Name: N-[gamma-Maleimidobutyryloxy]sulfo-succinimide ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

1-[4-(2,5-dioxopyrrol-1-yl)butanoyloxy]-2,5-dioxopyrrolidine-3-sulfonic acid;

IUPAC Name

1-[4-(2,5-dioxopyrrol-1-yl)butanoyloxy]-2,5-dioxopyrrolidine-3-sulfonic acid

Canonical SMILES

C1C(C(=O)N(C1=O)OC(=O)CCCN2C(=O)C=CC2=O)S(=O)(=O)O

InChI

InChI=1S/C12H12N2O9S/c15-8-3-4-9(16)13(8)5-1-2-11(18)23-14-10(17)6-7(12(14)19)24(20,21)22/h3-4,7H,1-2,5-6H2,(H,20,21,22)

InChIKey

LCZVQHWMSQLWSC-UHFFFAOYSA-N

Appearance

Soild powder

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-20°C (International: -20°C)

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Please store the product under the recommended conditions in the Certificate of Analysis.

Pictograms

Irritant

Signal Word

Warning

N-[gamma-Maleimidobutyryloxy]sulfo-succinimide ester, commonly known as sulfo-GMBS, is a versatile cross-linking reagent widely utilized in bioconjugation endeavors. Here, we explore four key applications of N-[gamma-Maleimidobutyryloxy]sulfo-succinimide ester:

Protein Conjugation: Within the realm of protein conjugation, sulfo-GMBS shines as a go-to choice for linking sulfhydryl groups to primary amines. This trait is particularly advantageous in the domain of antibody labeling, where the modification of one molecule with a maleimide group enables steadfast attachment to another molecule housing free thiol groups.

Immobilization of Biomolecules: Leveraging its cross-linking capabilities, sulfo-GMBS finds applications in the effective immobilization of enzymes, antibodies, or other proteins onto solid supports like beads or microplate surfaces. By forging covalent bonds between biomolecules and surfaces, sulfo-GMBS elevates the stability and reusability of biosensors and diagnostic assays.

Development of Proteomics Tools: In the dynamic field of proteomics, sulfo-GMBS emerges as a pivotal tool for unraveling protein interactions by cross-linking interacting partners within complex molecular frameworks. This innovative approach aids in pinpointing and stabilizing transient or weak interactions that elude conventional detection methods.

Surface Modification: A catalyst for surface modification, sulfo-GMBS imparts surfaces with reactive maleimide groups that engage seamlessly with thiol-containing molecules, propelling advancements in biotechnology applications. This transformative capability empowers the enhancement of material surfaces to bolster biocompatibility and functionalization for tailored applications. These modified surfaces find diverse applications in realms such as tissue engineering, biomaterials development, and designing innovative drug delivery systems, underscoring the versatility of sulfo-GMBS in driving progressive bioengineering solutions.

1. Progress and Current Trends in the Synthesis of Novel Polymers with Enhanced Mucoadhesive Properties

Vitaliy V Khutoryanskiy, Ruairí P Brannigan Macromol Biosci . 2019 Oct;19(10):e1900194. doi: 10.1002/mabi.201900194.

Mucoadhesion is defined as the adherence of a synthetic or natural polymer to a mucosal membrane via physical or chemical interactions. Mucoadhesive materials are widely used to develop dosage forms for transmucosal drug delivery via ocular, nasal, esophageal, oral, vaginal, rectal, and intravesical routes of administration. This review will discuss some of the most prominent and recent synthetic methodologies employed to modify polymeric materials in order to enhance their mucoadhesive properties. This includes chemical conjugation of polymers with molecules bearing thiol-, catechol-, boronate-, acrylate-, methacrylate-, maleimide-, and N-hydroxy(sulfo)succinimide ester- groups.

2. On the unusual stability of succinimidyl esters in pNIPAm-AAc microgels

Justin D Debord, L Andrew Lyon Bioconjug Chem . 2007 Mar-Apr;18(2):601-4. doi: 10.1021/bc060248z.

In this contribution, we describe the effects of amide coupling reactions on the physical properties of thermoresponsive hydrogel microparticles (microgels). These microgels, when treated via aqueous carbodiimide/sulfo-succinimide coupling protocols, displayed a dramatic modulation of the microgel phase transition thermodynamics. UV spectrophotometry was used to determine that this modulation was due to remarkably stable hydrogel conjugates of sulfo-NHS that resisted degradation under standard hydrolysis protocols. These intermediates result in a shift of the phase transition, along with a large increase in equilibrium microgel swelling degree, due to an increase in chain-chain Coulombic repulsion. Only aggressive hydrolysis protocols resulted in the recovery of the native microgel phase transition, suggesting that an unusually stable succinimidyl ester is formed in the microgel during coupling.

3. Interaction of N-hydroxy(sulfo) succinimide active esters with the reduced folate/methotrexate transport system from human leukemic CCRF-CEM cells

G Jansen, G R Westerhof, G Rijksen, J H Schornagel Biochim Biophys Acta . 1989 Nov 3;985(3):266-70. doi: 10.1016/0005-2736(89)90411-2.

The membrane impermeant protein cross-linker 3,3'-dithiobissulfosuccinimidyl propionate (DTSSP) is a well-known inhibitor of human erythrocyte band 3-mediated inorganic anion transport. We observed that DTSSP is also a potent inhibitor of reduced folate/methotrexate transport in human CCRF-CEM leukemia cells. An interaction of DTSSP with the reduced folate/MTX is substantiated by findings that: (a) like MTX transport itself, the concentration of DTSSP required for half-maximal inhibition of [3H]methotrexate transport varied substantially with the anionic composition of the external medium. In a saline buffer and an anion-deficient buffer the I50 values were 7 and 1 microM, respectively; (b) saturation of the carrier with 1-5 microM methotrexate completely protected the transport system from interaction by DTSSP; (c) methotrexate transport activity in DTSSP-treated cells could be restored after cleavage of the disulfide bond in DTSSP under mild reducing conditions; and (d) pretreatment of cells with DTSSP reduced the incorporation of [3H]methotrexate after labeling with an N-hydroxysuccinimide ester of [3H]methotrexate (NHS-MTX), another potent inhibitor of methotrexate transport. Comparison of DTSSP- and NHS-MTX-induced inhibition of methotrexate transport showed that DTSSP inhibition, in contrast to NHS-MTX inhibition, was (a) less potent, (b) dependent on buffer conditions, (c) reversible by reducing agents, and (d) required only a very low molar ratio of methotrexate over DTSSP to afford maximal protection.