5-anilino-penta-2,4-dienal-phenylimine | 5608-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-anilino-penta-2,4-dienal-phenylimine
• 英文别名: N-[5-(phenylamino)-2,4-pentadienylidene]aniline monohydrochloride；N-[5-(phenylimino)penta-1,3-dien-1-yl]aniline；N-(5-anilino-penta-2,4-dienylidene)-aniline；5-Anilino-penta-2,4-dienal-phenylimin；Glutaconaldehyd-bis-phenylimin；Pentendial-bis-phenylimin；N-[5-(Phenylimino)-1,3-pentadien-1-yl]aniline；N-(5-phenyliminopenta-1,3-dienyl)aniline
• CAS: 5608-83-3
• 化学式: C₁₇H₁₆N₂
• mdl: MFCD00570915
• 分子量: 248.327
• InChiKey: UDWRJSSBFBSTOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-anilino-penta-2,4-dienal-phenylimine 在 乙酸酐 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Spectroscopic Characterization of Heptamethine Cyanine Dyes for the Interaction with the CN^-and F^-

  摘要：

  The selectivity and sensitivity of a benzoindolium heptamethine cyanine dyes toward CN- and F- in DMSO are described. These anions interact with Dye-1 and Dye-2 forming anion-Dye adducts, the formation of which was supported by the Pariser-Parr-Pople molecular orbital (PPP MO) calculation. The different optical responses in Dye-1 stimulated by addition of CN- (blue to pale yellow) and F- (blue to pink) allow simultaneous estimation of CN- and F-.

  DOI：

  10.1080/15421406.2012.701121
• 作为产物：
  描述：

  1-<(Benzoyloxy)phenylmethyl>pyridinium-chlorid 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 5-anilino-penta-2,4-dienal-phenylimine
  参考文献：
  名称：

  Kuhn,R.; Teller,E., Justus Liebigs Annalen der Chemie, 1968, vol. 715, p. 106 - 121

  摘要：

  DOI：

文献信息

• Synthetic probes for in vitro purification and in vivo tracking of hepatocytes derived from human pluripotent stem cells
  作者：Ji Young Park、Jiyou Han、Hyo Sung Jung、Gyunggyu Lee、Hyo Jin Kim、Gun-Sik Cho、Han-Jin Park、Choongseong Han、Jong Seung Kim、Jong-Hoon Kim

  DOI：10.1016/j.biomaterials.2019.119431

  日期：2019.11

  Hepatocytes derived from human pluripotent stem cells (hPSCs) are promising candidates for cell therapy and drug discovery. However, it remains challenging to efficiently purify hepatocytes from undesired cell types after differentiation and to accurately monitor grafted cells after transplantation. Indocyanine Green (ICG), an FDA-approved, near-infrared (NIR) dye, has been used for various clinical

  源自人类多能干细胞（hPSC）的肝细胞有望用于细胞治疗和药物开发。然而，在分化后从不期望的细胞类型中有效纯化肝细胞以及在移植后准确地监测移植的细胞仍然具有挑战性。吲哚菁绿（ICG）是FDA批准的近红外（NIR）染料，已用于各种临床目的，并且仅被肝细胞吸收。但是，ICG的发射波长长（λem  > 800 nm），超出了荧光激活细胞分选（FACS）系统的检测范围。此外，它很容易从肝细胞中清除，从而阻碍了其在近红外成像中的应用。在这里，我们根据ICG的特性设计和合成了两种不同的探针。1）肝细胞净化剂（HPA， λ EM  = 562纳米），用于体外排序和2）肝细胞成像剂（HIA， λ EM  = 817 nm）的为高效的体内NIR成像。我们使用基于HPA探针的FACS纯化从各种hPSC系中获得了高度富集的hPSC衍生肝细胞（hPSC-Heps）群体。此外，通过HIA标记和NIR成像，可以直接观察
• Acridine-based dyes as high-performance near-infrared Raman reporter molecules for cell imaging
  作者：Jiasheng Du、Jinming Li、Yuzhan Li、Dong Wang、Hui Cao、Wanli He、Yang Zhou

  DOI：10.1039/d1ra08827k

  日期：——

  A surface-enhanced Raman scattering (SERS) nanoprobe has been proven to be a promising tool for near-infrared (NIR) biomedical imaging and diagnosis because of its high sensitivity and selectivity. However, the development of NIR SERS reporters has been a bottleneck impeding the preparation of ultrasensitive SERS probes. Herein, we report the design and synthesis of a series of SERS reporters in the

