: Potsdam, Germany
• [Presentation] biological recognition at molecular and cellular levels, and applications in medicinal chemistry (2010)
  • Author(s): Kiso, M., Ishida, H. and Ando, H.: Synthetic sialosides
  • Organizer: Assiut Univ. 7th International Pharmaceutical Science Conference
  • Place of Presentation: Assiut, Egypt
• [Presentation] Novel gangliosides synthesis toward applications in medicinal chemistry and cell biology (2010)
  • Author(s): Kiso, M., Ishida, H., Ando, H.
  • Organizer: 13th International Conference on Biology and Chemistry of Sialic Acids-SialoGlyco 2010
  • Place of Presentation: ポツダム(ドイツ)
• [Book] Renewed synthetic approach to SAα2-3Galβ1-3GalNAc-R SAα2-3Galβ1-3GalNAc-RSAα26SAα2-3Galβ1-3GalNAc-OR , SAα2-3Galβ1-3GalNAc-ORSAα26ST6GALNAC5gangliosides exploiting versatile and powerful synthetic units, in Methods In Enzymology, Glycomics, F. Minoru, Editor. (2010)
  • Author(s): Ando, H., Ishida, H. and Kiso, M
  • Total Pages: 478
  • Publisher: Elsevier: Amsterdam, Boston, Heidelberg, London, New York, Oxford, Paris, San Diego, San Francisco, Singapore, Sydney, Tokyo
• [Book] コールドスプリングハーバー 糖鎖生物学 第2 版 (2010)
  • Author(s): 秋元義弘, 安形高志, 安藤弘宗, 池北雅彦, 石田秀治, 岡島徹也, 掛樋一晃, 神奈木玲児, 木曽真, 北島健, 木下タロウ, 木全弘治, 久野淳, 佐藤ちひろ, 鈴木康夫, 竹川薫, 館野浩章, 谷口直之, 永井尚子, 羽渕脩躬, 浜村和紀, 平林淳, 古川圭子, 古川鋼一, 堀戸重臣, 宮坂昌之, 矢部富雄、山内祥生
  • Publisher: 鈴木康夫、木全弘治監訳, 丸善
• [Book] コールドスプリングハーバー糖鎖生物学第2版 (2010)
  • Author(s): 秋元義弘, 安形高志, 安藤弘宗, 池北雅彦, 石田秀治, 岡島徹也, 掛樋一晃, 神奈木玲児, 木曽真, 北島健, 木下タロウ, 木全弘治, 久野淳, 佐藤ちひろ, 鈴木康夫, 竹川薫, 館野浩章, 谷口直之, 永井尚子, 羽渕脩躬, 浜村和紀, 平林淳, 古川圭子, 古川鋼一, 堀戸重臣, 宮坂昌之, 矢部富雄, 山内祥生
  • Total Pages: 651
  • Publisher: 丸善
• [Remarks]
  • URL: http://www1.gifu-u.ac.jp/~kassei1/
• [Remarks] 生理活性物質学
  • URL: http://www1.gifu-u.ac.jp/~kassei1/
• [Remarks]
  • URL: http://www1.gifu-u.ac.jp/~kassei/
• [Remarks]
  • URL: http://wwwl.gifu-u.ac.jp/~kassei/