The Convergent Synthesis of Poly(glycerol‐succinic acid) Dendritic Macromolecules

Luman, Nathanael R.; Smeds, Kimberly A.; Grinstaff, Mark W.

doi:10.1002/chem.200305172

Cited by 42 publications

(30 citation statements)

References 78 publications

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“…For example, photoinitiated control of polymerization allows for their application as injectable biomaterials [18,19] with a non-cytotoxic polymerization process.…”

mentioning

confidence: 99%

A Combinatorial Library of Photocrosslinkable and Degradable Materials

Anderson¹,

Tweedie²,

Hossain³

et al. 2006

Advanced Materials

137

191

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Photocrosslinkable and degradable polymers are finding a broad range of applications as drug-delivery vehicles, tissueengineering scaffolds, and in the fabrication of microdevices. [1][2][3] However, the synthesis of multifunctional macromers that form these degradable networks commonly involves multiple functionalization and purification steps, which makes the development of large numbers of polymers with diverse properties difficult. Here, we develop the first combinatorial library of degradable photocrosslinked materials. A library of acrylate-terminated poly(b-amino ester)s was synthesized in parallel via a condensation reaction that combines primary or secondary amines with diacrylates. This library of macromers was then photopolymerized to form degradable networks, with a wide range of degradation times (< 1 day to minimal mass loss after three months), mass-loss profiles, and mechanical properties (∼ 4 to 350 MPa). We believe this library approach will allow for the rapid screening and design of degradable polymers for a variety of applications. The spatial and temporal control afforded during photoinitiated polymerizations has motivated their wide application in the general field of biomaterials. [1,2] For example, photocrosslinkable hydrogels are used for the delivery of cells to injured tissues, [4][5][6][7][8] for the encapsulation and controlled delivery of biological molecules, [9][10][11] and for controlled fluid flow and cell confinement in microfluidics. [12,13] Additionally, highly crosslinked photopolymers are currently used in dentistry [14] and are being developed as bone-replacement materials [15,16] and for the fabrication of microdevices.[17] Many of these applications are only possible owing to the controlled nature of this type of polymerization. For example, photoinitiated control of polymerization allows for their application as injectable biomaterials [18,19] with a non-cytotoxic polymerization process.[20]Additionally, through use of masks and lasers, the spatial control of the polymerization process allows for unique patterning and construction of complex materials.[21]Numerous photopolymerizable and degradable materials have been developed, including polyanhydrides, poly(propylene fumarates), poly(ethylene glycol), and polysaccharides, [8,15,16,18] all utilizing multiple reaction and purification steps for synthesis of the photopolymerizable precursors. Despite this work, it has proven challenging to predict specific desirable properties (e.g., degradation and mechanics) from known chemical and structural details of the network precursors. These properties are essential in the design of degradable polymers. For instance, it may be desirable to synthesize a very hard material for some applications (e.g., orthopaedics), whereas a soft material is advantageous for other applications (e.g., tissue adhesive). [22,23] One potential solution to the inability to predict physical behavior is the generation of a higher-throughput approach to rapidly synthesize and screen photopolymerizable li...

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“…For example, photoinitiated control of polymerization allows for their application as injectable biomaterials [18,19] with a non-cytotoxic polymerization process.…”

mentioning

confidence: 99%

A Combinatorial Library of Photocrosslinkable and Degradable Materials

Anderson¹,

Tweedie²,

Hossain³

et al. 2006

Advanced Materials

137

191

View full text Add to dashboard Cite

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“…G1-core, G2-core, and G3-core were prepared using known procedures, 31,34 as shown in Scheme 1. First, the 1,3-diol of glycerol was protected as 1,3-benzylideneglycerol 1 by treatment with p-TsOH and benzaldehyde.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Poly(glycerol-succinic acid)-dithiocarbamate and Poly(glycerol-succinic acid)-1,3,4-thiadiazole Dendrimers and Their Use as Anti-Wear Oil Additives

Kim¹,

Hoang²,

Kim³

et al. 2013

Bulletin of the Korean Chemical Society

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A series of poly(glycerol-succinic acid) dithiocarbamate and 1,3,4-thiadiazole dendrimers, which have potential as anti-wear oil additives, were synthesized. Their anti-wear properties in three different oils (100N, DB-51, and soybean) were evaluated using a four-ball wear tester. The results indicated that thiocarbamate dendrimers have moderate anti-wear properties in DB-51 oil, and 1,3,4-thiadiazole dendrimers exhibited good anti-wear properties in 100N and DB-51 oils. However, dithiocarbamate and 1,3,4-thiadiazole dendrimers were not effective anti-wear additives in soybean oil.

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“…A solution of DIC (82 mL, 0.5 mmol) in dry DCM (0.5 mL) in a syringe was added in intervals over a period of 30 min. After 1 h additional stirring on the ice bath, the reaction mixture was placed in the refrigerator for 16 h. The mixture was transferred to a separation funnel and acetone (20 mL), water (20 mL) and O-tert-Butyl-G1-lithium carboxylate dendron (15). In a threenecked 100 mL reaction flask O-tert-butyl-G1-methyl ester dendron 6 (0.69 g, 1.43 mmol) and LiI (1.54 g, 11.5 mmol) were dissolved in dry THF (25 mL).…”

Section: General Methodsmentioning

confidence: 99%

Convergent synthesis of degradable dendrons based on l-malic acid

2015

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New degradable polyester dendrons based on the cellular tricarboxylic acid cycle component L-malic acid were synthesized up to the third generation by convergent synthesis. The dendron wedges could be introduced in a stepwise, highly regioselective fashion. HMBC-NMR revealed that the C1-carbonyl on malic acid was exclusively esterified, before the reaction of the second dendron wedge at C4 took place.Degradation studies on a first generation dendron analyzed by HPLC showed that hydrolytic degradation of the dendron most profoundly takes place at pH 4 and pH 9 with the highest degradation rate at alkaline pH. NMR shows that the dendron degrades to malic acid and fumaric acid derivatives. Preliminary studies performed in the cell culture show low toxicity of the dendrons in concentrations of up to 50 mg mL À1 .

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The Convergent Synthesis of Poly(glycerol‐succinic acid) Dendritic Macromolecules

Cited by 42 publications

References 78 publications

A Combinatorial Library of Photocrosslinkable and Degradable Materials

A Combinatorial Library of Photocrosslinkable and Degradable Materials

Synthesis of Poly(glycerol-succinic acid)-dithiocarbamate and Poly(glycerol-succinic acid)-1,3,4-thiadiazole Dendrimers and Their Use as Anti-Wear Oil Additives

Convergent synthesis of degradable dendrons based on l-malic acid

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