生体材料

デンドロンおよび超分岐ポリマー

デンドロン

bis-MPA dendron

デンドロン(図1)はくさび形をした単分散デンドリマーのセグメントであり、複数の末端基と、中心部分(focal point)に反応性の高い官能基を1つ持ちます。デンドリマー特有の性質に加えて、性質の異なる中心の官能基と表面基を利用したオルトゴナル(orthogonal)反応を行うこともできます。例えば、デンドロンをある表面や他のデンドロン1、または他の高分子2にグラフトすることが可能です。シグマ アルドリッチの2,2-ビス(ヒドロキシメチル)プロパン酸(bis-MPA)デンドロン製品は、アルキンまたはカルボン酸の中心官能基を持つ3種類のgenerationでご提供しています。アルキン官能基は、アジド化合物との触媒的な付加環化反応「クリックケミストリー」図2)に適しています。カルボン酸は、EDCを媒介としたカップリングなどでアミンと選択的に反応します。表面にある多数の水酸基は、無水物やハロゲン化アシルとの反応によってさらに誘導体化することが可能です(図3)。

 

dendronの反応式

図2 デンドロンのクリックケミストリー

dendronの誘導体化

図3 デンドロンの誘導体化

超分岐ポリマー

超分岐ポリマー(図4)は、デンドリマーに似た性質を持つ多分散の樹枝状高分子ですが、1段階の重合反応で合成されます。これはデンドリマーに比べると分岐が不完全で、末端官能基の数は平均的(正確ではなく)ですが、完全なデンドリマー製品に比べてコスト効率に優れています。完全な構造が必要ない場合に超分岐ポリマーを用いることで、デンドリマーの利点をはるかに低コストで利用することができます。弊社のbis-超分岐ポリマー製品は純度が高く(97%以上)、溶解しやすい凍結乾燥粉末の状態でお届けします。

超分岐ポリマーの特徴と利点

いずれのポリエステルデンドロンと超分岐ポリマーも、水と極性有機溶媒(メタノール、THF、DMF、DMSO)に可溶です。bis-MPA樹枝状高分子は生体適合性と生分解性を持ち、有害な分解生成物を出さないことが確認されています。そのため、薬物輸送やその他の生体材料への応用に特に適しています4

  • 多数の末端水酸基(-OH)を持つため、無水物やハロゲン化アシルとの反応などによって、さらに化学的機能化を進めることができます。
  • 樹枝状/直線状のハイブリッド材料の汎用的な前駆体として応用できます3
  • 高度に枝分かれしているので、高溶解性かつ低粘性です(溶液および溶融状態において)。
  • 開環重合と熱硬化において、多官能性開始剤および架橋剤として有用です。
  • 紫外-可視光領域の波長に対して透明性を持ちます。
製品番号 製品名 End Group Functionality Generation  Number of Surface Groups
686603 Hyperbranched bis-MPA polyester-16-hydroxyl, generation 2 Hydroxyl 2 16
686581 Hyperbranched bis-MPA polyester-32-hydroxyl, generation 3 3 32
686573 Hyperbranched bis-MPA polyester-64-hydroxyl, generation 4 4 64

