Macrocyclic bile acids: from molecular recognition to degradable biomaterial building blocks

Gautrot, Julien E.; Zhu, Xiaoxia

doi:10.1039/b821340b

Cited by 33 publications

(22 citation statements)

References 111 publications

(157 reference statements)

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“…The development of multifunctional nanomaterials combining diagnostic and therapeutic purpose has recently attracted intensive interests [1][2][3][4][5][6]. Semiconductor nanocrystals known as quantum dots (QDs) are particularly appealing for bioimaging and labeling probes due to their unique optical properties, including broad absorption with narrow photoluminescence (PL) spectra, high quantum yield, low photobleaching, and resistance to chemical degradation [2][3][4][5][6][7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

In-situ immobilization of quantum dots in polysaccharide-based nanogels for integration of optical pH-sensing, tumor cell imaging, and drug delivery

et al. 2010

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Section: Introductionmentioning

confidence: 99%

In-situ immobilization of quantum dots in polysaccharide-based nanogels for integration of optical pH-sensing, tumor cell imaging, and drug delivery

et al. 2010

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“…Bile acids are large steroidal structures that are naturally derived and possess several hydroxy sites for functionalization, as shown in Scheme for cholic acid (CA). Bile acid‐based polymers have shown potential for the tuning of thermo‐mechanical properties, as well as thermal shape memory . In 2010, Manzini et al performed enzyme‐catalyzed polymerization reactions involving macrocycles of various sizes, with and without large steroidal structures .…”

Section: Recent Erop Techniques and Architectures Using Calbmentioning

confidence: 99%

“…Bile acid-based polymers have shown potential for the tuning of thermo-mechanical properties, as well as thermal shape memory. [16,95,134,135] In 2010, Manzini et al performed enzyme-catalyzed polymerization reactions involving macrocycles of various sizes, with and without large steroidal structures. [136] Although most reactions were successful, attempts at polymerizing dimers and trimers of lithocholic acid (LCA) gave no polymer.…”

Section: Polymerization Of Bulky Substratesmentioning

confidence: 99%

Recent Developments and Optimization of Lipase-Catalyzed Lactone Formation and Ring-Opening Polymerization

Champagne

Strandman

Zhu

2016

Macromol. Rapid Commun.

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To obtain materials useful for the biomedical field, toxic catalysts should be removed from the synthetic route of polymerization reactions and of their precursors. Lipase-catalyzed ring-opening polymerization and the synthesis of cyclic precursors can be performed with the same catalyst under different conditions. Here, we highlight the use of lipases as catalysts and optimization of their performance for both ring-closing and ring-opening polymerization, via varying parameters such as ring size, concentration, substrate molar ratio, temperature, and solvent. While the conditions for ring-closing reactions and ring-opening polymerizations of small molecules, such as ε-caprolactone, have been extensively explored using Candida antarctica lipase B (CALB), the optimization of macrocyclization, especially for more bulky substrates is surveyed here. Finally, recent methods and polymer architectures are summarized with an emphasis on new procedures for more sustainable chemistry, such as the use of ionic liquids as solvents and recycling of polyesters by enzymatic pathways.

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“…This concept was applied to the synthesis of bile acid-based polyesters (BAPs) and led to materials displaying elastomeric properties with Young's moduli near 1-2 MPa at 37°C, which make them suitable for soft tissue engineering. 21,23,24 Herein we report the high-performance shape memory properties of BAPs, both in the warm and cold drawing modes. We also extend this new family of polymers to mono-and bis-amides, as well as cholic acid, and draw structure-property relationships.…”

Section: Introductionmentioning

confidence: 98%

Shape Memory Polymers Based on Naturally-Occurring Bile Acids

Gautrot

Zhu

2009

Macromolecules

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Naturally occurring bile acids are ideal building blocks for a new generation of biomaterials displaying low systemic toxicity and engineered properties. Herein we report the synthesis of bile acid-based polyesters using entropy-driven ring-opening metathesis polymerization (ED-ROMP) and characterization of the structure of the resulting polymers. The materials synthesized display high molecular weights (M n above 100000), typical of ED-ROMPs. The mechanical and responsive behavior of these bile acid-based polyesters (BAPs) is studied by dynamic mechanical analysis (DMA) and thermomechanical cycling. Although BAPs are amorphous thermoplastics, they display typical rubber-like elasticity with tunable mechanical behavior, glass transitions close to body temperature, and outstanding shape memory properties. By introducing small changes in the chemical structure of BAPs (amide bonds or additional hydroxyl groups), we were able to correlate the materials' stiffness, their T g and shape recovery temperature to their structure. In addition, we show that BAPs can be deformed to high strains even at low temperature and still display shape recovery.

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Macrocyclic bile acids: from molecular recognition to degradable biomaterial building blocks

Cited by 33 publications

References 111 publications

In-situ immobilization of quantum dots in polysaccharide-based nanogels for integration of optical pH-sensing, tumor cell imaging, and drug delivery

In-situ immobilization of quantum dots in polysaccharide-based nanogels for integration of optical pH-sensing, tumor cell imaging, and drug delivery

Recent Developments and Optimization of Lipase-Catalyzed Lactone Formation and Ring-Opening Polymerization

Shape Memory Polymers Based on Naturally-Occurring Bile Acids

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