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CN-121974937-A - Conjugated double six-membered ring-containing metal coordination compound, and preparation method and application thereof

CN121974937ACN 121974937 ACN121974937 ACN 121974937ACN-121974937-A

Abstract

The invention belongs to the technical field of antibacterial material preparation, and discloses a conjugated double six-membered ring-containing metal coordination compound, and a preparation method and application thereof. By coordinating transition metal ions with dicyandiamide, a series of coordination compounds with conjugated double six-membered ring structures are constructed, and controllable preparation from small molecules to polymers is realized by introducing different linkers. Specifically, N-dimethylformamide is used as a solvent, dicyandiamide, metal chloride and a connector are used as raw materials, the raw materials react for 24 hours at a specific ratio at 70 ℃, and a micromolecular material and a polymer material are respectively obtained after suction filtration, washing and drying. The preparation method is simple, the raw materials are wide, all the materials have higher surface positive potential, and the antibacterial agent has high-efficiency antibacterial performance on escherichia coli and staphylococcus aureus.

Inventors

  • HE JINGHUI
  • WANG CHENNAN
  • CHEN SONG
  • LI BIN

Assignees

  • 苏州大学

Dates

Publication Date
20260505
Application Date
20260408

Claims (9)

  1. 1. The preparation method of the conjugated double six-membered ring-containing metal coordination compound is characterized by comprising the following steps of, S1, dissolving dicyandiamide in sufficient N, N-dimethylformamide to form a dicyandiamide solution; S2, adding a transition metal chloride into a sufficient amount of N, N-dimethylformamide, performing ultrasonic treatment to form a transition metal ion solution uniformly, then dripping the transition metal ion solution into a dicyandiamide solution, adding a connector under intense stirring, continuously stirring at 70 ℃, dripping the reacted solution into a large amount of continuously stirred deionized water to precipitate a product, performing suction filtration, and washing with water and acetone for three times respectively; S3, drying the cleaned solid in a vacuum oven at 50 ℃ overnight, and collecting the dried solid to obtain a metal coordination compound; Wherein the transition metal chloride is CuCl 2 、CoCl 2 or ZnCl 2 , and the linker is selected from n-hexanol or 1, 6-hexanediol.
  2. 2. The method for preparing a conjugated double six-membered ring containing metal coordination compound according to claim 1, wherein when the linker is n-hexanol, the molar ratio of dicyandiamide, transition metal ions and n-hexanol is 2:1:2, and the obtained metal coordination compound is a small molecular material, which is denoted by M-DCHe.
  3. 3. The method for preparing a conjugated double six-membered ring containing metal coordination compound according to claim 1, wherein when the linker is 1, 6-hexanediol, the molar ratio of dicyandiamide, transition metal ions and 1, 6-hexanediol is 2:1:1, and the obtained metal coordination compound is a polymer material, which is denoted by M-DCHDO.
  4. 4. A conjugated double six-membered ring-containing metal complex compound produced based on the production method according to any one of claims 1 to 3.
  5. 5. The conjugated double-six-membered ring containing metal complex according to claim 4, wherein the conjugated double-six-membered ring containing metal complex comprises a conjugated double-six-membered ring core structural unit formed by coordination of dicyandiamide and transition metal ions, zeta potential > +30 mV can efficiently target and bind to a negatively charged bacterial membrane, is stably dispersed in water, and has high surface positive charges.
  6. 6. The use of a conjugated double six-membered ring containing metal complex compound according to claim 4 for the preparation of an antibacterial material.
  7. 7. The use according to claim 6, wherein the antibacterial comprises resistance to one or both of escherichia coli or staphylococcus aureus.
  8. 8. The use according to claim 7, wherein the metal complex exhibits excellent antibacterial properties against both escherichia coli and staphylococcus aureus in the absence of light, and the minimum inhibitory concentration is in the range of 0.3-5 μg/mL.
  9. 9. An antibacterial material comprising the conjugated double six-membered ring-containing metal complex compound according to claim 4.