dendronの誘導体化

図4 Generation 3の超分岐 bis-MPA polyester(製品番号:686581

デンドリマー・デンドロン・多官能性PEG製品リスト

製品番号 製品名 Core End Group Functionality Generation Number of Surface Groups
806145 Bis-MPA-Acetylene dendrimer, trimethylol propane core, generation 1 Trimethylol Propane Acetylene 1 6
806153 Bis-MPA-Acetylene dendrimer, trimethylol propane core, generation 3 3 24
806161 Bis-MPA-Acetylene dendrimer, trimethylol propane core, generation 5 5 96
806137 Bis-MPA-Azide dendrimer, trimethylol propane core, generation 1 Azide 1 6
806129 Bis-MPA-Azide dendrimer, trimethylol propane core, generation 3 3 24
806110 Bis-MPA-Azide dendrimer, trimethylol propane core, generation 5 5 96
806099 Bis-MPA-COOH dendrimer, trimethylol propane core, generation 1 Carboxyl 1 6
806064 Bis-MPA-COOH dendrimer, trimethylol propane core, generation 2 2 12
806080 Bis-MPA-COOH dendrimer, trimethylol propane core, generation 3 3 24
806072 Bis-MPA-COOH dendrimer, trimethylol propane core, generation 4 4 48
901333 Bis-MPA-NHBoc dendrimer, trimethylol propane core, generation 1 NH-Boc 1 6
901330 Bis-MPA-NHBoc dendrimer, trimethylol propane core, generation 2 2 12
901329 Bis-MPA-NHBoc dendrimer, trimethylol propane core, generation 3 3 24
901322 Bis-MPA-NHBoc dendrimer, trimethylol propane core, generation 4 4 48
805920 Bis-MPA-OH dendrimer, trimethylol propane core, generation 1 Hydroxyl 1 6
805939 Bis-MPA-OH dendrimer, trimethylol propane core, generation 2 2 12
805947 Bis-MPA-OH dendrimer, trimethylol propane core, generation 3 3 24
805955 Bis-MPA-OH dendrimer, trimethylol propane core, generation 4 4 48
製品番号 製品名 Core End Group
Functionality
Generation Number of Surface Groups
412368 PAMAM dendrimer, ethylenediamine core, generation 0.0 solution, 20 wt. % in methanol Ethylenediamine core (2-carbon core) Amine 0.5 4
412384 PAMAM dendrimer, ethylenediamine core, generation 1.0 solution, 20 wt. % in methanol 1 8
412406 PAMAM dendrimer, ethylenediamine core, generation 2.0 solution, 20 wt. % in methanol 2 16
412422 PAMAM dendrimer, ethylenediamine core, generation 3.0 solution, 20 wt. % in methanol 3 32
412449 PAMAM dendrimer, ethylenediamine core, generation 4.0 solution, 10 wt. % in methanol 4 64
536709 PAMAM dendrimer, ethylenediamine core, generation 5.0 solution, 5 wt. % in methanol 5 128
536717 PAMAM dendrimer, ethylenediamine core, generation 6.0 solution, 5 wt. % in methanol 6 256
536725 PAMAM dendrimer, ethylenediamine core, generation 7.0 solution, 5 wt. % in methanol 7 512
536741 PAMAM dendrimer, ethylenediamine core, generation 8.0 solution, 5 wt. % in methanol 8 1024
536768 PAMAM dendrimer, ethylenediamine core, generation 9.0 solution, 5 wt. % in methanol 9 2048
536776 PAMAM dendrimer, ethylenediamine core, generation 10.0 solution, 5 wt. % in methanol 10 4096
664138 PAMAM Dendrimer Kit, generations 0-3 0-3 4-32
664049 PAMAM Dendrimer Kit, generations 4-7 4-7 64-512
526142 PAMAM dendrimer, ethylenediamine core, generation 0 (powder) Sodium carboxylate 0 4
412376 PAMAM dendrimer, ethylenediamine core, generation 0.5 solution, 20 wt. % in methanol 0.5 8
412392 PAMAM dendrimer, ethylenediamine core, generation 1.5 solution, 20 wt. % in methanol 1.5 16
412414 PAMAM dendrimer, ethylenediamine core, generation 2.5 solution, 10 wt. % in methanol 2.5 32
412430 PAMAM dendrimer, ethylenediamine core, generation 3.5 solution, 10 wt. % in methanol 3.5 64
470457 PAMAM dendrimer, ethylenediamine core, generation 4.5 solution, 5 wt. % in methanol 4.5 128
536784 PAMAM dendrimer, ethylenediamine core, generation 5.5 solution, 5 wt. % in methanol 5.5 256
