Succinimidyl 4-(''N''-maleimidomethyl)cyclohexane-1-carboxylate

Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate
Names
IUPAC name
Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate
Other names
SMCC, 4-(N-maleimidomethyl)cyclohexanecarboxylic acid N-succinimidyl ester
Identifiers
3D model (JSmol)
ChemSpider
Properties
C16H18N2O6
Molar mass 334.33 g·mol−1
Appearance White solid
Melting point 175 °C (347 °F; 448 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC) is a heterobifunctional amine-to-sulfhydryl crosslinker, which contains two reactive groups at opposite ends: NHS-ester and maleimide, reactive with amines and thiols respectively. SMCC is often used in bioconjugation to link proteins with other functional entities (fluorescent dyes, tracers, nanoparticles, cytotoxic agents).[1] For example, a targeted anticancer agent – trastuzumab emtansine (antibody-drug conjugate containing an antibody trastuzumab chemically linked to a highly potent drug DM-1) – is prepared using SMCC reagent.

References

  1. Hermanson, Greg. Bioconjugate Techniques. Elsevier. p. 299-239. ISBN 978-0-12-382239-0.
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