  表面增强拉曼散射 (SERS) 纳米探针已被证明是一种很有前途的近红外 (NIR) 生物医学成像和诊​​断工具，因为它具有高灵敏度和选择性。然而，近红外 SERS 报告分子的发展一直是阻碍超灵敏 SERS 探针制备的瓶颈。在此，我们报告了基于 10-甲基吖啶 (AD) 的 NIR 区域中一系列 SERS 报告基因的设计和合成。AD 纳米标签（金纳米星-AD 分子-BSA、AuNS-AD-BSA）表现出明显的 SERS 信号，并且可以在低至亚皮摩尔水平下检测到。体外成像实验结果表明，它可用于活细胞描绘。
• [EN] COMPOUNDS AND COMPOSITIONS FOR RETINAL INJURY DETECTION AND METHODS OF USING SAME<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR LA DÉTECTION DE LÉSIONS RÉTINIENNES ET PROCÉDÉS POUR LES UTILISER
  申请人：MOLECULAR TARGETING TECH INC

  公开号：WO2021158219A1

  公开（公告）日：2021-08-12

  Described are compounds, compositions, and methods suitable for diagnosing individuals with eye injuries and/or diseases. The compounds of the present disclosure have fluorescent groups and bis-dipicolylamine groups, which may be substituted or unsubstituted. The fluorescent group and bis-dipicolylamine group are connected by linking groups. The compositions may be formulated and administered as an eye drop. The methods may be used to track and/or label dying cells associated with eye injuries and/or diseases, such as, for example, retinal degenerations including, but not limited to, retinitis pigmentosa, glaucoma, diabetic retinopathy, and age-related macular degeneration.

  本文描述了适用于诊断患有眼部损伤和/或疾病的个体的化合物、组合物和方法。本公开的化合物具有荧光基团和双二吡啶胺基团，可以是取代或未取代的。荧光基团和双二吡啶胺基团通过连接基团连接在一起。这些组合物可以配制并作为眼药水进行给药。这些方法可以用于追踪和/或标记与眼部损伤和/或疾病相关的垂死细胞，例如视网膜退行性疾病，包括但不限于视网膜色素变性、青光眼、糖尿病性视网膜病变和年龄相关性黄斑变性。
• PYRAZOLE-BASED CYANINE DYE CONTAINING QUATERNARY AMMONIUM CATION
  申请人：Yamamoto Naoyuki

  公开号：US20120046474A1

  公开（公告）日：2012-02-23

  Problem Provided is a novel cyanine dye derivative having high fluorescence intensity in a short wavelength region, a structure where a pyrazole skeleton and an indole skeleton are bound to a polymethine chain, and also a controllable migration velocity by further introducing a quaternary ammonium cation into a molecule having said structure. Solution The present invention is the invention of a compound represented by the general formula [1] or a salt thereof: [wherein R 1 to R 6 each independently represent an alkyl group having, as a substituent, a group represented by the general formula [101]: (wherein R 101 to R 104 each independently represent a hydrogen atom or an alkyl group of C 1 to C 3 and m represents an integer from 2 to 6, and two or three of R 102 to R 104 together with a nitrogen atom to which they are bound may form a heterocyclic ammonium cation); or a group derived from a carboxylic acid represented by the general formula [2] which may have an amide bond: —COOR 12 [2] (wherein R 12 represents a hydrogen atom, an alkyl group of C 1 to C 10 , an alkali metal atom, an organic ammonium ion, an ammonium ion or anion); or an alkyl group which may have, as a substituent, a group derived from a sulfonic acid represented by the general formula [3] which may have an amide bond: —SO 3 R 13 [3] (wherein R 13 represents a hydrogen atom, an alkali metal atom, an organic ammonium ion, an ammonium ion or anion); R 7 to R 10 each independently represent an alkyl group, an alkynyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylsulfonyl group, an arylsulfonyl group, an amino group, a group derived from a carboxylic acid represented by the general formula [2], a group derived from a sulfonic acid represented by the general formula [3], a halogen atom, a hydrogen atom, a hydroxyl group, a cyano group or a nitro group; R 11 represents a hydrogen atom, an alkyl group, an alkynyl group or an aryl group, and n represents an integer from 0 to 3, and at least one of R 1 to R 6 is an alkyl group having, as a substituent, a group represented by the general formula [101]].

