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Research ArticleSpecial Issue on Drug Delivery Technologies

Injectable Pasty Biodegradable Polyesters Derived from Castor Oil and Hydroxyl-Acid Lactones

Noam Y. Steinman and Abraham J. Domb
Journal of Pharmacology and Experimental Therapeutics September 2019, 370 (3) 736-741; DOI: https://doi.org/10.1124/jpet.119.259077
Noam Y. Steinman
Institute of Drug Research, School of Pharmacy, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem, Israel
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Abraham J. Domb
Institute of Drug Research, School of Pharmacy, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem, Israel
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  • Fig. 1.
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    Fig. 1.

    Biodegradable pasty polymers may be injected through a syringe. These injectable polymers have the potential to be incorporated with drugs and used as site-specific drug-eluting implants.

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    Fig. 2.

    Preparation of polymers from secondary alcohols on castor oil or 12-hydroxystearic acid. The cyclic monomers used were Ɛ-caprolactone, trimethylene carbonate, or a 6:1 molar ratio of D,L-lactide and glycolide.

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    Fig. 3.

    Fourier-transform infrared spectroscopy spectra of pasty polymers confirmed polymerization. Characteristic C=O bands between 1746 and 1723 cm−1 were observed for polymers, as well as the disappearance of the characteristic hydroxyl bands in CO and HS.

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    Fig. 4.

    Viscosity was measured at varying shear rates. Polymers with the highest molecular weight were the most viscous. Any further increase in molecular weight resulted in solid polymers.

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    Fig. 5.

    Hydrolytic degradation of pasty polymer in each series I–VI was determined in phosphate buffer (pH 7.4) at 37°C. Weight loss was determined by drying the sample at each time point to determine the weight of the polymer.

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    TABLE 1

    Six series of polymers were synthesized, each with its own fatty acid: polymer pair

    InitiatorPolymerSeries Indentification
    COPCLI
    COPTMCII
    COPLGAIII
    HSPCLIV
    HSPTMCV
    HSPLGAVI
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    TABLE 2

    Molecular weight and fatty acid:polymer ratios of all polymers within series I–VI (Table 1)

    EntrySeriesaInitiator:PolymerbMwcMnbViscositydFlow Behaviore
    w/wkDakDaPa·s
    1I71:293.01.30.13Newtonian
    2I60:405.01.625Pseudoplastic
    3I41:596.12.381Pseudoplastic
    4I30:708.23.11.1 × 104Pseudoplastic
    5II80:202.71.21.2Newtonian
    6II68:323.11.41.6Newtonian
    7II56:443.81.72.8Newtonian
    8II44:564.42.17.4Newtonian
    9II23:777.24.063Newtonian
    10III92:81.91.00.92Newtonian
    11III69:312.62.32.8Newtonian
    12IV60:403.20.5017Pseudoplastic
    13IV50:503.50.6133Pseudoplastic
    14IV41:594.20.742.5 × 102Pseudoplastic
    15V46:543.20.653.0Newtonian
    16V24:765.81.335Newtonian
    17VI66:342.10.4627Newtonian
    18VI56:442.20.535.7Newtonian
    19VI43:572.70.7027Newtonian
    • GPC, gel permeation chromatography; Mn, number average molecular weight; Mw, weight average molecular weight.

    • ↵a Series number according to the data in Table 1.

    • ↵b The relative amounts (w/w) of fatty acid initiator and polymer as well as the true polymer Mn values were calculated from relative 1H NMR peaks of either component.

    • ↵c Mw was estimated by GPC relative to polystyrene standards and is reported in kilodaltons.

    • ↵d Viscosity at shear rate 0.1 second−1.

    • ↵e Flow behavior from shear rate 0.1–100 second−1.

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      Figures S1-S19. 

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Journal of Pharmacology and Experimental Therapeutics: 370 (3)
Journal of Pharmacology and Experimental Therapeutics
Vol. 370, Issue 3
1 Sep 2019
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Research ArticleSpecial Issue on Drug Delivery Technologies

Pasty Biodegradable Polyesters and Polycarbonates

Noam Y. Steinman and Abraham J. Domb
Journal of Pharmacology and Experimental Therapeutics September 1, 2019, 370 (3) 736-741; DOI: https://doi.org/10.1124/jpet.119.259077

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Research ArticleSpecial Issue on Drug Delivery Technologies

Pasty Biodegradable Polyesters and Polycarbonates

Noam Y. Steinman and Abraham J. Domb
Journal of Pharmacology and Experimental Therapeutics September 1, 2019, 370 (3) 736-741; DOI: https://doi.org/10.1124/jpet.119.259077
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