Ethyl acetate

All solvents were of analytical grade and used without further purification. [Rh(η⁶-C₅Me₅)(μ-Cl)Cl]₂, [Ru(η⁶-p-cymene)(μ-Cl)Cl]₂, 5-nitro-8-hydroxyquinoline, L-proline, aqueous formaldehyde (30% (v/v)), bpy, tetrabutylammonium nitrate (TBAN), KH-phthalate, n-octanol, D₂O, doxorubicin, 2-(N-morpholino)ethanesulfonic acid (MES), human serum, Dulbecco’s Modified Eagle Medium (DMEM) and RPMI media, HSA (A8763, essentially globulin free), DG, 1-methylimidazole, 4,4-dimethyl-4-silapentane-1-sulfonic acid (DSS) were Sigma-Aldrich (Darmstadt, Germany) products and were used without further purification. Ac-Ala-His-Ala-NH₂ (AHA) and Ac-Phe-His-Ala-NH₂ (FHA) peptides were purchased from GenScript (Piscataway, NJ, USA). HQCl-L-Pro was prepared according to our former report [12 (link)]. NaH₂PO₄, Na₂HPO₄, KH₂PO₄, KCl, KNO₃, NaCl, KOH, HNO₃, ethanol, ethyl acetate, dichloromethane, n-hexane, diethyl-ether, and methanol were purchased from Molar Chemicals (Halásztelek, Hungary) or VWR (Budapest, Hungary).

Acetone, dichloromethane (DCM), n-hexane, 2-propanol, toluene (reagent grade) were obtained from Molar Chemicals, Hungary, and they were purified by atmospheric pressure distillation. Furthermore, acetonitrile (MeCN), tetrahydrofuran (THF), methanol (MeOH), dimethyl-formamide (DMF), dimethyl-sulfoxide (DMSO), pyridine (HPLC grade, VWR, Darmstadt, Germany), ethylacetate (EtOAc), (reagent grade, Molar Chemicals, Hungary), 1,4-dioxane (reagent grade, Reanal, Hungary), 1,4-diaminonaphthalene (Sigma-Aldrich, Schnelldorf, Germany) were used without further purification. 2,6-diaminonaphthalene was purchased from Manchester Organics (London, UK) and purified by column chromatography.
The 1-amino-4-isocyanonaphthalene (1,4-ICAN) and the 2-amino-6-isocyanonaphthalene (2,6-ICAN) isomers were synthesized from the corresponding diamines (1,4- and 2,6-diaminonaphthalene), and the obtained products were characterized similarly to that reported for the 1-amino-5-isocyanonaphthalene [15 (link)]. The details of the synthesis and the characterization of 1,4-ICAN and 2,6-ICAN are given in the Supporting Information.

Chloroform, ethyl acetate and methanol of reagent grade as well as HPLC-grade methanol and acetonitrile were purchased from Molar Chemicals Kft. (Halásztelek, Hungary). Dimethyl sulfoxide (DMSO), n-dodecane, sodium chloride (NaCl), hydrochloric acid (HCl), disodium hydrogen phosphate heptahydrate (Na₂HPO₄∙7H₂O) and sodium dihydrogen phosphate monohydrate (NaH₂PO₄∙H₂O) were obtained from Reanal-Ker (Budapest, Hungary), while phosphatidylcholine, cholesterol and the porcine polar brain lipid extract were purchased from Merck (Darmstadt, Germany). Acetic acid 100% for HPLC LiChropur™, pyruvate and PBS tablet (Phosphate Buffered Saline, pH 7.4) were acquired from Sigma-Aldrich (Steinheim, Germany). Roswell Park Memorial Institute 1640 medium (RPMI-1640) and Dulbecco’s Modified Eagle’s Medium (DMEM) were supplied by Lonza (Basel, Switzerland). Fetal bovine serum (FBS) was purchased from Biosera (Nuaille, France). Non-essential amino acids, penicillin/streptomycin (10,000 units penicillin and 10 mg streptomycin/mL) and trypsin were obtained from Gibco (Thermo Fisher Scientific, Waltham, MA, USA). High-purity water was gained by a Millipore Direct Q5 Water Purification System (Billerica, MA, USA).