N-[gamma-Maleimidobutyryloxy]sulfo-succinimide ester - CAS 158018-81-6

N-[gamma-Maleimidobutyryloxy]sulfo-succinimide ester - CAS 158018-81-6 Catalog number: BADC-00368

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N-[gamma-Maleimidobutyryloxy]sulfo-succinimide ester is a highly significant and versatile compound that plays a pivotal role in the realm of biomedicine. Specifically designed for the purpose of labeling and conjugating biomolecules, this remarkable product has garnered immense attention in the field. Its wide-ranging applications span the development of targeted therapies, imaging agents, and drug delivery systems. By virtue of its maleimide group, which exhibits exceptional specificity, it empowers researchers to precisely target sulfhydryl-containing proteins or antibodies, thereby rendering feasible the treatment of an array of diseases, including but not limited to cancer or autoimmune disorders.

Category
ADCs Linker
Product Name
N-[gamma-Maleimidobutyryloxy]sulfo-succinimide ester
CAS
158018-81-6
Catalog Number
BADC-00368
Molecular Formula
C12H12N2O9S
Molecular Weight
360.30
N-[gamma-Maleimidobutyryloxy]sulfo-succinimide ester

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Description
N-[gamma-Maleimidobutyryloxy]sulfo-succinimide ester is a highly significant and versatile compound that plays a pivotal role in the realm of biomedicine. Specifically designed for the purpose of labeling and conjugating biomolecules, this remarkable product has garnered immense attention in the field. Its wide-ranging applications span the development of targeted therapies, imaging agents, and drug delivery systems. By virtue of its maleimide group, which exhibits exceptional specificity, it empowers researchers to precisely target sulfhydryl-containing proteins or antibodies, thereby rendering feasible the treatment of an array of diseases, including but not limited to cancer or autoimmune disorders.
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
Purity
≥98%
Shipping
-20°C (International: -20°C)
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Pictograms
Irritant
Signal Word
Warning
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.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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