Enzymatic Polymerization of Cyclic Monomers in Ionic Liquids as a Prospective Synthesis Method for Polyesters Used in Drug Delivery Systems
Abstract
:1. Introduction
2. Polymeric Carriers
3. Macromolecular Conjugates of Active Substances
4. Aliphatic Polyesters as a Carriers of Therapeutic Agents
Polyesters | Therapeutic Agent | Ref. |
---|---|---|
poly(lactide-co-glycolide) (PLG) | Amphotericin B | [23,24] |
Ciprofloxacin | [25,26] | |
Cisplatin | [27] | |
Docetaxel | [28] | |
Doxorubicin | [29,30] | |
Paclitaxel | [31,32] | |
Rifampicin | [33] | |
r-hGH (recombinant human growth hormone) | [34] | |
polylactide (PLA) | Camptothecin | [35,36] |
Doxorubicin | [37,38] | |
5-fluorouracil | [39] | |
poly(ε-caprolactone) (PCL) | Amphotericin B | [40] |
Ciprofloxacin | [41] | |
Citropin | [42] | |
Vancomycin | [43] |
5. Ring Opening Polymerization of Cyclic Esters
6. Biocatalytic Synthesis of Polymers for Biomedical Applications
Origin of Lipases | Ref. |
---|---|
Aspergillus niger | [70] |
Candida antarctica | [45,71,72,73,74,75,76,77,78] |
Candida cylindracea | [45,70,78] |
Candida rugosa | [70] |
Penicillium roqueforti | [70] |
Porcine pancreatic | [45,70,78,79,80,81,82] |
Pseudomonas cepacia | [45,70,76,78] |
Pseudomonas fluorescens | [45,70,76,78] |
Yarrowia lipolytica | [83] |
6.1. Influence of the Reaction Media on Activity of Biocatalysts
6.2. Ionic Liquids
ILs | Abbreviation |
---|---|
1-Butyl-3-methylimidazolium tetrafluoroborate | [bmim][BF4] |
1-Butyl-3-methylimidazolium bis((trifluoromethyl)-sulfonyl)imide | [bmim][NTf2] |
1-Butyl-3-methylimidazolium hexafluorophosphate | [bmim][PF6] |
1-Butyl-3-methylimidazolium trifluoromethanesulfonate | [bmim][OTf] |
1-Ethyl-3-methylimidazolium tetrafluoroborate | [emim][BF4] |
1-Hexyl-3-methylimidazolium hexafluorophosphate | [hmim][PF6] |
1,4-bis(3-Hexylimidazolium-1-yl)butane bishexafluorophosphate | [C4(C6Im)2][PF6] |
1-Dodecyl-3-methylimidazolium bis((trifluoromethyl)-sulfonyl)imide | [C12MIm][NTf2] |
1-Dodecyl-3-methylimidazolium hexafluorophosphate | [C12MIm][PF6] |
6.2.1. Enzyme Stability in Ionic Liquids
6.2.2. Polarity of Ionic Liquids
6.2.3. Hydrophobicity/Hydrophilicity
ILs | Polarity ETN (RT) | Mw (g·mol−1) | Melting Point (°C) | Viscosity in 20 °C (cP) | Density (g·cm−3) | Conductivity (S·m−1) | Water Solubility (WS) (%w/v) |
---|---|---|---|---|---|---|---|
[bmim][BF4] | 0.680 | 226 | −82 | 233 | 1.17 | 0.17 | 100 |
[bmim[Tf2N] | 0.645 | 419 | −4 | 52 | 1.43 | 0.39 | 1.40 |
[bmim][PF6] | 0.676 | 284 | −8 | 312 | 1.362 | 0.14 | 0.13 |
6.2.4. Viscosity
6.2.5. Effect of Impurities
7. Ionic Liquids as a Medium for the Enzymatic Ring-Opening Polymerization of Cyclic Esters
Monomer | ILs | Purity of ILs (%) | Enzyme | Temp. (°C) | Time (h) | Mn (Da) | PDI | Y/C (%) | Ref. |
