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730300

Sigma-Aldrich

Methacrylic acid N-hydroxysuccinimide ester

98%

Sinónimos:

N-(Methacryloxy)succinimide, N-(Methacryloyloxy)succinimide

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About This Item

Fórmula empírica (notación de Hill):
C8H9NO4
Número de CAS:
38862-25-8
Peso molecular:
183.16
MDL number:
MFCD15072193
UNSPSC Code:
12162002
PubChem Substance ID:
329764554
NACRES:
NA.23

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.

pictograms

Exclamation mark
GHS07

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

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Chitosan functionalized poly-?-caprolactone electrospun fibers and 3D printed scaffolds as antibacterial materials for tissue engineering applications
Myriam G. Tardajos, et al.
Carbohydrate Polymers, 191, 127-135 (2018)
Electrosprayed cysteine-functionalized degradable amphiphilic block copolymer microparticles for low pH-triggered drug delivery
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Introduction to Polymer Chemistry, 10 (2019)
Fabrication of Unique Magnetic Bionanocomposite for Highly Efficient Removal of Hexavalent Chromium from Water
Zhong Y, et al.
Scientific reports, 6(17), 31090-31090 (2016)
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
Postpolymerization modification of poly (pentafluorophenyl methacrylate): Synthesis of a diverse water-soluble polymer library
Gibson MI, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 47(17), 4332-4345 (2009)
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