Heptafluorobutyric acid

Manufactured by Merck Group

Sourced in United States, United Kingdom, Switzerland, Germany

Heptafluorobutyric acid is a fluorinated organic compound with the chemical formula C3F7COOH. It is a clear, colorless liquid. The compound is used as a reagent in various laboratory applications.

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Lab products found in correlation

Formic acid, by Merck Group (9 mentions) Acetonitrile, by Merck Group (5 mentions) Acetonitrile, by Thermo Fisher Scientific (4 mentions) Dithiothreitol (dtt), by Thermo Fisher Scientific (3 mentions) Acetone, by Merck Group (3 mentions) Serotonin hydrochloride, by Merck Group (2 mentions) Bovine serum albumin (bsa), by Merck Group (2 mentions) Tiamulin fumarate standard, by LGC (2 mentions) Internal standard of sulfaphenazole, by LGC (2 mentions) Hydrophilic polyvinylidene fluoride pvdf membrane syringe filters, by Restek (2 mentions) Acetonitrile, by Avantor (2 mentions) Nanosep centrifugal filters, by Pall Corporation (2 mentions) Bio inert, by Pall Corporation (2 mentions) Sulfaphenazole, by Pall Corporation (2 mentions) Itraq reagent kit 200 assay, by AB Sciex (2 mentions) Hplc grade acetonitrile, by Merck Group (2 mentions) Iodoacetamide, by Merck Group (2 mentions) Trifluoroacetic acid, by Thermo Fisher Scientific (2 mentions) Trichloroacetic acid, by Merck Group (2 mentions) Methylglyoxal, by Merck Group (2 mentions)

21 protocols using heptafluorobutyric acid

Quantification of Pharmacological Compounds

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Caffeine (CAF), Cytotoxicity Detection Kit (LDH) Roche, D-mannitol (MAN), D-Mannitol Colorimetric Assay Kit, disodium fumarate, deoxynivalenol (DON), L-glutamate, lucifer yellow (LY), and sodium pyruvate were obtained from Sigma Aldrich (St. Louis, MO, USA). All inorganic salts required for preparing Krebs Bicarbonate Buffer (KRB), ethanol, and glucose were purchased from Avantor (Gliwice, Poland). Amoxicillin trihydrate (AMX) and doxycycline hyclate (DOX) were generously donated by the pharmaceutical company Biofaktor Sp. z o.o. (Skierniewice, Poland) The quality of antibiotics was consistent with the monographs of the European Pharmacopoeia and corresponded to the quality of active substances used in the production of veterinary drugs.
Tissue transportation, preparation, and incubation were performed in Krebs Bicarbonate Buffer (KRB) containing 108 mM NaCl, 4.7 mM KCl, 1.8 mM Na₂HPO₄, 0.4 mM KH₂PO₄, 15 mM NaHCO₃, 1.2 mM MgSO₄, 1.25 mM CaCl₂, 11.5 mM glucose, 4.9 mM L-glutamate, 5.4 mM disodium furmate, and 4.9 mM sodium pyruvate at pH 7.4, and saturated with oxygen using a 95%/5% O₂/CO₂ mixture by gassing for 60 min [37 (link)].
For HPLC and LC-MS/MS analysis, acetonitrile, methanol, and formic acid (HPLC grade) were obtained from Avantor Chemicals (Radnor, PA, USA), trichloracetic acid and heptafluorobutyric acid were obtained from Sigma Aldrich (St. Louis, MO, USA).

Mendel M., Karlik W., Latek U., Chłopecka M., Nowacka-Kozak E., Pietruszka K, & Jedziniak P. (2022). Does Deoxynivalenol Affect Amoxicillin and Doxycycline Absorption in the Gastrointestinal Tract? Ex Vivo Study on Swine Jejunum Mucosa Explants. Toxins, 14(11), 743.