536792 PAMAM dendrimer, ethylenediamine core, generation 6.5 solution, 5 wt. % in methanol 6.5 512
477834 PAMAM-OH dendrimer, generation 2 solution, 20 wt. % in methanol Amidoethanol 2 16
477842 PAMAM-OH dendrimer, generation 3 solution, 20 wt. % in methanol 3 32
477850 PAMAM-OH dendrimer, generation 4 solution, 10 wt. % in methanol 4 64
536814 PAMAM-OH dendrimer, generation 5 solution, 5 wt. % in methanol 5 128
536822 PAMAM-OH dendrimer, generation 6 solution, 5 wt. % in methanol 6 256
536830 PAMAM-OH dendrimer, generation 7 solution, 5 wt. % in methanol 7 512
536857 PAMAM-50% C12 dendrimer, generation 2 solution, 20 wt. % in methanol 50% Amino and 50% [N-(2-hydroxydodecyl)] 2 16
536970 PAMAM-50% C12 dendrimer, generation 4 solution, 10 wt. % in methanol 4 64
536849 PAMAM-25% C12 dendrimer, generation 2 solution, 20 wt. % in methanol 75% Amino and 25% [N-(2-hydroxydodecyl)] 2 16
536865 PAMAM-25% C12 dendrimer, generation 3 solution, 20 wt. % in methanol 3 32
536962 PAMAM-25% C12 dendrimer, generation 4 solution, 10 wt. % in methanol 4 64
595861 PAMAM dendrimer, 1,4-diaminobutane core, generation 1.0 solution, 20 wt. % in methanol 1,4-Diaminobutane core (4-carbon core) Amine 1 8
596426 PAMAM dendrimer, 1,4-diaminobutane core, generation 6.0 solution, 10 wt. % in methanol 6 256
635227 PAMAM dendrimer, 1,4-diaminobutane core, generation 6, solution, 10 wt. % in methanol Amidoethanol 6 256
641146 PAMAM dendrimer, 1,4-diaminobutane core, generation 2 solution, 10 wt. % in methanol Amidoethylethanolamine 2 16
641162 PAMAM dendrimer, 1,4-diaminobutane core, generation 5 solution, 10 wt. % in methanol 5 128
635871 PAMAM dendrimer, 1,4-diaminobutane core, generation 4 solution, 10 wt. % in H2O Succinamic Acid 4 64
635898 PAMAM dendrimer, 1,4-diaminobutane core, generation 5 solution, 10 wt. % in H2O 5 128
636088 PAMAM dendrimer, 1,6-diaminohexane core, generation 4 solution, 10 wt. % in H2O 1,6-Diaminohexane core (6-carbon core) 4 64
636118 PAMAM dendrimer, 1,6-diaminohexane core, generation 6 solution, 10 wt. % in H2O 6 256
636169 PAMAM dendrimer, 1,12-diaminododecane core, generation 6 solution, 10 wt. % in H2O 1,12-Diaminododecane core (12-carbon core) Succinamic Acid 6 256
648299 PAMAM dendrimer, 1,12-diaminododecane core, generation 6 solution, 10 wt. % in H2O Tris(Hydroxymethyl)Amidomethane 6 256
647829 PAMAM dendrimer, cystamine core, generation 2.0 solution, 20 wt. % in methanol Cystamine Amine 2 16
648159 PAMAM dendrimer, cystamine core, generation 5, solution, 10 wt. % in methanol 5 128
552054 Cyclotriphosphazene-PMMH-6 dendrimer, generation 1.0 Cyclotriphosphazene Dichlorophosphinothioyl 1 6
551694 Thiophosphoryl-PMMH-12 dendrimer, generation 2.5 Thiophosphoryl chloride Aldehyde 2.5 12
551716 Thiophosphoryl-PMMH-24 dendrimer, generation 3.5 3.5 24
製品番号 製品名 Focal Point End Group
Functionality
Generation Number of Surface Groups
767328 Polyester bis-MPA dendron, 2 hydroxyl, 1 acetylene, generation 1, 95% Acetylene Hydroxyl 1 2
767301 Polyester bis-MPA dendron, 4 hydroxyl, 1 acetylene, generation 2, 95% 2 4
686646 Polyester-8-hydroxyl-1-acetylene bis-MPA dendron, generation 3 3 8
686638 Polyester-16-hydroxyl-1-acetylene bis-MPA dendron, generation 4, 96% 4 16
686611 Polyester-32-hydroxyl-1-acetylene bis-MPA dendron, generation 5, 97% 5 32
901317 Polyester bis-MPA dendron, 2 NHBoc, 1 acetylene (core), generation 1 NH-Boc 1 2
901313 Polyester bis-MPA dendron, 16 NHBoc, 1 acetylene (core), generation 4 4 16
