4-(N-马来酰亚胺甲基)环己烷羧酸 -N-琥珀酰亚胺酯(SMCC)

CAS: 64987-85-5 货号: N159712 分子式: C16H18N2O6 分子量: 334.33 EC号: 694-914-2
有货
级别和纯度: ≥98%(HPLC)
别名
N-琥珀酰亚胺基4-(马来酰亚胺基甲基)环己烷羧酸酯 | 4-[(2,5-二氧代-2,5-二氢-1H-吡咯-1-基)甲基]环己烷-1-甲酸2,5-二氧代吡咯烷-1-基酯
储存条件
-20°C储存,充氩
运输条件
超低温运输
应用
Antibody Drug Conjugates(ADC), 药物输送、表面改性, 蛋白质、肽和寡聚物的聚乙二醇化
★
规格
库存
价格
数量
25mg
N159712-25mg
期货 Stock Image
¥29.90
250mg
N159712-250mg
现货 Stock Image
¥49.90
1g
N159712-1g
现货 Stock Image
¥109.90
5g
N159712-5g
现货 Stock Image
¥485.90
25g
N159712-25g
现货 Stock Image
¥1,980.90
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为什么选择此级别

提供 ≥98%(HPLC) 纯度,适用于对基线干扰要求严格的色谱和分析工作流程。

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储存与运输

-20°C储存,充氩。超低温运输 。请查阅批次 COA 获取详细规格。

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质量文档

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文献证明

在色谱分析、有机合成和交叉偶联反应领域已被 53 篇同行评审文献引用。

概述

4-(N-马来酰亚胺基甲基)环己烷羧酸 N-羟基琥珀酰亚胺酯(SMCC)是一种异双功能交联剂,其包含一个具有胺和巯基反应性的延长间隔基。[1]它通常首先通过酰胺键(pH7.5(6.5-8.5)缓冲)与含有伯胺的分子进行偶联。第二次偶联通过硫醚键(pH6.8(6.5-7.0)缓冲)与含有游离巯基的分子进行特异性偶联。SMCC包含九个原子连接子。与芳族间隔基相比,延伸的脂族间隔基可在偶联之前稳定马来酰亚胺。

4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester (SMCC) is a heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. It is typically coupled initially to molecules containing primary amine by amide bond buffered at pH 7.5 (6.5-8.5). The second coupling is specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). SMCC contains nine atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers.
A heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. Typically coupled initially to molecules containing primary amine by amide bond buffered at pH 7.5 (6.5-8.5). The second coupling is specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Contains 9 atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers.

规格

别名
N-琥珀酰亚胺基4-(马来酰亚胺基甲基)环己烷羧酸酯 | 4-[(2,5-二氧代-2,5-二氢-1H-吡咯-1-基)甲基]环己烷-1-甲酸2,5-二氧代吡咯烷-1-基酯
英文别名
BCP10445 | 4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester, >=98%, powder | DB01429 | Mal-AMCHC-OSu | FT-0604078 | KBio2_007073 | AKOS015900701 | 2,5-dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexa
规格或纯度
≥98%(HPLC)
英文名称
N-Succinimidyl 4-(N-Maleimidomethyl) cyclohexanecarboxylate(SMCC)
储存条件
-20°C储存,充氩
运输条件
超低温运输
纯度
≥98%(HPLC)
名称和识别符
PubChem SID
EC号
694-914-2
分子类型
小分子
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexane-1-carboxylate
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
InChi Key
JJAHTWIKCUJRDK-UHFFFAOYSA-N
Smiles
C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)ON3C(=O)CCC3=O
Isomeric SMILES
C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)ON3C(=O)CCC3=O
分子量
334.33
Reaxy-Rn
1555271
Reaxys-RN link address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1555271&ln=

技术文档

📋 安全数据表 (SDS)

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🔬 规格说明书

该级别的完整质量属性和验收标准。

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高级数据

系统学分类

分类树(Taxonomy Tree)