---|---|---|---|---|---|---|---|---|---|
[bmim][BF4] | - | CA | 60 | 168 | 4200 | 2.7 | 97C | [123] | |
[bmim][BF4] | ≥99 | CA | 60 | 24 | 12,700 | 1.8 | 35Y | [124] | |
[bmim][BF4] | - | YLL | 100 | 16 | 1758 | 1.7 | - | [113] | |
[bmim][BF4] | - | YLL | 150 | 6 | 3092 | 2.5 | - | [113] | |
[bmim][PF6] | - | CA | 60 | 72 | 540 | 4.2 | 62C | [123] | |
[bmim][PF6] | ≥99 | CA | 60 | 24 | 12,200 | 1.7 | 30Y | [124] | |
CL | [bmim][NTf2] | ≥99 | CA | 60 | 24 | 10,500 | 2.1 | 44Y | [124] |
[bmim][NTf2] | ≥97 | CA | 90 | 24 | 8100 | - | 85Y | [102] | |
[C4(C6Im)2][PF6] | - | CA | 90 | 48 | 26,200 | - | 62Y | [125] | |
[C12MIm][PF6] | - | CA | 90 | 48 | 11,700 | - | 37Y | [125] | |
[C12MIm][NTf2] | - | CA/ILs | 60 | 48 | 35,600 | - | 62Y | [125] | |
[C12MIm][NTf2] | - | CA | 60 | 48 | 20,300 | - | 54Y | [125] | |
LLA | [bmim][BF4] | ≥99 | CA | 110 | 24 | 54,600 | 1.25 | 24.3Y96.2C | [126] |
[bmim][PF6] | ≥99 | CA | 65 | 264 | 581 | 1.2 | 29.5Y | [127] | |
[bmim][PF6] | - | CA | 90 | 120 | 19,600 | 1.2 | - | [128] | |
[bmim][PF6] | ≥99 | CA | 120 | 24 | 3900 | 1.19 | 0.1Y90.4C | [126] | |
[hmim][PF6] | ≥97 | CA | 90 | 168 | 37,800 | 1.3 | 63.2Y | [129] | |
[hmim][PF6] | ≥97 | CA | 65 | 120 | 1700 | 1.3 | 16.5Y | [129] | |
[bmim][NTf2] | ≥99 | CA | 120 | 24 | 50,100 | 1.42 | 10.5Y | [126] | |
DO | [bmim][PF6] | ≥99 | CA/ILs | 70 | 18 | 182,100 | - | - | [130] |
[bmim][PF6] | ≥99 | CA | 70 | 24 | 27,700 | - | - | [130] | |
GA | [bmim][PF6] | ≥99 | CA | 65 | 96 | - | - | - | [127] |
LLA:GA (1:3) | [hmim][PF6] | ≥97 | CA | 65 | 120 | 3500 | 1.3 | 40.2Y | [129] |
[bmim][PF6] | ≥99 | CA | 65 | 96 | 2400 | 1.1 | 36.7Y | [127] | |
LLA:GA (3:1) | [bmim][PF6] | ≥99 | CA | 90 | 144 | 18,500 | 1.1 | - | [127] |
7.1. Effect of Monomer and Polymer Solubility in ILs
7.2. Effect of Temperature
7.3. Effect of Enzyme Preparations
7.4. Structure of Polyesters Obtained in ILs
7.5. Kinetics of Polyester Enzymatic Synthesis in ILs
8. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Piotrowska, U.; Sobczak, M. Enzymatic Polymerization of Cyclic Monomers in Ionic Liquids as a Prospective Synthesis Method for Polyesters Used in Drug Delivery Systems. Molecules 2015, 20, 1-23. https://doi.org/10.3390/molecules20010001
Piotrowska U, Sobczak M. Enzymatic Polymerization of Cyclic Monomers in Ionic Liquids as a Prospective Synthesis Method for Polyesters Used in Drug Delivery Systems. Molecules. 2015; 20(1):1-23. https://doi.org/10.3390/molecules20010001
Chicago/Turabian StylePiotrowska, Urszula, and Marcin Sobczak. 2015. "Enzymatic Polymerization of Cyclic Monomers in Ionic Liquids as a Prospective Synthesis Method for Polyesters Used in Drug Delivery Systems" Molecules 20, no. 1: 1-23. https://doi.org/10.3390/molecules20010001