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US 2026/0240867 A1Published application
Multinuclear heterocyclic metal carbene complex for wound healing
AssigneeKing Abdulaziz University
InventorsMohammad ASAD, Ayesha RIAZ, Muhammad Adnan IQBAL, Haq Nawaz BHATTI, Muhammad Nadeem ARSHAD, Abdullah M. ASIRI, Khalid A. ALZAHRANI, Naved AZUM
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Abstract
A complex includes at least two N-heterocyclic carbene (NHC) ligands with the formula I, and two to six silver atoms. R is selected from a group consisting of a propyl functional group, a butyl functional group, and a benzyl functional group. The silver atoms are bonded to the at least two NHC ligands.
Claims20
1:
- A complex, including:
- at least two N-heterocyclic carbene (NHC) ligands with the formula I:
- wherein R is selected from a group consisting of a propyl functional group, a butyl functional group, and a benzyl functional group, and
- two to six silver atoms,
- wherein each of the silver atoms are bonded to the at least two NHC ligands.
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2:
- The complex of claim 1, wherein the NHC ligand of formula I is made by a process, including:
- refluxing a 1-X-1H-benzimidazole with a 1,2-dibromoethane to form a 3-(2-bromoethyl)-1-X-1H-benzoimidazolium,
- wherein X is selected from a group consisting of propyl, butyl, and benzyl,
- refluxing a 1,3-bis((1H-imidazol-1-yl)methyl)benzene with the 3-(2-bromoethyl)-1-X-1H-benzoimidazolium in an organic solution to form a tetrakis-benzamidazolium precursor;
- refluxing the tetrakis-benzamidazolium precursor with 3-(2-bromoethyl)-1-X-1H-benzoimidazolium in 1,4-dioxane to form a salt of formula 1.
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3:
- The complex of claim 2, wherein X is propyl and the tetrakis-benzamidazolium precursor has a percent yield of 45 to 50% based on an initial weight of reactants.
4:
- The complex of claim 2, wherein X is butyl and the tetrakis-benzamidazolium precursor has a percent yield of 42 to 48% based on an initial weight of reactants.
5:
- The complex of claim 2, wherein X is benzyl and the tetrakis-benzamidazolium precursor has a percent yield of 45 to 50% based on an initial weight of reactants.
6:
- The complex of claim 1, wherein the complex is made by a process including:
- mixing the NHC ligand of formula I with a silver salt in a polar solvent in the absence of light for 45 to 50 hours (h) to form a mixture;
- filtering the mixture;
- collecting a filtrate;
- and
- mixing a hexafluorophosphate salt with the filtrate in a polar solvent to form the complex.
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7:
- A method of healing wounds, including:
- administering the complex of claim 1 to an open wound;
- and
- closing the open wound to form a healed wound,
- wherein a surface area of the healed wound is smaller compared to an initial surface area of the open wound.
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8:
- The method of claim 7, wherein the administering the complex to the open wound occurs at least 2 times a day.
9:
- The method of claim 7, wherein the administering the complex to the open wound occurs for at least 1 to 15 days.
10:
- The method of claim 7, wherein after the administering the complex to the open wound and the closing the open wound, the wound heals with a percent wound contraction of 70 to 85% based on the initial surface area of the open wound.
11:
- A method of anti-angiogenesis, including:
- administering the complex of claim 1 to a subject;
- and
- reducing growth of blood vessels in the subject.
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12:
- The method of claim 11, further including:
- dissolving blood vessels during the reducing.
13:
- The complex of claim 1, further including:
- at least two NHC ligands with the formula II:
14:
- The complex of claim 1, further including:
- at least two NHC ligands with the formula III:
- wherein R is selected from a group consisting of a propyl functional group, a butyl functional group, a hexyl functional group, a benzyl functional group, and an ethyl phenyl functional group.
15:
- The complex of claim 1, further including:
- at least two NHC ligands with the formula IV:
- wherein R is a diphenyl methane functional group.
16:
- The complex of claim 13, wherein the complex has a percent yield of 75 to 85% based on an initial weight of reactants.
17:
- The complex of claim 14, wherein the complex has a percent yield of 65 to 90% based on an initial weight of reactants.
18:
- The complex of claim 15, wherein the complex has a percent yield of 80 to 85% based on an initial weight of reactants.
19:
- The complex of claim 14, wherein the functional group is the hexyl functional group, and the complex has a unit cell volume of 1650 to 1700 cubic angstroms (Å3).
20:
- A pharmaceutical composition, including:
- the complex of claim 1;
- a filler;
- a stabilizer;
- a surfactant;
- a binder;
- a glidant;
- and
- a lubricant.
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