1,3,5,7-tetramethyl-2,6-bis(2-carboxyethyl)-8-[4-(N,N-diethylamino)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene | 1000870-48-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,3,5,7-tetramethyl-2,6-bis(2-carboxyethyl)-8-[4-(N,N-diethylamino)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 1,3,5,7-tetramethyl-2,6-bis(2-carboxyethyl)-8-(p-diethylamino)phenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene；bis-carboxylic acid (1,3,5,7-tetramethyl-2,6-bis(2-carboxyethyl)-8-(p-diethylaminophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene)；3-[11-(2-Carboxyethyl)-8-[4-(diethylamino)phenyl]-2,2-difluoro-4,6,10,12-tetramethyl-1-aza-3-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-3,5,7,9,11-pentaen-5-yl]propanoic acid；3-[11-(2-carboxyethyl)-8-[4-(diethylamino)phenyl]-2,2-difluoro-4,6,10,12-tetramethyl-1-aza-3-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-3,5,7,9,11-pentaen-5-yl]propanoic acid
• CAS: 1000870-48-3
• 化学式: C₂₉H₃₆BF₂N₃O₄
• 分子量: 539.43
• InChiKey: VNUBOFVPGVEKHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3,5,7-tetramethyl-2,6-bis(2-carboxyethyl)-8-[4-(N,N-diethylamino)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene 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 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Targeted pH-dependent fluorescent activity-based cathepsin probes

  摘要：

  研究人员开发了双功能、可激活 pH 值的 BODIPY 染料，并将其纳入含甘露糖簇的半胱氨酸蛋白酶活性探针中。树突状细胞依赖甘露糖受体摄取探针，然后将探针转运到酸性细胞区，通过活细胞成像看到荧光，随后抑制酪蛋白酶。

  DOI：

  10.1039/c1cc12947c
• 作为产物：
  描述：

  N,N-二乙基-4-氨基苯甲醛 在 三氟乙酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.67h， 生成 1,3,5,7-tetramethyl-2,6-bis(2-carboxyethyl)-8-[4-(N,N-diethylamino)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Targeted pH-dependent fluorescent activity-based cathepsin probes

  摘要：

  研究人员开发了双功能、可激活 pH 值的 BODIPY 染料，并将其纳入含甘露糖簇的半胱氨酸蛋白酶活性探针中。树突状细胞依赖甘露糖受体摄取探针，然后将探针转运到酸性细胞区，通过活细胞成像看到荧光，随后抑制酪蛋白酶。

  DOI：

  10.1039/c1cc12947c

文献信息

• In Vivo Fluorescence Imaging of Bone-Resorbing Osteoclasts
  作者：Toshiyuki Kowada、Junichi Kikuta、Atsuko Kubo、Masaru Ishii、Hiroki Maeda、Shin Mizukami、Kazuya Kikuchi

  DOI：10.1021/ja2064582

  日期：2011.11.9

  Osteoclasts are giant polykaryons responsible for bone resorption. Because an enhancement or loss of osteoclast function leads to bone diseases such as osteoporosis and osteopetrosis, real-time imaging of osteoclast activity in vivo can be of great help for the evaluation of drugs. Herein, pH-activatable chemical probes BAp-M and BAp-E have been developed for the detection of bone-resorbing osteoclasts in vivo. Their acid dissociation constants (pK(a)) were determined as 4.5 and 6.2 by fluorometry in various pH solutions. These plc values should be appropriate to perform selective imaging of bone-resorbing osteoclasts, because synthesized probes Cannot fluoresce intrinsically at physiological pH and the pH in the resorption pit is lowered to about 4.5. Furthermore, BAp-M and BAp-E have a bisphosphonate Moiety that enabled the probes to localize. on bone tissues. The hydroxyapatite (HA) binding assay in vitro was, therefore, performed to confirm the tight binding of the probes to the bone tissues. Our probes showed :intense fluorescence at pH values but no fluorescence signal under physiological pH conditions on HA. Finally, we applied the probes to in vivo imaging of osteoclasts by using intravital two-photon microscopy. As expected, the fluorescence signals of the probes were locally observed between; the osteoclasts and bone tissues, that is in resorption pits. These results indicate that our pH-activatable probe g will prove to be a powerful tool for the selective detection of bone-resorbing osteoclasts in vivo, because this is the first instance Where in vivo imaging has been conducted in a low-pH region created by bone-resorbing osteoclasts.
• Kowada, Toshiyuki; Kikuta, Junichi; Kubo, Atsuko, Journal of the American Chemical Society
  作者：Kowada, Toshiyuki、Kikuta, Junichi、Kubo, Atsuko、Ishii, Masaru、Maeda, Hiroki、et al.

  DOI：——

  日期：——
• PH-SENSITIVE FLUORESCENT PROBE
  申请人：The University of Tokyo

  公开号：EP2098529B1

  公开（公告）日：2014-06-18