64987-85-5
中文名稱
4-(N-馬來酰亞胺基甲基)環(huán)己烷-1-羧酸琥珀酰亞胺酯
英文名稱
N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate
CAS
64987-85-5
分子式
C16H18N2O6
MDL 編號
MFCD00009634
分子量
334.32
MOL 文件
64987-85-5.mol
更新日期
2026/05/28 18:03:22
64987-85-5 結(jié)構(gòu)式
基本信息
中文別名
4-(N-馬來酰亞胺基甲基)環(huán)己烷-1-羧酸琥珀酰亞胺酯 英文別名
4-(N-MALEIMIDOMETHYL)CYCLOHEXANE-1-CARBOXYLIC ACID N-HYDROXYSUCCINIMIDE ESTER4-(N-MALEIMIDOMETHYL)CYCLOHEXANECARBOXYLIC ACID N-HYDROXYSUCCINIMIDE ESTER
N-SUCCINIMIDYL 4-(MALEIMIDOMETHYL)CYCLOHEXANE-1-CARBOXYLATE
N-SUCCINIMIDYL 4-(MALEIMIDOMETHYL)CYCLOHEXANECARBOXYLATE
SMCC
SUCCINIMIDYL 4-[N-MALEIMIDO-METHYL]CYCLOHEXANE-1-CARBOXYLATE
SUCCINIMIDYL TRANS-4-(MALEIMIDYLMETHYL)CYCLOHEXANE-1-CARBOXYLATE
SUCCINIMIDYL-TRANS-4-(N-MALEIMIDOMETHYL)CYCLOHEXANE-1-CARBOXYLATE
SUCCINIMIDYL-TRANS-4-(N-MALEIMIDYLMETHYL)CYCLOHEXANE-1-CARBOXYLATE
TRANS-4-(N-MALEIMIDYLMETHYL)-CYCLO-HEXANE-1-CARBOXYLATE-N-HYDROXYSUCCINIMIDE ESTER
n-(4-carboxycyclohexylmethyl)maleimiden-hydroxysuccinimideester
N-succinimidyl 4-(maleimidome.)cyclo-hexanecarboxylate
4-(N-MALEIMIDOMETHYL)-CYCLOHEXANE-1-CARBOXYLIC ACID N-HYDROXYSUCCINIMIDE ESTER CRYSTALLINE
N-Succinimidyl-4-(N-maleimidomethyl)-cyclohexane-1-carboxylate
4-(maleimidomethyl)-1-cyclohexanecarboxylic acid N-hydroxy
N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate, SMCC
所屬類別
有機(jī)原料：羧酸類化合物及衍生物物理化學(xué)性質(zhì)
熔點(diǎn)180-182 °C(lit.)
沸點(diǎn)501.7±42.0 °C(Predicted)
密度1.42±0.1 g/cm3(Predicted)
儲存條件2-8°C
溶解度chloroform: 50 mg/mL
酸度系數(shù)(pKa)-2.24±0.20(Predicted)
形態(tài)powder
顏色白色至灰白色
敏感性Moisture & Light Sensitive
BRN1555271
InChIInChI=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
InChIKeyJJAHTWIKCUJRDK-UHFFFAOYSA-N
SMILESC1(C(ON2C(=O)CCC2=O)=O)CCC(CN2C(=O)C=CC2=O)CC1
CAS 數(shù)據(jù)庫64987-85-5(CAS DataBase Reference)
安全數(shù)據(jù)
警示詞警告
危險性描述H315-H319-H335
危險品標(biāo)志Xi
危險類別碼R36/37/38
安全說明S26-S36
WGK Germany3
海關(guān)編碼29280000
存儲類別11 - Combustible Solids
應(yīng)用領(lǐng)域
用途1
單克隆的SMCC抗體衍生化與低(聚)核苷酸結(jié)合，用于兩步放射免疫療法中；雙異官能團(tuán)交聯(lián)試劑，將胺以及巰基反應(yīng)性合并入擴(kuò)展間隔片，典型地，在pH7.5緩沖液(6.5-8.5)中，通過酰胺鍵偶聯(lián)至包含伯胺的分子，在pH6.8緩沖液(6.5-7.0)中，通過硫醚連接，次級偶聯(lián)至特別的包含自由巰基的分子；用于制備酶的免疫交聯(lián)物以及半抗原載體分子結(jié)合體，包含了9個原子連接；一種擴(kuò)展的脂肪質(zhì)的間隔片，與芳香族間隔片相比，使順丁烯二酰亞胺穩(wěn)定地優(yōu)先偶聯(lián)用途2
A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(ab’2 fragments to 脽-galactosidase. Conjugates hIgG to alkaline phosphatase.常見問題列表
交聯(lián)標(biāo)記試劑
SMCC是常用的異雙功能交聯(lián)劑，交聯(lián)后提供一個8.3 ?的鏈接。SMCC兩端自帶馬來酰亞胺（maleimide）和NHS活化酯，可和巰基（thiol）和氨基（amine）反應(yīng)交聯(lián)，生成穩(wěn)定的巰醚鍵（thioester）和酰胺鍵。SMCC上環(huán)己烷（Cyclohexane）結(jié)構(gòu)可以加持馬來酰亞胺（maleimide）的穩(wěn)定性，甚至在pH 7.5條件下這種結(jié)構(gòu)的馬來酰亞胺仍然穩(wěn)定，例如，在4 oC下，0.1 M磷酸鈉緩沖液中可穩(wěn)定長達(dá)64小時。
生物活性
SMCC 是一種蛋白質(zhì)交聯(lián)劑。SMCC 接合抗原耦合脾臟細(xì)胞來誘導(dǎo)抗原特異性免疫反應(yīng)。體外研究
SMCC or sulfo-SMCC can use to conjugate keyhole limpet hemocyanin (KLH) and ovalbumin (OVA). In the the conjugation system, 300 μl KLH or OVA (3 mg) and 30 μl SMCC or Sulfo-SMCC (the final concentration of 0.1 mM) are added in PBS with final volume of 3 ml.
體內(nèi)研究
Using the SMCC-conjugation method is able to induce potent immune responses to whole protein or peptide antigens by injection of antigen-coupled syngeneic splenic mononuclear cells in mice.