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16 mercaptohexadecanoic acid

Manufactured by Merck Group
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Sourced in Germany, United States

16-mercaptohexadecanoic acid is a chemical compound used in various laboratory applications. It is a long-chain fatty acid with a sulfhydryl (thiol) group at the 16th carbon position. This compound is commonly used as a linker or modifier in surface functionalization and self-assembled monolayer (SAM) formation on metal surfaces.

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Lab products found in correlation

11 mercapto 1 undecanol, by Merck Group (8 mentions) N hydroxysuccinimide nhs, by Merck Group (4 mentions) Bovine serum albumin (bsa), by Merck Group (3 mentions) Sodium borohydride, by Merck Group (3 mentions) Dimethylformamide, by Merck Group (3 mentions) 1 ethyl 3 3 dimethylaminopropyl carbodiimide edc, by Merck Group (3 mentions) Ethanolamine, by Merck Group (2 mentions) Hydrochloric acid (hcl), by Merck Group (2 mentions) Chloroform, by Merck Group (2 mentions) Pentafluorophenyl, by Merck Group (2 mentions) Silver nitrate, by Merck Group (2 mentions) Sodium citrate, by Merck Group (2 mentions) N hydroxysuccinimide, by Merck Group (2 mentions) 1 ethyl 3 3 dimethylaminopropyl carbodiimide, by Merck Group (2 mentions) 1 dodecanethiol, by Merck Group (2 mentions) N n diisopropylethylamine, by Merck Group (2 mentions) N 3 dimethylaminopropyl n ethylcarbodiimide hydrochloride, by Merck Group (2 mentions) 11 mercaptoundecanol, by Merck Group (2 mentions) Ethanol, by Merck Group (2 mentions) Meat extract, by BD (1 mentions)

30 protocols using 16 mercaptohexadecanoic acid

1

Antibody-Based Detection of E. coli

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Phosphate buffer saline (PBS) and ultra-pure water were purchased from Gibco Italia. Peptone, meat extract, tryptone, yeast extract, and Noble Agar were purchased from BD Diagnostics (Milan, Italy,. Ethanolamine, 16-mercaptohexadecanoic acid, 1-ethyl-3-(3-(dimethylamino)-propyl) carbodiimide (EDC), N-hydroxy succinimide (NHS), and bovine serum albumin (BSA) were purchased from Merck KGaA, (Darmstadt, Germany). Antibodies anti-Human Serum Albumin (Monoclonal anti-HSA-11 A6684) were purchased from Merck KGaA, (Darmstadt, Germany) and anti-E. coli (Polyclonal anti-E. coli ab13627) from Abcam (Cambridge, UK). Customized primers and a probe for qPCR-based detection of E. coli were purchased from Primm Srl. TaqMan Universal Master Mix with Rox and 96-well reaction plates were purchased from Invitrogen. Colilert-18 reagent, sample vessels, and Quanti-Tray/2000 were purchased from IDEXX. Amicon Ultra centrifugal filter units of 50 kDa and Whatman filter membranes of 0.22, 5, and 20 μm porosity were purchased from Sigma-Aldrich (Darmstadt, Germany.
La Spina R., António D.C., Desmet C., Valsesia A., Bombera R., Norlén H., Lettieri T, & Colpo P. (2019). Dark Field Microscopy-Based Biosensors for the Detection of E. coli in Environmental Water Samples. Sensors (Basel, Switzerland), 19(21), 4652.
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2

