SMCC
(Synonyms: 4-(N-马来酰亚胺基甲基)环己烷-1-羧酸琥珀酰亚胺酯) 目录号 : GC38695
A protein cross-linking reagent
Cas No.:64987-85-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
SMCC is a heterobifunctional cross-linking reagent that contains an amine-reactive N-hydroxysuccinimide ester and a sulfhydryl-reactive maleimide group that can be used in click chemistry reactions in the conjugation of proteins.1,2,3 It has been used to cross-link the anticancer agent DM1 to an IgG1 monoclonal antibody to form the antibody-drug conjugate DM1-SMCC .4 Immunization of mice with SMCC-coupled keyhole limpet hemocyanin (KLH) antigen and syngeneic splenocytes increases the percentage of proliferating T cells in isolated splenocytes from recipient mice compared to mice immunized with KLH and the adjuvant LPS.3
1.Bieniarz, C., Husain, M., Barnes, G., et al.Extended length heterobifunctional coupling agents for protein conjugationsBioconjug. Chem.7(1)88-95(1996) 2.Hermanson, G.T.The reactions of bioconjugationBioconjugate Techniques(2013) 3.Guo, Y., Werbel, T., Wan, S., et al.Potent antigen-specific immune response induced by infusion of spleen cells coupled with succinimidyl-4-(N-maleimidomethyl cyclohexane)-1-carboxylate (SMCC) conjugated antigensInt. Immunopharmacol.31158-168(2019) 4.Luo, Q., Chung, H.H., Borths, C., et al.Structural characterization of a monoclonal antibody-maytansinoid immunoconjugateAnal. Chem.88(1)695-702(2016)
| Cas No. | 64987-85-5 | SDF | |
| 别名 | 4-(N-马来酰亚胺基甲基)环己烷-1-羧酸琥珀酰亚胺酯 | ||
| Canonical SMILES | O=C(C1CCC(CN2C(C=CC2=O)=O)CC1)ON3C(CCC3=O)=O | ||
| 分子式 | C16H18N2O6 | 分子量 | 334.32 |
| 溶解度 | DMSO: 25 mg/mL (74.78 mM) | 储存条件 | 4°C, away from moisture and light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.9911 mL | 14.9557 mL | 29.9115 mL |
| 5 mM | 0.5982 mL | 2.9911 mL | 5.9823 mL |
| 10 mM | 0.2991 mL | 1.4956 mL | 2.9911 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The TRAP/SMCC/Mediator complex and thyroid hormone receptor function
Trends Endocrinol Metab 2001 Apr;12(3):127-34.PMID:11306338DOI:10.1016/s1043-2760(00)00355-6.
The TRAP/SMCC/Mediator complex is a mammalian transcriptional regulatory complex that contains over 25 polypeptides and is, in part, phylogenetically conserved. It was originally isolated as a thyroid hormone receptor (TR)-associated protein (TRAP) complex that mediates TR-activated transcription from DNA templates in conjunction with the general transcription machinery, and probably acts in vivo after the action of other receptor-interacting coactivators involved in chromatin remodeling. Subsequently, the TRAP complex was identified as a more broadly used coactivator complex for a wide variety of activators. The TRAP220 subunit mediates ligand-dependent interactions of the complex with TR and other nuclear receptors; and genetic ablation of murine TRAP220 has revealed that it is essential both for optimal TR function and for a variety of early developmental and adult homeostasis events in mice, but not for cell viability per se.
TRAP/SMCC/mediator-dependent transcriptional activation from DNA and chromatin templates by orphan nuclear receptor hepatocyte nuclear factor 4
Mol Cell Biol 2002 Aug;22(15):5626-37.PMID:12101254DOI:10.1128/MCB.22.15.5626-5637.2002.
The orphan nuclear receptor hepatocyte nuclear factor 4 (HNF-4) regulates the expression of many liver-specific genes both during development and in the adult animal. Towards understanding the molecular mechanisms by which HNF-4 functions, we have established in vitro transcription systems that faithfully recapitulate HNF-4 activity. Here we have focused on the coactivator requirements for HNF-4, especially for the multicomponent TRAP/SMCC/Mediator complex that has emerged as the central regulatory module of the transcription apparatus. Using a system that has been reconstituted from purified transcription factors, as well as one consisting of unfractionated nuclear extract from which TRAP/SMCC/Mediator has been depleted by specific antibodies, we demonstrate a strong dependence of HNF-4 function on this coactivator. Importantly, we further show a TRAP/SMCC/Mediator-dependence for HNF-4 transcriptional activation from chromatin templates. The latter involves cooperation with the histone acetyltransferase-containing coactivator p300, in accord with a synergistic mode of action of the two divergent coactivators. We also show that HNF-4 and TRAP/SMCC/Mediator can interact physically. This interaction likely involves primary HNF-4 activation function 2 (AF-2)-dependent interactions with the TRAP220 subunit of TRAP/SMCC/Mediator and secondary (AF-2-independent) interactions with TRAP170/RGR1. Finally, recruitment experiments using immobilized templates strongly suggest that the functional consequences of the physical interaction probably are manifested at a postrecruitment step in the activation pathway.
