4 4 6 dimethoxy 1 3 5 triazin 2 yl 4 methylmorpholinium chloride dmt mm

Poly-l-lysine⋅hydrobromide (PLL⋅HBr, Mw: 1–5 kDa), deoxycholic acid (DOCA), methoxy polyethylene glycol acetic acid (MPEG-COOH, Mw: 5K), CUR, pyrene, deuterium oxide (D₂O), dimethyl solfoxide-_d6 (DMSO-_d6), and phosphate-buffered saline (PBS, pH 7.4) were purchased from Sigma-Aldrich (St. Louis, MO). Cyanine 5.5 carboxylic acid (cy5.5-COOH) was obtained from Lumiprobe Corporation (Hallandale Beach, FL). 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) was supplied from Wako Pure Chemical Industries (Osaka, Japan). Dialysis tubes (Spectrum Laboratories Inc., Rancho Dominguez, CA) were used for purification. Acidic PBS (pH 5.5 and 6.8) was adjusted using hydrochloric acid (HCl). The human hepatoma Hep3B cell line was supplied by the Korean Cell Line Bank (Seoul, Republic of Korea). High glucose Dulbecco’s modified eagle medium (DMEM), fetal bovine serum (FBS), and penicillin–streptomycin (PS) were used for cell culture. Cell counting kit-8 (CCK-8) was purchased from Dojindo Molecular Technologies, Inc. (Kumamoto, Japan). The nuclei of the cells were counterstained with ProLong^® Gold anti-fade reagent with 4′,6-diamidino-2-phenylindole (DAPI, Invitrogen, OR). The AP In Situ Cell Death Detection Kit was purchased from Roche Life Science (Indianapolis, IN). All chemicals were used as received without further purification.

Glycol chitosan (GC) and glycidyl methacrylate (GM) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Bone morphogenetic protein-2 (BMP-2) and transforming growth factor-beta1 (TGF-β1) were purchased from Thermo Fisher Scientific (Waltham, MA, USA). 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) was obtained from Wako Pure Chemical Industries (Osaka, Japan). Dialysis tubes (Spectrum Laboratories Inc., Rancho Dominguez, CA, USA) were used for purification. The MC3T3-E1 cell line was purchased from the American Type Culture Collection (ATCC; Manassas, VA, USA). α-Minimum Eagle’s medium, fetal bovine serum (FBS), and penicillin and streptomycin (PS) were supplied by Life Technologies (Grand Island, NY, USA). All chemicals were used as received.

N-Carboxyanhydride of ε-trifluoroacetyl-L-lysine (NCA-Lys(TFA)) was purchased from Chuo Kasei Co., Ltd. (Osaka, Japan). MeAIB was purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). 11-Azido-3,6,9-trioxaundecan-1-amine, Boc-L-glutamic acid 1-benzyl ester (Boc-Glu-OBzl), Boc-L-glutamic acid 5-benzyl ester (Boc-Glu(OBzl)-OH), RPMI 1640 medium, Dulbecco’s modified Eagle’s medium (DMEM), penicillin/streptomycin, BCH, and trypsin/EDTA were purchased from Sigma Aldrich Corporation (St. Louis, MO). Dimethylsulfoxide (DMSO), triethylamine (TEA), N-methyl-2-pyrolidone (NMP), BzlSer, Gln, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM), and D-PBS(-) were purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan). DMSO was purified by distillation under reduced pressure before use. Dibenzocyclooctyne-Cy5 (Cy5-DBCO) was purchased from Click Chemistry Tools (Scottsdale, AZ). Fetal bovine serum (FBS), and Hoechst 33342 were purchased from Thermo Fisher Scientific, Inc. (Waltham, MA). Bovine serum albumin (BSA) was purchased from Nacalai Tesque, Inc. (Kyoto, Japan).