Synthesis of Metal-Organic SURMOF Films

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Copper acetate monohydrate (≥98%), palladium chloride (99%), MUD (11-mercapto-1-undecanol, 97%), bdc (1,4-benzenedicarboxylate, 98%), 16-mercaptohexadecanoic acid (MHDA), dabco(1,4-diazabicyclo(2.2.2)octane (≥99%) and DCTB (trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene] malononitrile, ≥99%), hydrochloric acid (37%), glacial acetic acid, tetrahydrofuran (THF, (≥99.9%)) and chloroform (≥99.5%) were purchased from Merck, Germany. Methyl propiolate (99%) was purchased from Alfa-Aesar, Germany. Absolute ethanol (≥99.8%) was purchased from VWR chemicals. The substrates used for SURMOF synthesis consisted of a 100 nm Au/5 nm Ti metal bilayer deposited on p-doped (100) Si wafers and plain p-doted (100) Si wafers. The Au surface was functionalized by a self-assembled monolayer of MUD before SURMOF synthesis. All chemicals were used as received, without further purification.
Sen B ., Santos JCC ., Haldar R ., Zhang Q ., Hashem T ., Qin P ., Li Y ., Kirschhöfer F ., Brenner-Weiss G ., Gliemann H ., Heinke L ., Barner-Kowollik C ., Knebel A , & Wöll C . (2020). Introducing electrical conductivity to metal-organic framework thin films by templated polymerization of methyl propiolate. Nanoscale, 12(48).
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3

Synthesis of Colloidal Metal Nanoparticles

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Silver nitrate, hydrochloric acid, ethanol, sodium citrate and citric acid were purchased from POCH S. A. Copper chloride, ascorbic acid, 16-mercaptohexadecanoic acid, dimethylamine, sodium borohydride, hexadecyltrimethylammonium chloride (CTAC), tetraethyl orthosilicate (TEOS), and 4-mercaptobenzoic acid (p-MBA) were acquired from Sigma-Aldrich. A 30% HAuCl4 solution in dilute HCl (99.99% trace metals basis) and platinum sheets were purchased from the Polish State Mint. The water used in all the experiments was purified in the Millipore Milli-Q manner. All materials were of high purity and were used as received without further purification or treatment.
Krajczewski J., Kędziora M., Kołątaj K, & Kudelski A. (2019). Improved synthesis of concave cubic gold nanoparticles and their applications for Raman analysis of surfaces. RSC Advances, 9(32), 18609-18618.
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4

Synthesis of Gold Nanoparticles

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Cetrimonium bromide (CTAB), chloroauric acid tetrahydrate (HAuCl4), silver nitrate (AgNO3), sodium borohydride (NaBH4), sodium citrate (Na3C6H5O7), L-ascorbic acid (C6H8O6), 16—mercaptohexadecanoic acid (MHDA), dimethylformamide (DMF), pentafluorophenyl (PFP), N, Ndiisopropylethylamine (DIPEA), N-cyclohexyl-N′-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate (CMC) and all other chemicals were purchased from Sigma–Aldrich (Darmstadt, Germany).
Depciuch J., Miszczyk J., Maximenko A., Zielinski P.M., Rawojć K., Panek A., Olko P, & Parlinska-Wojtan M. (2020). Gold Nanopeanuts as Prospective Support for Cisplatin in Glioblastoma Nano-Chemo-Radiotherapy. International Journal of Molecular Sciences, 21(23), 9082.
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5

Formation of Cu-BDC Thin Films

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For the formation of Cu-BDC films, 16-mercaptohexadecanoic
acid [MHDA] (90%), 11-mercapto-1-undecanol [MUD] (97%), copper(II)
acetate monohydrate [Cu(CH3COO)2·H2O] (≥98%), and terephthalic acid [H2BDC]
(98%) were purchased from Sigma-Aldrich. Absolute, anhydrous ethanol
(200 proof ACS/USP grade) was purchased from Pharmco by Greenfield
Global. Gold-coated (100 nm) silicon wafers with an adhesive titanium
layer (5 nm) were purchased from Platypus Technologies.
Dhanapala B.D., Maglich D.L, & Anderson M.E. (2023). Impact of Surface Functionalization and Deposition Method on Cu-BDC surMOF Formation, Morphology, Crystallinity, and Stability. Langmuir, 39(34), 12196-12205.
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6

