Adipic acid dihydrazide

Manufactured by Merck Group

Sourced in United States

Adipic acid dihydrazide is a chemical compound used as a laboratory reagent. It is a dihydrazide derivative of adipic acid and serves as a bifunctional linker or cross-linking agent in various applications.

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Lab products found in correlation

Dimethyl sulfoxide (dmso), by Merck Group (7 mentions) N hydroxysuccinimide, by Merck Group (5 mentions) Ethylene glycol, by Merck Group (4 mentions) Triethylamine, by Merck Group (4 mentions) N n dicyclohexylcarbodiimide, by Merck Group (4 mentions) Fetal bovine serum (fbs), by Thermo Fisher Scientific (4 mentions) Sodium periodate, by Merck Group (4 mentions) N 3 dimethylaminopropyl n ethylcarbodiimide hydrochloride, by Merck Group (3 mentions) Activated charcoal, by Merck Group (3 mentions) 4 dimethylaminopyridine, by Merck Group (3 mentions) Hyaluronic acid, by Merck Group (3 mentions) Paraformaldehyde (pfa), by Merck Group (3 mentions) Streptomycin, by Welgene (3 mentions) Penicillin, by Welgene (3 mentions) Trypsin, by Welgene (3 mentions) Chlorin e6 ce6, by Frontier Scientific (3 mentions) Bovine serum albumin (bsa), by Merck Group (2 mentions) Phosphate buffered saline (pbs), by Merck Group (2 mentions) 1 hydroxybenzotriazole, by Merck Group (2 mentions) Mitoxantrone, by Merck Group (2 mentions)

Spelling variants of this product

Adipic acid (35 citations) Adipic acid dihydrazide agarose beads (9 citations) Adipic acid dihydrazide (ADH) (8 citations) Adipic dihydrazide (5 citations) Adipic acid dihydrazide agarose (2 citations)

29 protocols using adipic acid dihydrazide

Synthesis of Coumarin-6-Labeled Hyaluronic Acid

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Adipic acid dihydrazide (ADH), coumarin-6, dimethyl sulfoxide (DMSO), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDC), and thioacetamide (TAA) were obtained from Sigma-Aldrich Co. (St. Louis, MO, USA). DMSO (extra dry) was purchased from Acros Co. (Geel, Belgium). N-hydroxysuccinimide (NHS) and N,N’-dicyclohexylcarbodiimide (DCC) were obtained from Fluka Ltd. (Buchs, Switzerland). Poly(d,l)-lactide (M_w 16,000–35,000 Da) was purchased from Green Square (Taichung, Taiwan). Hyaluronic acid was provided by Dr. Shih-lan Hsu. All other reagents were of the highest grade commercially available.

Chen Y.N., Hsu S.L., Liao M.Y., Liu Y.T., Lai C.H., Chen J.F., Nguyen M.H., Su Y.H., Chen S.T, & Wu L.C. (2016). Ameliorative Effect of Curcumin-Encapsulated Hyaluronic Acid–PLA Nanoparticles on Thioacetamide-Induced Murine Hepatic Fibrosis. International Journal of Environmental Research and Public Health, 14(1), 11.

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Biopolymer-Based Hydrogel Fabrication

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Sodium alginate was purchased from Pronova Biopolymers (Oslo, Norway) with an average molecular weight of ~250 kDa and with high guluronate content (Protoanal LF 20/40). Adipic acid dihydrazide (AAD), 1-ethyl-3-(dimethylaminopropyl) carbodiimide (EDC), MES, 1-hydroxybenzotriazole (HOBT), iron (II,III) oxide powder (< 5 micron), mitoxantrone, phosphate buffered saline (PBS), bovine serum albumin (BSA), Sigmacote, Fluorescein isothiocyanate (FITC)-dextrans, Rhodamine-dextran, and FITC-Diethylaminoethyl (DEAE)-dextrans were all purchased from Sigma-Aldrich (St. Louis, MO). Mouse Bone Morphogenetic Protein-2 (BMP-2), Thymus Chemokine-1 (TCK-1), and Enzyme-linked Immunosorbent Assay (ELISA) kits and kit reagents were purchased from R&D Systems (Minneapolis, MN).

