A water-soluble protein cross-linking reagent
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Sulfo-SMCC (sodium salt)

Item No. 35692

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)methyl]-cyclohexanecarboxylic acid, 2,5-dioxo-3-sulfo-1-pyrrolidinyl ester, monosodium salt
CAS Number
92921-24-9
Synonyms
  • Sulfosuccinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate
Molecular Formula
C16H17N2O9S • Na
Formula Weight
436.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleWater: Soluble
SMILES
O=C1C=CC(N1CC2CCC(CC2)C(ON3C(CC(S(=O)([O-])=O)C3=O)=O)=O)=O.[Na+]
InChi Code
InChI=1S/C16H18N2O9S.Na/c19-12-5-6-13(20)17(12)8-9-1-3-10(4-2-9)16(23)27-18-14(21)7-11(15(18)22)28(24,25)26;/h5-6,9-11H,1-4,7-8H2,(H,24,25,26);/q;+1/p-1
InChi Key
VUFNRPJNRFOTGK-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    Product Description

    Sulfo-SMCC is a water-soluble protein cross-linking reagent that contains an anime-reactive sulfo-N-hydroxysuccinimide (sulfo-NHS) ester and a sulfhydryl-reactive maleimide group that can be used in the conjugation of proteins.1,2 It has been used to conjugate anti-programmed cell death ligand 1 (PD-L1) antibodies to the surface of platelets to induce antitumor immunity in xenograft models, as well as to conjugate Golgi-targeting peptides to platelet microparticle-mimetic nanoplatforms for the delivery of all-trans retinoic acid (Item No. 11017) to isolated human synovial fibroblasts from patients with rheumatoid arthritis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gao, Y., Chen, X., Wang, B., et al. Engineering platelets with PDL1 antibodies and iron oxide nanoparticles for postsurgical cancer immunotherapy. ACS Appl. Bio Mater. 6(1), 257-266 (2023).

    2. Deng, C., Zhao, X., Chen, Y., et al. Engineered platelet microparticle-membrane camouflaged nanoparticles for targeting the golgi apparatus of synovial fibroblasts to attenuate rheumatoid arthritis. ACS Nano 16(11), 18430-18447 (2022).