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

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Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate
SMCC.png
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)
ChEBI
ChemSpider
EC Number
  • 613-734-7
UNII
  • InChI=1S/C16H18N2O6/c19-12-5-6-13(20)17(12)9-10-1-3-11(4-2-10)16(23)24-18-14(21)7-8-15(18)22/h5-6,10-11H,1-4,7-9H2
    Key: JJAHTWIKCUJRDK-UHFFFAOYSA-N
  • O=C(C1CCC(CN2C(C=CC2=O)=O)CC1)ON3C(CCC3=O)=O
Properties
C16H18N2O6
Molar mass 334.328 g·mol−1
Appearance White solid
Melting point 175 °C (347 °F; 448 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC) is a heterobifunctional amine-to-sulfhydryl crosslinker, which contains two reactive groups at opposite ends: N-hydroxysuccinimide-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[edit]

  1. ^ Hermanson, Greg (2013). Bioconjugate Techniques. Elsevier. p. 299–339. ISBN 978-0-12-382239-0.