Kennedy S., Roco C., Déléris A., Spoerri P., Cezar C., Weaver J., Vandenburgh H, & Mooney D. (2018). Improved magnetic regulation of delivery profiles from ferrogels. Biomaterials, 161, 179-189.

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Hydrazide-Based Polymer Synthesis and Characterization

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Propanoic acid hydrazide (≥90%), O-ethylhydroxylamine hydrochloride (97%), adipic acid dihydrazide (≥98%,), O,O′-1,3-propanediylbishydroxylamine dihydrochloride (98%), propyl isocyanate, hexamethylenediisocyanate, hydrazine monohydrate, activated charcoal (Norit), sodium periodate (NaIO₄) and ethylene glycol were purchased from Sigma-Aldrich. Propyl semicarbazide and N,N′-(hexane-1,6-diyl)bis(hydrazinecarboxamide) (HDCA) (¹H NMR structures shown in Figures S1 and S2 in Supplementary Information) were synthesized according to literature [38 (link)]. Sodium alginate was purchased from FMC (Manugel GMB, Lot No. G9402001, Dialysis membrane (Spectra/Por^®) with molecular weight cut off (MWCO) 3500 Dalton (Da) from VWR, Netherlands.
Dulbecco’s modified Eagle’s medium (DMEM, high glucose and supplemented with GlutaMAX™ and Sodium Pyruvate), DEME-F12 (low glucose), Dulbecco’s phosphate buffer saline (PBS), fetal bovine serum (FBS), penicillin/streptomycin (P/S), calcein AM, ethidium homodimer, Alexa Fluor^® 488 Phalloidin, DAPI and PrestoBlue™ cell viability reagent were purchased from Thermo Fisher Scientific.

Hafeez S., Ooi H.W., Morgan F.L., Mota C., Dettin M., van Blitterswijk C., Moroni L, & Baker M.B. (2018). Viscoelastic Oxidized Alginates with Reversible Imine Type Crosslinks: Self-Healing, Injectable, and Bioprintable Hydrogels. Gels, 4(4), 85.

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Hyaluronic Acid-Based Theranostic Nanoparticles

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Hyaluronic acid (HA, Mw = 4.8 kDa), 3-(diethylamino)propylamine (DEAP), N-hydroxysuccinimide (NHS), N,N’-dicyclohexylcarbodiimide (DCC), triethylamine (TEA), deoxycholic acid (DOCA), 4-dimethylamino pyridine (DMAP), pyridine, dimethyl sulfoxide (DMSO), sodium tetraborate, adipic acid dihydrazide (ADH), doxorubicin hydrochloride (DOX), paraformaldehyde, heparin, and Triton X-100, 4′,6-diamidino-2-phenylindole dihydrochloride (DAPI) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Chlorin e6 (Ce6) was purchased from Frontier Scientific Inc (Logan, UT, USA). RPMI-1640 medium, DMEM medium, fetal bovine serum (FBS), phosphate buffered saline (PBS), ethylene diamine tetra-acetic acid (EDTA), penicillin, trypsin, and streptomycin were purchased from Welgene Inc (Seoul, Korea). EV-depleted FBS was purchased from System Biosciences Inc. (Palo Alto, CA, USA). Cell Counting Kit-8 (CCK-8) was purchased from Dojindo Molecular Technologies Inc. (Santa Clara, CA, USA). Wheat Germ Agglutinin Alexa Fluor^® 488 Conjugate (WGA-Alexa Fluor^® 488), fluorescein isothiocyanate (FITC) were purchased from Life Technologies (Carlsbad, CA, USA).

Park J., Lee H., Youn Y.S., Oh K.T, & Lee E.S. (2020). Tumor-Homing pH-Sensitive Extracellular Vesicles for Targeting Heterogeneous Tumors. Pharmaceutics, 12(4), 372.

