6-carboxyfluorescein N-hydroxysuccinimide ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-carboxyfluorescein N-hydroxysuccinimide ester
• 英文别名: 6-carboxyfluorescein succinimidyl ester；fluorescein NHS；Flurescein-NHS ester；4-(2,5-dioxopyrrolidin-1-yl)oxycarbonyl-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• 化学式: C₂₅H₁₅NO₉
• 分子量: 473.395
• InChiKey: LXFOCXWFKJWFEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-carboxyfluorescein N-hydroxysuccinimide ester 在 4-二甲氨基吡啶 、 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Artificial Ligands of Streptavidin (ALiS): Discovery, Characterization, and Application for Reversible Control of Intracellular Protein Transport

  摘要：

  Artificial ligands of streptavidin (ALiS) with association constants of similar to 10(6) M-1 were discovered by high-throughput screening of our chemical library, and their binding characteristics, including X-ray crystal structure of the streptavidin complex, were determined. Unlike biotin and its derivatives, ALiS exhibits fast dissociation kinetics and excellent cell permeability. The streptavidin-ALiS system provides a novel, practical compound-dependent methodology for repeated reversible cycling of protein localization between intracellular organella.

  DOI：

  10.1021/jacs.5b05672
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 6-carboxyfluorescein 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 6-carboxyfluorescein N-hydroxysuccinimide ester
  参考文献：
  名称：

  Artificial Ligands of Streptavidin (ALiS): Discovery, Characterization, and Application for Reversible Control of Intracellular Protein Transport

  摘要：

  Artificial ligands of streptavidin (ALiS) with association constants of similar to 10(6) M-1 were discovered by high-throughput screening of our chemical library, and their binding characteristics, including X-ray crystal structure of the streptavidin complex, were determined. Unlike biotin and its derivatives, ALiS exhibits fast dissociation kinetics and excellent cell permeability. The streptavidin-ALiS system provides a novel, practical compound-dependent methodology for repeated reversible cycling of protein localization between intracellular organella.

  DOI：

  10.1021/jacs.5b05672

文献信息

• [EN] BONE ACTIVE NITROGEN-CONTAINING BISPHOSPHONATES WITH A NEAR INFRARED FLUORESCENT LABEL<br/>[FR] BISPHOSPHONATES CONTENANT DE L'AZOTE ACTIFS DANS L'OS AYANT UN MARQUEUR FLUORESCENT DANS LE PROCHE INFRAROUGE
  申请人：UNIV SOUTHERN CALIFORNIA

  公开号：WO2017053486A1

  公开（公告）日：2017-03-30

  A compound of Formula (I) has the structure: wherein G is a straight, branched or cyclic alkyl group having 2 to 50 carbon atoms or an ether group, and R is a fluorescent dye. In some embodiments, G is selected from the group consisting of -(CH2)n- and -(CH2OCH2)m-, wherein n is an integer from 2 to 18, m is an integer from 2 to 18.

  式（I）的化合物具有以下结构：其中G是具有2到50个碳原子的直链、支链或环烷基基团或醚基团，R是荧光染料。在某些实施例中，G从组中选择，该组由-(CH2)n-和-( O )m-组成，其中n是从2到18的整数，m是从2到18的整数。
• [EN] INTEGRIN ANTAGONIST CONJUGATES FOR TARGETED DELIVERY TO CELLS EXPRESSING VLA-4<br/>[FR] CONJUGUÉS D'ANTAGONISTES D'INTÉGRINE POUR CIBLER DES CELLULES EXPRIMANT LE VLA-4
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013110680A1

  公开（公告）日：2013-08-01

  The invention relates to compounds of formula I: wherein R1, R2, and n are defined in the detailed description and claims. In particular, the present invention relates to the compounds of formula I for use in the manufacture and delivery of conjugated moieties such as small molecules, peptides, nucleic acids, fluorescent moieties, and polymers which are linked to VLA-4 integrin antagonists to target cells expressing VLA-4.

  该发明涉及以下式I的化合物：其中R1、R2和n在详细说明和权利要求中有定义。具体而言，本发明涉及式I的化合物，用于制造和传递共轭基团，如小分子、肽、核酸、荧光基团和聚合物，这些基团与VLA-4整合素拮抗剂连接，以靶向表达VLA-4的细胞。
• [EN] TUNABLE FLUORESCENCE USING CLEAVABLE LINKERS<br/>[FR] FLUORESCENCE RÉGLABLE À L'AIDE DE LIEURS CLIVABLES
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2014171899A1

  公开（公告）日：2014-10-23

  The invention relates to cleavable chemistry in general, and in particular, to tunable fluoresence using cleavable linkers present in fluorochrome-quencher conjugates.

  这项发明涉及可切割化学反应，特别是利用存在于荧光染料-猝灭剂共轭物中的可切割连接物来实现可调节荧光。
• [EN] INTEGRIN ANTAGONIST CONJUGATES FOR TARGETED DELIVERY TO CELLS EXPRESSING ALPHA-V-BETA-3<br/>[FR] CONJUGUÉS D'ANTAGONISTE DE L'INTÉGRINE POUR UNE ADMINISTRATION CIBLÉE À DES CELLULES EXPRIMANT L'ALPHA-V-BÊTA-3
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013110578A1

  公开（公告）日：2013-08-01

  The invention relates to compounds of formula (I): wherein R1, R2, and n are defined in the detailed description and claims. In particular, the present invention relates to the compounds of formula (I) for use in the manufacture and delivery of conjugated moieties such as small molecules, peptides, nucleic acids, fluorescent moieties, and polymers which are linked to alpha-V-beta-3 integrin antagonists to target cells expressing alpha-V-beta-3.

  本发明涉及如下公式(I)的化合物：其中R1、R2和n在详细描述和权利要求中定义。特别是，本发明涉及用于制造和输送与alpha-V-beta-3整合素拮抗剂连接的共轭部分，如小分子、肽、核酸、荧光部分和聚合物，以针对表达alpha-V-beta-3的细胞的公式(I)的化合物。
• APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES
  申请人：Kunzer Aaron R.

  公开号：US20100184766A1

  公开（公告）日：2010-07-22

  Disclosed are compounds which inhibit the activity of anti-apoptotic Bcl-2 proteins, compositions containing the compounds and methods of treating diseases during which is expressed anti-apoptotic Bcl-2 protein.

  公开了抑制抗凋亡Bcl-2蛋白活性的化合物，包含这些化合物的组合物以及治疗表达抗凋亡Bcl-2蛋白疾病的方法。