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Polyanhydrides: Synthesis and characterization

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Biopolymers I

Part of the book series: Advances in Polymer Science ((POLYMER,volume 107))

Abstract

The delivery of drugs from biodegradable polymeric materials for human and animal use has attracted considerable attention of investigators throughout the scientific community. Various types of polymers have been synthesized and tested for this purpose which include: poly(α-esters), poly(aliphatic esters), polyorthoesters, polyphosphazenes, poly(phosphate esters), polymers based on amino acids, natural and synthetic peptides and proteins, polysaccharides and polyanhydrides. Comprehensive reviews on various biodegradable polymers and their advantages have been published [1–5]. This chapter concentrates on the polyanhydride class of polymers.

Polyanhydrides are useful bioabsorbable materials for controlled drug delivery. They are hydrolytically unstable and hydrolyze to diacid monomers in contact with body fluids. Since their introduction to the field of controlled drug delivery, about 10 years ago, extensive research has been conducted to study their chemistry as well as their toxicity and medical applications. Several review articles have been published on polyanhydrides and the focus has been on controlled drug delivery applications [1, 2].

A major part of this chapter will review recent developments in the chemistry and properties of polyanhydrides, which includes new synthetic methods, new polymeric structures, and in depth characterization of polyanhydrides. The degradation and drug release properties and applications that were not reviewed previously are included. A review article by the same authors concentrating on polyanhydride applications and toxicity is in preparation [6].

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Abbreviations

ACDA:

acetylenedicarboxylic acid

BTC:

1,3,5-benzenetricarboxylic acid

Co:

drug load in gm/cc

CPH:

1,6-bis(p-carboxyphenoxy) hexane

CPP:

1,3-bis(carboxyphenoxy) propane

CPV:

carboxphenoxy valerate

DMF:

N,N-dimethylformamide

DSC:

Differential Scanning Calorimetry

Et3N:

triethylamine

FA:

fumaric acid

FAD:

dimer fatty acid

Gelfoam:

absorbable gelatin sponge

Gliadel:

Polyanhydride brain tumor implant containing BCNU

GPC:

gel permeation chromatography

4HC:

4-hydroperoxycyclophosphamide

IPA:

isophthalic acid

Ln:

average length of sequence

MIT:

Massachusetts Institute of Technology

Mw:

weight average molecular weight

Mn:

number average molecular weight

PA:

poly(adipic acid)

PAA:

poly(acrylic acid)

PAZ:

poly(azelaic acid)

PLA:

poly(lactic acid)

PCL:

poly(caprolactone)

PDP:

poly(phenylenedicarboxylic acid)

PHB:

poly(hydroxybutyrate)

PSA:

poly(sebacic acid)

PSU:

poly(suberic acid)

SA:

sebacic acid

SEM:

Scanning Electron Microscope

Septicin:

polyanhydride antibacterial bone implant

STDA:

4,4′stilbenedicarboxylic acid

Surgicel:

oxidized cellulose absorbable hemostat

TA:

terephthalic acid

Tg:

glass transition temperature

Tm:

melting point

TMA-gly:

trimellitimide-glycine

ToF-SIMS:

time-of-flight secondary ion mass spectroscopy

VPO:

vapor pressure osmometry

Vycryl:

synthetic absorbable suture

Xc:

degree of crystallinity

XPS:

X-ray photoelectron spectroscopy

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Authors and Affiliations

  1. School of Pharmacy, Faculty of Medicine, Hebrew University of Jerusalem, 91120, Jerusalem, Israel

    Abraham J. Domb

  2. Drug Delivery Laboratories, Nova Pharmaceutical Corporation, 21224, Baltimore, MD, USA

    Abraham J. Domb, Shimon Amselem & Manoj Maniar

  3. Department of Pharm. Sci., Medical University of South California, 29425, Charleston, SC, USA

    Jaymin Shah

Authors
  1. Abraham J. Domb
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  2. Shimon Amselem
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  3. Jaymin Shah
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  4. Manoj Maniar
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Robert S. Langer Nicholas A. Peppas

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© 1993 Springer-Verlag

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Domb, A.J., Amselem, S., Shah, J., Maniar, M. (1993). Polyanhydrides: Synthesis and characterization. In: Langer, R.S., Peppas, N.A. (eds) Biopolymers I. Advances in Polymer Science, vol 107. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0027552

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  • DOI: https://doi.org/10.1007/BFb0027552

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  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-56148-4

  • Online ISBN: 978-3-540-47478-4

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