7-amino-4-methyl-6-sulfocoumarin-3-acetic acid succinimidyl ester | 200554-19-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-amino-4-methyl-6-sulfocoumarin-3-acetic acid succinimidyl ester
• 英文别名: Alexa Fluor 350 carboxylic acid succinimiddyl ester；7-amino-3-((((succinimidyl)oxy)carbonyl)methyl)-4-methylcoumarin-6-sulfonic acid；Alexa Fluor 350 NHS ester；Alex Fluor 350 NHS ester；Alexa Fluor 350；7-amino-3-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethyl]-4-methyl-2-oxochromene-6-sulfonic acid
• CAS: 200554-19-4
• 化学式: C₁₆H₁₄N₂O₉S
• 分子量: 410.361
• InChiKey: IKYJCHYORFJFRR-UHFFFAOYSA-N

物化性质

• 密度：
  1.74±0.1 g/cm3(Predicted)
• 溶解度：
  易溶于水、二甲基亚砜、甲醇
• 最大波长(λmax)：
  346nm (Buffer pH 7); 353nm (MeOH)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  179
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(2-氨基乙基)马来酰亚胺三氟乙酸盐 、 7-amino-4-methyl-6-sulfocoumarin-3-acetic acid succinimidyl ester 在 N,N-二异丙基乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 以67%的产率得到7-amino-3-((((2-maleimidyl)ethylamino)carbonyl)methyl)-4-methylcoumarin-6-sulfonic acid
  参考文献：
  名称：

  Sulfonated derivatives of 7-aminocoumarin

  摘要：

  本发明描述了在3-、6-和/或8-位置被磺酸或磺酸盐取代一次或多次的7-氨基香豆素染料，该染料可用作荧光探针或用于酶底物、被笼罩的探针或与还原糖形成加合物的制备中。本发明的染料可以选择性地具有用于制备荧光共轭物的反应基团，本发明描述了这些共轭物及其制备方法。

  公开号：

  US05696157A1
• 作为产物：
  描述：

  7-carboethoxyamido-4-methylcoumarin-3-acetic acid ethyl ester 在 吡啶 、 硫酸 作用下， 生成 7-amino-4-methyl-6-sulfocoumarin-3-acetic acid succinimidyl ester
  参考文献：
  名称：

  7-Amino-4-methyl-6-sulfocoumarin-3-acetic acid: a novel blue fluorescent dye for protein labeling

  摘要：

  7-Amino-4-methyl-6-sulfocoumarin-3-acetic acid (AMCA-S, also called Alexa(TM) 350) 2 was synthesized as a new water-soluble blue fluorescent dye for protein labeling. Compared with its nonsulfonated counterpart (AMCA) 1 the new dye gave significantly higher fluorescence quantum yields on proteins. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00364-9

文献信息

• SITE-SPECIFIC LABELING OF AFFINITY TAGS IN FUSION PROTEINS
  申请人：LIFE TECHNOLOGIES CORPORATION

  公开号：US20160025713A1

  公开（公告）日：2016-01-28

  The present invention provides methods and fluorescent compounds that facilitate detecting and labeling of a fusion protein by being capable of selectively binding to an affinity tag. The fluorescent compounds have the general formula A(B)n, wherein A is a fluorophore, B is a binding domain that is a charged chemical moiety, a protein or fragment thereof and n is an integer from 1-6 with the proviso that the protein or fragment thereof not be an antibody or generated from an antibody. The present invention provides specific fluorescent compounds and methods used to detect and label fusion proteins that contain a poly-histidine affinity tag. These compounds have the general formula A(L)m(B)n wherein A is a fluorophore, L is a linker, B is an acetic acid binding domain, m is an integer from 1 to 4 and n is an integer from 1 to 6. The acetic acid groups interact directly with the positively charged histidine residues of the affinity tag to effectively label and detect a fusion protein containing such an affinity tag when present in an acidic or neutral environment.

