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Heterocyclyl polymethine ir chromophores

a technology of chromophores and polymethine, which is applied in the field of heterocyclyl polymethine ir chromophores, can solve the problems of limited materials that emit in this region, the need for cnts as a swir contrast agent, and the key limitation of photomedicine, and achieves low or negligible quantum yields

Pending Publication Date: 2021-11-25
RGT UNIV OF CALIFORNIA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present patent provides small molecules that can be used for optical imaging, photothermal therapy, and photodynamic therapy. These molecules have improved properties and can absorb and emit light in the NIR and SWIR regions. These molecules have high quantum yields and can be used for in vivo imaging. The patent also includes methods for preparing and using these molecules for sensing and cargo delivery.

Problems solved by technology

Despite its potential, photomedicine has encountered a key limitation: the penetration of light into tissue, defined as the point in which ⅔ of the light has been scattered or absorbed by endogenous biomolecules.
The main limitation was the need for CNTs as a SWIR contrast agent, as there are concerns regarding the biocompatibility of CNTs.
While the potential of the SWIR has been demonstrated, materials that emit in this region are limited.
However, all these materials are sizeable and do not represent a direct comparison to the fluorophores that have been enormously successful in vitro.

Method used

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  • Heterocyclyl polymethine ir chromophores
  • Heterocyclyl polymethine ir chromophores
  • Heterocyclyl polymethine ir chromophores

Examples

Experimental program
Comparison scheme
Effect test

example 1

on of Exemplary Dimethylaminoflavylium Dyes

7-Dimethylaminoflavylium heptamethine Dye (3, Flav7)

[0323]4-((E)-2-((E)-2-chloro-3-(2-((E)-7-(dimethylamino)-2-phenyl-4H-chromen-4-ylidene)ethylidene)cyclohex-1-en-1-yl)vinyl)-7-(dimethylamino)-2-phenylchromenylium perchlorate 7-N,N-dimethylamino-4-methyl-flavylium perchlorate (1) (31.1 mg, 0.0855 mmol, 2.1 equiv), N-[(3-(anilinomethylene)-2-chloro-1-cyclohexen-1-yl)methylene]aniline 6 (13.0 mg, 0.040 mmol, 1.0 equiv.) and anhydrous sodium acetate (9 mg, 0.1 mmol, 2.5 equiv.) were dissolved in EtOH (0.78 mL, anhydrous) and heated to 90° C. for 6 hours. The solution was cooled to room temperature and evaporated onto silica gel. Dye 3 was purified via silica gel chromatography, eluting with a DCM / MeOH solvent gradient of 200:1, 150:1, 100:1, 80:1, 67:1 and 50:1. This procedure gave pure 3 (11.1 mg, 0.0145 mmol, 36%). 1H NMR (500 MHz, DMSO-d6): δ 8.21 (d, J=10 Hz, 2H), 8.14-8.10 (m, 6H), 7.70-7.53 (m, 8H), 7.06 (d, J=15 Hz, 2H), 6.96 (dd, J=10...

example 2

f Dimethylaminoflavylium Dyes

[0327]The absorbance spectra in FIG. 2 and FIGS. 4A-4G were obtained in DCM on a JASCO V-770 UV-Visible / NIR spectrophotometer with a 2000 nm / min or 4000 nm / min scan rate. Plotted are the baseline corrected and normalized data. The emission spectra in FIG. 2 were taken in DCM on either a Horiba Instruments PTI QuantaMaster Series fluorometer (6), a Fluoromax-3 spectrofluorometer (1, 3-5), or home-built InGaAs array detector (Princeton Instruments). For 6 the following parameters were used: ex. 610 nm, emission collected from 620-900 nm, slits 5 nm, step size 1 nm, integration time 1 s. Plotted is the DCM corrected, baseline corrected, normalized data. For 1, and 3-5, the following parameters were used: slits 5 nm, step size 1 nm, integration time, 0.25 s. Excitation values and emission collection were as follows: 1 (ex. 460, collection 470-800 nm), 5 (ex. 675 nm, collection 685-950 nm), 4 (ex. 840 nm, emission 850-1100 nm), 3 (ex. 730 nm, emission 950-140...

