4-[(2Z)-2-[(2E)-2-[2-chloro-3-[(E)-2-[5-methoxy-3,3-dimethyl-1-(4-sulfobutyl)indol-1-ium-2-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-5-methoxy-3,3-dimethylindol-1-yl]butane-1-sulfonate | 162411-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-[(2Z)-2-[(2E)-2-[2-chloro-3-[(E)-2-[5-methoxy-3,3-dimethyl-1-(4-sulfobutyl)indol-1-ium-2-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-5-methoxy-3,3-dimethylindol-1-yl]butane-1-sulfonate
• CAS: 162411-22-5
• 化学式: C₄₀H₅₁ClN₂O₈S₂
• 分子量: 787.439
• InChiKey: MNVASHPKEQOKQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  53
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-[(2Z)-2-[(2E)-2-[2-chloro-3-[(E)-2-[5-methoxy-3,3-dimethyl-1-(4-sulfobutyl)indol-1-ium-2-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-5-methoxy-3,3-dimethylindol-1-yl]butane-1-sulfonate 在 N-羟基丁二酰亚胺 、 四(三苯基膦)钯 、 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.5h， 生成 4-(2-(2-(4'-(3-((5-(2-fluoropropanamido)pentyl)amino)-3-oxopropyl)-6-(2-(5-methoxy-3,3-dimethyl-1-(4-sulfobutyl)indolin-2-ylidene)ethylidene)-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)vinyl)-5-methoxy-3,3-dimethyl-3H-indol-1-ium-1-yl)butane-1-sulfonate
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS OF DIAGNOSING OCULAR DISEASES
  [FR] COMPOSITIONS ET PROCÉDÉS DE DIAGNOSTIC DE MALADIES OCULAIRES

  摘要：

  该发明提供了用于病理细胞追踪的新型多模态探针，允许使用新的探针标记垂死细胞，并通过非侵入性成像技术跟踪它们，以诊断眼部疾病、确定疾病进展并评估治疗效果。该发明的分子探针可通过局部、局部或全身给药用于诊断和监测任何眼部疾病的改善或进展。

  公开号：

  WO2014092958A1
• 作为产物：
  描述：

  5-甲氧基-2,3,3-三甲基-1-（4-磺丁基）-吲哚鎓内盐 、 (E)-2-chloro-3-(hydroxymethylene)cyclohex-1-ene-1-carbaldehyde 以 正丁醇 、 苯 为溶剂， 反应 16.0h， 以72%的产率得到4-[(2Z)-2-[(2E)-2-[2-chloro-3-[(E)-2-[5-methoxy-3,3-dimethyl-1-(4-sulfobutyl)indol-1-ium-2-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-5-methoxy-3,3-dimethylindol-1-yl]butane-1-sulfonate
  参考文献：
  名称：

  A New Method for the Synthesis of Heptamethine Cyanine Dyes: Synthesis of New Near-Infrared Fluorescent Labels

  摘要：

  A new uncatalyzed synthesis of heptamethine cyanine dyes is described. The reaction involves heating a mixture of N-alkyl-substituted quaternary salts derived from 2,3,3-trimethylindole or 2,3,3-trimethylbenzindole and 2-chloro-1-formyl-3-(hydroxymethylene)cyclohex-1-ene to reflux in a mixture of 1-butanol and benzene (7:3) as solvent. No catalyst is used, and water is removed as an azeotrope. The resulting chloro compounds possess strong absorption and fluorescence properties in the near-infrared region and are converted to dyes bearing reactive functionalities such as hydroxy and isothiocyanate groups useful as fluorescent tags for nucleic acids and proteins. Several symmetric and nonsymmetric dyes have been synthesized in high yields.

  DOI：

  10.1021/jo00113a018

文献信息

• MOLECULAR PROBES FOR MULTIMODALITY IMAGING OF ANIONIC MEMBRANE SURFACES
  申请人：Molecular Targeting Technologies, Inc.