Multiplex Cytokine Sandwich Immunoassay

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The following reagents were from Sigma–Aldrich (St. Louis, MO, USA); 16-mercaptohexadecanoic acid, cysteamine, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide, succinic anhydride and N-hydroxysuccinimide. Triethylamine, dimethylformamide and bovine serum albumin (BSA) were from Fisher Scientific (Pittsburgh, PA, USA). Six-armed-poly(ethyleneglycol)–amine was from SunBio (South Korea). PBS (Cat#70011-036) and Tween-20 were from Life Technologies (Grand Island, NY, USA).
Sandwich antibody pairs for IL-20 were produced by Novo Nordisk A/S. Capture anti-IL-20 antibody was of the IgG1 isotype. Unspecific binding was assessed using a IgG1 isotype control from R&D Systems (MAB002, Minneapolis, MN, USA). IRDye-800 streptavidin conjugate was from LiCor Biosciences (Lincoln, NE, USA). Mouse, goat and bovine IgG were from Jackson ImmunoResearch (West Grove, PA, USA).
Purified cytokine antigen standards and sandwich antibody pairs for IL-1β (MAB601, BAF201), IL-10 (MAB2172, BAF217), IL-6 (MAB206, BAF206), and TNFα (MAB610, BAF210) were purchased from R&D systems. All capture antibodies were of the IgG1 isotype.
Valentina M., Jan F., Peder N.L., Bo Z., Hongjie D, & Pernille K. (2015). Cytokine detection and simultaneous assessment of rheumatoid factor interference in human serum and synovial fluid using high-sensitivity protein arrays on plasmonic gold chips. BMC Biotechnology, 15, 73.
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7

Synthesis and Characterization of Organometallic Compounds

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1,3,5-tris(4-carboxyphenyl)benzene [BTB] (98%), 1,3,5-tris(4’carboxy[1,1᾿-biphenyl]-4-yl)benzene [BBC] (95%), copper (II) acetate monohydrate, 16-mercaptohexadecanoic acid [MHDA] (90%), 11-mercapto-1-undecanol [MUD] (97%), 1-octadecanethiol [ODT] (98%), hydrochloric acid (ACS reagent, 37%), anhydrous propylene carbonate [PC], and anhydrous dimethyl sulfoxide [DMSO] are from Sigma Aldrich (St. Louis, MO). Absolute, anhydrous ethanol (200 proof, ACS/USP Grade) was obtained from Phamco-Aaper (Shelbyville, KY). These chemicals were used as received. Ferrocene (Fc, Sigma Aldrich) and tetrabutylammonium tetrafluoroborate (TBATFB, Sigma Aldrich) were dried at 120 °C under vacuum for 12 h prior to transferring to an Ar-filled glovebox (less than 1 ppm O2/H2O). Silicon wafers with a 5 nm Ti adhesion layer and a 100 nm Au layer were obtained from Platypus Technologies (New Orleans, LA). Ge (100) wafers were obtained from MTI Corporation (Richmond, CA).
Lau J., Trojniak A.E., Maraugha M.J., VanZanten A.J., Osterbaan A.J., Serino A.C., Ohnsorg M.L., Cheung K.M., Ashby D.S., Weiss P.S., Dunn B.S, & Anderson M.E. (2019). Conformal Ultrathin Film Metal–Organic Framework Analogues: Characterization of Growth, Porosity, and Electronic Transport. Chemistry of materials : a publication of the American Chemical Society, 31(21), 8977-8986.
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8

Isolation and Activation of CD4+ T Cells

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CD4+ T cells were purchased from
Innovative Research and preserved according to the manufacturer’s
instructions (details provided in the Supporting Information). CD4 recombinant human protein (PHS0044), CD3D
and CD3E recombinant human protein (10981-H08H), magnetic beads functionalized
with streptavidin (Dynabeads M280), and phosphate-buffered saline
(PBS, pH = 7.4) were purchased from Invitrogen. Bovine serum albumin
(BSA), monoclonal biotinylated human CD3 antibody produced in mouse
(SHAB4700047), poly(l-lysine) (PLL) (0.1%, w/v, molecular
weight 150,000−300,000), glutaraldehyde (25 wt % in H2O), tetradecanethiol, 16-mercaptohexadecanoic acid (98%), N-hydroxysuccinimide (NHS), and N-(3-(dimethylamino)propyl)-N′-ethylcarbodiimide hydrochloride (EDC) were purchased
from Sigma-Aldrich. The 0.5 M EDTA solution obtained from Ambion was
used as received. Biotinylated anti-CD4 antibody (MEM-241) was obtained
from Abcam. Isolation buffer was prepared from PBS with 0.1% BSA and
2 mM EDTA.
Chen Y.T., Jamison A.C., Lee T.R, & Xu S. (2016). Quantitatively Resolving Ligand–Receptor Bonds on Cell Surfaces Using Force-Induced Remnant Magnetization Spectroscopy. ACS Central Science, 2(2), 75-79.
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9