Description

Conjugated double six-membered ring-containing metal coordination compound, and preparation method and application thereof Technical Field The invention belongs to the field of antibacterial materials, and particularly relates to a conjugated double six-membered ring-containing metal coordination compound, and a preparation method and application thereof. Background Microorganisms are widely distributed in the earth ecological system, penetrate through various scenes of human production and living, and are closely related to human health. Clinically common infections are mostly induced by gram-positive bacteria, gram-negative bacteria and other strains, and can cause various serious diseases. Antibiotics have been the key means to combat bacterial infections, but due to their irrational and overuse, multi-drug resistant strains are rapidly emerging and spread, and new antibiotics are developed over long periods and at high cost, traditional antibiotic therapy systems are severely impacted. Therefore, there is a need to explore effective strategies against multiple resistant strains, to prevent the transmission of "superbacteria", and the development and use of antibacterial materials is an important direction to solve the above problems. Therefore, there is an urgent need to develop novel antibacterial materials, particularly antibacterial materials which are not liable to cause bacterial resistance. In response to the challenge of increasing bacterial resistance, researchers have continuously explored novel antibacterial strategies in recent years, and particularly remarkable progress has been made in the fields of cationic polymers, metal complexes, monoatomic nanoenzymes and the like. For example, yu et al review Cationic Antibacterial Polymers (CAPs) such as quaternary ammonium, guanidine, and quaternary phosphonium salt materials, utilize electrostatic interactions between their positive charges and bacterial cell membranes to achieve high efficacy sterilization, and have a lower risk of drug resistance than traditional antibiotics (Coordination CHEMISTRY REVIEWS 447 (2021) 214128). Gong et al constructed a supramolecular structure formed by the assembly of the cell penetrating peptide octapolyarginine (R8) with the anionic surfactant SDS, wherein the bactericidal rate of the layered aggregates against staphylococcus aureus and escherichia coli reached 99.9% at a concentration of 25 μg/mL, and significantly promoted wound healing in a mouse infection model (ADVANCED MATERIALS 2025, 202411388). Zhang et al prepared PSACNZs-N 2 -C material by adjusting the Co-N coordination number in cobalt monoatomic nanoenzyme, which had a sterilizing rate of 99.7% against Staphylococcus aureus at a concentration of 400. Mu.g/mL (Acta Biomaterialia 164 (2023) 563-576). Zhao et al developed a guanidino-functionalized polyamino acid PArg 20 that achieved rapid killing of candida albicans within 10 minutes by a "adsorption-penetration-disruption" phage-like mechanism, MIC values as low as 2-4 μg/mL, and significantly reduced fungal burden in mouse cornea and systemic infection models (ACS Nano 2025,19 (49), 41605-41622). Zigale et al further designed Co-N-C monoatomic nanoenzymes with oxidase activity to achieve >99% kill of tetracycline-resistant bacteria by generating reactive oxygen species without the addition of H 2O2 and to effectively promote healing of infected wounds (ACS appl. Mater. Interfaces 2026, 18, 3669-3683). Although various antibacterial strategies are continuously updated, so that the antibacterial effect of the nano material is continuously improved, the bacterial killing effect of the prior art is still unsatisfactory. Therefore, it is important to find a material with a low minimum antimicrobial concentration and an antimicrobial strategy with excellent killing effect on high concentration bacteria in a short light time. The guanidine functional group provides ideas for designing novel antibacterial materials due to the unique properties. Researches show that the guanidine band has positive charges, and can form specific double-tooth hydrogen bonds with negatively charged phosphate groups in a phospholipid layer of a bacterial cell membrane, so that efficient targeted combination and physical membrane rupture are realized, and compared with quaternary ammonium salts and the like, the guanidine band has lower cytotoxicity. The metal coordination compound has wide application prospect in the fields of catalysis, biological medicine and the like due to structural designability, various geometric configurations and rich physicochemical properties. By coordination and assembly of the organic ligand with targeting membrane rupture capability and the metal ion with antibacterial activity, the novel material with targeting identification and multi-mechanism synergistic antibacterial effect is hopeful to be constructed. However, how to design a metal complex compound with definite synthetic structure, good s