  提供的问题是一种新型青菁染料衍生物，在短波长区域具有高荧光强度，具有吡唑骨架和吲哚骨架结合到聚甲烯链的结构，通过进一步将季铵阳离子引入具有所述结构的分子，还具有可控的迁移速度。 解决方案是一种由通用式[1]表示的化合物或其盐的发明： [其中R1至R6各自独立地表示具有作为取代基的烷基基团的基团的烷基基团，所述基团由通用式[101]表示： （其中R101至R104各自独立地表示氢原子或C1至C3的烷基基团，m表示2至6的整数，且R102至R104中的两个或三个与它们结合的氮原子可能形成杂环铵阳离子）；或者源自可能具有酰胺键的通用式[2]所表示的羧酸的基团： —COOR12 （其中R12表示氢原子、C1至C10的烷基基团、碱金属原子、有机铵离子、铵离子或阴离子）；或者可能具有源自可能具有酰胺键的通用式[3]所表示的磺酸的基团： —SO3R13 （其中R13表示氢原子、碱金属原子、有机铵离子、铵离子或阴离子）；R7至R10各自独立地表示烷基基团、炔基基团、芳基基团、烷氧基团、芳氧基团、烷基磺基团、芳基磺基团、氨基团、源自通用式[2]所表示的羧酸的基团、源自通用式[3]所表示的磺酸的基团、卤素原子、氢原子、羟基、氰基或硝基；R11表示氢原子、烷基基团、炔基基团或芳基基团，n表示0至3的整数，且R1至R6中至少有一个是具有作为取代基的基团的烷基基团，所述基团由通用式[101]表示]。
• Sensitive and Selective Fluorescent Probe for Selenol in Living Cells Designed via a p<i>K</i>_a Shift Strategy
  作者：Shengrui Zhang、Qin Wang、Xiawei Liu、Jianjian Zhang、Xiao-Feng Yang、Zheng Li、Hua Li

  DOI：10.1021/acs.analchem.8b00066

  日期：2018.3.20

  Selenocysteine (Sec) is a primary kind of reactive selenium species in cells, and its vital roles in physiological processes have been featured. Thus, the development of highly sensitive and selective methods for the sensing of Sec is of great significance. This work reports a turn-on fluorescent probe for selenol based on the unique fluorescence OFF–ON switching between the Schiff base (SB) and its complementary protonated Schiff base (PSB) form of merocyanine dyes. The probe consists of a merocyanine Schiff base fluorophore and a 2,4-dinitrobenzenesulfonamide moiety that reacts especially with selenol. The fluorescence turn-on response of MC-Sec is realized via the selective removal of the strongly electron withdrawing 2,4-dinitrobenzenesulfonyl group by Sec, leading to a shift in the pKa of the imine nitrogen of the probe from 6.40 to 9.04 and thus significantly increasing the population of the fluorescent PSB form of the dye at physiological pH. MC-Sec shows good selectivity and sensitivity for Sec and has been applied in the imaging of exogenous and endogenous selenol in living cells by confocal fluorescence microscopy. The proposed mechanism should be useful for developing future probes directed to other target molecules by employing this simple but effective pKa shift strategy.

  硒代半胱氨酸（Sec）是细胞中的一种主要活性硒物种，在生理过程中发挥着重要作用。因此，开发高灵敏度和高选择性的 Sec 检测方法具有重要意义。本研究报告了一种硒酚荧光探针，该探针基于梅洛菁染料的席夫碱（SB）及其互补质子化席夫碱（PSB）形式之间独特的荧光 "关-开 "切换。该探针由美蓝希夫碱荧光团和 2,4-二硝基苯磺酰胺分子组成，后者特别能与硒酚发生反应。MC-Sec 的荧光开启响应是通过 Sec 选择性地去除强夺电子的 2,4-二硝基苯磺酰基实现的，这导致探针的亚胺氮的 pKa 从 6.40 变为 9.04，从而显著增加了生理 pH 值下该染料的荧光 PSB 形式的数量。MC-Sec 对 Sec 具有良好的选择性和灵敏度，已被应用于通过共聚焦荧光显微镜对活细胞中的外源性和内源性硒酚进行成像。通过采用这种简单而有效的 pKa 值移动策略，所提出的机制将有助于开发针对其他目标分子的探针。