Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media
TL;DR: Hydrogels with two different types of carboxyl group locations were employed as substrates containing the carboxylic acid, while ethylenediamine and benzylamine were used as amine to study the mechanism of amide formation between carboxYlic acid and amine in aqueous media using 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride.
About: This article is published in Bioconjugate Chemistry.The article was published on 1995-01-01. It has received 707 citations till now. The article focuses on the topics: Carboxylic acid & Acrylic acid.
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TL;DR: A bioinspired design for adhesives consisting of an adhesive surface with a flexible matrix to develop an adhesive that has the right level of stick but moves with the surrounding tissues, which is effective in the presence of blood and thus might work during wound repair.
Abstract: Adhesion to wet and dynamic surfaces, including biological tissues, is important in many fields but has proven to be extremely challenging. Existing adhesives are cytotoxic, adhere weakly to tissues, or cannot be used in wet environments. We report a bioinspired design for adhesives consisting of two layers: an adhesive surface and a dissipative matrix. The former adheres to the substrate by electrostatic interactions, covalent bonds, and physical interpenetration. The latter amplifies energy dissipation through hysteresis. The two layers synergistically lead to higher adhesion energies on wet surfaces as compared with those of existing adhesives. Adhesion occurs within minutes, independent of blood exposure and compatible with in vivo dynamic movements. This family of adhesives may be useful in many areas of application, including tissue adhesives, wound dressings, and tissue repair.
919 citations
TL;DR: This review surveys the design and the applications of cellulose-based hydrogels, which are extensively investigated due to the large availability of cellulosity in nature, the intrinsic degradability of cellulOSE and the smart behaviour displayed by some cellulose derivatives.
Abstract: Hydrogels are macromolecular networks able to absorb and release water solutions in a reversible manner, in response to specific environmental stimuli. Such stimuli-sensitive behaviour makes hydrogels appealing for the design of ‘smart’ devices, applicable in a variety of technological fields. In particular, in cases where either ecological or biocompatibility issues are concerned, the biodegradability of the hydrogel network, together with the control of the degradation rate, may provide additional value to the developed device. This review surveys the design and the applications of cellulose-based hydrogels, which are extensively investigated due to the large availability of cellulose in nature, the intrinsic degradability of cellulose and the smart behaviour displayed by some cellulose derivatives. Keywords: Hydrogels; cellulose; biodegradation. 1. Introduction Hydrophilic polymers can swell and absorb water without dissolving, provided that chemical or physical crosslinks exist among the macromolecular chains. The polymer network resulting from the crosslinks swells in the aqueous solvent, until the thermodynamic force of swelling is totally counterbalanced by the elastic, retractive force exerted by the crosslinks. This ‘solid-like solution’ of polymer and water resulting at equilibrium is known as a hydrogel. The amount of water retained by
649 citations
Cites background from "Mechanism of Amide Formation by Car..."
...functionalization of cellulose with several biomolecules, able to promote specific cell functions, due to the ability of the carbodiimide to crosslink various polypeptides [84,85]....
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TL;DR: In this article, six commonly used wet chemical oxidants were evaluated in terms of their effects on the surface chemistry and structure of MWCNTs using a combination of analytical techniques, including X-ray photoelectron spectroscopy (XPS) and energy dispersive spectrograph (EDX).
627 citations
Cites background from "Mechanism of Amide Formation by Car..."
...For example, Nakajima and Ikada proposed that in the presence of excess DTBC, the N-acyl urea, 3, is produced when the O-acyl isourea activated complex, 2, that initially forms from the reaction of DTBC with carboxylic acid groups, undergoes an irreversible rearrangement [45]....
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TL;DR: The purpose of this paper is to review the various chemical modification methods and synthetic routes to obtain HA derivatives, encompassing all applications.
579 citations
Cites background from "Mechanism of Amide Formation by Car..."
...(2007) described this method for the study of the hydrolytic egradation of HA during the crosslinking process with EDC....
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...Indeed, carboxylic acid activation by EDC is best performed in an acidic environment (pH 3.5–4.5) (Nakajima & Ikada, 1995), whereas amide formation is best done at high pH, when the amine is deprotonated....
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...HA–tyramine was first synthesized with EDC and HOBt....
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...However, reagents need to be added in large quantities as some hydrolysis of EDC cannot be avoided and the amine is mostly protonated at the required pH reaction range....
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...This way, degrees of substitution of up to 60–80% were obtained, suggesting that EDC hydrolysis was minimized....
