Claims for Patent: 10,369,221

Summary for Patent: 10,369,221

Title:	Conjugated porphyrin carbon quantum dots for targeted photodynamic therapy
Abstract:	The present disclosure relates to porphyrin containing carbon quantum dots useful for bioimaging and/or phytodynamic therapy.
Inventor(s):	Zhu; Xunjin (Hong Kong, HK), Wong; Wai Kwok (Hong Kong, HK), Wu; Fengshou (Hong Kong, HK)
Assignee:	Hong Kong Baptist University (Hong Kong, HK)
Application Number:	15/806,514
Patent Claims:	1. A nanoparticle comprising a carbon matrix and one or more moieties present on the surface of the carbon matrix, wherein the one or more moieties is selected from the group consisting of --CO.sub.2H and --C(.dbd.O)NH(CH.sub.2CH.sub.2O).sub.nCH.sub.2CH.sub.2NHR, wherein n is a whole number selected from 3-100 and R is a hydrogen or a targeting group; and the carbon matrix comprises a compound of Formula I: ##STR00014## wherein, M is a metal selected from the group consisting of Co, Ni, Mn, Zn, Pt, and Pd; or M represents two hydrogen, each of which is covalently bound to a nitrogen; and ##STR00015## represents a covalent nitrogen-carbon bond between the compound of Formula I and the carbon matrix. 2. The nanoparticle of claim 1, wherein n is a whole number selected from 3-40. 3. The nanoparticle of claim 1, wherein the nanoparticle has an average diameter of about 3 to about 3.5 nm. 4. The nanoparticle of claim 1, wherein the carbon matrix comprises graphitic carbon. 5. The nanoparticle of claim 1, wherein the targeting group is selected from the group consisting of an antibody, an antibody fragment, a peptide, an aptamer, and a small molecule. 6. The nanoparticle of claim 5, wherein the antibody is cetuximab or panitumumab; the peptide is a cyclic RGD peptide; and the aptamer is anti-nucleolin aptamer AS1411. 7. The nanoparticle of claim 1, wherein the nanoparticle has an average diameter of about 3 to about 3.5 nm; n is whole number selected from 3-40; the carbon matrix comprises graphitic carbon; M is Zn; or M represents two hydrogen, each of which is covalently bound to a nitrogen; and R is cetuximab. 8. A method for treating non-small cell lung cancer in a patient in need thereof, comprising the step of administering a therapeutically effective amount of the nanoparticle of claim 7 to the patent. 9. A method for imaging a cell that overexpresses epidermal growth factor receptor (EGFR), comprising the step of contacting the cell with the nanoparticle of claim 7 and detecting the fluorescence of the nanoparticle of claim 7. 10. A method of synthesizing the nanoparticle of claim 1, comprising the steps of: a) contacting an organic acid selected from the group consisting of aspartic acid, citric acid, ethylenediaminetetraacetic acid (EDTA), glutamic acid, and tartaric acid with a compound of Formula II: ##STR00016## wherein, M is a metal selected from the group consisting of Co, Ni, Mn, Zn, Pt, and Pd; or M represents two hydrogen, each of which is covalently bound to a nitrogen; thereby forming a polymerized polyamide; b) subjecting the polymerized polyamide to hydrothermal carbonization thereby forming an unfunctionalized nanoparticle comprising a carbon matrix and one or more --CO.sub.2H present on the surface of the carbon matrix; and the carbon matrix comprises a compound of Formula I: ##STR00017## wherein, M is a metal selected from the group consisting of Co, Ni, Mn, Zn, Pt, and Pd; or M represents two hydrogen, each of which is covalently bound to a nitrogen; and ##STR00018## represents a covalent nitrogen-carbon bond between the compound of Formula I and the carbon matrix; c) contacting the unfunctionalized nanoparticle with NH.sub.2(CH.sub.2CH.sub.2O).sub.nCH.sub.2CH.sub.2NH.sub.2, wherein n is a whole number selected from 3-100, under conditions for forming an amide bond, thereby forming an amine terminated nanoparticle; and d) optionally contacting the amine terminated nanoparticle with a targeting group comprising an activated carbonyl thereby forming the nanoparticle of claim 1. 11. The method of claim 10, wherein the step of contacting the compound of Formula II and the organic acid, the compound of Formula II and organic acid are present in a mass to mass ratio of about 1:10 to about 5:15 of the compound of Formula II to the organic acid. 12. The method of claim 10, wherein the organic acid is citric acid. 13. The method of claim 10, wherein n is a whole number selected from 3-40. 14. The method of claim 13, wherein the step of contacting the contacting the unfunctionalized nanoparticle with NH.sub.2(CH.sub.2CH.sub.2O).sub.nCH.sub.2CH.sub.2NH.sub.2, the unfunctionalized nanoparticle and NH.sub.2(CH.sub.2CH.sub.2O).sub.nCH.sub.2CH.sub.2NH.sub.2 are present in a mass to mass ratio of about 1:4 to about 5:95 the unfunctionalized nanoparticle to the NH.sub.2(CH.sub.2CH.sub.2O).sub.nCH.sub.2CH.sub.2NH.sub.2. 15. A nanoparticle made according to the method of claim 14. 16. The method of claim 10, wherein the targeting group is selected from the group consisting of an antibody, an antibody fragment, a peptide, an aptamer, and a small molecule. 17. The method of claim 10, further comprising the step of purifying the unfunctionalized nanoparticle by dialysis. 18. The method of claim 10, wherein the hydrothermal carbonization is conducted at a temperature between about 160.degree. C. to about 240.degree. C. 19. The method of claim 10, wherein the nanoparticle has an average diameter of about 3 to about 3.5 nm; n is whole number selected from 3-40; the carbon matrix comprises graphitic carbon; M is Zn; or M represents two hydrogen, each of which is covalently bound to a nitrogen; and the targeting group comprising an activated carbonyl is cetuximab comprising an activated carbonyl. 20. A nanoparticle made according to the method of claim 19.

Details for Patent 10,369,221

Applicant	Tradename	Biologic Ingredient	Dosage Form	BLA	Approval Date	Patent No.	Expiredate
Eli Lilly And Company	ERBITUX	cetuximab	Injection	125084	02/12/2004		2036-11-08
Eli Lilly And Company	ERBITUX	cetuximab	Injection	125084	03/28/2007		2036-11-08
Amgen, Inc.	VECTIBIX	panitumumab	Injection	125147	09/27/2006		2036-11-08