Mercaptoundecanoic acid

4-aminothiophenol (4-ATP or pATP), cysteamine (CYS), cystamine, L-cysteine, mercaptopropionic acid (MPA), mercaptoundecanoic acid (MUA), 4-mercaptobenzoic acid (4-MB), hexanethiol (HT), imidazole, 2,6-dimethoxyphenol (DMP), NHS (N-hydroxysuccinimide), EDC (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride), Na₂HPO₄, NaH₂PO₄H₂O, and sodium chloride (NaCl) were obtained from Sigma-Aldrich. Sodium fluoride (NaF) and sodium azide (NaN₃) were obtained from Merck-Suprapur. All chemicals were used as received without further purification.

Sodium citrate, hydrogen tetrachloroaurate trihydrate, sulfuric acid, ubiquinone-1, 1-mercaptohexanol (MCH), 1-hexanethiol (HT), mercaptohexanoic acid (MHA), mercaptoundecanoic acid (MUA), 3,3′-dithiodipropionic acid di(N-hydroxysuccinimide ester) (DTSP), dimethyl sulfoxide (DMSO), Nα′,Nα″-bis(carboxymethyl)-l-lysine, and nickel sulfate were purchased from Sigma (St-Louis, MO, USA); potassium phosphate dibasic trihydrate from Acros Organics (Geel, Belgium); mercaptopropionic acid and cysteamine (cyst) from Tokyo Chemical Industry (Tokyo, Japan). The 1,2-dioleoyl-sn-glycero-3-phospho-rac-(1-glycerol) (sodium salt) (PG) and 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (PE) were provided by Avanti Polar Lipids Inc. (Alabaster, AL, USA). These chemicals were used without any additional purification. Thiols were dissolved in ethanol, and lipids were prepared in a 1/3 (v/v) mixture of ethanol and chloroform.

Gold(III) chloride hydrate (HAuCl₄∙xH₂O), cetyl trimethylammonium bromide (CTAB), sodium borohydride (NaBH₄), silver nitrate (AgNO₃), ascorbic acid, FeCl₃·6H₂O, sodium citrate dihydrate, polyacrylamide, tetraethoxysilane (TEOS), (3-aminopropyl)triethoxysilane (APTES), mercaptoundecanoic acid (MUA), (3-mercaptopropyl)trimethoxysilane (MPTMS), N-hydroxysuccinimide (NHS), and N-ethyl-N’-(3-(dimethylamino)propyl)carbodiimide hydrochloride (EDC), were purchased from Sigma Aldrich, (Paris, France). Millipore water and reagent grade ethanol (EtOH) were used.

Horse heart cyt c, 2,3-dimethoxy-5-methyl-p-benzoquinone (Q₀), mercaptoundecanoic acid,
and mercaptoundecanol were purchased from Sigma-Aldrich. Milli-Q water
(Millipore, MA) was used in all preparations and procedures. Planar
disc 2 mm Ag electrodes were purchased from CH Instruments, Austin,
TX. Reference electrodes, counter electrodes, and potentiostats were
purchased from Metrohm Autolab BV, Utrecht, Netherlands. A high-power
multiarray LED (870-66-60) centered at 870 nm was purchased from Roither-Lasertechnik
GmbH, Wien, Austria.

Tetrachloroauric acid (HAuCl4.3H2O; ≥99.9% trace metals basis), sodium citrate monobasic (Na3C6H5O7; purum p.a., anhydrous, ≥99.0%), mercaptoundecanoic acid (MUA; 95%), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC; purum, ≥98.0%) and N—hydroxisuccinimide (NHS; 98%) were purchased from Sigma-Aldrich. 2-(N-morpholino) ethanesulfonic acid (MES; 99%) was supplied by Vetec. All the samples were prepared by using deionized water (Direct Q 3 UV-MilliQ, Merck Millipore; Darmstadt, Germany). The peptides C7H2 (YISCYNGATSYNQKFK) and HuAL1 (RASQSVSSYLA) were supplied by Peptide 2.0 (≥95% of purity). RPMI (Gibco) and DMEM (Gibco) medium were prepared in deionized water. Fetal bovine serum (FBS), streptomycin, and ampicillin were used to supplement the medium and were supplied by Cultilab and ThermoFisher Scientific, respectively. For cell viability assay, it was used trypan blue (solution 0.4%) and trypsin, both purchased from Sigma Aldrich. The antimicrobial studies were carried out in agar Muller-Hinton (Kasvi) and agar Sabouraud (Kasvi). Brain Heart Infusion (BHI, KASVI) was used to prepare pre-inocula of the strains. The in vivo experiments were carried out according to the Animal Use Ethics Committee (CEUA) of the Federal University of São Paulo (ethical approval code: 2210300817; 8-11-2017).