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US-12622966-B2 - Compound for photothermal cancer therapy, composition including the same, and method for photothermal cancer therapy

US12622966B2US 12622966 B2US12622966 B2US 12622966B2US-12622966-B2

Abstract

Provided are a new compound for photothermal cancer therapy, a composition including the same, and a method for photothermal cancer therapy, and more particularly, a compound that is an organic photosensitizer based on an indan structure, a nanoparticle as a self-assembly thereof, a composition including the same, and a method for photothermal therapy using the same.

Inventors

  • Song Yi Lee
  • Thanh Chung Pham

Assignees

  • PUKYONG NATIONAL UNIVERSITY INDUSTRY-UNIVERSITY COOPERATION FOUNDATION

Dates

Publication Date
20260512
Application Date
20230131
Priority Date
20220419

Claims (11)

  1. 1 . A compound represented by Chemical Formula 1: wherein R 1 is selected from a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, and an alkynyl group having 2 to 10 carbon atoms; and wherein when R 1 is selected from a substituted cycloalkyl group having 3 to 6 carbon atoms, a substituted cycloalkenyl group having 3 to 6 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, and a substituted heteroaryl group having 5 to 12 carbon atoms, the substitution is selected from one of an alkyl having 1 to 5 carbon atoms, alkenyl having 2 to 5 carbon atoms, alkynyl having 2 to 5 carbon atoms, and a halogen atom.
  2. 2 . The compound of claim 1 , wherein the compound is provided in the form of an aggregate nanoparticle.
  3. 3 . The compound of claim 2 , wherein the nanoparticle has a size of 500 nm or less, and the nanoparticle emits heat at a temperature of 45° C. or higher by a light irradiation.
  4. 4 . The compound of claim 2 , wherein a photothermal conversion efficiency of the nanoparticle is 60% or higher.
  5. 5 . A composition comprising: the compound represented by Chemical Formula 1 of claim 1 .
  6. 6 . The composition of claim 5 , wherein the composition is used for photothermal therapy, and emits thermal energy during a light irradiation to remove or kill target cells.
  7. 7 . The composition of claim 6 , wherein the target cells comprise cancer cells, tumor cells or hyperproliferative cells.
  8. 8 . The composition of claim 5 , further comprising: water, an organic solvent, or both, wherein the compound in the composition is included in an active ingredient content.
  9. 9 . A method for photothermal therapy, the method comprising: contacting the composition of claim 5 with a target cell in vivo or ex vivo; and irradiating light to a region of the target cell contacting the composition.
  10. 10 . The method of claim 9 , wherein the irradiating of the light comprises heating a target cell region to a temperature of 45° C. or more by irradiating a red light laser of 1 second or more and 1 W/cm 2 or more and removing or killing the target cell.
  11. 11 . The method of claim 9 , further comprising: after the irradiating of the light, acquiring and analyzing an infrared thermal image of the target cell region.

Description

CROSS-REFERENCE TO RELATED APPLICATION This application claims the benefit of Korean Patent Application No. 10-2022-0048172 filed on Apr. 19, 2022, in the Korean Intellectual Property Office, the entire disclosure of which is incorporated herein by reference for all purposes. BACKGROUND 1. Field of the Invention One or more embodiments relate to a new compound for photothermal cancer therapy, a composition including the same, and a method for photothermal cancer therapy. 2. Description of the Related Art Chemotherapy, radiation therapy, and surgery, which have been applied to cancer treatment so far, often cause serious side effects. In contrast, photothermal therapy has advantages such as low side effects, very low drug resistance, local destruction of tumor, and the like. Photothermal therapeutic agents are mostly based on inorganic materials, but organic photothermal agents have better biocompatibility. Among organic photothermal agents, polymers generally exhibit molecular polydispersity with low reproducibility, and supramolecules are not always stable under physiological conditions, and the polymers and the supramolecules have disadvantages of biodegradation toxicity. Several efficient small organic photothermal agents have been reported, but in order to make these organic photothermal agents having a photothermal effect, a bulky chain, an aromatic ring, etc. are introduced to perform several stages of organic reaction, resulting in a low yield, so that economic disadvantages also occur in commercialization, clinical trials and applications. Some small organic photothermal agents have problems such as low photostability of cyanide derivatives, low water solubility of porphyrins and phthalocyanines, and low photothermal conversion efficiency of BODIPY derivatives, and a molecular design for nanoscale-level organic photothermal agents for acquiring excellent photothermal conversion efficiency (η) may generate obstacles to rapidly access biological and clinical trials. SUMMARY An aspect of the present disclosure is to provide a new compound that is a photosensitizer having a simple synthesis process (e.g., a single-step organic reaction), excellent photothermal conversion efficiency and excellent biocompatibility and may be used as a photothermal material. Another aspect of the present disclosure is to provide nanoparticles that are a nano-aggregation platform prepared by self-assembly of the compound according to the present disclosure, and may be utilized as a photothermal material having excellent photothermal conversion efficiency and excellent biocompatibility. Another aspect of the present disclosure is to provide a composition that includes the compound, nanoparticles or both according to the present disclosure and may be utilized as a photothermal therapeutic agent. Another aspect of the present disclosure is to provide a photothermal therapy method using the composition according to the present disclosure. However, technical aspects of the present disclosure are not limited to the aforementioned purpose and other aspects which are not mentioned may be clearly understood to those skilled in the art from the following description. According to an aspect of the present disclosure, there is provided a new compound represented by Chemical Formula 1 below: In Chemical Formula 1, R1 and R2 are selected from hydrogen, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, and an alkynyl group having 2 to 20 carbon atoms, respectively, however, at least one of R1 and R2 is selected from a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms. R3 to R5 are selected from hydrogen, halogen, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, and an alkynyl group having 2 to 10 carbon atoms, respectively.) According to an embodiment of the present disclosure, at least one of the R1 and R2 may be selected from a substituted or unsubstituted aryl group having 6 to 12 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 carbon atoms. According to an embodiment of the present disclosure, the compound of Chemical Formula 1 may be selected from Chemical Formula 1-1. In Chemical Formula 1-1, R1 is selected from hydrogen, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 6 ca