Sodium hyaluronan (35,000 Da) was purchased from Lifecore Biomedical (Chaska, MN).PPa was purchased from Frontier Scientific (Logan, Utah). 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b] pyridinium 3-oxid hexafluorophosphate (HATU) was purchased from Chem-Impex International, Inc. (Wood Dale, IL). N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDC•HCl), adipic acid dihydrazide (ADH) and TWEEN® 80 were purchased from Sigma-Aldrich Co. (St. Louis, MO). Other chemicals and organic solvents, N, N-Diisopropylethylamine (DIPEA), N, N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO), and cell culture supplies were purchased from Fisher Scientific (Pittsburgh, PA). Dulbecco’s Modified Eagle’s Medium (DMEM) was purchased from Lonza (Allendale, NJ). LysoTracker® Blue DND-22 (ex/em, 373/422 nm), 4’, 6-Diamidino-2-Phenylindole (DAPI, ex/em, 358/461 nm) and Singlet Oxygen Sensor Green (SOSG) were purchased from Life Technologies™ (Grand Island, NY). The MDA-1986 human oral squamous carcinoma cell line was kindly provided by Dr. Jeffery Myers (The University of Texas, M.D. Anderson Cancer Center, Houston, TX). Double distilled water (ddH2O) was used for preparing all of the aqueous solutions.
Adipic acid dihydrazide adh
Manufactured by Merck Group
Sourced in United States
Adipic acid dihydrazide (ADH) is a chemical compound used in various industrial applications. It serves as a cross-linking agent, primarily utilized in the production of polyurethane and epoxy resins.
Automatically generated - may contain errors
Lab products found in correlation
N 3 dimethylaminopropyl n ethylcarbodiimide hydrochloride edc hcl, by Merck Group (1 mentions)
Lysotracker blue dnd 22, by Thermo Fisher Scientific (1 mentions)
Singlet oxygen sensor green (sosg), by Thermo Fisher Scientific (1 mentions)
4 6 diamidino 2 phenylindole (dapi), by Thermo Fisher Scientific (1 mentions)
Tween 80, by Merck Group (1 mentions)
Dulbecco s modified eagle s medium dmem, by Lonza (1 mentions)
Daunorubicin, by Cayman Chemical (1 mentions)
Acetonitrile, by Thermo Fisher Scientific (1 mentions)
Methanol, by Thermo Fisher Scientific (1 mentions)
N n dimethylformamide (dmf), by Thermo Fisher Scientific (1 mentions)
Dimethyl sulfoxide (dmso), by Thermo Fisher Scientific (1 mentions)
Fetal bovine serum (fbs), by Merck Group (1 mentions)
Phosphate buffered saline (pbs), by GE Healthcare (1 mentions)
Dulbecco s modified eagle medium dmem, by GE Healthcare (1 mentions)
Trypsin 1 mm edta, by Thermo Fisher Scientific (1 mentions)
Lc ms grade formic acid, by Thermo Fisher Scientific (1 mentions)
Hplc grade water, by Thermo Fisher Scientific (1 mentions)
Heparin, by Pfizer (1 mentions)
Calcium sulfate, by Merck Group (1 mentions)
2 n morpholino ethanesulfonic acid hydrate mes, by Merck Group (1 mentions)
8 protocols using adipic acid dihydrazide adh
1
Synthesis and Characterization of Hyaluronic Acid Conjugates
2
Doxorubicin and Drug Preparation Protocols
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Doxorubicin
and fetal bovine serum (FBS) were purchased from Sigma-Aldrich (St.
Louis, MO). Daunorubicin was purchased from Cayman Chemical Co. (Ann
Arbor, MI). BD syringes and needles, HPLC grade water, methanol, acetonitrile,
LC–MS grade formic acid, methanol, DMSO, DMF, and other organic
solvents were obtained from Fisher Scientific (Hampton, NH). 4-(p-Iodophenyl) butyric acid (IPBA) was purchased from Santa
Cruz (Dallas, TX). Adipic acid dihydrazide (ADH) was purchased from
Sigma-Aldrich (St. Louis, MO). Heparin was obtained from Pfizer (New
York, NY). Dulbecco’s Modified Eagle Medium (DMEM) and phosphate-buffered
saline (PBS) were purchased from GE healthcare Bio-Sciences (Pittsburgh,
PA). 0.25% w/v trypsin/1 mM EDTA was purchased from Gibco Life Technologies
(Grand Island, NY).
and fetal bovine serum (FBS) were purchased from Sigma-Aldrich (St.