example 3

l Exemplary Preparations of Dimethylaminoflavylium Dyes

[0330]

7-(Dimethylamino)-2-phenyl-4H-chromen-4-one (S2a)

[0331]3-(dimethylamino)phenol (500 mg, 3.64 mmol, 1 equiv.) and ethyl benzoylacetate (1.10 mL, 6.37 mmol, 1.75 equiv.) were combined in a 10 mL flask and heated at 180° C. for 24 h. The solution was cooled to room temperature, evaporated onto silica gel and purified via column chromatography with a 50:1 to 1:4, followed by a second column in 6:1 to 1:1 hexanes / EtOAc gradient. The procedure gave a beige solid (493 mg, 1.86 mmol, 51%). Rf=0.4 in 1:1 hexanes / EtOAc 1H NMR (500 MHz, Chloroform-d) δ 8.01 (d, J=9.0 Hz, 1H), 7.91-7.84 (m, 2H), 7.54-7.44 (m, 3H), 6.73 (dd, J=9.0, 2.4 Hz, 1H), 6.67 (s, 1H), 6.55 (d, J=2.4 Hz, 1H), 3.07 (s, 6H). 13C NMR (126 MHz, Chloroform-d) δ 177.9, 162.3, 158.4, 154.2, 132.3, 131.1, 129.0, 126.6, 126.1, 113.7, 110.9, 107.3, 97.2, 40.3. HRMS (ESI+) calcd for C17H16NO2+ [M+H]+: 266.1176; found: 266.1178. Absorbance (CH2Cl2): 229, 274, 358 nm.

7-(Dimet...

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Abstract

The present disclosure provides NIR- and SWIR-active small molecule polymethine dyes with improved properties for use in optical imaging, photothermal therapy, and photodynamic therapy.

Description

RELATED APPLICATIONS[0001]This application claims the benefit of U.S. Provisional Application No. 62 / 775,788 filed Dec. 5, 2018, the contents of which are fully incorporated by reference herein.BACKGROUND[0002]Photomedicine broadly refers to the use of light for diagnostic or therapeutic procedures, including optical imaging, photothermal therapy (thermal ablation of cells) and photodynamic therapy (reactive oxygen species induced apoptosis or necrosis). (See Hamblin, M. R.; Huang, Y. Y. Handbook of Photomedicine; CRC Press: Boca Raton, 2014.) The low toxicity of light coupled with the direct control of localization and dosage make phototherapy a promising avenue for increasing the therapeutic index of disease treatment. (See Yuan, A.; Wu, J.; Tang, X.; Zhao, L.; Xu, F.; Hu, Y. J. Pharm. Sci. 2013, 102, 6-28.) Additionally, the inexpensive nature of lasers and detectors poise photoimaging platforms as cost-effective preventative healthcare screening procedures. (See Massoud, T. F.; ...

Claims

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Application Information

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IPC IPC(8): C07D311/58C07D311/92C07D311/30C07D405/14C07D405/04C07D491/16C07D519/00A61K49/00
CPCC07D311/58C07D311/92C07D311/30A61K49/0032C07D405/04C07D491/16C07D519/00C07D405/14G06Q10/10G06Q30/0206G06Q40/04G06Q10/083G06Q40/02H04L9/3239H04L2209/56G06F21/6254G06F21/64H04L63/0421H04L63/0442H04L63/10G06Q20/02G06Q2220/00H04L9/50G06Q20/108G06Q20/3678G06Q20/42G06Q20/3829G06F16/27G06F16/2379G06F21/602H04L9/30H04L9/0637
Inventor SLETTEN, ELLEN M.COSCO, EMILY D.SPEARMAN, ANTHONYPENGSHUNG, MONICA
Owner RGT UNIV OF CALIFORNIA
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