SMCC - CAS 64987-85-5

SMCC - CAS 64987-85-5 Catalog number: BADC-00712

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SMCC is a heterobifunctional protein crosslinker for antibody-drug-conjugation (ADC).

Category
ADCs Linker
Product Name
SMCC
CAS
64987-85-5
Catalog Number
BADC-00712
Molecular Formula
C16H18N2O6
Molecular Weight
334.32
SMCC

Ordering Information

Catalog Number Size Price Quantity
BADC-00712 5 g $298
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Description
SMCC is a heterobifunctional protein crosslinker for antibody-drug-conjugation (ADC).
Synonyms
4-(N-Maleimidomethyl)cyclohexane-1-carboxylic Acid N-Hydroxysuccinimide Ester; NSC 344483; N-Succinimidyl 4-(Maleimidomethyl)cyclohexane-1-carboxylate
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexane-1-carboxylate
Canonical SMILES
C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)ON3C(=O)CCC3=O
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
InChIKey
JJAHTWIKCUJRDK-UHFFFAOYSA-N
Density
1.42±0.1 g/cm3(Predicted)
Solubility
Soluble in chloroform, ethyl acetate
Melting Point
172-174 ℃
LogP
0.20080
Appearance
White to off-white solid
Purity
98 %
Shipping
Room temperature
Storage
Store at -20 ℃
Pictograms
Irritant
Signal Word
Warning
Boiling Point
501.7±42.0 ℃ (Predicted)
1.A novel anti-CD37 antibody-drug conjugate with multiple anti-tumor mechanisms for the treatment of B-cell malignancies.
Deckert J1, Park PU, Chicklas S, Yi Y, Li M, Lai KC, Mayo MF, Carrigan CN, Erickson HK, Pinkas J, Lutz RJ, Chittenden T, Lambert JM. Blood. 2013 Nov 14;122(20):3500-10. doi: 10.1182/blood-2013-05-505685. Epub 2013 Sep 3.
CD37 has gathered renewed interest as a therapeutic target in non-Hodgkin lymphoma (NHL) and chronic lymphocytic leukemia (CLL); however, CD37-directed antibody-drug conjugates (ADCs) have not been explored. Here, we identified a novel anti-CD37 antibody, K7153A, with potent in vitro activity against B-cell lines through multiple mechanisms including apoptosis induction, antibody-dependent cellular cytotoxicity, antibody-dependent cellular phagocytosis, and complement-dependent cytotoxicity. The antibody was conjugated to the maytansinoid, DM1, a potent antimicrotubule agent, via the thioether linker, N-succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC), and the resulting ADC, IMGN529, retained the intrinsic antibody activities and showed enhanced cytotoxic activity from targeted payload delivery. In lymphoma cell lines, IMGN529 induced G2/M cell cycle arrest after internalization and lysosomal processing to lysine-N(ε)-SMCC-DM1 as the sole intracellular maytansinoid metabolite.
2.Trastuzumab emtansine: first global approval.
Ballantyne A1, Dhillon S. Drugs. 2013 May;73(7):755-65. doi: 10.1007/s40265-013-0050-2.
Genentech and ImmunoGen are collaborating on the development of trastuzumab emtansine, a HER2 antibody-drug conjugate that comprises Genentech's trastuzumab antibody linked to ImmunoGen's anti-mitotic agent, mertansine (a maytansine derivative; also known as DM1). The conjugate combines two strategies: the anti-HER2 activity of trastuzumab, and the targeted intracellular delivery of mertansine, a tubulin polymerisation inhibitor which interferes with mitosis and promotes apoptosis. The linker in trastuzumab emtansine is a non-reducible thioether linker, N-succinimidyl-4-(N-maleimidomethyl) cyclohexane-1-carboxylate (SMCC, designated MCC after conjugation). Trastuzumab emtansine (Kadcyla™) has been launched in the USA as second-line monotherapy for HER2-positive metastatic breast cancer, and has been filed for approval in the EU and Japan in this indication. Trastuzumab emtansine is in phase III development as first-line combination therapy or monotherapy for metastatic HER2-positive breast cancer, and as third-line monotherapy for metastatic HER2-positive breast cancer.
3.Synthesis of a stable and specific surface plasmon resonance biosensor surface employing covalently immobilized peptide nucleic acids.
Burgener M1, Sänger M, Candrian U. Bioconjug Chem. 2000 Nov-Dec;11(6):749-54.
Biosensors allow the real-time and label-free observation of biochemical reactions between various ligands including antigen-antibody reactions and nucleic acids hybridizations. In our studies, we used a surface plasmon resonance biosensor to elucidate the hybridization characteristics of a peptide nucleic acid (PNA) ligand immobilized on sensor surfaces either through covalent or streptavidin-biotin coupling. A biotin-labeled PNA was employed in the latter approach whereas the covalent immobilization included the following steps: A maleimide group was attached to the N-terminal of the PNA using N-succinimidyl 4-(N-maleimidomethyl)-cyclohexane-1-carboxylate (SMCC). To generate free thiol groups for coupling, a carboxylated dextran matrix of the sensor surface was activated with N-hydroxysuccinimide (NHS) and N-ethyl-N'-(dimethylaminopropyl)-carbodiimide (EDC) and thiolated by addition of cystamine dihydrochloride followed by reduction with 1, 4-dithioerythrite (DTE).
4.Dual potency anti-HER2/neu and anti-EGFR anthracycline immunoconjugates in chemotherapeutic-resistant mammary carcinoma combined with cyclosporin A and verapamil P-glycoprotein inhibition.
Coyne CP1, Ross MK, Bailey JG. J Drug Target. 2009 Jul;17(6):474-89. doi: 10.1080/10611860903012802.
Immunoconjugates of epirubicin were synthesized with monoclonal antibodies against the epidermal growth factor receptors, HER2/neu and EGFR, by creating a sulfhydryl-reactive epirubicin intermediate applying heterobifunctional succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC), which was introduced at alpha-monoamide groups of the epirubicin carbohydrate moiety. In parallel, N-succinimidyl-S-acetylthioacetate (SATA) was used to incorporate a sulfhydryl group into immunoglobulin at the terminal amine position of -lysine amino acid residues. Eprirubicin-SMCC-SATA-IgG immunoconjugates were produced by reacting epirubicin-SMCC and SATA-IgG at appropriate molar ratios. Epirubicin-(anti-HER2/neu) and epirubicin-(anti-EGFR) had greater potency against chemotherapeutic-resistant SKBr-3 mammary carcinoma than did epirubicin at epirubicin-equivalent concentrations. Epirubicin-(anti-HER2/neu) was more potent than epirubicin-(anti-EGFR), and a synergistic level of antineoplastic activity was detected with an epirubicin immunoconjugate 50/50 combination.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Historical Records: γ-Fagarine | SMCC

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