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Antibacterial Assay with FITC-Labeled P. aeruginosa

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Ciprofloxacin, trimethylamine, methylene chloride, heptafluorobutyric acid, perfluoropentanoic acid, fluorescein isothiocyanate (FITC) and perfluoroheptanoic acid were purchased from Sigma-Aldrich (St. Louis, MO) and used without further purification. Pseudomonas aeruginosa strain 19660 was purchased from ATCC. A telomerase transformed human corneal epithelial cell line (hTCEpi) [66 (link)] was used for in vitro studies.

Qin G., Zhu Z., Li S., McDermott A.M, & Cai C. (2017). Development of Ciprofloxacin-loaded contact lenses using fluorous chemistry. Biomaterials, 124, 55-64.

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Quantification of Biogenic Amines by UPLC-MS/MS

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The concentrations of agmatine, cadaverine, histamine, 2-phenylethylamine, putrescine, spermidine, spermine, tryptamine, and tyramine were quantified with external calibration, in triplicate, by UPLC-MS/MS, using an Acquity system equipped with an HSS T3 column (Waters), as described previously (Van der Veken et al., 2020 (link)). Samples were prepared by addition of 300 μL of acetonitrile (Merck) with 0.2% heptafluorobutyric acid (Sigma-Aldrich) to 300 μL of aqueous extracts, followed by microcentrifugation at 18,000 × g for 15 min, and filtering with a 0.2-μm LG H-PTFE filter (Millex; Merck) before injection (5 μL) into the column.

Decadt H., Weckx S, & De Vuyst L. (2023). The rotation of primary starter culture mixtures results in batch-to-batch variations during Gouda cheese production. Frontiers in Microbiology, 14, 1128394.

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Serotonin Quantification Protocol

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Serotonin hydrochloride, formic acid (FA), and heptafluorobutyric acid were obtained from Sigma Aldrich (St. Louis, MO). Serotonin-d4 hydrochloride was obtained from Santa Cruz Biotech (Dallas, TX). Optima LC/MS-grade water and acetonitrile (ACN) were obtained from Thermo-Fisher Scientific (Waltham, MA). Individual calibration standards were prepared at serotonin concentrations of 0.98, 3.9, 15.6, 62.5, 250, and 1000 ng/mL using an aqueous internal standard solution that contains 450 ng/mL of serotonin-d4 as the diluent.

Engevik M.A., Luck B., Visuthranukul C., Ihekweazu F.D., Engevik A.C., Shi Z., Danhof H.A., Chang-Graham A.L., Hall A., Endres B.T., Haidacher S.J., Horvath T.D., Haag A.M., Devaraj S., Garey K.W., Britton R.A., Hyser J.M., Shroyer N.F, & Versalovic J. (2020). Human-Derived Bifidobacterium dentium Modulates the Mammalian Serotonergic System and Gut–Brain Axis. Cellular and Molecular Gastroenterology and Hepatology, 11(1), 221-248.

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Purification and Crystallization of DHFR

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For all stock solutions, test compounds were dissolved in dimethylsulfoxide (DMSO; Sigma-Aldrich, St. Louis, MO). Buffers required for purification of recombinant DHFR were prepared with dithiothreitol, ethylenediaminetetraacetic acid (EDTA), glycerol, and Tris base purchased from Fisher Scientific (Hampton, NH). Crystallization solution was prepared with γ-butyrolactone; 4-morpholineethanesulfonic acid sodium salt; nicotinamide adenine dinucleotide phosphate (NADPH); polyethylene glycol 10,000; and sodium acetate purchased from Sigma-Aldrich. Hydroxypropyl methylcellulose (HPMC; Sigma-Aldrich) and potassium phosphate buffer (BD Biosciences, San Jose, CA) were used throughout microsomal experiments. Acetonitrile [high-performance liquid chromatography (HPLC) grade] was purchased from Fisher Scientific. Ethyl acetate (HPLC grade) was purchased from MilliporeSigma (Burlington, MA). Heptafluorobutyric acid was purchased from Sigma-Aldrich. All mobile phases were filtered using 2.0-μm filtration discs from MilliporeSigma.

