5-amino-5′-methyl BAPTA tetramethyl ester | 1329676-54-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-amino-5′-methyl BAPTA tetramethyl ester
• 英文别名: 5-amino-5'-methyl-BAPTA tetramethyl ester；methyl 2-[2-[2-[5-amino-2-[bis(2-methoxy-2-oxoethyl)amino]phenoxy]ethoxy]-N-(2-methoxy-2-oxoethyl)-4-methylanilino]acetate
• CAS: 1329676-54-1
• 化学式: C₂₇H₃₅N₃O₁₀
• 分子量: 561.589
• InChiKey: LBNAUOQCEJJZCF-UHFFFAOYSA-N

物化性质

• 沸点：
  682.8±55.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  40
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  、 5-amino-5′-methyl BAPTA tetramethyl ester 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Development of a Far-Red to Near-Infrared Fluorescence Probe for Calcium Ion and its Application to Multicolor Neuronal Imaging

  摘要：

  To improve optical imaging of Ca2+ and to make available a distinct color window for multicolor imaging, we designed and synthesized CaSiR-1, a far-red to near-infrared fluorescence probe for Ca2+, using Si-rhodamine (SiR) as the fluorophore and the well-known Ca2+ chelator BAPTA. This wavelength region is advantageous, affording higher tissue penetration, lower background autofluorescence, and lower phototoxicity in comparison with the UV to visible range. CaSiR-1 has a high fluorescence off/on ratio of over 1000. We demonstrate its usefulness for multicolor fluorescence imaging of action potentials (visualized as increases in intracellular Ca2+) in brain slices loaded with sulforhodamine 101 (red color; specific for astrocytes) that were prepared from transgenic mice in which some neurons expressed green fluorescent protein.

  DOI：

  10.1021/ja205809h
• 作为产物：
  描述：

  5-methyl-5'-nitro-BAPTA tetramethyl ester 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以47%的产率得到5-amino-5′-methyl BAPTA tetramethyl ester
  参考文献：
  名称：

  Development of a Far-Red to Near-Infrared Fluorescence Probe for Calcium Ion and its Application to Multicolor Neuronal Imaging

  摘要：

  To improve optical imaging of Ca2+ and to make available a distinct color window for multicolor imaging, we designed and synthesized CaSiR-1, a far-red to near-infrared fluorescence probe for Ca2+, using Si-rhodamine (SiR) as the fluorophore and the well-known Ca2+ chelator BAPTA. This wavelength region is advantageous, affording higher tissue penetration, lower background autofluorescence, and lower phototoxicity in comparison with the UV to visible range. CaSiR-1 has a high fluorescence off/on ratio of over 1000. We demonstrate its usefulness for multicolor fluorescence imaging of action potentials (visualized as increases in intracellular Ca2+) in brain slices loaded with sulforhodamine 101 (red color; specific for astrocytes) that were prepared from transgenic mice in which some neurons expressed green fluorescent protein.

  DOI：

  10.1021/ja205809h

文献信息

• DEEP RED FLUORESCENT PROBE
  申请人：The University of Tokyo

  公开号：US20200087326A1

  公开（公告）日：2020-03-19

  A near-infrared fluorescent probe has fluorescence in the near-infrared region. Like CaSiR-1, the probe has rhodamines as the fluorescent mother nucleus and accumulates in the cytoplasm. The probe makes it possible to visualize concentration fluctuations in metal ions, such as calcium ions, within the body. The fluorescent probe includes a compound represented by the following general formula or a salt of the compound:

  一个近红外荧光探针在近红外区域有荧光。像CaSiR-1一样，该探针以罗丹明作为荧光母核，并在细胞质中积累。该探针使得可视化体内金属离子，如钙离子的浓度波动成为可能。荧光探针包括由以下通用公式表示的化合物或该化合物的盐：
• A far-red fluorescent probe based on a phospha-fluorescein scaffold for cytosolic calcium imaging
  作者：Hiroaki Ogasawara、Marek Grzybowski、Riho Hosokawa、Yoshikatsu Sato、Masayasu Taki、Shigehiro Yamaguchi

  DOI：10.1039/c7cc07344e

  日期：——

  The far-red emissive fluorescent probe CaPF-1 based on a phospha-fluorescein scaffold enables the detection of cytosolic calcium ions in living cells. The probe can be excited in the red region (λabs = 636 nm) and exhibits a sufficiently high fluorescence turn-on response in the far-red region (λem = 663 nm) upon complexation with calcium ions. The hydrophilic and anionic characteristics of this phospha-fluorescein

  基于磷酸荧光素支架的远红外发射荧光探针CaPF-1能够检测活细胞中的胞质钙离子。所述探针可以在红色区域（激发λ ABS = 636纳米），并显示出足够高的荧光接通在远红光区域响应（λ EM = 663纳米）在络合钙离子。这种磷酸荧光素荧光团的亲水和阴离子特性使得CaPF-1可以在细胞质中定位。此外，有可能使用CaPF-1观察HeLa细胞中组胺诱导的钙振荡。
• US8962338B2
  申请人：——

  公开号：US8962338B2

  公开（公告）日：2015-02-24