4-(N-Maleimidomethyl)cyclohexane-1-carboxylic acid 3-sulfo-N-hydroxysuccinimide ester sodium salt , CAS No.92921-24-9

CAS: 92921-24-9 Cat. No.: M123456 Peso molecular: 436.37 Número EC: 618-887-3

Synonyms

Sulfo-SMCC Sodium Salt

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Application

Antibody Drug Conjugates(ADC), Drug Delivery, Surface Modification, PEGylation of Protein, Peptide & Oligo

Descripción general

4-(N-Maleimidomethyl)cyclohexane-1-carboxylic acid 3-sulfo-N-hydroxysuccinimide ester sodium salt (sulfoSMCC) is a heterobifunctional protein/peptide cross-linker and a suitable cross-coupling reagent.

Specifications

Sinónimos

Sulfo-SMCC Sodium Salt

Mecanismos bioquímicos y fisiológicos

4-(N-Maleimidomethyl)cyclohexane-1-carboxylic acid 3-sulfo-N-hydroxysuccinimide ester sodium salt is known to introduce a well-defined number of maleimide groups into the protein which confers them a long shelf-life at low temperatures and can be further

Condiciones de almacenamiento de almacenamiento

Store at -20°C, Argon charged

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Nombres e identificadores

• Pubchem Sid: 504763085
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763085
• Sonrisas canónicas: C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)ON3C(=O)CC(C3=O)S(=O)(=O)[O-].[Na+]
• IUPAC Name: sodium;1-[4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexanecarbonyl]oxy-2,5-dioxopyrrolidine-3-sulfonate
• InChIKey: VUFNRPJNRFOTGK-UHFFFAOYSA-M
• 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
• Isómeros SMILES: C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)ON3C(=O)CC(C3=O)S(=O)(=O)[O-].[Na+]
• WGK Alemania: 3
• Peso molecular: 436.37
• Reaxy-Rn: 9374793
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9374793&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Pyrrolidines
      • Subclass Pyrrolidones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Pyrrolidines
• Subclass: Pyrrolidones
• Intermediate Tree Nodes: Not available
• Direct Parent: Maleimides
• Alternative Parents: Pyrrolidine-2-ones N-substituted carboxylic acid imides Sulfonyls Pyrrolines Organosulfonic acids Alkanesulfonic acids Dicarboximides Lactams Azacyclic compounds Monocarboxylic acids and derivatives Organonitrogen compounds Hydrocarbon derivatives Organic oxides Carbonyl compounds Organic sodium salts Organic cations
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Maleimide - Carboxylic acid imide, n-substituted - 2-pyrrolidone - Carboxylic acid imide - Dicarboximide - Pyrroline - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Organosulfonic acid - Sulfonyl - Alkanesulfonic acid - Lactam - Monocarboxylic acid or derivatives - Azacycle - Organic alkali metal salt - Carboxylic acid derivative - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Organic nitrogen compound - Organic salt - Organic sodium salt - Organic cation - Aliphatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as maleimides. These are compounds containing a 2,5-pyrroledione moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Solubilidad: soluble in water (2.5 mg/ml) and DMF
• Sensibilidad: heat & Moisture sensitive
• Peso molecular: 436.400 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 436.055 Da
• Monoisotopic Mass: 436.055 Da
• Topological Polar Surface Area: 167.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 853.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

Referencias

1. Jing Xu, Yujin Li, Yinbing Liu, Xu Wu, Ke-jing Huang.  (2023)  Ultra-sensitive self-powered sensor based on the hollow Rubik's cube substrate and multiple signal amplification strategy for real-time heavy metal detection.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2023.134377]

2. Jing Xu, Yinbing Liu, Ke-Jing Huang, Renjie Wang, Xiaoxuan Sun.  (2023)  An ingenious designed dual mode self-powered biosensing platform based on graphdiyne heterostructure substrate for instant hepatocarcinoma marker detection.  TALANTA,      [PMID:37209584] [10.1016/j.talanta.2023.124656]

3. Ruijin Zeng, Linghui Lin, Hexiang Gong, Yuxuan Li, Jianhui Xu, Lingting Huang, Weijun Wang, Sen Lin, Dianping Tang, Shaojun Guo.  (2023)  Tuning the rate-determining step of uric acid electrooxidation over single-atom-site metal centers for high-performing sensing.  Chem Catalysis,      [PMID:] [10.1016/j.checat.2023.100514]

4. Fu-Ting Wang, Yang-Yang Hou, Xuecai Tan, Ke-Jing Huang, Jing Xu, Ren Cai.  (2022)  Real-time multiple signal amplification self-powered biosensing platform for ultrasensitive detection of MicroRNA.  BIOSENSORS & BIOELECTRONICS,      [PMID:36470063] [10.1016/j.bios.2022.114933]

5. Yayun An, Dafeng Jiang, Nan Zhang, Wei Jiang.  (2022)  Cascade primer exchange reaction-based amplification strategy for sensitive and portable detection of amyloid β oligomer using personal glucose meters.  ANALYTICA CHIMICA ACTA,      [PMID:36257732] [10.1016/j.aca.2022.340440]