Lombardo M.N., G-Dayanandan N., Keshipeddy S., Zhou W., Si D., Reeve S.M., Alverson J., Barney P., Walker L., Hoody J., Priestley N.D., Obach R.S, & Wright D.L. (2019). Structure-Guided In Vitro to In Vivo Pharmacokinetic Optimization of Propargyl-Linked Antifolates. Drug Metabolism and Disposition, 47(9), 995-1003.

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Isotope Labeling Protocol for Mass Spectrometry

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All isotopic reagents used for the synthesis
of labels were purchased from Isotec (Miamisburg, OH). Mass spec grade
trypsin/Lys C mix and dithiothreitol (DTT) were purchased from Promega
(Madison, WI). Urea, ammonium bicarbonate, ACS grade methanol (MeOH),
ACS grade dichloromethane (DCM), ACS grade acetonitrile (ACN), Optima
UPLC grade ACN, Optima UPLC grade water, and Optima LC/MS grade formic
acid were purchased from Fisher Scientific (Pittsburgh, PA). Sodium
cyanoborohydride (NaBH₃CN), l-leucine, formaldehyde
(CH₂O), hydrogen chloride gas (HCl), iodoacetamide (IAA),
tris hydrochloride, trifluoroacetic acid (TFA), triethylammonium bicarbonate
(TEAB), N,N-dimethylformamide (DMF),
4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium tetrafluoroborate
(DMTMM), N-methylmorpholine (NMM), heptafluorobutyric
acid (HFBA), dimethyl sulfoxide (DMSO), and bovine serum albumin (BSA)
were purchased from Sigma-Aldrich (St. Louis, MO). Hydroxylamine solution
was purchased from Alfa Aesar (Ward Hill, MA).

Frost D.C., Greer T, & Li L. (2014). High-Resolution Enabled 12-Plex DiLeu Isobaric Tags for Quantitative Proteomics. Analytical Chemistry, 87(3), 1646-1654.

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Quantitative Analysis of Tiamulin Fumarate

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All organic solvents used were of an analytical grade. The tiamulin fumarate standard and internal standard (IS) of sulfaphenazole were purchased from LGC Standards (Teddington, Middlesex, UK). Acetonitrile was from J.T. Baker (Deventer, the Netherlands). Heptafluorobutyric acid and formic acid were from Sigma-Aldrich (St. Louis, MO, USA). Hydrophilic polyvinylidene fluoride (PVDF) membrane syringe filters, 0.22 μm, were provided by Restek (College, PA, USA). Nanosep centrifugal filters with 0.2 µm of Bio-Inert were from Pall Corporation (New York, NY, USA).
A tiamulin and sulfaphenazole stock standard solution at a concentration of 1000 μg/mL in methanol was kept stable for 6 months by storing at −18 °C in the dark. Working solutions were made in ultrapure water from a diluted stock solution and stored at 4–8 °C for 1 month.

Cybulski P., Gajda A., Bilecka M, & Jabłoński A. (2023). Determination of Tiamulin Concentration in Sow Milk and in Sera of Suckling Piglets. Molecules, 28(19), 6940.

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Quantification of Neurotransmitters and Cigarette Constituents

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Dopamine hydrochloride, γ-aminobutyric acid (GABA), serotonin hydrochloride, glutamine, glutamate, epinephrine (internal standard, IS), formic acid, and heptafluorobutyric acid (HFBA) were obtained from Sigma-Aldrich (St. Louis, MO, USA). Trifluoroacetic acid (TFA) was acquired from Fisher Scientific (Loughborough, Leics, UK). LC/MS grade water, methanol, and acetonitrile were purchased from Honeywell Burdick and Jackson (Muskegon, MI, USA). Milli-Q water was supplied by a Milli-Q^® water purification system (Millipore, Bedford, MA, USA). Liggett Ducat blue cigarettes cruise (LD, 0.6 mg of nicotine, 0.8 mg of tar, and 0.01 mg of carbon monoxide) were purchased from the local market.

