Cholesteryl-(L-lactic acid) building blocks for self-assembling biomaterials

Harm Anton Klok, Julia J. Hwang, Subramani N. Iyer, Samuel I Stupp

Research output: Contribution to journalArticle

101 Citations (Scopus)

Abstract

The synthesis and properties of a novel set of building blocks for the preparation of self-assembling biomaterials are described. These molecules consist of a relatively short oligo(L-lactic acid) segment (n̄ = 10-40) that is substituted with a cholesterol moiety as an end group and in some cases has a second biofunctional substituent at its other terminus. The cholesterol moiety not only serves to induce liquid crystalline properties and drive the self-assembly of these oligomers, but also is expected to have an effect on the interaction of cells with these materials. The cholesteryl-(L-lactic acid) (CLA) oligomers form thermotropic liquid crystals and self-assemble into lamellar structures consisting of interdigitated bilayers. In addition, the CLA oligomers can be homogeneously blended with poly(L-lactic acid), thereby offering the possibility to improve the cell interaction properties of this common surgical biomaterial. Furthermore, the secondary alcohol terminus of the CLA oligomers allows the opportunity to introduce additional bioactive substituents such as cholesterol, indomethacin (an antiinflammatory drug), and pyrene and rhodamine B (which can act as fluorescent labels for bioimaging purposes) and various α-amino acids. These biofunctional CLA oligomers can also be homogeneously mixed with the unsubstituted CLA oligomers and thus could enable a further noncovalent functionalization of self-assembling biomaterials.

Original languageEnglish
Pages (from-to)746-759
Number of pages14
JournalMacromolecules
Volume35
Issue number3
DOIs
Publication statusPublished - Jan 29 2002

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Biocompatible Materials
Lactic acid
Oligomers
Biomaterials
Lactic Acid
Cholesterol
rhodamine B
Thermotropic liquid crystals
Lamellar structures
Indomethacin
Pyrene
Self assembly
Labels
Anti-Inflammatory Agents
Amino acids
Alcohols
Crystalline materials
Amino Acids
Molecules
Liquids

ASJC Scopus subject areas

  • Materials Chemistry

Cite this

Cholesteryl-(L-lactic acid) building blocks for self-assembling biomaterials. / Klok, Harm Anton; Hwang, Julia J.; Iyer, Subramani N.; Stupp, Samuel I.

In: Macromolecules, Vol. 35, No. 3, 29.01.2002, p. 746-759.

Research output: Contribution to journalArticle

Klok, Harm Anton ; Hwang, Julia J. ; Iyer, Subramani N. ; Stupp, Samuel I. / Cholesteryl-(L-lactic acid) building blocks for self-assembling biomaterials. In: Macromolecules. 2002 ; Vol. 35, No. 3. pp. 746-759.
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