FC8-325A

• 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: FC8-325A
• 英文别名: (4-sulfamoylphenylmethyl)thioureido-fluorescein；2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)-5-[3-(4-sulfamoyl-benzyl)-thioureido]-benzoic acid；2-(3-hydroxy-6-oxoxanthen-9-yl)-5-[(4-sulfamoylphenyl)methylcarbamothioylamino]benzoic acid
• 化学式: C₂₈H₂₁N₃O₇S₂
• 分子量: 575.623
• InChiKey: MWYSNECAHMAFGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  209
• 氢给体数：
  5
• 氢受体数：
  9

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-aminofluorescein	——	C20H13NO5	347.327
  ——	Fluorescein isothiocyanate	1173-43-9	C21H11NO5S	389.388

反应信息

• 作为产物：
  描述：

  磺胺米隆 、 Fluorescein isothiocyanate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 FC8-325A
  参考文献：
  名称：

  Carbonic Anhydrase Inhibitors. Design of Fluorescent Sulfonamides as Probes of Tumor-Associated Carbonic Anhydrase IX That Inhibit Isozyme IX-Mediated Acidification of Hypoxic Tumors

  摘要：

  Sulfonamides inhibit the catalytic activity of carbonic anhydrases (CAs, EC 4.2.1.1), enzymes participating in the regulation of acid-base balance and ion transport in many tissues. Carbonic anhydrase IX (CA IX), a transmembrane isoform with predominant association with tumors and limited distribution in normal tissues, is strongly overexpressed by hypoxia. Hypoxia increases the catalytic performance of CA IX contributing to microenvironmental acidosis, which influences cancer progression and treatment outcome. CA IX represents a target for detection and therapy of hypoxic tumors. Sulfonamide CA IX selective inhibitors accumulate only in hypoxic cells containing CA IX, reversing acidification mediated by this enzyme. The design of fluorescent sulfonamides that preferentially inhibit the activity of CA IX, showing reduced penetration through the plasma membranes and binding to hypoxic cells expressing CA IX, is reported here. These inhibitors represent promising candidates for developing anticancer therapies based on tumor-associated CA isozyme inhibition and offer interesting tools for imaging and further investigation of hypoxic tumors.

  DOI：

  10.1021/jm0501073

文献信息

• Sulfonamide Derivatives Having Carbonic Anhydrase Inhibiting Activity and their Use as Therapeutic and Diagnostic Agents
  申请人：Supuran Claudiu T.

  公开号：US20080138291A1

  公开（公告）日：2008-06-12

  The present invention discloses sulfonamide A-(Q)n—Ar—SChNHR which are CA IX-selective inhibitors, which selectively bind to the enzyme under hypoxic conditions and are able to reverse the tumor acidification mediated by the enzyme. These compounds are useful in anticancer therapies based on tumor-associated CA isozyme inhibition as well as for hypoxic tumor imaging.
• US7833734B2
  申请人：——

  公开号：US7833734B2

  公开（公告）日：2010-11-16
• US7833739B2
  申请人：——

  公开号：US7833739B2

  公开（公告）日：2010-11-16
• Carbonic Anhydrase Inhibitors. Design of Fluorescent Sulfonamides as Probes of Tumor-Associated Carbonic Anhydrase IX That Inhibit Isozyme IX-Mediated Acidification of Hypoxic Tumors
  作者：Alessandro Cecchi、Alzbeta Hulikova、Jaromír Pastorek、Silvia Pastoreková、Andrea Scozzafava、Jean-Yves Winum、Jean-Louis Montero、Claudiu T. Supuran

  DOI：10.1021/jm0501073

  日期：2005.7.1

  Sulfonamides inhibit the catalytic activity of carbonic anhydrases (CAs, EC 4.2.1.1), enzymes participating in the regulation of acid-base balance and ion transport in many tissues. Carbonic anhydrase IX (CA IX), a transmembrane isoform with predominant association with tumors and limited distribution in normal tissues, is strongly overexpressed by hypoxia. Hypoxia increases the catalytic performance of CA IX contributing to microenvironmental acidosis, which influences cancer progression and treatment outcome. CA IX represents a target for detection and therapy of hypoxic tumors. Sulfonamide CA IX selective inhibitors accumulate only in hypoxic cells containing CA IX, reversing acidification mediated by this enzyme. The design of fluorescent sulfonamides that preferentially inhibit the activity of CA IX, showing reduced penetration through the plasma membranes and binding to hypoxic cells expressing CA IX, is reported here. These inhibitors represent promising candidates for developing anticancer therapies based on tumor-associated CA isozyme inhibition and offer interesting tools for imaging and further investigation of hypoxic tumors.