1-([4-([([dodecylsulfanyl]methanethioyl)sulfanyl]methyl)phenyl]methyl)-3,4-bis[(2-hydroxyethyl)sulfanyl]-2,5-dihydro-1H-pyrrole-2,5-dione | 1424958-03-1

• 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: 1-([4-([([dodecylsulfanyl]methanethioyl)sulfanyl]methyl)phenyl]methyl)-3,4-bis[(2-hydroxyethyl)sulfanyl]-2,5-dihydro-1H-pyrrole-2,5-dione
• 英文别名: 1-[[4-(Dodecylsulfanylcarbothioylsulfanylmethyl)phenyl]methyl]-3,4-bis(2-hydroxyethylsulfanyl)pyrrole-2,5-dione
• CAS: 1424958-03-1
• 化学式: C₂₉H₄₃NO₄S₅
• 分子量: 629.995
• InChiKey: GQEKVMFOPBKWJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  39
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  211
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-巯基乙醇 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 反应 3.0h， 以35%的产率得到1-([4-([([dodecylsulfanyl]methanethioyl)sulfanyl]methyl)phenyl]methyl)-3,4-bis[(2-hydroxyethyl)sulfanyl]-2,5-dihydro-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Conjugation-Induced Fluorescent Labeling of Proteins and Polymers Using Dithiomaleimides

  摘要：

  Dithiomaleimides (DTMs) with alkyl substituents are shown to be a novel class of highly emissive fluorophores. Variable solubility and further functionalization can easily be tailored through the choice of N and S substituents. Inclusion of a DTM unit into a ROP/RAFT initiator or insertion into the disulfide bond of salmon calcitonin (sCT) demonstrates the utility for fluorescent labeling of polymers and proteins. Simultaneous PEGylation and fluorescent labeling of sCT is also demonstrated, using the DTM unit as both a linker and a fluorophore. It is anticipated that DTMs will offer an attractive alternative to commonly used bulky, planar fluorophores.

  DOI：

  10.1021/ja3105494

文献信息

• New Functional Handle for Use as a Self-Reporting Contrast and Delivery Agent in Nanomedicine
  作者：Mathew P. Robin、Anne B. Mabire、Joanne C. Damborsky、Elizabeth S. Thom、Ursula H. Winzer-Serhan、Jeffery E. Raymond、Rachel K. O’Reilly

  DOI：10.1021/ja403587c

  日期：2013.6.26

  The synthesis and photophysical characterization of a chromophore-bridged block copolymer system is presented. This system is based on a dithiomaleimide (DTM) functional group as a highly emissive functionality which can readily be incorporated into polymeric scaffolds. A key advantage of this new reporter group is its versatile chemistry, ease of further functionalization, and notably small size, which allows for ready incorporation without affecting or disrupting the self-assembly process critical to the formation of core shell polymeric contrast and drug delivery agents. We demonstrate the potential of this functionality with a diblock system which has been shown to be appropriate for micellization and, when in the micellar state, does not self quench The block copolymer is shown to be significantly more emissive than the lone dye, with a concentration independent emission and anisotropy profile from 1.5 mM to 0.15 mu M. An emission lifetime and anisotropy decay comparison of the block copolymer to its micelle displays that time-domain fluorescence lifetime imaging (FLIM) is able to rapidly resolve differences in the supramolecular state of this block dye block polymer system. Furthermore, the ability to resolve these differences in the supramolecular state means that the DTM micelles are capable of self reporting when disassembly occurs, simply by monitoring with FLIM. We demonstrate the great potential for in vitro applications that this system provides: by using :FLIM to Observe micelle disassembly in different vascular components of rat hippocampal tissue. In total this system represents a new class of in chain emitter which is appropriate for application in quantitative imaging and the tracking of particle degradation/disassembly events in biological environments.