6. Mohammad Javad Afshari, Cang Li, Jianfeng Zeng, Jiabin Cui, Shuwang Wu, Mingyuan Gao.  (2022)  Self-illuminating NIR-II bioluminescence imaging probe based on silver sulfide quantum dots.  ACS Nano,      [PMID:36178795] [10.1021/acsnano.2c06667]

7. Fu-Ting Wang, Hu Luo, Yang-Yang Hou, Yu Ya, Ke-Jing Huang, Shu-Peng Li, Lan-Rui Wang, Ya-Lin Song, Xuecai Tan.  (2022)  Dual microRNAs-driven enzyme biofuel cells: Visualization biosensing system with capacitor assistance output signal amplification.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2022.131970]

8. Wenting He, Hao Shen, Zixin Zhou, Ze Huang, Hao Chao, Jiayi Song, Ping Su, Yi Yang.  (2021)  Janus DNA bridges metal-organic frameworks and graphene oxide for convenient and efficient multienzyme co-immobilization with boosted activity.  APPLIED SURFACE SCIENCE,      [PMID:] [10.1016/j.apsusc.2021.151242]

9. Yuan-Yuan Jiang, Xu Zhao, Li-Jian Chen, Cheng Yang, Xue-Bo Yin, Xiu-Ping Yan.  (2021)  A dual-colored persistent luminescence nanosensor for simultaneous and autofluorescence-free determination of aflatoxin B1 and zearalenone.  TALANTA,      [PMID:34074391] [10.1016/j.talanta.2021.122395]

10. Jiayi Song, Wenting He, Hao Shen, Zixin Zhou, Mengqi Li, Ping Su, Yi Yang.  (2020)  Exquisitely designed magnetic DNA nanocompartment for enzyme immobilization with adjustable catalytic activity and improved enzymatic assay performance.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2020.124488]

11. Zixin Zhou, Zijing Gao, Hao Shen, Mengqi Li, Wenting He, Ping Su, Jiayi Song, Yi Yang.  (2020)  Metal–Organic Framework in Situ Post-Encapsulating DNA–Enzyme Composites on a Magnetic Carrier with High Stability and Reusability.  ACS Applied Materials & Interfaces,      [PMID:31971363] [10.1021/acsami.9b23526]

12. Anwei Zhou, Junjie Du, Mengying Jiao, Daping Xie, Qianqian Wang, Lingjing Xue, Caoyun Ju, Zichun Hua, Can Zhang.  (2019)  Co-delivery of TRAIL and siHSP70 using hierarchically modular assembly formulations achieves enhanced TRAIL-resistant cancer therapy.  JOURNAL OF CONTROLLED RELEASE,      [PMID:31078569] [10.1016/j.jconrel.2019.05.013]

13. Jiayi Song, Wenting He, Hao Shen, Zixin Zhou, Mengqi Li, Ping Su, Yi Yang.  (2019)  Construction of multiple enzyme metal–organic frameworks biocatalyst via DNA scaffold: A promising strategy for enzyme encapsulation.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2019.01.138]

14. Lu Xuewen, mei Ting, Guo Qi, Zhou Wenjing, Li Xiaomei, Chen Jitao, Zhou Xinke, Sun Ning, Fang Zhiyuan.  (2018)  Improved performance of lateral flow immunoassays for alpha-fetoprotein and vanillin by using silica shell-stabilized gold nanoparticles.  MICROCHIMICA ACTA,  186  (1): (1-7).  [PMID:30515570] [10.1007/s00604-018-3107-9]

15. Fengchun Zhao, Yuan Tian, Qiang Shen, Ruxia Liu, Ruirui Shi, Huimin Wang, Zhengyou Yang.  (2018)  A novel nanobody and mimotope based immunoassay for rapid analysis of aflatoxin B1.  TALANTA,      [PMID:30625581] [10.1016/j.talanta.2018.11.013]

16. Jiayi Song, Hao Shen, Ye Yang, Zixin Zhou, Ping Su, Yi Yang.  (2018)  Multifunctional magnetic particles for effective suppression of non-specific adsorption and coimmobilization of multiple enzymes by DNA directed immobilization.  Journal of Materials Chemistry B,  6  (36): (5718-5728).  [PMID:32254978] [10.1039/C8TB01842A]

17. Jiayi Song, Ting Lei, Ye Yang, Nan Wu, Ping Su, Yi Yang.  (2018)  Attachment of enzymes to hydrophilic magnetic nanoparticles through DNA-directed immobilization with enhanced stability and catalytic activity.  NEW JOURNAL OF CHEMISTRY,  42  (11): (8458-8468).  [PMID:] [10.1039/C8NJ00426A]

18. Jing Xu, Xinqi Luo, Yujin Li, Yinbing Liu, Jianqi Lu, Xi Lin, Ke-Jing Huang.  (2024)  A self-powered sensor based on hollow bimetallic sulfide and double-strand TSDR amplification achieves sensitive miRNA-21 detection.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2024.136487]