  本发明提供了一种方法和荧光化合物，通过选择性地与亲和标签结合，从而促进融合蛋白的检测和标记。所述荧光化合物具有通式A(B)n，其中A是荧光团，B是带电化学基团、蛋白质或其片段的绑定域，n是1-6的整数，但该蛋白质或其片段不是抗体或由抗体产生的。本发明还提供了特定的荧光化合物和方法，用于检测和标记含有聚组氨酸亲和标签的融合蛋白。这些化合物具有通式A(L)m(B)n，其中A是荧光团，L是连接器，B是醋酸绑定域，m是1到4的整数，n是1到6的整数。醋酸基团直接与亲和标签中的正电荷组氨酸残基相互作用，有效地标记和检测含有此类亲和标签的融合蛋白，当其存在于酸性或中性环境中时。
• [EN] DESIGN, SYNTHESIS AND EVALUATION OF PROCASPASE ACTIVATING COMPOUNDS AS PERSONALIZED ANTI-CANCER DRUGS<br/>[FR] CONCEPTION, SYNTHÈSE ET ÉVALUATION DE COMPOSÉS ACTIVATEURS DE PROCASPASE EN TANT QUE MÉDICAMENTS ANTICANCÉREUX PERSONNALISÉS
  申请人：UNIV ILLINOIS

  公开号：WO2010091382A1

  公开（公告）日：2010-08-12

  Compositions and methods are disclosed in embodiments relating to induction of cell death such as in cancer cells. Compounds and related methods for synthesis and use thereof, including the use of compounds in therapy for the treatment of cancer and selective induction of apoptosis in cells are disclosed. Compounds are disclosed that have lower neurotoxicity effects than other compounds.

  本发明公开了涉及诱导细胞死亡（例如癌细胞）的组合物和方法。公开了用于合成和使用这些化合物的相关方法，包括在癌症治疗中使用化合物以及在细胞中选择性诱导凋亡。公开了具有比其他化合物更低神经毒性效应的化合物。
• Fluorophore Assisted Photolysis of Thiolato-Cob(III)alamins
  作者：Zachary L. Rodgers、Thomas A. Shell、Alexander M. Brugh、Hannah L. Nowotarski、Malcolm D. E. Forbes、David S. Lawrence

  DOI：10.1021/acs.inorgchem.5b02036

  日期：2016.3.7

  investigated the photolysis of N-acetylcysteinyl cob(III)alamin at several wavelengths within the ultraviolet and visible spectrum. To aid in photolysis, we show that attaching fluorophore “antennae” to the cobalamin scaffold can improve photolytic efficiency by up to an order of magnitude. Additionally, electron paramagnetic resonance confirms previous conjectures that the photolysis of thiolato-cobalamins

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• Unraveling Tetrazine-Triggered Bioorthogonal Elimination Enables Chemical Tools for Ultrafast Release and Universal Cleavage
  作者：Jonathan C. T. Carlson、Hannes Mikula、Ralph Weissleder

  DOI：10.1021/jacs.7b11217

  日期：2018.3.14

  achieves only partial release and is incompletely understood, which has limited its application. Investigating the mechanistic features of this reaction’s performance, we discovered profound pH sensitivity, exploited it with acid-functionalized tetrazines that both enhance and markedly accelerate release, and ultimately uncovered an unexpected dead-end isomer as the reason for poor release. Implementing facile

  键裂解反应的最新发展已将生物正交化学的范围扩大到点击连接之外，并为探针激活和治疗递送提供了新的策略。然而，这些应用仍处于起步阶段，需要进一步创新以实现体内多功能和广泛有用的工具所需的效率。在这些化学反应中，四嗪/反式环辛烯点击释放反应具有示范性的动力学和适应性，但仅实现了部分释放且尚未完全了解，限制了其应用。研究该反应性能的机械特征，我们发现了深刻的 pH 敏感性，将其与酸官能化的四嗪一起使用，既增强又显着加速释放，并最终发现了一个意想不到的死端异构体，这是释放不良的原因。通过实施简单的方法来防止这种死胡同的形成，我们取得了非凡的效率，在整个生理 pH 范围内基本上完全释放，增强了药物递送策略并扩大了生物正交开/关控制的动态范围。
• FLUORESCENT COMPOUNDS
  申请人：Mao Fei

  公开号：US20090305410A1

  公开（公告）日：2009-12-10

  The present invention relates to fluorescent dyes in general. The present invention provides a wide range of fluorescent dyes and kits containing the same, which are applicable for labeling a variety of biomolecules, cells and microorganisms. The present invention also provides various methods of using the fluorescent dyes for research and development, forensic identification, environmental studies, diagnosis, prognosis, and/or treatment of disease conditions.

  本发明涉及一般的荧光染料。本发明提供了一系列广泛的荧光染料和包含这些染料的试剂盒，适用于标记各种生物分子、细胞和微生物。本发明还提供了利用荧光染料进行研究和开发、法医鉴定、环境研究、诊断、预后和/或治疗疾病状况的各种方法。