Louis, MO). Daunorubicin was purchased from Cayman Chemical Co. (Ann
Arbor, MI). BD syringes and needles, HPLC grade water, methanol, acetonitrile,
LC–MS grade formic acid, methanol, DMSO, DMF, and other organic
solvents were obtained from Fisher Scientific (Hampton, NH). 4-(p-Iodophenyl) butyric acid (IPBA) was purchased from Santa
Cruz (Dallas, TX). Adipic acid dihydrazide (ADH) was purchased from
Sigma-Aldrich (St. Louis, MO). Heparin was obtained from Pfizer (New
York, NY). Dulbecco’s Modified Eagle Medium (DMEM) and phosphate-buffered
saline (PBS) were purchased from GE healthcare Bio-Sciences (Pittsburgh,
PA). 0.25% w/v trypsin/1 mM EDTA was purchased from Gibco Life Technologies
(Grand Island, NY).
3
Hyaluronate-Alginate Hydrogel Synthesis
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Sodium hyaluronate was purchased from Lifecore
(Mw = 700, 1500, 2500 kDa; Chaska, MN)
and Humedix (Mw = 1000 kDa; Anyang, Korea).
Sodium alginate (ALG) (Mw = 250 kDa, guluronate
unit content = 66%) was purchased from FMC Biopolymer (Sandvika, Norway).
RGD peptide (GGGGRGDSP) and HAV peptide (GGGGSHAVSS) were purchased
from Anygen (Seoul, Korea). 1-Ethyl-3-(dimethylaminopropyl)carbodiimide
(EDC) hydrochloride was purchased from Proteochem (Hurricane, UT). N-Hydroxysulfosuccinimide sodium salt (sulfo-NHS) was purchased
from Covachem (Loves Park, IL). Adipic acid dihydrazide (ADH), 2-(N-morpholino)ethanesulfonic acid (MES) hydrate, calcium
sulfate, deuterium oxide (D2O), Alcian blue, and direct
red 80 were purchased from Sigma-Aldrich (St. Louis, MO). Dulbecco’s
phosphate-buffered saline (DPBS), fetal bovine serum (FBS), Dulbecco’s
modified Eagle’s medium nutrient mixture F-12 (DMEM/F-12),
penicillin–streptomycin (P–S), and trypsin–ethylenediaminetetraacetic
acid (EDTA) were procured from Gibco (Grand Island, NY). The Ez-Cytox
kit was purchased from DoGenBio (Daejeon, Korea), and the Live/Dead
Viability/Cytotoxicity kit was purchased from Invitrogen (Waltham,
MA).
(Mw = 700, 1500, 2500 kDa; Chaska, MN)
and Humedix (Mw = 1000 kDa; Anyang, Korea).
Sodium alginate (ALG) (Mw = 250 kDa, guluronate
unit content = 66%) was purchased from FMC Biopolymer (Sandvika, Norway).
RGD peptide (GGGGRGDSP) and HAV peptide (GGGGSHAVSS) were purchased
from Anygen (Seoul, Korea). 1-Ethyl-3-(dimethylaminopropyl)carbodiimide
(EDC) hydrochloride was purchased from Proteochem (Hurricane, UT). N-Hydroxysulfosuccinimide sodium salt (sulfo-NHS) was purchased
from Covachem (Loves Park, IL). Adipic acid dihydrazide (ADH), 2-(N-morpholino)ethanesulfonic acid (MES) hydrate, calcium
sulfate, deuterium oxide (D2O), Alcian blue, and direct
red 80 were purchased from Sigma-Aldrich (St. Louis, MO). Dulbecco’s
phosphate-buffered saline (DPBS), fetal bovine serum (FBS), Dulbecco’s
modified Eagle’s medium nutrient mixture F-12 (DMEM/F-12),
penicillin–streptomycin (P–S), and trypsin–ethylenediaminetetraacetic
acid (EDTA) were procured from Gibco (Grand Island, NY). The Ez-Cytox
kit was purchased from DoGenBio (Daejeon, Korea), and the Live/Dead
Viability/Cytotoxicity kit was purchased from Invitrogen (Waltham,
MA).
4
Adipic Acid Dihydrazide-Modified Hyaluronic Acid Synthesis
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ADH-HA was produced by modifying the carboxylic acid moieties of the D-glucuronic acid with adipic acid dihydrazide. Adipic acid dihydrazide (ADH) (≥98%; Sigma-Aldrich, Saint Louis, MO, USA) was added to a 1 wt.% HA (Mw~1.5–1.8 MDa; Sigma-Aldrich, Saint Louis, MO, USA) solution prepared in Milli-Q water, at a molar ratio of 1 (ADH:HA). Then, the reaction occurred in the presence of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (≥98.0% Sigma-Aldrich, Saint Louis, MO, USA) (molar ratio 0.25; EDCI:HA) at pH 4.75, by addition of HCl dropwise, at room temperature, until no further pH variation was observed. The solution was then dialyzed firstly against diluted HCl containing 0.1 M NaCl (3 × 5 L, 48 h), followed by dialysis in diluted HCl (pH 3.5) (3 × 5 L, 24 h) and finally, against Milli-Q water. The resultant solution was frozen at −80 °C, recovered by freeze-drying, and stored until further use at −20 °C [11 (link)].