Covalent Immobilization of Proteins on Self-Assembled Monolayers

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SAG, Fn and Coll proteins were covalently immobilized, in a random orientation, onto self-assembled monolayers (SAMs) of carboxyl-terminated alkanethiols. Glass coverslips coated with a thin (~30 nm) gold layer were immersed overnight in ethanol solutions containing 1 mM 16-mercaptohexadecanoic acid (Sigma-Aldrich, Belgium) and 11-mercapto-1-undecanol (Sigma-Aldrich) in a 1:9 ratio and then rinsed with ethanol and dried. A brief (~30 s) sonication was applied to remove loosely bound alkanethiol aggregates. The resulting monolayers were further immersed for 30 min in a solution containing 20 mg/mL N-hydroxysuccinimide (NHS) (Sigma-Aldrich) and 50 mg/mL 1-ethyl-3-(3-(dimethylamino)propyl)-carbodiimide (EDC) (Sigma-Aldrich) and subsequently rinsed with water. The activated surfaces were then incubated with either 100 ng/mL SAG,83 (link) 0.2 mg/mL Fn (from human plasma, Sigma-Aldrich), or 1 mg/mL collagen (Type 1 from rat tail, Sigma-Aldrich), in PBS for at least 2 h, followed by rinsing with the same buffer.
For preparing hydrophobic and hydrophilic substrates, gold-coated glass coverslips were immersed overnight in a solution of 1 mM of either 1-dodecanethiol (Sigma-Aldrich) or 11-mercapto-1-undecanol (Sigma-Aldrich), then rinsed with ethanol and dried under N2. All surfaces were freshly prepared and used the same day.
Sullan R.M., Li J.K., Crowley P.J., Brady L.J, & Dufrêne Y.F. (2015). Binding Forces of Streptococcus mutans P1 Adhesin. ACS nano, 9(2), 1448-1460.
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10

Multifunctional Nanoparticle Synthesis

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Tetraethyl ortho-silicate (TEOS, 99.0%), (3-aminopropyl)triethoxysilane (APTES, 99%), polyoxyethylene (5) nonylphenylether (Igepal CO-520), tetrakis(hydroxymethyl)phosphonium chloride (THPC, 80% solution in H2O), hydrogen tetrachloroaurate(iii) hydrate (HAuCl4·3H2O, 99.9% metals basis), 16-mercaptohexadecanoic acid (16-MHDA), dimethylformamide (DMF), pentafluorophenyl (PFP), N,N-diisopropylethylamine (DIPEA) and N-cyclohexyl-N-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (CMC) were purchased from Sigma Aldrich (USA). Ferric chloride hexahydrate (FeCl3·6H2O, 99%), sodium oleate (NaOA, 95%) were purchased from Carl Roth. 1-Octadecene (ODE, tech. 90%), oleic acid (OA, tech. 90%), potassium carbonate (K2CO3, 99.0%) were purchased from Alfa-Aesar Chemicals. Cyclohexane (C6H12, 99.5%), hexane (C6H12, 97.0%), acetone (C3H6O, 99.5%), ammonia solution (NH3·H2O, 25%), chloroform (CHCl3), ethanol (C2H5OH, 96%) were bought from POCH. Ultrapure water was used throughout the experiments. All the chemicals were used as received without further purification.
Maximenko A., Depciuch J., Łopuszyńska N., Stec M., Światkowska-Warkocka Ż., Bayev V., Zieliński P.M., Baran J., Fedotova J., Węglarz W.P, & Parlinska-Wojtan M. (2020). Fe3O4@SiO2@Au nanoparticles for MRI-guided chemo/NIR photothermal therapy of cancer cells. RSC Advances, 10(44), 26508-26520.
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