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TL;DR: In this review, different strategies to stabilize multimeric enzymes at different levels are revised and special emphasis is put on the new immobilization strategies specifically designed to involve the maximum amount of enzyme subunits in the immobilization (and thus, in the further multipoint covalent attachment).
567 citations
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TL;DR: A sensitive method to determine the free amino groups in proteins is presented that makes use of the reagent 2,4,6-trinitrobenzenesulfonic acid and found that sodium dodecyl sulfate was bound to some of the ϵ-amino groups of lysine in bovine serum albumin, ovalbumin, and human γ-globulin and rendered the involved amino groups unreactive toward TNBS.
1,972 citations
TL;DR: The kinetics of the reaction indicates that there are limits to the variation of carbodiimide and nucleophile when quantitative modification is desired, but that a wide variety of reagents can be used if quantitative reaction is not essential.
904 citations
Book•
18 Aug 1991
TL;DR: This chapter discusses cross-linking techniques for Cross-Linking Analysis of Cross-Linked Products Reaction Complications and Preparation of Immunotoxins Using Avidin-Biotin Linkage Miscellaneous Coupling Methods.
Abstract: INTRODUCTION REACTIVE GROUPS OF PROTEINS AND THEIR MODIFYING AGENTS Compositions of Proteins Functional Groups of Proteins Group Directed Reagents CHOICE AND DESIGN OF CROSS-LINKING REAGENTS Nucleophilic Reactions Electrophilic Reactions Group Directed Reactions Nonspecific Reactions Cleavable Reagents Labeled Cross-Linking Reagents Hydrophobicity and Hydrophilicity of Reagents HOMOBIFUNCTIONAL CROSS-LINKING REAGENTS Amino Group Directed Cross-Linkers Sulfhydryl Group Directed Cross-Linkers Carboxyl Group Directed Cross-Linking Reagents Phenolate and Imidazolyl Group Directed Cross-Linking Reagents Arginine Residue Directed Cross-Linker Nondiscriminatory Photoactivatable Cross-Linkers Noncovalent Homobifunctional Cross-Linking Reagents Miscellaneous Bifunctional Reagents HETEROBIFUNCTIONAL CROSS-LINKERS Group Selective Heterobifunctional Cross-Linking Reagents Photosensitive Heterobifunctional Cross-Linking Reagents Disguised or Masked Reagents ZERO-LENGTH CROSS-LINKING REAGENTS Carboxyl Group Activating Reagents Reagents for Carbohydrate Activation Reagents for Disulfide Formation Enzymes as Zero-Length Cross-Linkers PROCEDURES, ANALYSIS, AND COMPLICATIONS Procedures for Cross-Linking Analysis of Cross-Linked Products Reaction Complications APPLICATION OF CHEMICAL CROSS-LINKING TO SOLUBLE PROTEINS Interresidue Distance Determinations Nearest Neighbor Analysis Conformational Analysis Structural Stability CROSS-LINKING OF MEMBRANE PROTEINS General Methodology of Membrane Cross-Linking Possible Artifacts of Membrane Cross-Linking Identification of Membrane Receptors Nearest-Neighbor Analysis of Membrane Components Membrane Protein Conformational Analysis Stabilization of Membrane Proteins PREPARATION OF ENZYME IMMUNOCONJUGATES AND OTHER IMMUNOASSAY COMPONENTS Components of Enzyme Immunoassays Conjugation of Enzymes to Antibodies and their Fragments Coupling Proteins to Antibodies and their Fragments Coupling Enzymes to Proteins and Antigens Characterization of Conjugation Methods PREPARATION OF IMMUNOTOXINS AND OTHER DRUG CONJUGATES FOR TARGETING THERAPEUTICS Selection of Cross-Linking Reagents and Toxins Conjugation through Disulfide Bond Conjugation through Thioether Linkage Conjugation with Actuvated Chlorambucil Conjugation with Acid-Labile and Photocleaveable Cross-Linkers Conjugation through Carbohydrate Residues Preparation of Immunotoxins Using Avidin-Biotin Linkage Miscellaneous Coupling Methods CONJUGATION OF PROTEINS TO SOLID MATRICES Functionalities of Matrices Protein Immobilization by Matrix Activation Cross-Linking Reagents Used in Protein Immobilization Cross-Linking through Carbohydrate Chains OTHER APPLICATIONS AND FUTURE PROSPECTS Application to Nucleic Acids Cross-Linking Small Molecules to Proteins Synopsis INDEX Note: Each chapter also contains an Introduction and References
718 citations
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