5
Hydrogel Erosion Kinetics Comparison
6
Alginate Oligomers and Trimannuronate Synthesis
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Guluronic acid oligomers (G oligomer) with two different molecular weight distributions were prepared 10 from partially acid hydrolysed, high guluronate alginate from Laminaria hyperborea stipes by acid precipitation to give oligomers with a number average degree of polymerization (DPn) of 21 and a fraction of guluronic acid (FG) of 0.90 (determined by NMR). Samples with DPn of 4 and 10 were prepared by further hydrolysis.
Trimannuronate was an inhouse sample prepared according to previously described methods. 11, 12 Dextran T-2000 (Mw = 2 000 000 g/mol) was purchased from Pharmacia Fine Chemicals. Maltotriose, trigalacturonic acid, adipic acid dihydrazide (ADH), O,O'-1,3,-propanediylbishydroxylamine dihydrochloride (PDHA) and 2-methylpyridine borane complex (α-picoline borane) was purchased from Sigma-Aldrich. PEG linkers were purchased from BroadPharma, US. All other chemicals were obtained from commercial sources and of analytical grade.
Trimannuronate was an inhouse sample prepared according to previously described methods. 11, 12 Dextran T-2000 (Mw = 2 000 000 g/mol) was purchased from Pharmacia Fine Chemicals. Maltotriose, trigalacturonic acid, adipic acid dihydrazide (ADH), O,O'-1,3,-propanediylbishydroxylamine dihydrochloride (PDHA) and 2-methylpyridine borane complex (α-picoline borane) was purchased from Sigma-Aldrich. PEG linkers were purchased from BroadPharma, US. All other chemicals were obtained from commercial sources and of analytical grade.
7
Preparation of PA-OMVs-DT Conjugate
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PA-OMVs were covalently conjugated to DT as a carrier protein using the adipic acid dihydrazide (ADH) (Sigma, USA) as a spacer molecule and 1-ethyl-3- (3- dimethyl aminopropyl) carbodiimide (EDAC) (Sigma, USA) as a linker. At first, 2 mg/ml of PA-OMVs was exposed to EDAC (final concentration of 0.1 M), and then reacted with ADH for 5 h at pH: 8. Thin-layer chromatography (TLC) was used to monitor the reaction's solution for 6 h. The conjugation of PA-OMVs and ADH was then purified for 24 h using three water changes and a 2 kDa cut-off dialysis bag against water at 4 °C. Then, 2 mg/ml of this solution reacted with DT containing 1 mg/ml protein in the presence of EDAC for 24 h. Then, PA-OMVs-DT conjugate was purified via Sephadex G-750 gel filtration chromatography (Sigma, USA).
The fractions were collected and centrifuged as a PA-OMVs-DT conjugate after being measured at 280 nm (protein) in the obtained fractions. Finally, the conjugated molecules were lyophilized in glass vials with a volume of 1 ml, passed through a 0.45 mm Millipore filter (USA), and kept at − 20 °C until injection.
The fractions were collected and centrifuged as a PA-OMVs-DT conjugate after being measured at 280 nm (protein) in the obtained fractions. Finally, the conjugated molecules were lyophilized in glass vials with a volume of 1 ml, passed through a 0.45 mm Millipore filter (USA), and kept at − 20 °C until injection.
8
Chondrogenic and Adipogenic Potential of MSCs
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Dextrin used in this study was Tackidex B 167 (Batch E 1445), a generous gift from Roquette (Lestrem, France). ECM from porcine SIS was a gift from Cook Biotech Inc. (West Lafayette, IN, USA). LLKKK18 (KEFKRIVKRIKKFLRKLV) was purchased from Schafer-N (Copenhagen, Denmark). Sodium m-periodate, diethylene glycol, adipic acid dihydrazide (ADH), silver nitrate, sodium thiosulphate, dexamethasone, ascorbic acid-2-phosphate, β-glycerphoshate, Alcian Blue, acetic acid, sodium carbonate (Na2CO3), calcium fluoride (CaF2), calcium hydrogen phosphate (CaHPO4), di-phosphorus penta-oxide (P2O5) and polyvinyl alcohol, formaldehyde, pepsin and hydrochloric acid (HCl) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Dulbecco's Modified Eagle Medium (DMEM) with GlutaMAX™ and without nucleosides, foetal bovine serum, streptomycin, penicillin, amphotericin B, HEPES Buffer solution, StemPro® Adipogenesis Differentiation kit and StemPro® Chondrogenesis Differentiation kit were obtained from Gibco®. AccutaseTM Cell detachment solution, Stain Buffer and CD90, CD105, CD44, CD34, CD19, CD11b, CD45, MHC Class II antibodies were obtained from BD Biosciences©.
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