14-core gold phosphine sulfur cluster compound as well as preparation method and application thereof

A cluster compound and phosphine sulfur technology, which is applied to 14-nucleated gold phosphine sulfur cluster compound and its preparation, and the application field of lysosome targeting probe in cell imaging, which can solve the application of high cytotoxicity, which is difficult to achieve. Long-term tracking of organelles, etc., to achieve the effects of low cytotoxicity, good lysosome targeting, and broadening the scope of application

Active Publication Date: 2019-01-04
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most commercial small molecule fluorescent probes such as Lyso Tracker DND series and neutral red series exhibit high pH dependence in fluorescent labeling, making it difficult to achieve long-term tracking of organelles (see: Y.P.Ho, K.W.Leong, Nanoscale, 2010, 2, 60–68.)
Quantum dots or gold nanoparticles can properly extend the imaging period, but their high cytotoxicity still limits their application in long-term tracking

Method used

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  • 14-core gold phosphine sulfur cluster compound as well as preparation method and application thereof
  • 14-core gold phosphine sulfur cluster compound as well as preparation method and application thereof
  • 14-core gold phosphine sulfur cluster compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: Binuclear gold phosphine chloride complex [(AuCl) 2 Preparation of bdppmapy]

[0048] Au(tht)Cl (0.1605g, 0.5mmol) and ligand bdppmapy (0.1225g, 0.25mmol) were added to 10mL of dichloromethane solvent at room temperature, and a clear solution was formed after stirring with a magnetic stirrer for three hours. The supernatant was placed in a diffusion tube, and 25 mL of n-hexane was used to cover the upper layer of the filtrate by the diffusion method. After 2 days, a colorless block crystal [(AuCl) was precipitated. 2 bdppmapy]. The crystals were collected, then fully washed with n-hexane, and finally placed in a vacuum oven at 30°C for drying. Yield: 0.2223g (purity: 93.1%, calculated based on gold)

[0049] Elemental analysis (%): C 31 h 28 Au 2 Cl 2 N 2 P 2 (M.W.=955.33), Theoretical: C, 38.95; H, 2.93; N, 2.93%; Found: 38.79; H, 3.03; N, 2.87%.

[0050] Infrared spectrum (potassium bromide tablet method): 3416(m), 3146(m), 3051(m), 1599(s), 154...

Embodiment 2

[0055] Embodiment 2: Preparation of 14 nuclei gold phosphine sulfur cluster compound Au14

[0056] The precursor [(AuCl) 2 bdppmapy] (0.0955g, 0.1mmol) in dichloromethane (5mL) was added to Na 2 S·9H 2 O (0.0240 g, 0.1 mmol) in ethanol solution (5 mL), was stirred with a magnetic stirrer for 3 hours to obtain a yellow solution and a gray precipitate, which was filtered to obtain a yellow clear liquid. Put this clear solution in a diffusion tube, cover the upper layer of the filtrate with 25mL ether by diffusion method, after 3 to 5 days, yellow-green massive crystals [Au 14 S 6 (bdpp mapy) 5 ] Cl 2 . The crystals were collected, washed thoroughly with ether, and finally dried in a vacuum oven at 30°C. Yield: 0.0710g (purity: 91.0%, calculated based on gold).

[0057] Cluster [Au 14 S 6 (bdpp mapy) 5 ] Cl 2 The structure is as image 3 As shown, in order to better demonstrate its structure, Figure 4 Its front and top views are shown.

Embodiment 3

[0058] Example 3: Basic characterization and fluorescence test of the 14-nuclear gold phosphine-sulfur cluster compound Au14

[0059] Au14 was characterized by infrared, elemental analysis and X-ray single crystal diffraction, and its fluorescence properties were studied. The specific results are as follows.

[0060] Table 2. Clusters [Au 14 S 6 (bdpp mapy) 5 ] Cl 2 The crystallographic parameters of

[0061]

[0062] Elemental analysis (%): C1 55 h 136 Au 14 Cl 2 N 10 P 10 S 6 (M.W.=5469.22), Theoretical: C, 34.01; H, 2.49; N, 2.56%; Found: C, 33.97; H, 2.33; N, 2.67%.

[0063] Infrared spectrum (potassium bromide tablet method): 3442(s), 1628(m), 1592(s), 1474(s), 1435(s), 1400(m), 1384(m), 1314(w) ,1218(w),1158(w),1099(s),1084(s),998(m),859(s),741(m),691(m),508(m),481(w) cm -1 .

[0064] The above data show that the present embodiment has successfully obtained 14 nuclear gold phosphine sulfur clusters Au14, namely [Au 14 S 6 (bdpp mapy) 5 ] Cl 2 .

[...

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Abstract

The invention discloses a double-core gold phosphine sulfur cluster compound and a 14-core gold phosphine sulfur cluster compound. The cluster compound is a bulky crystal, the molecular formula of which is C155H136Au14Cl2N10P10S6 and the chemical formula of which is [Au14S6(bdppmapy)5]Cl2, wherein bdppmapy represents N,N-di(diphenylphosphine methyl)-2-aminopyridine; the 14-core gold phosphine sulfur cluster compound is a triclinic system, the space group of which is Pi and the cell parameters of which are shown in a formula, wherein alpha is equal to 87.453(3) degrees, beta is equal to 76.042(2) degrees and gamma is equal to 75.797(2) degrees. The invention further discloses an application of the 14-core gold phosphine sulfur cluster compound as a lysosome targeted probe. The 14-core goldphosphine sulfur cluster compound has a relatively good fluorescent property, a relatively high quantum yield and relatively low cytotoxicity.

Description

technical field [0001] The invention relates to the technical field of metal clusters, in particular to a 14-nuclear gold phosphine-sulfur cluster and its preparation method, as well as its application in cell imaging as a lysosome targeting probe. Background technique [0002] In recent years, organelle-specific markers have attracted considerable attention in order to visualize organelle functions and activities in cells. Among them, lysosome, as an important organelle, is a part of the inner membrane system of the cell, and plays a vital role in a series of cellular biological activities, such as plasma membrane repair, immune response, energy metabolism and cell homeostasis. (See: J. Chan, S. C. Dodani, C. J. Chang, Nat. Chem., 2012, 4, 973-984.). In order to reveal the morphology and function of lysosomes, the design and synthesis of lysosome-targeted fluorescent probes has also become a research hotspot for scientists. [0003] Traditional dye-based fluorescent probe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/12C09K11/06G01N21/64
CPCC07B2200/13C07F1/005C09K11/06C09K2211/1007C09K2211/1029C09K2211/188G01N21/6428G01N21/6486
Inventor 郎建平刘春玉陈亮任志刚
Owner SUZHOU UNIV
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