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Nisin A-Based Antimicrobial Hydrogel Synthesis

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Nisin A (95%, isolated from Lactococcus lactis in sauerkraut) was obtained from Handary, Belgium. Dextran (from Leuconostoc mesenteroides, 100–200 kDa), Dextran 60 (from L. mesenteroides, ~ 60 kDa), alginic acid (from brown algae, low viscosity (4–12 cps), M/G ratio 1.43 as determined by ¹³C SS-NMR below), sodium (meta) periodate (> 99%), ethylene glycol (99%), N-hydroxysulfosuccinimide sodium salt (S-NHS, > 98%), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC, crystalline), adipic acid dihydrazide (ADH, > 98%), hydroxylamine hydrochloride, glycol chitosan (degree of deacetylation: > 60%), trifluroacetic acid (TFA, > 99%), acetonitrile (ACN, > 99.9%), phosphate-buffered saline (tablets, PBS), and sodium dodecyl sulphate were all purchased from Sigma-Aldrich, Ireland. Dimethyl sulfoxide (DMSO, for molecular biology) was purchased from VWR International. Liquid nitrogen was supplied by BOC Gases (Ireland). Glycine (lab grade), 2,4,6-trinitrobenzene sulfonic acid (5% w/v, MeOH), potassium chloride (99%) and hydrochloric acid (37%, fuming) were purchased from Fisher Scientific, Ireland. Pullulan/Dextran standards for light scattering/tetra detection (TDS3030) were provided by Particular Sciences, Dublin, Ireland. Staphylococcus aureus (DSM 20231) was purchased from the Leibniz Institute DSMZ-German collection of Microorganisms and Cell Cultures.

Flynn J., Culebras M., Collins M.N, & Hudson S.P. (2022). The impact of varying dextran oxidation levels on the inhibitory activity of a bacteriocin loaded injectable hydrogel. Drug Delivery and Translational Research, 13(1), 308-319.

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Protein Conjugation Protocol

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N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), N-Hydroxysulfosuccinimide (sNHS), Adipic acid dihydrazide (ADH) and a 25% solution of Glutaraldehyde (GA) in water were obtained from Sigma-Aldrich (St. Louis, MO). N-(ε-maleimidocaproyloxy)succinimide (EMCS), N-(ε-maleimidocaproyloxy)sulfo-succinimide sodium salt (sulfo-EMCS), and S-acetylthioglycolic acid N-hydroxysuccinimidyl ester (SATA) were purchased from Pierce Biotechnology Inc. (Rockford, IL). CFD10 and CFD100 Amicon centrifugal filtration devices with 10 kDa and 100 kDa MWCO respectively were obtained from Millipore (Billerica, MA).

Scaria P.V., Chen B., Rowe C.G., Jones D.S., Barnafo E., Fischer E.R., Anderson C., MacDonald N.J., Lambert L., Rausch K.M., Narum D.L, & Duffy P.E. (2017). Protein-protein conjugate nanoparticles for malaria antigen delivery and enhanced immunogenicity. PLoS ONE, 12(12), e0190312.

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Multifunctional Nanoparticle Drug Delivery System

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γ-Cyclodextrin (γ-CD), succinic anhydride (SA), dimethylsulfoxide (DMSO), N,N’-dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP), 3-(diethylamino)propylamine (DEAP), hydroxysuccinimide (NHS), triethylamine (TEA), sodium tetraborate, adipic acid dihydrazide (ADH), N-phenylacetic acid (PA), methanol (MeOH), triiron dodecacarbonyl (FeCO), acetonitrile (HPLC grade), deionized water (HPLC grade), sodium azide, tween 80, hemoglobin (Hb), sodium dithionite, 4′,6-diamidino-2-phenylindole dihydrochloride (DAPI), and formaldehyde were purchased from Sigma-Aldrich (St. Louis, MO, USA). Sodium hyaluronate (HA, M_w = 4.8 kDa) was purchased from Lifecore Biomedical Inc. (Chaska, MN, USA). Paclitaxel (PTX) was purchased from Samyang Biopharm (Seoul, Republic of Korea). RPMI-1640, fetal bovine serum (FBS), penicillin, streptomycin, trypsin, and ethylene diamine tetra-acetic acid (EDTA) were purchased from Welgene Inc. (Seoul, Republic of Korea). Chlorin e6 (Ce6) was purchased from Frontier Scientific Inc. (Logan, UT, USA). Wheat Germ Agglutinin Alexa Fluor^® 488 conjugate (WGA-Alexa Fluor^® 488) was purchased from Life Technologies (Carlsbad, CA, USA). Cell Counting Kit-8 (CCK-8) was purchased from Dojindo Molecular Technologies Inc. (Rockville, MD, USA).