界(kingdom) 有机化合物
超类(Superclass) 有机杂环化合物
类(Class) 吡咯烷
亚类(Subclass) 吡咯烷酮
中间层级节点(Intermediate Tree Nodes) 暂无
直接上位类(Direct Parent) 马来酰亚胺
其他上位类(Alternative Parents) 吡咯烷-2-酮  N-取代羧酸酰亚胺  吡咯啉  二羧酰亚胺  内酰胺类  羧酸盐  一元羧酸及其衍生物  氮杂环化合物  有机光子化合物  有机氮化合物  有机盐  有机氧化物  碳氢化合物衍生物  羰基化合物  
分子骨架(Molecular Framework) 脂肪族杂单环化合物
取代基(Substituents) 2-吡咯烷酮 - 脂肪族杂单环化合物 - 氮杂环 - 羰基 - 羧酸衍生物 - 羧酸酰亚胺 - 羧酸亚胺,正位取代 - 羧酸盐 - 二羧酰亚胺 - 烃衍生物 - 肟 - 甲酰亚胺 - 单羧酸或其衍生物 - 有机硝基化合物 - 有机氧化物 - 有机氧化合物 - 有机盐 - 有机氮化合物 - 有机氧化合物 - 有机氮化合物 - 吡咯烷酮
描述(Description) 该化合物属于马来酰亚胺类有机化合物。这类化合物含有2,5-吡咯烷酮结构单元。
外部描述符(External Descriptors) maleimides - N-hydroxysuccinimide ester
三维结构
交互式化学结构模型





化学和物理性质
敏感性
对热敏感 ;对光线敏感 ;对湿度敏感
熔点
177 °C
分子量
334.320 g/mol
XLogP3
-0.100
氢键供体数Hydrogen Bond Donor Count
0
氢键受体数Hydrogen Bond Acceptor Count
6
可旋转键计数Rotatable Bond Count
5
精确质量Exact Mass
334.116 Da
单同位素质量Monoisotopic Mass
334.116 Da
拓扑极表面积Topological Polar Surface Area
101.000 Ų
重原子数Heavy Atom Count
24
形式电荷Formal Charge
0
复杂度Complexity
598.000
同位素原子数Isotope Atom Count
0
定义的原子立体中心计数Defined Atom Stereocenter Count
0
未定义的原子立体中心计数Undefined Atom Stereocenter Count
0
定义的键立体中心计数Defined Bond Stereocenter Count
0
未定义的键立体中心计数Undefined Bond Stereocenter Count
0
所有立体化学键的总数The total count of all stereochemical bonds
0
共价键合单元计数Covalently-Bonded Unit Count
1
安全和危险性(GHS)
象形图
信号词
警告
危险声明

H315: 引起皮肤刺激

H319: 引起严重眼睛刺激

预防措施声明

P264: 处理后要彻底洗手。

P280: 戴防护手套/穿防护服/戴防护眼罩/戴防护面具。

P302+P352: 如皮肤沾染:用水充分清洗。

P305+P351+P338: 如进入眼睛:用水小心冲洗几分钟。如戴隐形眼镜并可方便地取出,取出隐形眼镜。继续冲洗。

P332+P313: 如发生皮肤刺激:求医/就诊。

P337+P313: 如仍觉眼刺激:求医/就诊。

P362+P364: 脱掉沾污的衣服,清洗后方可重新使用。

质检证书(CoA,COO,BSE/TSE 和分析图谱)
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批号(Lot Number) 证书类型 货号
D2622626 分析证书 N159712
D2622615 分析证书 N159712
D2622623 分析证书 N159712
D2622624 分析证书 N159712
C2626096 分析证书 N159712
K2513100 分析证书 N159712
H2529718 分析证书 N159712
H2529717 分析证书 N159712
H2529471 分析证书 N159712
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H2217047 分析证书 N159712
B2420070 分析证书 N159712
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K2316322 分析证书 N159712
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I2215635 分析证书 N159712
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I2215632 分析证书 N159712
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D2323899 分析证书 N159712
D2501089 分析证书 N159712
D2514016 分析证书 N159712
H2423037 分析证书 N159712
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技术文档和文章
连接子 - 抗体与药物结合的关键因素
Linkers - A Crucial Factor in Antibody–Drug Conjugates
氨基反应探针标记实验方案
链霉亲和素修饰蛋白的专业指南
Professional Guide to Streptavidin-Modified Proteins
无脊椎动物氧载体蛋白在免疫与疫苗研究中的作用
Invertebrate Oxygen Carrier Proteins in Immunology and Vaccine Research
从官能团到实验判断:蛋白质交联剂选择与实验要点
From Functional Groups to Experimental Decision-Making: Protein Crosslinker Selection and Experimental Essentials
Amine-Reactive Probe Labeling Experimental Protocol
ADC 连接子:调控抗体药物偶联物体内稳定性、载荷释放及疗效安全性的关键单元
ADC Linkers: Key Units That Regulate the In Vivo Stability, Payload Release, and Efficacy and Safety of Antibody–Drug Conjugates
ADC热门抗肿瘤靶标:信号机制与靶向治疗进展
Leading ADC Targets in Oncology: Signaling Mechanisms and Therapeutic Advances
此产品的引用文献
引用文献
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