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Chiral cyclen compounds and their uses

A kind of anodine, chiral technology, applied in the field of chiral anodine compound and its application

Pending Publication Date: 2019-07-02
THE HONG KONG POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite having a large g lum value, but lanthanide(III) adducts are generally only water sensitive and stable in nonpolar solutions 49,50

Method used

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  • Chiral cyclen compounds and their uses
  • Chiral cyclen compounds and their uses
  • Chiral cyclen compounds and their uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0341] Synthesis of chiral DOTA metal complexes

[0342] 1. Synthesis of chiral DOTA-based ligands L1-L4

[0343] The synthetic route to prepare chiral DOTA-based ligands is as follows Figure 1A shown. Chiral rhodophonines (3a-3d) from aziridines 1a-1d in the presence of TsOH (step (a)) or Lewis acids (step (b), boron trifluoride and diethyl ether complexes) Synthesize. The cyclized tetrameric products 2a-2d were purified by column chromatography or recrystallization. In step (c), deprotection of the four benzyl groups in 2a-2d yields chiral rotenin 3a-3d. In step (d), the chiral tertenin 3a-3d is reacted with tert-butyl 2-bromoacetate to obtain the chiral tertenin 4a-4d. In steps (e) and (f), the tert-butyl group in the chiral tertenin 4a-4d was deprotected by acid to give DOTA-based ligands L1-L4.

[0344] 2. Synthesis of chiral DOTA-based metal complexes from L1-L4

[0345] exist Figure 1A In step (g), according to [LnDOTA] known in the art - The classical pr...

Embodiment 2

[0429] Synthesis of Metal Complexes Based on Chiral DO3A

[0430] 1. Materials and General Methods.

[0431] Unless otherwise stated, all chemicals were of reagent grade, purchased from Sigma-Aldrich or Acros Organics, which were used without further purification. Humidity-sensitive synthetic procedures were performed under nitrogen atmosphere using standard Schlenk techniques. Davisil silica gel (40-63m) was obtained from Grace Davison. Using analytical reagent grade solvents, acetonitrile was dried over calcium hydride and distilled under nitrogen. High performance liquid chromatography (HPLC) was performed by a Vision HT C18HL 5 mm column using an Agilent 1100 series device with a UV visible detector (UV detection range 220 to 350 nm). Use Waters PrepC18 5m OBDTM (19x 250mm) or (19x 100mm) column for reverse phase semi-preparative purification on an Agilent HPLC system (UV detection range 220 to 360nm). Recorded on a Bruker Ultrashield 400Plus NMR spectrometer (at...

Embodiment 3

[0483] Formation of Copper Complexes Based on Chiral DOTA

[0484] synthesis:

[0485] Chiral DOTA-based lithium salts 29-c and 29-d were synthesized according to similar reaction conditions as described in Examples 1 and 2 ( Figure 29 ).

[0486] LC-MS analysis

[0487] method:

[0488] LC-MS conditions: column: Agilent Eclipse Plus C18RRHD 1.8 μm column (50×2.1 mm), eluent A: water containing 0.01% formic acid, eluent B: acetonitrile.

[0489] [260] Gradient: 2% B, 0-2 minutes; 2-50% B, 2-15 minutes.

[0490] Experimental procedure:

[0491] (1) Inject lithium salt 29-c for analysis.

[0492] (2) Dissolve lithium salt 29-c (7.8 mg, 1.0 eq) in 3 ml NaOAc buffer (1.0 M, pH 5.50), then add CuCl 2 (1.94 mg, 1.0 equiv).

[0493] (3) After the following 5 conditions, 20 μL of the reaction mixture was taken, then diluted with 0.5 mL of NaOAc buffer, and then 5 μL was injected for analysis.

[0494] a) Add CuCl 2 After that, just stir for a few seconds;

[0495] ...

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Abstract

The present invention relates to the preparation of a series of chiral DOTA, D03A, D02A, DO1A, cyclen and their metal complexes, which display properties superior to those of previous DOTA- based compounds, and hence are potentially valuable as a platform for diagnostic applications. The chiral DOTAs reveal a high abundance of twisted square antiprism (TSA) geometry favoring them to be used as potential MRI contrast agents, whereas their rapid labelling properties at mild conditions make them excellent candidates for use as radiometal chelators.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of U.S. Provisional Application No. 62 / 396,785, filed September 19, 2016. The entire content and disclosure of the aforementioned applications are incorporated by reference into this application. [0003] Throughout this application, various publications are referenced. The entire disclosures of these publications in their entireties are incorporated into this application by reference to more fully describe the state of the art to which this invention pertains. [0004] field of invention [0005] The present invention relates to a sterically controlled synthetic strategy to obtain chiral sendanine ligands with increased rigidity, higher stability and water solubility for various biomedical applications . Background technique [0006] It is known that the tetraazacycloalkanes, especially the triazacyclododecane (1,4,7,10-tetraazacyclododecane) derivatives form very stable lanthanid...

Claims

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Application Information

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IPC IPC(8): C07D257/02A61K31/395A61K49/22
CPCA61K49/22C07D257/02C07D401/14C07F9/65583C07D401/06C07D403/14C07D409/14C07F5/003A61K51/0482A61K51/088
Inventor 罗嘉丽戴利雄
Owner THE HONG KONG POLYTECHNIC UNIV
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