Lee E, & Lee E.S. (2023). Development of pH-Responsive Hyaluronic Acid-Conjugated Cyclodextrin Nanoparticles for Chemo-/CO-Gas Dual Therapy. Pharmaceutics, 15(7), 1818.

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Crosslinked Hyaluronic Acid Hydrogel

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Materials, growth factors and cells used in the present study were purchased from varying suppliers. HA with an average molecular weight of

8.8 \times 10^{5}

Da was purchased from Bloomage Freda Biopharm Co., Ltd. (Harrogate, UK); sodium periodate (NaIO₄), ethylene glycol, adipic acid dihydrazide (ADH), paraformaldehyde (PFA), and sucrose from Sigma-Aldrich Co. (St. Louis, MO, USA); trizol from Thermo Fisher Scientific (Waltham, MA, USA); DEPC from Biotopped (Beijing, People's Republic of China); and neutral balsam and 50 kDa cellulose dialysis from Shanghai Yuanye Bio-Technology Co., Ltd. (Shanghai, People's Republic of China). TGF-β1 and IL-6 were from MedChemExpress (Shanghai, People's Republic of China); and human Tenon's capsule fibroblasts (HTFs) and human umbilical vein endothelial cells (HUVECs) from the Institute of Biochemistry and Cell Biology and the Chinese Academy of Sciences (Shanghai, People's Republic of China). Dulbecco's Modified Eagle Medium (DMEM) and fetal bovine serum (FBS) were from Thermo Fisher Scientific; hematoxylin and eosin stain from Solarbio (Beijing, People's Republic of China); TGF-β1 polyclonal antibody from Boster Biological Technology Co., Ltd. (Wuhan, People's Republic of China); and IL-6 polyclonal antibody from Affinity Biosciences Co., Ltd. (Beijing, People's Republic of China).

Wang R., Chen B., Wei H., Yan W., Wu Y., Wang C., Zhang B., Liu F., Tian H., Chen X, & Tian W. (2022). Collecting and deactivating TGF-β1 hydrogel for anti-scarring therapy in post-glaucoma filtration surgery. Materials Today Bio, 14, 100260.

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Doxorubicin-Loaded Hyaluronic Acid Hydrogels

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Hyaluronic acid (HA, M_w = 4.8 kDa), adipic acid dihydrazide (ADH), N,N′-dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (NHS), dimethyl sulfoxide (DMSO), triethylamine (TEA), 2,3-dimethylmaleic anhydride (DMA), sodium hydroxide (NaOH), ferrous chloride tetrahydrate (FeCl₂·4H₂O), doxorubicin hydrochloride (DOX), formaldehyde, and triton X-100 were purchased from Sigma-Aldrich (St. Louis, MO, USA). Phosphate buffered saline (PBS), Roswell Park Memorial Institute-1640 (RPMI-1640), fetal bovine serum (FBS), penicillin, streptomycin, trypsin, and ethylene diaminetetraacetic acid (EDTA) were purchased from Welgene Inc. (Seoul, Korea). Cell Counting Kit-8 (CCK-8) was purchased from Dojindo Molecular Technologies Inc. (Rockville, MD, USA).

Bae Y., Kim Y, & Lee E.S. (2021). Endosomal pH-Responsive Fe-Based Hyaluronate Nanoparticles for Doxorubicin Delivery. Molecules, 26(12), 3547.

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Aptamer-Hyaluronic Acid Conjugate Synthesis

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5TR1 aptamer (5TR1) (5′–COOH–GAAGTGAAAATGACAGAACACAACA-3′) was produced by MicroSynth (Switzerland). Hyaluronic acid (MW = 50,000 Da) (HA) was purchased from Creative PEGworks. The following materials were bought from Sigma-Aldrich in Munich, Germany: N-hydroxysulfosuccinimide (NHS), Adipic acid dihydrazide, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC), Epirubicin, and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). Merck in Darmstadt, Germany, supplied the other necessary materials.

Jamshidi Z., Dehghan R., Nejabat M., Abnous K., Taghdisi S.M, & Hadizadeh F. (2024). Dual-targeting CD44 and mucin by hyaluronic acid and 5TR1 aptamer for epirubicin delivery into cancer cells: Synthesis, characterization, in vitro and in vivo evaluation. Heliyon, 10(2), e24833.

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