5(6)-carboxy-tetramethylrhodamine | 212389-93-0

• 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: 5(6)-carboxy-tetramethylrhodamine
• 英文别名: TAMRA；5-Carboxy methylrhodamine；[9-(2,4-dicarboxyphenyl)-6-(dimethylamino)xanthen-3-ylidene]-dimethylazanium
• CAS: 212389-93-0；1236195-98-4
• 化学式: C₂₅H₂₃N₂O₅
• 分子量: 431.468
• InChiKey: YMZMTOFQCVHHFB-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  90.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5(6)-carboxy-tetramethylrhodamine 、 N-(6-aminohexyl)-azidoacetamide 在 1-羟基苯并三唑 、 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 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以18.2%的产率得到N-(6-azidoacetamidehexyl)-5-carbamide-tetramethylrhodamine
  参考文献：
  名称：

  Jiang, Hong; Congleton, Johanna; Liu, Qun, Journal of the American Chemical Society, 2009, vol. 131, p. 1658 - 1659

  摘要：

  DOI：
• 作为产物：
  描述：

  在 copper dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以80%的产率得到5(6)-carboxy-tetramethylrhodamine
  参考文献：
  名称：

  From Spirolactam Mixtures to Regioisomerically Pure 5- and 6-Rhodamines: A Chemodosimeter-Inspired Strategy

  摘要：

  Inspired by the ring-open reaction of rhodamine spriolactams as typical chemodosimeters, a general strategy is proposed to conveniently and efficiently synthesize isomerically pure 5- and 6-R-tetramethylrhodamine on a larger scale.

  DOI：

  10.1021/ol300523m

文献信息

• The one-pot nonhydrolysis Staudinger reaction and Staudinger or SPAAC ligation
  作者：Longhuai Cheng、Xueying Kang、Dan Wang、Yasi Gao、Long Yi、Zhen Xi

  DOI：10.1039/c9ob00528e

  日期：——

  azide than that the Staudinger-Bertozzi or SPAAC ligation with alkyl azide, as revealed by HPLC analysis and fluorescence kinetics. Based on the tandem NSR and Staudinger-Bertozzi ligation, we prepare a molecular beacon 7 from 1 in one-pot synthesis with a recovery yield of 32%. When a faster SPAAC ligation is used instead of the Staudinger-Bertozzi ligation, compound 8 is prepared in the tandem NSR and

  两种生物正交反应的组合使用可以在生理条件下为各种应用提供异双功能分子。基于非水解施陶丁格反应（NSR），我们设计和开发了一种双叠氮杂连接子1，用于化学选择性双官能化，而无需使用无催化剂和一锅法进行保护。HPLC分析和荧光动力学表明，四氟化芳族叠氮化物的NSR比Staudinger-Bertozzi或SPAAC与烷基叠氮化物的连接要快得多。基于串联NSR和Staudinger-Bertozzi连接，我们从一锅法合成中从1个制备分子信标7，回收率达32％。如果使用更快的SPAAC结扎代替Staudinger-Bertozzi结扎，在串联NSR和SPAAC反应中制备化合物8，回收率为59％。作为概念验证研究，双色生物成像显示，串联NSR和SPAAC连接可进一步在活细胞中产生基于FRET的二元组。这项工作表明，NSR可以与其他生物正交反应结合使用，而无需一锅得到保护。
• NOVEL PHOTOACTIVABLE FLUORESCENT DYES FOR OPTICAL MICROSCOPY AND IMAGING TECHNIQUES
  申请人：Hell Stefan W.

  公开号：US20120202216A1

  公开（公告）日：2012-08-09

  The present invention relates to novel photoactivable rhodamine or carbopyronine derivatives of the following general formulae G1-G4 (I), G1: A1=O, A2=N, A3=C; G2: A1=S, A2=N, A3=C; G3: A1=O, A2=O, A3=N; G4: A1=S, A2=O, A3=N; comprising UV light absorbing chromophores which after photolysis by irradiation at 254-490 nm (preferably at 375-420 nm) generate fluorescent rhodamine or carbopyronine derivatives and small non-toxic fragments such as N 2 or N 2 O. The invention also relates to methods for preparing such compounds and to the use of these compounds for optical microscopy and imaging techniques.