  公开号：US20130323172A1

  公开（公告）日：2013-12-05

  Embodiments provide dual modality probes for imaging phosphatidylserine (PS) exposure and other anionic membrane surfaces. In various embodiments, the probes were constructed by utilizing a) the high selectivity of synthetic zinc (II) dipicolylamine coordination complexes (Zn-DPA) for targeting externalized PS which over-expresses in apoptotic and necrotic cells, b) a near-infrared (NIR) dye for optical imaging, and c) a widely used clinically approved radionuclide for PET (or SPECT) imaging. A variety of linking elements were incorporated into the probes between the Zn-DPA and radionuclide motif to modulate the pharmacokinetics. The in vitro and in vivo data of radiolabeled dipicolylamine probes demonstrated their utilities for imaging PS exposure with multiple imaging modalities.

  实施例提供了用于成像磷脂酰丝氨酸（PS）暴露和其他阴离子膜表面的双模探针。在各种实施例中，探针是通过利用a）合成锌（II）二吡啶胺配位配合物（Zn-DPA）对外显PS的高选择性，该PS在凋亡和坏死细胞中过度表达，b）用于光学成像的近红外（NIR）染料，以及c）用于PET（或SPECT）成像的广泛使用的临床批准放射性核素来构建的。在探针中，Zn-DPA和放射性核素基序之间结合了各种连接元素以调节药代动力学。放射性标记的二吡啶胺探针的体外和体内数据证明了它们在多种成像模式下成像PS暴露的效用。
• Optical Imaging of Bacterial Infection in Living Mice Using a Fluorescent Near-Infrared Molecular Probe
  作者：W. Matthew Leevy、Seth T. Gammon、Hua Jiang、James R. Johnson、Dustin J. Maxwell、Erin N. Jackson、Manuel Marquez、David Piwnica-Worms、Bradley D. Smith

  DOI：10.1021/ja0665592

  日期：2006.12.1

  An optical imaging probe was synthesized by attaching a near-infrared carbocyanine fluorophore to an affinity group containing two zinc(II) dipicolylamine (Zn-DPA) units. The probe has a strong and selective affinity for the surfaces of bacteria, and it was used to image infections of Gram-positive S. aureus and Gram-negative E. coli bacteria in living nude mice. After intravenous injection, the probe selectively accumulates at the sites of localized bacterial infections in the thigh muscles of the mice.
• A New Method for the Synthesis of Heptamethine Cyanine Dyes: Synthesis of New Near-Infrared Fluorescent Labels
  作者：Narasimhachari Narayanan、Gabor Patonay

  DOI：10.1021/jo00113a018

  日期：1995.4

  A new uncatalyzed synthesis of heptamethine cyanine dyes is described. The reaction involves heating a mixture of N-alkyl-substituted quaternary salts derived from 2,3,3-trimethylindole or 2,3,3-trimethylbenzindole and 2-chloro-1-formyl-3-(hydroxymethylene)cyclohex-1-ene to reflux in a mixture of 1-butanol and benzene (7:3) as solvent. No catalyst is used, and water is removed as an azeotrope. The resulting chloro compounds possess strong absorption and fluorescence properties in the near-infrared region and are converted to dyes bearing reactive functionalities such as hydroxy and isothiocyanate groups useful as fluorescent tags for nucleic acids and proteins. Several symmetric and nonsymmetric dyes have been synthesized in high yields.
• [EN] COMPOSITIONS AND METHODS OF DIAGNOSING OCULAR DISEASES<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE DIAGNOSTIC DE MALADIES OCULAIRES
  申请人：MOLECULAR TARGETING TECHNOLOGIES INC

  公开号：WO2014092958A1

  公开（公告）日：2014-06-19

  The invention provides novel multi-modality probes for pathologic cell tracking which allow labeling of dying cells with new probes and tracking them via non-invasive imaging techniques to diagnose ocular diseases, determine disease progression and evaluate effectiveness of treatment. The molecular probes of the invention can be topically, locally, or systemically administered for diagnosing and monitoring improvement or progression of any ocular diseases.

  该发明提供了用于病理细胞追踪的新型多模态探针，允许使用新的探针标记垂死细胞，并通过非侵入性成像技术跟踪它们，以诊断眼部疾病、确定疾病进展并评估治疗效果。该发明的分子探针可通过局部、局部或全身给药用于诊断和监测任何眼部疾病的改善或进展。