Abstract
Patterned immobilization of synthetic and biological ligands on material surfaces with controlled surface densities is important for various bioanalytical and cell biological purposes. This paper describes the synthesis, characterization, and application of a novel silane coupling agent bearing a photoremovable succinimidyl carbonate, which enables the photopatterning of various primary amines on glass and silicon surfaces. The silane coupling agent is 1-[5-methoxy-2-nitro-4-(3-trimethoxysilylpropyloxy)phenyl]ethyl N-succinimidyl carbonate. The distinct feature of this molecule is that it has a photocleavable 2-nitrobenzyl switch between a trimethoxysilyl group and a succinimidyl carbonate, each reactive to the hydroxy groups of inorganic oxides and primary amines. Based on this molecular design, the compound allows for the one-step introduction of succinimidyl carbonates onto the surface of glass and silicon, immobilization of primary amines, and region-selective and dose-dependent release of the amines by near-UV irradiation. Therefore, we were able to pattern amine ligands on the substrates in given surface densities and arbitrary geometries by controlling the doses and regions of photoirradiation. These features were verified by UV-vis spectroscopy, contact angle measurements, infrared (IR) spectroscopy, X-ray photoelectron spectroscopy (XPS), ellipsometry, and atomic force microscopy (AFM). The compound was applied to form a chemical density gradient of amino-biotin on a silicon substrate in a range of 0.87-0.12 chains/nm2 by controlling photoirradiation under a standard fluorescence microscope. Furthermore, we also succeeded in forming a chemical density gradient at a lower surface density range (0.15-0.011 chains/nm2) on the substrate by diluting the feed amino-biotin with an inert control amine.
| Original language | English |
|---|---|
| Pages (from-to) | 88-97 |
| Number of pages | 10 |
| Journal | Colloids and Surfaces B: Biointerfaces |
| Volume | 76 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2010 Mar 1 |
| Externally published | Yes |
Fingerprint
Keywords
- Caged compound
- Cell adhesion
- Gradient
- Patterning
- Silane coupling agent
- XPS
ASJC Scopus subject areas
- Biotechnology
- Colloid and Surface Chemistry
- Physical and Theoretical Chemistry
- Surfaces and Interfaces
Cite this
Silane coupling agent bearing a photoremovable succinimidyl carbonate for patterning amines on glass and silicon surfaces with controlled surface densities. / Nakayama, Hidekazu; Nakanishi, Jun; Shimizu, Takahiro; Yoshino, Yutaro; Iwai, Hideo; Kaneko, Shingo; Horiike, Yasuhiro; Yamaguchi, Kazuo.
In: Colloids and Surfaces B: Biointerfaces, Vol. 76, No. 1, 01.03.2010, p. 88-97.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Silane coupling agent bearing a photoremovable succinimidyl carbonate for patterning amines on glass and silicon surfaces with controlled surface densities
AU - Nakayama, Hidekazu
AU - Nakanishi, Jun
AU - Shimizu, Takahiro
AU - Yoshino, Yutaro
AU - Iwai, Hideo
AU - Kaneko, Shingo
AU - Horiike, Yasuhiro
AU - Yamaguchi, Kazuo
PY - 2010/3/1
Y1 - 2010/3/1
N2 - Patterned immobilization of synthetic and biological ligands on material surfaces with controlled surface densities is important for various bioanalytical and cell biological purposes. This paper describes the synthesis, characterization, and application of a novel silane coupling agent bearing a photoremovable succinimidyl carbonate, which enables the photopatterning of various primary amines on glass and silicon surfaces. The silane coupling agent is 1-[5-methoxy-2-nitro-4-(3-trimethoxysilylpropyloxy)phenyl]ethyl N-succinimidyl carbonate. The distinct feature of this molecule is that it has a photocleavable 2-nitrobenzyl switch between a trimethoxysilyl group and a succinimidyl carbonate, each reactive to the hydroxy groups of inorganic oxides and primary amines. Based on this molecular design, the compound allows for the one-step introduction of succinimidyl carbonates onto the surface of glass and silicon, immobilization of primary amines, and region-selective and dose-dependent release of the amines by near-UV irradiation. Therefore, we were able to pattern amine ligands on the substrates in given surface densities and arbitrary geometries by controlling the doses and regions of photoirradiation. These features were verified by UV-vis spectroscopy, contact angle measurements, infrared (IR) spectroscopy, X-ray photoelectron spectroscopy (XPS), ellipsometry, and atomic force microscopy (AFM). The compound was applied to form a chemical density gradient of amino-biotin on a silicon substrate in a range of 0.87-0.12 chains/nm2 by controlling photoirradiation under a standard fluorescence microscope. Furthermore, we also succeeded in forming a chemical density gradient at a lower surface density range (0.15-0.011 chains/nm2) on the substrate by diluting the feed amino-biotin with an inert control amine.
AB - Patterned immobilization of synthetic and biological ligands on material surfaces with controlled surface densities is important for various bioanalytical and cell biological purposes. This paper describes the synthesis, characterization, and application of a novel silane coupling agent bearing a photoremovable succinimidyl carbonate, which enables the photopatterning of various primary amines on glass and silicon surfaces. The silane coupling agent is 1-[5-methoxy-2-nitro-4-(3-trimethoxysilylpropyloxy)phenyl]ethyl N-succinimidyl carbonate. The distinct feature of this molecule is that it has a photocleavable 2-nitrobenzyl switch between a trimethoxysilyl group and a succinimidyl carbonate, each reactive to the hydroxy groups of inorganic oxides and primary amines. Based on this molecular design, the compound allows for the one-step introduction of succinimidyl carbonates onto the surface of glass and silicon, immobilization of primary amines, and region-selective and dose-dependent release of the amines by near-UV irradiation. Therefore, we were able to pattern amine ligands on the substrates in given surface densities and arbitrary geometries by controlling the doses and regions of photoirradiation. These features were verified by UV-vis spectroscopy, contact angle measurements, infrared (IR) spectroscopy, X-ray photoelectron spectroscopy (XPS), ellipsometry, and atomic force microscopy (AFM). The compound was applied to form a chemical density gradient of amino-biotin on a silicon substrate in a range of 0.87-0.12 chains/nm2 by controlling photoirradiation under a standard fluorescence microscope. Furthermore, we also succeeded in forming a chemical density gradient at a lower surface density range (0.15-0.011 chains/nm2) on the substrate by diluting the feed amino-biotin with an inert control amine.
KW - Caged compound
KW - Cell adhesion
KW - Gradient
KW - Patterning
KW - Silane coupling agent
KW - XPS
UR - http://www.scopus.com/inward/record.url?scp=74149087188&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=74149087188&partnerID=8YFLogxK
U2 - 10.1016/j.colsurfb.2009.10.020
DO - 10.1016/j.colsurfb.2009.10.020
M3 - Article
C2 - 19910170
AN - SCOPUS:74149087188
VL - 76
SP - 88
EP - 97
JO - Colloids and Surfaces B: Biointerfaces
JF - Colloids and Surfaces B: Biointerfaces
SN - 0927-7765
IS - 1
ER -