Modification of fluorous substrates with oligo(ethylene glycol) via "click" chemistry for long-term resistance of cell adhesion

Rafael Contreras-Caceres; Catherine M Santos; Siheng Li; Amit Kumar; Zhiling Zhu; Satya S Kolar; Miguel A Casado-Rodriguez; Yongkai Huang; Alison McDermott; Juan Manuel Lopez-Romero; Chengzhi Cai

doi:10.1016/j.jcis.2015.07.033

Modification of fluorous substrates with oligo(ethylene glycol) via "click" chemistry for long-term resistance of cell adhesion

J Colloid Interface Sci. 2015 Nov 15:458:112-8. doi: 10.1016/j.jcis.2015.07.033. Epub 2015 Jul 15.

Authors

Affiliations

¹ Department of Chemistry, University of Houston, Houston, TX 77204, USA; Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Málaga, 29071, Spain. Electronic address: rcontreras@uma.es.
² Department of Chemistry, University of Houston, Houston, TX 77204, USA. Electronic address: cmsantos@central.uh.edu.
³ Department of Chemistry, University of Houston, Houston, TX 77204, USA. Electronic address: sihengli9@gmail.com.
⁴ Department of Chemistry, University of Houston, Houston, TX 77204, USA. Electronic address: aks208@yahoo.com.
⁵ Department of Chemistry, University of Houston, Houston, TX 77204, USA. Electronic address: jeremial@gmail.com.
⁶ College of Optometry, University of Houston, Houston, TX 77204, USA. Electronic address: snkolar@uh.edu.
⁷ Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Málaga, 29071, Spain. Electronic address: miguelcasado204@gmail.com.
⁸ Department of Chemistry, University of Houston, Houston, TX 77204, USA. Electronic address: hykaiuh@gmail.com.
⁹ College of Optometry, University of Houston, Houston, TX 77204, USA. Electronic address: amcdermott@optometry.uh.edu.
¹⁰ Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Málaga, 29071, Spain. Electronic address: jmromero@uma.es.
¹¹ Department of Chemistry, University of Houston, Houston, TX 77204, USA. Electronic address: cai@uh.edu.

PMID: 26210101
DOI: 10.1016/j.jcis.2015.07.033

Abstract

In this work perfluorinated substrates fabricated from SiO2 glass slides are modified with oligo(ethylene glycol) (OEG) units for long-term resistance of cell adhesion purposes, based on fluorous interactions and click chemistry. Specifically, fluorous substrates, prepared by treatment of glass slides with 1H, 1H, 2H, 2H-perfluorodecyltrimethoxysilane (FAS17), were coated with ethynyl-OEG-C8F17, followed by covalent attachment of an azido-OEG via copper-catalyzed azide-alkyne cycloaddition (CuAAC) "click" reaction. We demonstrate that the resultant surface avoid fibrinogen adsorption and resisted cell adhesion for over 14days. X-ray photoemission spectroscopy (XPS) analysis and contact angle goniometry measurements confirm the presence of the OEG molecules on the fluorous substrates. Bright field optical images show total absence of 3T3 fibroblast cells on the OEG modified fluorinated substrate for 1 and 5days, and a remarkably decrease of cell adhesion at 14days.

Keywords: Cell adhesion resistance; Click reaction; Fluorinated substrate; Fluorine–fluorine interaction; OEG; Protein resistance.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Cell Adhesion
Click Chemistry*
Ethylene Glycol / chemistry*
Fluorine / chemistry*
Glass / chemistry
Molecular Structure
Silicon Dioxide / chemistry

Substances

Fluorine
Silicon Dioxide
Ethylene Glycol

Abstract

Publication types

MeSH terms

Substances

Grants and funding