5-羧基-X-罗丹明琥珀酰亚胺酯(单一化合物) | 209734-74-7

• 物质功能分类: 生物化工 - 生化试剂 - 荧光成像
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 5-羧基-X-罗丹明琥珀酰亚胺酯(单一化合物)
• 中文别名: 5-羧基-X-罗丹明SE；5-羧基-X-罗丹明 SE
• 英文名称: 5-carboxy-X-rhodamine N-succinimidyl ester
• 英文别名: 5-carboxy-X-rhodamine succinimidyl ester；5-ROX-SE；5-(2,5-dioxopyrrolidin-1-yl)oxycarbonyl-2-(3-oxa-23-aza-9-azoniaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1(27),2(17),4,9(28),13,15,18-heptaen-16-yl)benzoate
• CAS: 209734-74-7
• 化学式: C₃₇H₃₃N₃O₇
• 分子量: 631.685
• InChiKey: BTTBJYLMDASSAS-UHFFFAOYSA-N

物化性质

• 溶解度：
  在DMF中可溶

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  47
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3

制备方法与用途

用途

5-羧基-X-罗丹明 SE 被用作胺偶联剂，用于制备电荷修饰的染料标记双脱氧核苷酸三磷酸（ddNTP），以便实现“直接加载”DNA 测序。

反应信息

• 作为反应物：
  描述：

  4-哌啶甲酸 、 5-羧基-X-罗丹明琥珀酰亚胺酯(单一化合物) 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以13 mg的产率得到
  参考文献：
  名称：

  CELL TRACKING REAGENTS AND THEIR METHODS OF USE

  摘要：

  本文描述了一种用于短期和长期跟踪细胞增殖、分化和/或功能的化合物、方法和试剂盒。本文披露的化合物是基于罗丹明的细胞跟踪试剂，其在紫外/可见光谱的红色部分发出荧光，并且具有明亮的荧光强度、均匀的细胞染色以及在活细胞内良好的保留性，同时对细胞具有低毒性。

  公开号：

  US20170044372A1
• 作为产物：
  描述：

  5-羧基-X-罗丹明 、 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 5-羧基-X-罗丹明琥珀酰亚胺酯(单一化合物)
  参考文献：
  名称：

  Synthesis of 5- and 6-Carboxy-X-rhodamines

  摘要：

  An efficient route is reported to 5- and 6-carboxy-X-rhodamines (compounds 1 and 2) that contain multiple n-propylene or gamma,gamma-dimethylpropylene groups bridging terminal nitrogen atoms and the central xanthene core. Gram quantities of these dyes are synthesized from inexpensive starting materials. The isolated products are activated by selective transformation of the carboxylic acid group into N-hydroxysuccinimidyl esters in situ and then conjugated with an amino group of a molecule of interest.

  DOI：

  10.1021/ol801904k

文献信息

• SYNTHESIS OF NOVEL PIPERIDINYL LINKER BASED ENERGY TRANSFER TERMINATORS AND THEIR POTENTIAL USE IN DNA SEQUENCING
  作者：T. Sudhakar Rao、Satyam Nampalli、Weihong Zhang、Haiguang Xiao、Shiv Kumar

  DOI：10.1081/ncn-200060586

  日期：2005.4.1

  Synthesis of novel piperidinyl linker based ET cassettes and terminators is described. These novel terminators are evaluated in the DNA sequencing experiments using thermostable DNA polymerase.
• Unnatural amino acid derived FRET cassettes, terminators and their DNA sequencing potential
  作者：Satyam Nampalli、Weihong Zhang、T Sudhakar Rao、Haiguang Xiao、Lakshmi P Kotra、Shiv Kumar

  DOI：10.1016/s0040-4039(02)00196-x

  日期：2002.3

  An unnatural, tri-functional amino acid. t-BOC-L-para-amino-phenylalanine (1). was utilized in the design and syntheses of highly efficient FRET cassettes (4-7) and converted them into 2'.3'-dideoxynucleotide terminators (8-11) for investigating DNA sequencing potential coupled with a thermostable DNA polymerase. Thermo Sequenase(TM) II . (C) 2002 Elsevier Science Ltd. All rights reserved.
• Targeted Detection of Cyclooxygenase-1 in Ovarian Cancer
  作者：Paola Malerba、Brenda C. Crews、Kebreab Ghebreselasie、Cristina K. Daniel、Elma Jashim、Ansari M. Aleem、Redoan A. Salam、Lawrence J. Marnett、Md. Jashim Uddin

  DOI：10.1021/acsmedchemlett.9b00280

  日期：2020.10.8

  Overexpression of cyclooxygenase-1 (COX-1) is associated with the initiation and progression of ovarian cancer, and targeted imaging of COX-1 is a promising strategy for early detection of this disease. We report the discovery of N-[(5-carboxy-X-rhodaminyl)but-4-yl]-3-(1-(4-methoxyphenyl)-5-(p-tolyl)-1H-pyrazol-3-yl)propenamide (CMP) as the first COX-1-targeted optical agent for imaging of ovarian cancer. CMP exhibits light emission at 604 nm (lambda(max)), thereby minimizing tissue autofluorescence interference. In both purified enzyme and COX-1-expressing human ovarian adenocarcinoma (OVCAR-3) cells, CMP inhibits COX-1 at low nanomolar potencies (IC50 = 94 and 44 nM, respectively). CMP's selective binding to COX-1 in OVCAR-3 cells was visualized microscopically as intense intracellular fluorescence. In vivo optical imaging of xenografts in athymic nude mice revealed COX-1-dependent accumulation of CMP in COX-1-expressing mouse ovarian surface epithelial carcinoma (ID8NGL) and OVCAR-3 cells. These results establish proof-of-principle for the feasibility of targeting COX-1 in the development of new imaging and therapeutic strategies for ovarian cancer.
• FLUORESCENCE RESONANCE ENERGY TRANSFER DYE NUCLEOTIDE TERMINATORS: A NEW SYNTHETIC APPROACH FOR HIGH-THROUGHOUT DNA SEQUENCING
  作者：Satyam Nampalli、Mahesh Khot、John R. Nelson、Parke K. Flick、Carl W. Fuller、Shiv Kumar

  DOI：10.1081/ncn-100002307

  日期：2001.3.31

  Fluorescence resonance energy transfer (FRET) based dye-nucleotide terminators (10-13) were designed, synthesized, and formulated with Thermo Sequenase(TM) II DNA polymerase into a robust kit for high throughput DNA sequencing. The key energy transfer (ET) rigid and linear linker (2), required for the syntheses of energy transfer cassettes (6-9) was synthesized via Heck coupling reaction on t-Boc-L-4-iodo-phenylalanine (1) with N-TFA-propargylamine.
• FOUR COLOR FRET DYE NUCLEOTIDE TERMINATORS FOR DNA SEQUENCING
  作者：T. Sudhakar Rao、Satyam Nampalli、Kate Lavrenov、Weihong Zhang、Haiguang Xiao、John Nelson、Shiv Kumar

  DOI：10.1081/ncn-100002348

  日期：2001.3.31

  The synthesis of four color set of energy transfer-dye terminators (8a-8d) starting from p-iodo-beta -phenylalanine was accomplished and their utility in the sequencing reactions has been evaluated.