  本发明涉及以下通式G1-G4（I）的新型光致发色基础或羧基吡咯烷衍生物，其中：G1：A1=O，A2=N，A3=C；G2：A1=S，A2=N，A3=C；G3：A1=O，A2=O，A3=N；G4：A1=S，A2=O，A3=N；包括吸收紫外光的色团，经过254-490 nm的光解作用（最好在375-420 nm下），产生荧光的罗丹明或羧基吡咯烷衍生物和小的无毒碎片，例如N2或N2O。本发明还涉及制备这种化合物的方法以及将这些化合物用于光学显微镜和成像技术的使用。
• FLUORESCENT ISOTOPE TAGS AND THEIR METHOD OF USE
  申请人：Agnew Brian

  公开号：US20090017546A1

  公开（公告）日：2009-01-15

  The present invention provides novel reactive fluorescent compounds that incorporate stable isotopic (deuterium, 13-carbon, 15-nitrogen, 18-oxygen) substitutions. The invention includes the use of these compounds, in combination with non-isotopically substituted analogs, for the purification, identification and relative quantification of proteins, peptides, saccharides, metabolites, and other biologically important compounds by combining liquid chromatography (LC) and mass spectrometry (MS). Fluorescent labeling of target compounds in this manner provides orders-of-magnitude sensitivity enhancement over traditional stable isotope labels, and also affords the possibility of simultaneous multiplexed analysis due to the multiwavelength nature of different fluorophores.

  本发明提供了新型反应性荧光化合物，其中包含稳定同位素（氘，13-碳，15-氮，18-氧）取代。该发明包括使用这些化合物与非同位素取代的类似物结合，通过液相色谱（LC）和质谱（MS）相结合来纯化、鉴定和相对定量蛋白质、肽、糖、代谢物和其他生物重要化合物。以这种方式对目标化合物进行荧光标记提供了比传统的稳定同位素标记高几个数量级的灵敏度增强，并且由于不同荧光团的多波长性质，还提供了同时多重分析的可能性。
• Immunotargeting of Gram-Positive Pathogens <i>via</i> a Cell Wall Binding Tick Antifreeze Protein
  作者：Brianna E. Dalesandro、Marcos M. Pires

  DOI：10.1021/acs.jmedchem.2c01464

  日期：2023.1.12

  Immunological agents that supplement or modulate the host immune response have proven to have powerful therapeutic potential, although this modality is less explored against bacterial pathogens. We describe the application of a bacterial binding protein to re-engage the immune system toward pathogenic bacteria. More specifically, a hapten was conjugated to a protein expressed by Ixodes scapularis ticks

  补充或调节宿主免疫反应的免疫剂已被证明具有强大的治疗潜力，尽管这种方式对细菌病原体的探索较少。我们描述了一种细菌结合蛋白在使免疫系统重新接触病原菌方面的应用。更具体地说，将半抗原与肩突硬蜱表达的一种蛋白质结合，称为肩胛硬蜱抗冻糖蛋白 (IAFGP)，该蛋白对细菌肽聚糖上的d-丙氨酸残基具有高亲和力。我们发现该蛋白质的一个片段保留了高表面结合亲和力。此外，半抗原与该肽的结合导致半抗原显示在万古霉素抗性的细胞表面上粪肠球菌。半抗原展示然后诱导抗体的募集并促进免疫细胞对细菌病原体的摄取。这些结果证明了使用细胞壁结合剂作为一类细菌免疫疗法的基础的可行性。
• METHODS OF ANALYZING POLYNUCLEOTIDES EMPLOYING ENERGY TRANSFER DYES
  申请人：Lee G. Linda

  公开号：US20070154925A1

  公开（公告）日：2007-07-05

  Novel linkers for linking a donor dye to an acceptor dye in an energy transfer fluorescent dye are provided. These linkers faciliate the efficient transfer of energy between a donor and acceptor dye in an energy transfer dye. One of these linkers for linking a donor dye to an acceptor dye in an energy transfer fluorescent dye has the general structure R 21 Z 1 C(O)R 22 R 28 where R 21 is a C 1-5 alkyl attached to the donor dye, C(O) is a carbonyl group, Z 1 is either NH, sulfur or oxygen, R 22 is a substituent which includes an alkene, diene, alkyne, a five and six membered ring having at least one unsaturated bond or a fused ring structure which is attached to the carbonyl carbon, and R 28 includes a functional group which attaches the linker to the acceptor dye.