901316 Polyester bis-MPA dendron, 4 NHBoc, 1 acetylene (core), generation 2 2 4
901315 Polyester bis-MPA dendron, 8 NHBoc, 1 acetylene (core), generation 3 3 8
767298 Polyester bis-MPA dendron, 8 hydroxyl, 1 allyl, generation 3, 95% allyl Hydroxyl 3 8
767271 Polyester bis-MPA dendron, 16 hydroxyl, 1 allyl, generation 4 4 16
767255 Polyester bis-MPA dendron, 32 hydroxyl, 1 allyl, generation 5, 95% 5 32
767174 Polyester bis-MPA dendron, 8 carboxyl, 1 amine, generation 3 amine Carboxyl 3 8
767166 Polyester bis-MPA dendron, 16 carboxyl, 1 amine, generation 4 4 16
767263 Polyester bis-MPA dendron, 8 hydroxyl, 1 amine, generation 3 Hydroxyl 3 8
767247 Polyester bis-MPA dendron, 16 hydroxyl, 1 amine, generation 4 4 16
767239 Polyester bis-MPA dendron, 32 hydroxyl, 1 amine, generation 5, 95% 5 32
767220 Polyester bis-MPA dendron, 2 hydroxyl, 1 azide, generation 1, 97% azide Hydroxyl 1 2
767212 Polyester bis-MPA dendron, 4 hydroxyl, 1 azide, generation 2, 95% 2 4
767204 Polyester bis-MPA dendron, 8 hydroxyl, 1 azide, generation 3, 95% 3 8
767190 Polyester bis-MPA dendron, 16 hydroxyl, 1 azide, generation 4, 95% 4 16
767182 Polyester bis-MPA dendron, 32 hydroxyl, 1 azide, generation 5, 95% 5 32
901311 Polyester bis-MPA dendron, 2 NHBoc, 1 azide (core), generation 1 NH-Boc 1 2
901298 Polyester bis-MPA dendron, 16 NHBoc, 1 azide (core), generation 4 4 16
901297 Polyester bis-MPA dendron, 4 NHBoc, 1 azide (core), generation 2 2 4
901332 Polyester bis-MPA dendron, 8 NHBoc, 1 azide (core), generation 3 3 8
686670 Polyester-8-hydroxyl-1-carboxyl bis-MPA dendron, generation 3, >=97% Carboxyl Hydroxyl 3 8
686662 Polyester-16-hydroxyl-1-carboxyl bis-MPA dendron, generation 4 4 16
686654 Polyester-32-hydroxyl-1-carboxyl bis-MPA dendron, generation 5, >=97% 5 32
901393 Polyester bis-MPA dendron, 2 NHBoc, 1 carboxyl (core), generation 1 NH-Boc 1 2
901381 Polyester bis-MPA dendron, 16 NHBoc, 1 carboxyl (core), generation 4 4 16
901377 Polyester bis-MPA dendron, 4 NHBoc, 1 carboxyl (core), generation 2 2 4
901380 Polyester bis-MPA dendron, 8 NHBoc, 1 carboxyl (core), generation 3 3 8
901370 Polyester bis-MPA dendron, 2 acetylene, 1 NHBoc (core), generation 1 NH-Boc Acetylene 1 2
901374 Polyester bis-MPA dendron, 4 acetylene, 1 NHBoc (core), generation 2 2 4
901376 Polyester bis-MPA dendron, 8 acetylene, 1 NHBoc (core), generation 3 3 8
901355 Polyester bis-MPA dendron, 16 acetylene, 1 NHBoc (core), generation 4 4 16
901307 Polyester bis-MPA dendron, 2 azide, 1 NHBoc (core), generation 1 Azide 1 2
901335 Polyester bis-MPA dendron, 4 azide, 1 NHBoc (core), generation 2 2 4
901360 Polyester bis-MPA dendron, 8 azide, 1 NHBoc (core), generation 3 3 8
901369 Polyester bis-MPA dendron, 16 azide, 1 NHBoc (core), generation 4 4 16
901379 Polyester bis-MPA dendron, 2 carboxyl, 1 NHBoc (core), generation 1 Carboxyl 1 2
901408 Polyester bis-MPA dendron, 4 carboxyl, 1 NHBoc (core), generation 2 2 4
901398 Polyester bis-MPA dendron, 8 carboxyl, 1 NHBoc (core), generation 3 3 8
901394 Polyester bis-MPA dendron, 16 carboxyl, 1 NHBoc (core), generation 4 4 16
767131 Polyester bis-MPA dendron, 8 hydroxyl, 1 thiol, generation 3, 95% Thiol Hydroxyl 3 8
767123 Polyester bis-MPA dendron, 16 hydroxyl, 1 thiol, generation 4 4 16
767115 Polyester bis-MPA dendron, 32 hydroxyl, 1 thiol, generation 5, 95% 5 32
901300 Polyester bis-MPA dendron, 2 NHBoc, 1 thiol (core), generation 1 NH-Boc 1 2
901304 Polyester bis-MPA dendron, 16 NHBoc, 1 thiol (core), generation 4 4 16
901312 Polyester bis-MPA dendron, 4 NHBoc, 1 thiol (core), generation 2 2 4