19. Zhenhuan Jin, Wei Xiao, Lin Shen, Xiaoxue Shi, Jianping Li.  (2024)  An electrochemical method based on CRISPR-Cas12a and enzymatic reaction for the highly sensitive detection of tumor marker MUC1 mucin.  ANALYST,  149  (15): (3920-3927).  [PMID:38912896] [10.1039/D4AN00595C]

20. Qiu-Yue Pan, Yi-Fan Liang, Yu Wang, Yi-Hong He, Yan-Hong Chen, Jin-Yi Yang, Yu-Dong Shen, Zhen-Lin Xu, Bruce Hammock, Surat Hongsibsong, Hong Wang.  (2025)  Engineering bioluminescent immunoassay for mix-to-measure parathion detection in foodstuffs.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.112936]

21. Yan Zhao, Qianqian Yu, Miaolin Duan, Qi Zhang, Zhishang Li, Yan Zhang, Yana Liu, Han Wang, Xingmin Li, Ruitong Dai, Fei Jia.  (2024)  Locking-Fluorescence Signals Regulated CRISPR/Cas12a Biosensor Based on Metal–Organic Framework for Sensitive Detection of Salmonella typhimurium.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:39508638] [10.1021/acs.jafc.4c07681]

22. Fengchun Zhao, Guanqun Wang, Xinrui Cao, Wenxu Song, Min Guo, Huimin Wang, Zhengyou Yang.  (2025)  Non-competitive immunoassay for zearalenone based on phage display developed recombinant antibody and anti-immunocomplex peptide.  FOOD CHEMISTRY,      [PMID:39848053] [10.1016/j.foodchem.2025.142943]

23. Sun Huiwen, Wei Moris, Guo Amber, Zhang Ci, Wang Yuefeng, Huang Renhui, Li Xiaoxiao, Zhan Jeffrey, Wu Jonny, Jiang Bruce.  (2024)  Shrimp hemocyanin elicits a potent humoral response in mammals and is favorable to hapten conjugation.  Scientific Reports,  14  (1): (1-10).  [PMID:39039159] [10.1038/s41598-024-67715-1]

24. Xuefeng Zhang, Xuyang Huang, Diancheng Hang, Jiaqi Jin, Shanshan Li, Yufu Zhu, Hongmei Liu.  (2024)  Targeting pyroptosis with nanoparticles to alleviate neuroinflammatory for preventing secondary damage following traumatic brain injury.  Science Advances,  10  (2):   [PMID:38198543] [10.1126/sciadv.adj4260]

25. Hui Li, Zongshan Zhang, Wantong Hao, Huixin Shi, Ruiyang Yin, Jing Xu.  (2025)  Self-powered bio-chip for ultra-sensitive dual MiRNAs detection: A portable platform for cancer biomarker analysis.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40419043] [10.1016/j.ijbiomac.2025.144637]

26. Xiaonan Wei, Chaoquan Lai, Xiaoyang Zhu, Aiyan Ji, Yeshan Qin, Shu Gao, Qiuyu Liu, Yonghao Li, Xuanyan Zhao, Hongyue Lou, Chunrong Qu, Zhen Cheng.  (2025)  Construction of 89Zr-Radiolabeled Melanin-Based Nanoprobes with FAP-Targeted Motifs for Tumor PET Imaging.  MOLECULAR PHARMACEUTICS,      [PMID:41111236] [10.1021/acs.molpharmaceut.5c01192]

27. Xueying Zhao, JinJin Li, Yi Hao, Xiaolan Gao, Yifu Wang, Leiliang He, Yamin Xiong.  (2025)  Proximity Effect-Mediated DNA Self-Assembly for the Highly Specific Detection of Glioma-Derived Exosomes by Combining Multiple Exosomal Surface Markers.  ACS Sensors,      [PMID:41292412] [10.1021/acssensors.5c00951]

28. Li-Wen Zhang, Zhu-Ying Yan, Xu Zhao, Li-Xia Yan, Li-Jian Chen, Xiu-Ping Yan.  (2026)  Undoped zinc gallogermanate nanoparticles based persistent luminescence aptasensor for the determination of bisphenol a in aquatic products.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:41679186] [10.1016/j.saa.2026.127553]

29. Xu Zhao, Xue-Bing Qin, Zhu-Ying Yan, Li-Jian Chen, Xiu-Ping Yan.  (2026)  Complementary Strand-Free Persistent Luminescence Ratiometric Aptasensor for Ultrasensitive and Selective Carbendazim Assay.  ACS Sensors,      [PMID:] [10.1021/acssensors.5c04924]

30. Wenxu Song, Xinrui Cao, Wendi Yue, Fengchun Zhao, Qing Zhou, Zhengyou Yang.  (2026)  Signal-enhanced ultrasensitive photoelectrochemical immunosensor for detecting Aflatoxin B1 based on phage-anti-immunocomplex peptide and PCN-224@MXene.  BIOSENSORS & BIOELECTRONICS,      [PMID:] [10.1016/j.bios.2026.118641]