Simple and Rapid LC-MS/MS Methods for Quantifying Catabolites of Antibody-Drug Conjugates with SMCC Linker
J Chromatogr Sci 2021 Jun 21;59(7):642-649.PMID:33420505DOI:10.1093/chromsci/bmaa122.
The stability and exposure of toxin-related catabolites in system circulation contributes to the evaluation of the stability, targeted delivery and off-target toxicity for antibody-drug conjugates (ADC) at different stages during drug development. In this study, simple and rapid liquid chromatography-tandem mass spectrometry (LC-MS/MS) methods for determination catabolites of Mertansine (DM1), MCC-DM1 and Lys-MCC-DM1 in cynomolgus serum have been developed. The serum samples are processed by protein precipitation. The LC-MS/MS methods are applied on a Phenomenex C8 column (50 × 2.0 mm, 5 μm) with gradient elution with water-formic acid 0.1% (A) and acetonitrile-formic acid 0.1% (B) at a flow rate of 0.5 mL/min. The analytical run time is only 4.0 min and the calibration ranges of the standard curve are 0.500-200 ng/mL for DM1, 1.00-500 ng/mL for MCC-DM1 and 2.00-1000 ng/mL for Lys-MCC-DM1. Intra- and inter-day precision of low, middle and high quality controls was <15%, and accuracy was 99.2-110.9%. The methods were successfully applied to evaluate three catabolites of novel ADCs with N-succinimidyl-4-(N-maleimidomethyl)-cyclohexane-1-carboxylate linker in vitro and in vivo studies.
Design of smart neonatal health monitoring system using SMCC
Healthc Technol Lett 2016 Nov 2;4(1):13-19.PMID:28261491DOI:10.1049/htl.2016.0054.
Automated health monitoring and alert system development is a demanding research area today. Most of the currently available monitoring and controlling medical devices are wired which limits freeness of working environment. Wireless sensor network (WSN) is a better alternative in such an environment. Neonatal intensive care unit is used to take care of sick and premature neonates. Hypothermia is an independent risk factor for neonatal mortality and morbidity. To prevent it an automated monitoring system is required. In this Letter, an automated neonatal health monitoring system is designed using sensor mobile cloud computing (SMCC). SMCC is based on WSN and MCC. In the authors' system temperature sensor, acceleration sensor and heart rate measurement sensor are used to monitor body temperature, acceleration due to body movement and heart rate of neonates. The sensor data are stored inside the cloud. The health person continuously monitors and accesses these data through the mobile device using an Android Application for neonatal monitoring. When an abnormal situation arises, an alert is generated in the mobile device of the health person. By alerting health professional using such an automated system, early care is provided to the affected babies and the probability of recovery is increased.
Potent antigen-specific immune response induced by infusion of spleen cells coupled with succinimidyl-4-(N-maleimidomethyl cyclohexane)-1-carboxylate (SMCC) conjugated antigens
Int Immunopharmacol 2016 Feb;31:158-68.PMID:26735611DOI:10.1016/j.intimp.2015.12.023.
In the present study, we report our recently developed new approach to inducing antigen-specific immune response. We use two nucleophilic substitution "click" chemistry processes to successfully couple protein antigens or peptides to mouse spleen cells or T cells by a heterobifunctional crosslinker, succinimidyl-4-(N-maleimidomethyl cyclohexane)-1-carboxylate (SMCC) or sulfo-SMCC. SMCC and its water-soluble analog sulfo-SMCC contain N-hydroxysuccinimide (NHS) ester and maleimide groups, which allow stable covalent conjugation of amine- and sulfhydryl-containing molecules in trans. Protein coupling to cells relies on the free sulfhydryls (thiols) on cell surfaces and the free amines on protein antigens. Although the amount of protein coupled to cells is limited due to the limited number of cell surface thiols, the injection of spleen cells coupled with antigenic proteins, such as keyhole limpet hemocyanin (KLH) or ovalbumin (OVA), induces a potent antigen-specific immune response in vivo, which is even stronger than that induced by the injection of a large dose of protein plus adjuvants. In addition, short peptides coupled to purified splenic T cells also potently elicit peptide-specific T cell proliferation in vivo after injection. Further studies show that antigen-coupled spleen cell treatment leads to augmented IFN-γ-producing T cells. Our study provides a unique antigen delivery method that efficiently distributes antigen to the entire immune system, subsequently eliciting a potent antigen-specific immune response with enhanced IFN-γ production. The findings in the present study suggest that this antigen-cell coupling strategy could be employed in immunotherapy for cancers, infectious diseases as well as immune-mediated disorders.