DESIGN AND SYNTHESIS OF NEW POLYESTER DENDRIMERS, AND APPLICATION TO DRUG DELIVERY SYSTEM
| Project/Area Number |
18510106
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Nanomaterials/Nanobioscience
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| Research Institution | Toho University |
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Principal Investigator |
IWAMURA Michiko Toho University, その他部局等, PROFESSOR EMERITUS (90057597)
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| Co-Investigator(Kenkyū-buntansha) |
ICHIMURA Kunifiiro TOHO UNIVERSITY, Faculty of Science, PROFESSOR (90232412)
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| Project Period (FY) |
2006 – 2007
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| Project Status |
Completed (Fiscal Year 2007)
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| Budget Amount *help |
¥4,020,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥420,000)
Fiscal Year 2007: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2006: ¥2,200,000 (Direct Cost: ¥2,200,000)
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| Keywords | Polvesterdendrimer / Dendrimer synthesis / ESI-MS of dendrimers / Particle sizes of dendrimers / NMR of dendrimers / Cell recognition ability / Cvtotoxic activit / デンドリマーの粒子形状 / デンドリマーのNMR / デンドリマーの細胞内取り込み / ポリエステルデンドリマー合成 / デンドリマーの細菌毒性 |
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| Research Abstract |
1. The scope and limitation of our new Michael addition reaction in a 5M aqueous KOH solution. We found that this simple Michel reaction was useful only for the reaction of 1,3-ketoesters or 1.3-diesters with acrvlates both carrying bulky or stable alkyl groups in a basic solution.
2. Synthesis of "malonate dendrimer". The building block was prepared from the Michael addition of benzyl malonate to t-butyl acrylate, followed by the addition of ethylene glycol to the forcal carboxyl. The "malonate dendrimers" were synthesized up to [G3-32tBu] by repetition of [deprotection by HCOOH, then condensation by EDCI/DMAP] reactions.
3. Characterizion of the "malonate dendrimer". The molecular weights of these dendrimers were confirmed by ESI-MS measurements. The assignments of Hi and C^<13> chemical shifts of NMR spectra were carried out using various kinds of measurements such as COSY, HMBC and HMQC, etc. The back-folded shape of G3 dendrimer in CDCl_3 with the peripheral tBu located in the void space deeply inside was suggested from the analysis of NOESY measurements. The'particle size measurements in MeOH for G0~G3 were carried out using the dynamic light scattering method. The particle sizes of these dendrimers are ca. 40% smaller than those calculated for the stretched conformation.
4. Application of these dendrimers to drug delivery system. A polyester dendron with 16 mannose molecules (for targeting and increase of solubility in water) at the periphries and anthracene at the focal point was successfully synthesized. The bioassay using mouse peritoneal cells confirmed the efficient uptake of this dendron.
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Report
(3 results)
Research Products
(12 results)
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[Presentation] Design, synthesis and niolecular shapes of new aliphatic polyester dendrimers starting from acetoacetate, malonate and acrylate2007
Author(s)
Iwamura, M., Sakurai, R., Ichimura, K., Oshima, Y
Organizer
5th International Dendrimer Symposium
Place of Presentation
Toulouse, France
Description
「研究成果報告書概要(欧文)」より
Related Report
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[Presentation] A new drug delivery system consisting of caged compounds and sugars attached at the peripheries of dendrimers2006
Author(s)
Iwamura, M., Kamimae, K., Gotoh, Y, Shiraishi, K., Watanabe, S., Sasaki, S
Organizer
XIXth International Symposium on Medicinal Chemistry
Place of Presentation
Istanbul, Turkey
Description
「研究成果報告書概要(欧文)」より
Related Report
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[Presentation] New strategies in Prodrug Design2006
Author(s)
Iwamura, M., Kamimae, K., Gotoh, Y, Shiraishi, K., Watanabe, S., Kobayashi, Y.,Sasaki, S
Organizer
The 5th Joint Seminar on Biomedical Sciences among TU, PSU, CMU and KUMS
Place of Presentation
Kunming, China
Description
「研究成果報告書概要(欧文)」より
Related Report
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[Presentation] Synthesis and photophysical properties of new red fluorescent chromic dyes, 9,9'-biacridone-3,3'-diones2006
Author(s)
Yamada, S., Konno, A., Kohsaka, N., Ose, A., Iwamura, M
Organizer
XXI IUPAC Symposium on Photochemistry
Place of Presentation
Kyoto, Japan
Description
「研究成果報告書概要(欧文)」より
Related Report
