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Conjugation of Polymers with Biomolecules and Polymeric Vaccine Development Technologies
Published in Mesut Karahan, Synthetic Peptide Vaccine Models, 2021
In the covalent bonding method the peptide protein is the most preferred carbodiimide of direct cross-linking reagents used to form protein-protein conjugates. The carbodiimides, in which water-soluble and insoluble forms exist, mediate the binding of the carboxylate and primary amines with the amide bond, and the phosphamide bond of the phosphate and amino groups. The water-soluble carbodiimides are more preferred in biochemical conjugates because many macromolecules of biological origin are soluble in aqueous buffer solutions. Carbodiimides which are insoluble in water are generally used in peptide synthesis and in bioconjugation reactions where the molecules must be dissolved only in organic solvents. Products and byproducts that occur in these reactions can only be dissolved in organic solvents and are not soluble in water (Hermanson 1996; McCarthy et al. 2014) (Figure 5.5).The activation carboxyl group of polymers, and coupling with the peptide to obtain a polymer-peptide conjugate with [1-Ethyl-3- (3-dimethylaminopropyl)] EDC method (Mansuroğlu and Mustafaeva 2012).
The Modification Of Carboxyl Groups
Published in Roger L. Lundblad, Chemical Reagents for Protein Modification, 2020
There is additional evidence supporting the influence of solvent conditions on carbodiimide-mediated modification of proteins. Deen et al.37 demonstrated that the use of an N-methylimidazole buffer for EDC-mediated coupling of peptides to carrier proteins markedly reduced the incidence of neodeterminants strictly related to coupling chemistry (in this system, such neodeterminants likely arise as O-acylureas).
The Modification of Carboxyl Groups
Published in Roger L. Lundblad, Claudia M. Noyes, Chemical Reagents for Protein Modification, 1984
Roger L. Lundblad, Claudia M. Noyes
In addition to the information presented in Table 2, certain examples of carbodiimide-mediated modification should be discussed in greater detail. The inactivation of yeast hexokinase33 by reaction with l-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-/?-toluenesulfonate is shown in Figure 5. These experiments should be compared to those shown in Figure 6 with the same reagent in the presence of nitrotyrosine ethyl ester. The use of the nitrotyrosine derivative as the attacking nucleophile allowed the introduction of a “reporter group” onto the glutamyl residue modified in this study. The use of the nitro-tyrosyl derivative also permitted the facile determination of the extent of modification (in 0.1 M NaOH, thus the nitrotyrosyl derivative had Amax at 430 nm (e = 4.6 x 10 3 MHcm_l). Studies on the use of this carbodiimide in the modification of Phosphorylase b have been reported.34Figure 7 shows the reaction of rabbit muscle Phosphorylase with 1-cyclohexyl-3-(2-morpholinyl-(4)-ethyl) carbodiimide metho-p-toluenesulfonate (CMC) in the absence of added nucleophile while Figure 8 shows the effect of added nucleophiles on the rate of inactivation.
Hepatocyte-targeting and tumor microenvironment-responsive liposomes for enhanced anti-hepatocarcinoma efficacy
Published in Drug Delivery, 2022
Dongliang Cheng, Zhiwei Wen, Hui Chen, Shiyuan Lin, Wei Zhang, Xin Tang, Wei Wu
Aladdin Industrial Corporation (Shanghai, China) provided hydroxycamptothecin (HCPT, purity > 98%), soybean phospholipids (SPC, purity > 98%), 1,2-dioloyl-sn-glycero-3-phosphoethanolamine (DOPE), Mal-PEG2k-NHS, cholesterol (Chol, purity > 95%), and PBS buffer. Guangzhou Tanshui Technology Co., Ltd supplied the DSPE-PEG1k-TAT and DSPE-PEG1k. Glbiochem (Shanghai, China) produced MMP2-cleavable peptides (Gly-Pro-Leu-Gly-Ile-Ala-Gly-Gln) and myrcludex B peptides (myrB, HBV preS/12-47myr). Novoprotein (Shanghai, China) provided the human active MMP2 protein. Beyotime Biotech Inc. (Shanghai, China) supplied Hoechst 33258, and Absin Bioscience Inc. (Shanghai, China) provided an apoptosis assay kit (Annexin V-FICT). The hydrochloride of N-Ethyl-N'-(3-dimethylaminopropyl) carbodiimide (EDC) was obtained from Aladdin Reagent Database Inc. AAT Bioquest Co. Ltd (Shanghai, China) supplied the TRITC-phalloidin. Sigma (Taufkirchen, Germany) delivered the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). All other reagents were analytical grade, and all experiments were conducted using distilled water.
Study of FA12 peptide-modified PEGylated liposomal doxorubicin (PLD) as an effective ligand to target Muc1 in mice bearing C26 colon carcinoma: in silico, in vitro, and in vivo study
Published in Expert Opinion on Drug Delivery, 2022
Atefeh Biabangard, Ahmad Asoodeh, Mahmoud Reza Jaafari, Mohammad Mashreghi
Four peptides were chosen from our peptide bank randomly [20], which were chemically synthesized by GL Biochem (Shanghai, China) with 95% purity. DSPE-PEG2000-COOH (1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[carboxy(polyethylene glycol)-2000]) was purchased from Avanti Polar Lipids (Alabaster, AL). Isopropanol and chloroform were purchased from Merck (Darmstadt, Germany). MTT 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide was also purchased from Sigma-Aldrich (Germany). Commercially available PLD, Doxil, was acquired from Behestan Darou Company (Tehran, Iran). N-hydroxysuccinimide (Sulfo-NHS; ≥98%) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC; ≥99.0%) were obtained from Merck KGaA (Darmstadt, Germany). RPMI 1640 culture media and fetal bovine serum (FBS) were obtained from Gibco (Carlsbad, CA).
New generation of viral nanoparticles for targeted drug delivery in cancer therapy
Published in Journal of Drug Targeting, 2022
Nikta Alvandi, Maryam Rajabnejad, Zeynab Taghvaei, Neda Esfandiari
There are some linkers for VLPs conjugation categorised in carbodiimide chemistry. DCC (dicyclohexyl carbodiimide) is one of the first and frequented carbodiimides particularly in organic synthesis applications developed as a reagent. Usually, DCC is used for the formation of amide and ester bonds between water insoluble compounds or solid-phase peptide synthesis (Figure 5(E)). Another water-insoluble amide bond-forming agent is DIC (diisopropyl carbodiimide) which has some upsides over DCC, such as being liquid at room temperature and easier dispense than DCC (Figure 5(F)). EDC (1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide) is another water-soluble carbodiimide reagent used in multitudes of biochemical processes as a crosslinker. Its performance is similar to DCC and DIC (Figure 5(G)). Furthermore, another carbodiimide that is suitable for the chemical probing of RNA structure is CMC (1-cyclohexyl-(2-morpholinoethyl) carbidiimide as the metho-p-toluene sulphonate salt) considered as a water-soluble reagent for peptide synthesis or coupling ligands to carriers (Figure 5(H)) [47].