Hammad A.M., Alhusban A.A., Alzaghari L.F., Alasmari F, & Sari Y. (2023). Effect of Cigarette Smoke Exposure and Aspirin Treatment on Neurotransmitters’ Tissue Content in Rats’ Hippocampus and Amygdala. Metabolites, 13(4), 515.

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Derivatization of Amino Acids for iTRAQ

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The derivatization of 44 amino acids and related amines were conducted on the iTRAQ^® Reagent Kit 200 Assay (P/N: A1116, AB Sciex, USA), including phosphoserine (PSer), phosphoethanolamine (PEtN), taurine (Tau), asparagine (Asn), serine (Ser), hydroxyproline (Hyp), glycine (Gly), glutamine (Gln), aspartate (Asp), ethanolamine (EtN), histidine (His), threonine (Thr), citrulline (Cit), sarcosine (Sar), β-alanine (β-Ala), alanine (Ala), glutamate (Glu), 1-methylhistidine, (1MHis), 3-methylhistidine (3MHis), argininosuccinic acid (Asa), carnosine (Car), homocitrulline (Hcit), arginine (Arg), α-aminoadipic acid (Aad), γ-aminobutyric acid (GABA), β-aminoisobutyric acid (β-Aib), α-amino-N-butyric acid (α-Abu), anserine (Ans), δ-hydroxylysine (δ-Hyl), proline (Pro), ornithine (Orn), cystathionine (Cth), cystine (Cys), lysine (Lys), methionine (Met), valine (Val), norvaline (Nva), tyrosine (Tyr), homocysteine (Hcy), isoleucine (Ile), leucine (Leu), norleucine (Nle), phenylalanine (Phe), and tryptophan (Trp). Heptafluorobutyric acid (≥99.5%) was obtained from Sigma-Aldrich (Switzerland) for mobile phase preparation. Acetonitrile and formic acid were purchased from Merck (Darmstadt, Germany). All chemicals and reagents were of appropriate analytical grades.

An Z., Shi C., Li P, & Liu L. (2021). Stability of amino acids and related amines in human serum under different preprocessing and pre-storage conditions based on iTRAQ®-LC-MS/MS. Biology Open, 10(2), bio055020.

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Targeted Metabolomics Workflow Chemicals

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LC mobile phases consisting of HPLC-grade acetonitrile and the modifiers formic acid and heptafluorobutyric acid were purchased from Sigma-Aldrich, whereas water was generated by using an in-house Milli-Q water purification system. Other chemicals, including O-benzylhydroxylamine (OBHA), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, ethyl acetate, and methanol, were also purchased from Sigma-Aldrich. Internal standards for targeted metabolomics, including sodium lactate ¹³C₃, citric D₄ (2,2,4,4) acid, fumaric ¹³C₄ acid, sodium pyruvate ¹³C₃, α-ketoglutaric D₆ acid, butyryl-l-carnitine D₃, propionyl-l-carnitine D₃, acetyl-l- carnitine D₃, decanoyl-l-carnitine D₃, hexanoyl-l-carnitine D₃, isovaleryl-l-carnitine D₉, octadecanoyl-l-carnitine D₃, octanoyl-l-carnitine D₃, and tetradecanoyl-l-carnitine D₃, were purchased from Isotec (Sigma-Aldrich), whereas succinic D₆ acid and disodium-2-hydroxy-glutarate D₃ (2,3,3) were purchased from CDN Isotopes.

Marquis B.J., Hurren N.M., Carvalho E., Kim I.Y., Schutzler S., Azhar G., Wolfe R.R, & Børsheim E. (2017). Skeletal Muscle Acute and Chronic Metabolic Response to Essential Amino Acid Supplementation in Hypertriglyceridemic Older Adults. Current Developments in Nutrition, 1(11), e002071.

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