901303 Polyester bis-MPA dendron, 8 NHBoc, 1 thiol (core), generation 3 3 8
製品番号 製品名 Core End Group Functionality Generation Number of Surface Groups
806218 Hyperbranched G4-PEG6k-OH PEG 6K Hydroxyl Pseudo Generation 4 32
806226 Hyperbranched G5-PEG6k-OH Pseudo Generation 5 64
806234 Hyperbranched G6-PEG6k-OH Pseudo Generation 6 128
806242 Hyperbranched G2-PEG10k-OH PEG 10K Pseudo Generation 2 8
806250 Hyperbranched G3-PEG10k-OH Pseudo Generation 3 16
806269 Hyperbranched G4-PEG10k-OH Pseudo Generation 4 32
806277 Hyperbranched G5-PEG10k-OH Pseudo Generation 5 64
806285 Hyperbranched G6-PEG10k-OH Pseudo Generation 6 128
806293 Hyperbranched G2-PEG20k-OH PEG 20K Pseudo Generation 2 8
806307 Hyperbranched G3-PEG20k-OH Pseudo Generation 3 16
806323 Hyperbranched G4-PEG20k-OH Pseudo Generation 4 32
806315 Hyperbranched G5-PEG20k-OH Pseudo Generation 5 64
806331 Hyperbranched G6-PEG20k-OH Pseudo Generation 6 128
901359 Poly(ethylene glycol) linear dendron, NHBoc terminated, PEG Mn 2000, generation 1 PEG 2K NH-Boc 1 4
901404 Poly(ethylene glycol) linear dendron, NHBoc terminated, PEG Mn 2000, generation 2 2 8
901389 Poly(ethylene glycol) linear dendron, NHBoc terminated, PEG Mn 2000, generation 3 3 16
901405 Poly(ethylene glycol) linear dendron, NHBoc terminated, PEG Mn 2000, generation 4 4 32
901384 Poly(ethylene glycol) linear dendron, NHBoc terminated, PEG Mn 5000, generation 1 PEG 5K 1 4
901388 Poly(ethylene glycol) linear dendron, NHBoc terminated, PEG Mn 5000, generation 2 2 8
901400 Poly(ethylene glycol) linear dendron, NHBoc terminated, PEG Mn 5000, generation 3 3 16
901385 Poly(ethylene glycol) linear dendron, NHBoc terminated, PEG Mn 5000, generation 4 4 32
901353 Poly(ethylene glycol) linear dendrimer, NHBoc terminated, PEG Mn 6000, generation 1 PEG 6K 1 4
901382 Poly(ethylene glycol) linear dendrimer, NHBoc terminated, PEG Mn 6000, generation 2 2 8
901407 Poly(ethylene glycol) linear dendrimer, NHBoc terminated, PEG Mn 6000, generation 3 3 16
901397 Poly(ethylene glycol) linear dendrimer, NHBoc terminated, PEG Mn 6000, generation 4 4 32
760900 Poly(ethylene glycol), 4 acetylene dendron, generation 1, average Mn 6,300 PEG 6K Acetylene 1 4
760919 Poly(ethylene glycol), 8 acetylene dendron, generation 2, average Mn 6,900 2 8
760927 Poly(ethylene glycol), 16 acetylene dendron, generation 3, average Mn 8,000 3 16
760935 Poly(ethylene glycol), 4 acetylene dendron, generation 1, average Mn 20,000 PEG 20k 1 4
760943 Poly(ethylene glycol), 8 acetylene dendron, generation 2, average Mn 21,000 2 8
760951 Poly(ethylene glycol), 16 acetylene dendron, generation 3, average Mn 22,000 3 16
760862 Poly(ethylene glycol), 8 hydroxyl dendron, generation 2, average Mn 6,700 PEG 6K Hydroxyl 2 8
752371 Poly(ethylene glycol), 16 hydroxyl dendron, generation 3, average Mn 8,000 3 16
760870 Poly(ethylene glycol), 32 hydroxyl dendron, generation 4, average Mn 9,500 4 32
752398 Poly(ethylene glycol), 4 hydroxyl dendron, generation 1, average Mn 20,300 PEG 20K 1 4
760889 Poly(ethylene glycol), 8 hydroxyl dendron, generation 2, average Mn 21,000 2 8
752363 Poly(ethylene glycol), 16 hydroxyl dendron, generation 3, average Mn 21,600 3 16
760897 Poly(ethylene glycol), 32 hydroxyl dendron, generation 4, average Mn 24,000 4 32

References

  1. Wu, P. et al. Chem. Commun. 2005, 5775-5777.
  2. Gillies, E.R. et al. J. Am. Chem. Soc. 2002, 124, 14137-14146.
  3. Rojo et al. Bioconjugate Chem. 2003, 14, 817-823.
  4. Padilla de Jesus et al. Bioconjugate Chem. 2002, 13, 453-461.