α,ω-Bis(2-amino-3-phenylpropyl) poly(ethylene glycol) (PEG-Ph-NH₂) (M_n = 10,060, M_w/M_n = 1.02) was synthesized according to our previous report [24 (link)]. α,ω-Bisaminopropyl PEG (PEG-NH₂) (M_n = 10,200, M_w/M_n = 1.03) was obtained from NOF Corporation (Tokyo, Japan). α-Cyclodextrin (α-CD) was obtained from Ensuiko Sugar Refining (Tokyo, Japan). 4-(Azidomethyl)benzoic acid was synthesized according to the previous report [27 (link)]. 4-Azidobenzoic acid, 4-methylbenzoic acid, p-(tert-butyl)phenylacetylene, and 2-(2-hydroxyethoxy)ethylamine (HEEA) were obtained from TCI (Tokyo, Japan). 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) and copper(II) sulfate pentahydrate (CuSO₄) were obtained from Wako Pure Chemical Industries (Osaka, Japan). N,N’-Carbonyldiimidazole (CDI) and (+)-sodium L-ascorbate were obtained from Sigma-Aldrich (St. Louis, MO, USA). Dibenzocyclooctyne-fluor 488 (DF488) was obtained from Click Chemistry Tools (Scottsdale, AZ, USA). Other solvents were obtained from Kanto Chemicals (Tokyo, Japan).

EYPC was kindly donated by NOF Co. (Tokyo, Japan). 1,2-Cyclohexanedicarboxylic anhydride, OVA, fluorescein isothiocyanate (FITC), p-xylene-bis-pyridinium bromide (DPX) were purchased from Sigma (St. Louis, MO, USA). Dextran having molecular weight of 70,000, 1-aminodecane, pyranine and Triton X-100 were obtained from Tokyo Chemical Industries Ltd. (Tokyo, Japan). 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methyl morpholinium chloride (DMT-MM) was from Wako Pure Chemical Industries Ltd. (Osaka, Japan). 1,1′-Dioctadecyl-3,3,3′,3′-tetramethylindocarbocyanine perchlorate (DiI) was from Life Technologies. Dialysis tube (molecular weight cutoff: 10 kDa) was purchased from Sekisui Medical Co., Ltd. (Tokyo, Japan). FITC-OVA was prepared by reacting OVA (10 mg) with FITC (11.8 mg) in 0.5 M NaHCO₃ (4 mL, pH 9.0) at 4 °C for three days and subsequent dialysis [13 (link)]. 3-Methyl glutarylated Dextrans (MGlu65-Dex and MGlu67-Dex-C₁₀) were prepared as previously reported [15 (link)].

Amino-terminal ethylenediamine core polyamidoamine (PAMAM) dendrimers of generation-4 and generation-5 (G4 and G5) were purchased from Sigma–Aldrich Co. (St. Louis, MO, USA). 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) was purchased from FUJIFILM Wako Pure Chemical Co. (Tokyo, Japan). N-(tert-butoxycarbonyl)-1,2-diaminoethane (Boc-ethylenediamine) and fluorescein-4-isothiocyanate (FITC) were purchased from Tokyo Chemical Industry Co., Ltd (Tokyo, Japan). 2-(4-isothiocyanatobenzyl)-diethylenetriamine pentaacetic acid (p-SCN-Bn-DTPA) was purchased from Macrocyclics (Plano, TX, USA). ¹¹¹InCl₃ and HiLyte™ Fluor 488 acid, SE (HF488) were obtained from Nihon Medi-Physics Co., Ltd. (Tokyo, Japan) and AnaSpec Inc. (Fremont, CA, USA), respectively. Phycoerythrin (PE)-conjugated antibodies, such as CD3-PE (clone REA641) and CD45R (B220)-PE (Clone REA755), were purchased from Miltenyi Biotec, Ltd. (Bergisch Gladbach, Germany).

Egg yolk phosphatidylcholine (EYPC) was kindly donated by NOF Co. (Tokyo, Japan). Allyl-α-D-mannopyranoside, cysteamine hydrochloride, 3-methylglutaric anhydride, Curdlan from Alcaligenes faecalis, ovalbumin (OVA), bovine serum albumin (BSA), p-xylene-bis-pyridinium bromide (DPX) and calcein were purchased from Sigma (St. Louis, MO, USA). Triton X-100, 1-Aminodecane, and pyranine were obtained from Tokyo Chemical Industries Ltd. (Tokyo, Japan). Concanavalin A and 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methyl morpholinium chloride (DMT-MM) were obtained from Wako Pure Chemical Industries Ltd. (Osaka, Japan), while 1,1′-Dioctadecyl-3,3,3′,3′-tetramethylindocarbocyanine perchlorate (DiI) was from Life Technologies.