730300
Methacrylic acid N-hydroxysuccinimide ester
98%
Synonym(s):
N-(Methacryloxy)succinimide, N-(Methacryloyloxy)succinimide
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About This Item
Empirical Formula (Hill Notation):
C8H9NO4
CAS Number:
Molecular Weight:
183.16
NACRES:
NA.23
PubChem Substance ID:
UNSPSC Code:
12162002
MDL number:
Quality Level
assay
98%
form
solid
mp
101-105 °C
storage temp.
2-8°C
SMILES string
CC(=C)C(=O)ON1C(=O)CCC1=O
InChI
1S/C8H9NO4/c1-5(2)8(12)13-9-6(10)3-4-7(9)11/h1,3-4H2,2H3
InChI key
ACGJEMXWUYWELU-UHFFFAOYSA-N
General description
Methacrylic acid N-hydroxysuccinimide ester(NHS-MA) belongs to the class of reactive monomers known as N-hydroxysuccinimide (NHS) esters. It is commonly used for functionalizing biomolecules through amine-reactive coupling reactions infields such as bioconjugation, protein labeling, and peptide synthesis. It also serves as a crosslinking agent or linker molecule for the conjugation of drugs or targeting ligands to carrier materials.
Application
Methacrylic acid N-hydroxysuccinimide ester can be used:
- As a monomer to prepare degradable amphiphilic diblock copolymer microparticles via RAFT polymerization, for low pH-triggered drug delivery. NHS-MA can shield the drug molecule from degradation, enhance its solubility, and improve its pharmacokinetic properties.
- For the surface functionalization of poly-ε-caprolactone (PCL) scaffolds used for tissue engineering. NHS groups are used to couple with chitosan of various molecular weights.
- To prepare biocompatible polymer hydrogel for enzymatic biofuel cells. The hydrogel can serve as an enzyme-immobilizing matrix for enzymatic bioelectrodes.
signalword
Warning
Hazard Classifications
Acute Tox. 4 Inhalation - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Theato, P.
Journal of Polymer Science Part A: Polymer Chemistry, 46, 6677-6677 (2008)
Xiaolong Zhang et al.
Biomacromolecules, 17(3), 778-787 (2016-01-23)
It is important to synthesize materials to recapitulate critical functions of biological systems for a variety of applications such as tissue engineering and regenerative medicine. The purpose of this study was to synthesize a chimeric hydrogel as a promising extracellular
Myriam G Tardajos et al.
Carbohydrate polymers, 191, 127-135 (2018-04-18)
Tissue engineering (TE) approaches often employ polymer-based scaffolds to provide support with a view to the improved regeneration of damaged tissues. The aim of this research was to develop a surface modification method for introducing chitosan as an antibacterial agent