A polyethylene glycol copolymer for carrying and releasing multiple copies of cysteine-containing peptides

Shaei Yun Huang, Shahriar Pooyan, Jihong Wang, Indrani Choudhury, Michael J Leibowitz, Stanley Stein

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Two different methods were developed to prepare an adduct of a poly(ethylene glycol)-lysine copolymer with either cysteamine or 1-amino-2-methyl-2-propanethiol. Cysteine-containing peptides could then be disulfide-linked to the thiol groups on the polymer in a facile manner. In the described procedures, a coupling ratio of about 8 peptides/molecule of poly(ethylene glycol)-lysine copolymer (M(w) = 27 000) was typically attained. The products were stable at neutral pH, but the peptides could be released from the polymer in a physiologically relevant reducing environment. The release rate was highly dependent on the linker used for forming the disulfide bond. To illustrate the potential biomedical usefulness of this polymer carrier, a Tat peptide-PEG conjugate was shown to inhibit expression of a reporter gene fused to the TAR element of human immunodeficiency virus in a model cell assay.

Original languageEnglish (US)
Pages (from-to)612-617
Number of pages6
JournalBioconjugate Chemistry
Volume9
Issue number5
DOIs
StatePublished - Sep 1998
Externally publishedYes

Fingerprint

Peptides
Polyethylene glycols
Cysteine
Copolymers
Polymers
Disulfides
Cysteamine
Reporter Genes
Viruses
Sulfhydryl Compounds
Assays
Genes
HIV
Molecules
poly(ethylene glycol) lysine copolymer

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Clinical Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

A polyethylene glycol copolymer for carrying and releasing multiple copies of cysteine-containing peptides. / Huang, Shaei Yun; Pooyan, Shahriar; Wang, Jihong; Choudhury, Indrani; Leibowitz, Michael J; Stein, Stanley.

In: Bioconjugate Chemistry, Vol. 9, No. 5, 09.1998, p. 612-617.

Research output: Contribution to journalArticle

Huang, Shaei Yun ; Pooyan, Shahriar ; Wang, Jihong ; Choudhury, Indrani ; Leibowitz, Michael J ; Stein, Stanley. / A polyethylene glycol copolymer for carrying and releasing multiple copies of cysteine-containing peptides. In: Bioconjugate Chemistry. 1998 ; Vol. 9, No. 5. pp. 612-617.
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