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
CAS Number	64987-85-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:63174;
ChemSpider	111419 ;
ECHA InfoCard	100.123.863
EC Number	613-734-7;
PubChem CID	125175;
UNII	B357P1G1IF ;
CompTox Dashboard (EPA)	DTXSID30215307 ;
	InChI 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;
	SMILES O=C(C1CCC(CN2C(C=CC2=O)=O)CC1)ON3C(CCC3=O)=O;
Properties
Chemical formula	C16H18N2O6
Molar mass	334.328 g·mol−1
Appearance	White solid
Melting point	175 °C (347 °F; 448 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). 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: 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

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

[Hermanson2013-1] Hermanson, Greg (2013). Bioconjugate Techniques. Elsevier. pp. 299–339. ISBN 978-0-12-382239-0.

[1]