Carrageenan derivative, probe for labelling macrophages, and method for preparing same
AssigneesKorea University Research and Business Foundation, Seoul National University R&Db Foundation
InventorsHong Seog Seo, Yong Jik Lee, Jae Min Jeong, Yun Sang Lee, Ji Yong Park
Life of this patent
Estimating the term…
Abstract
A carrageenan derivative according to the present disclosure can quickly and easily detect and label the presence of inflammation-related macrophages and, particularly, can accurately and easily identify M1-type macrophages highly associated with early inflammation. In addition, the carrageenan derivative has advantages in that it can be produced easily, environmental pollution is minimized because a small amount of organic solvent is used, and initial cost is low.
Claims17
A carrageenan derivative formed as a hydroxy group of a galactose or 3,6-anhydrogalactose moiety of carrageenan having a repeat unit represented by Chemical Formula 1 is oxidized to an aldehyde group through periodate oxidation, and
- the aldehyde group is substituted with a compound represented by Chemical Formula 2 or Chemical Formula 3 and then reduced:
- wherein
- each of R1 to R4, which are identical to or different from each other, is any one selected from the group consisting of —H, —OH, —CH3, —CH2OH, —COOH, and —OSO3−,
- R5 is any one selected from the group consisting of —H, —OH, —CH3, —CH2OH, —COOH, —CH2OSO3−, and —OSO3−,
- n is an integer from 1 to 10,000, and
- o is an integer from 1 to 10.
A method for preparing a carrageenan derivative, comprising:
- 1) a step of preparing carrageenan-aldehyde having repeat units represented by Chemical Formulas 1 and 4 by reacting carrageenan having a repeat unit represented by Chemical Formula 1 with an oxidizing agent;
- 2) a step of substituting the aldehyde group of the carrageenan-aldehyde with a compound of Chemical Formula 2 or Chemical Formula 3 by reacting the carrageenan-aldehyde prepared in the step 1) with a compound represented by Chemical Formula 2 or Chemical Formula 3;
- and
- 3) a step of reacting the substituted carrageenan derivative prepared in the step 2) with a reducing agent:
- wherein
- each of R1 to R4, which are identical to or different from each other, is any one selected from the group consisting of —H, —OH, —CH3, —CH2OH, —COOH, and —OSO3−,
- R5 is any one selected from the group consisting of —H, —OH, —CH3, —CH2OH, —COOH, —CH2OSO3−, and —OSO3−,
- each of n and m is an integer from 1 to 10,000, and
- o is an integer from 1 to 10.
A method for preparing a probe for labeling macrophages, comprising:
- a) a step of preparing carrageenan-aldehyde having repeat units represented by Chemical Formulas 1 and 4 by reacting carrageenan having a repeat unit represented by Chemical Formula 1 with an oxidizing agent;
- b) a step of substituting an aldehyde group of the carrageenan-aldehyde with a compound of Chemical Formula 2 by reacting the carrageenan-aldehyde prepared in the step a) with a compound represented by Chemical Formula 2 or Chemical Formula 3;
- c) a step of reacting the substituted carrageenan derivative prepared in the step b) with a reducing agent;
- and
- d) a step of reacting the carrageenan derivative prepared in the step c) with a radioisotope or an isothiocyanate-modified fluorescent dye:
- wherein
- each of R1 to R4, which are identical to or different from each other, is any one selected from the group consisting of —H, —OH, —CH3, —CH2OH, —COOH, and —OSO3−,
- R5 is any one selected from the group consisting of —H, —OH, —CH3, —CH2OH, —COOH, —CH2OSO3−, and —OSO3−,
- each of n and m is an integer from 1 to 10,000, and
- o is an integer from 1 to 10.
A method for preparing a probe for labeling macrophages, comprising:
- i) a step of preparing carrageenan-aldehyde having repeat units represented by Chemical Formulas 1 and 4 by reacting carrageenan having a repeat unit represented by Chemical Formula 1 with an oxidizing agent;
- ii) a step of substituting an aldehyde group of the carrageenan-aldehyde with a compound of Chemical Formula 3 by reacting the carrageenan-aldehyde prepared in the step i) with a compound represented by Chemical Formula 2 or Chemical Formula 3;
- iii) a step of reacting the substituted carrageenan derivative prepared in the step ii) with a reducing agent;
- and
- iv) a step of conducting copper-free click reaction of the carrageenan derivative prepared in the step iii) with an azide compound represented by Chemical Formula 5:
- each of R1 to R4, which are identical to or different from each other, is any one selected from the group consisting of —H, —OH, —CH3, —CH2OH, —COOH, and —OSO3−,
- R5 is any one selected from the group consisting of —H, —OH, —CH3, —CH2OH, —COOH, —CH2OSO3−, and —OSO3−,
- each of n and m is an integer from 1 to 10,000, and
- o is an integer from 1 to 10;
- wherein
- A is any one selected from a group consisting of Cy3, Cy5, fluorescein isothiocyanate (FITC), tetramethylrhodamine isothiocyanate (RITC), Alexa, 4,4,-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY), Texas Red, NOTA, biotin, C-11, F-18, Ga-67, Ga-68, Cu-64, I-123, I-124, I-125, Zr-89, In-111, Tc-99m, Y-90, Re-186, Re-188, Lu-177, Ac-225, At-211 and I-131.
Dependencies are inferred from the claim text.