Amino-EG6-undecanethiol, hydrochloride


Application: SAM preparation, amine group coating, and hydrophilic surface

Chemical Description: 20-(11-Mercaptoundecanyloxy)-3, 6, 9, 12, 15, 18-hexaoxaeicosane-1-amine, hydrochloride
CAS: 496839-01-1 (free base)

Appearance: white or pale yellow powder
Purity: ≥90.0% (HPLC, derivatization)
MW: 504.16, C23H60ClNO6S

Storage Condition: -20ºC, protect from light and metal
Shipping Condition: ambient temperature


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Structural Formula

Product Description

Polyethyleneglycols (PEGs) are widely used for material modifications to improve hydrophilicity of the surface. PEG-coated materials are usually more stable under physiological conditions. Since Amino-EG6-undecanethiol has 6 ethylene glycol units, 11 carbon atoms, and an SH group at the end, it can be used to prepare a highly oriented and hydrophilic SAM on a gold surface. This is suitable for biomaterial labeling on the surface due to the improved hydrophilicity. The hydrophilic surface can prevent proteins or other biomaterials from non-specific binding. Therefore, the SAM prepared by this reagent will provide a better surface to develop biomaterial sensors or DNA/ protein microarrays. To prepare an Amino-EG6-SAM on a gold surface, hydroxy-EGn-undecanethiols (n=3, 6) are used to dilute the number of amino groups according to the density of the molecules being introduced onto the surface.

How to Prepare SAM
1. Soak a gold-coated glass plate in Piranha solutiona) for 10-15 minutes. Wash the plate with purified water.a)
2. Dissolve aminoalkanethiol compound in ethanol to prepare several mM to several ten mM solutions.
3. Soak the plate in the aminoalkanethiol solution for a certain time period.b)
4. Wash the SAM-coated plate with ethanol and then water.
5. Dry the plate under nitrogen atmosphere, if necessary.

a)Piranha solution: sulfuric acid and 30% hydrogen peroxide, 3:1. Piranha solution is a strong oxidizing agent. Extreme care is necessary when using it.
Do not apply Piranha solution to resin-coated plates; it may erode the resin.
b)To prepare a SAM-coated plate with the best performance, aminoalkanethiol concentration and soaking time should be individually determined.

Application of SAM-Preparation of DNA Array (Fig. 1)
1. Use SF10 glass slides (Schott Glass Technologies) coated with 5 nm chromium and 45 nm gold thin film.
2. Soak the glass slide in a 1 mM 1-octadecanethiol (ODT)/ethanol solution overnight to prepare ODT SAM-coated slide.
3. Draw 500 μm x 500 μm patterns on the ODT SAM-coated slide by UV irradiation with an Hg-Xe arc lamp.a)
4. Soak the slide in a 1 mM 11-amino-1-undecanethiol (AUT)/ethanol solution for 2 hours to form AUT SAM on the 500 μm x 500 μm photopatterned area.
5. Drop 2 mM SPDP solutionb) onto the slide and leave the slide at room temperature.
6. Wash the slide and dry under nitrogen atmosphere.
7. Apply 1 mM thiol-DNA solutionc) to each 500 μm x 500 μm pattern and incubate at room temperature overnight.
8. Incubate the slide with a sample solution for 10 minutes and wash with phosphate buffer, followed by SPR imaging.

a)Irradiation time: 1-1.5 hours
b)SPDP: N-succinimidyl 3-(2-pyridyldithio)propionate. Dissolve SPDP in DMSO to prepare 50 mM solution. Dilute it 25 times with 100 mM triethanolamine buffer, pH 7.0.
c)Dissolve thiol-DNA with 100 mM triethanolamine buffer, pH 8.0.

Fig. 1 DNA Array Preparation Scheme


When it is difficult to take out all the powder from the container,
please add the solvent into a container and dissolve it before its use.

1) C. Pale-Grosdemange, E. S. Simon, K. L. Prime, and G. M. Whitesides, Anal. Chem., 1999, 71, 777-790.
2) M. Kyo, K.Usui-Aoki, H. Koga, Anal. Chem, 2005, 77, 7115-7121.
3) G. B. Sigal, M. Mrksich, and G. M. Whitesides, J. Am. Chem. Soc., 1998, 120, 3464-3473.
4) Y. Li, H. J. Lee, and R. M. Corn, Nucleic Acids Research, 2006, 34, 6416-6424.

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Surface Chemistry

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