A photoresponsive pro-fragrance of an antibacterial peptide-fragrance linkage and application thereof

Abstract

The application provides an antibacterial peptide-flavor linked light response pro-perfume and an application thereof, and the pro-perfume is prepared by linking antibacterial peptides after the reaction of hydroxyl or carboxyl of an alcohol or carboxylic acid flavor molecule with (5-amino-2-nitrophenyl) methanol. The antibacterial peptide-flavor linked light response pro-perfume prepared by the application has good light response release performance, can prolong the flavor release duration and improve the fragrance retention, significantly improves the utilization rate of the flavor, breaks through the traditional passive release mode to realize active regulation, has high efficient broad-spectrum antibacterial activity, and the linked antibacterial peptides endow the pro-perfume with antibacterial performance to effectively inhibit the growth of microorganisms; in addition, the amino and amide groups of the antibacterial peptides improve the water solubility of the pro-perfume, and further broaden the application range of the pro-perfume. The raw materials are easy to obtain, the synthesis steps are simple, the conditions are mild, and the yield is high. The commercially available raw materials can be simply synthesized under mild conditions to realize large-scale production, and the application has wide market prospect and economic benefits.

Description

Technical Field

[0001] This invention belongs to the field of fragrance and flavor technology, specifically relating to a photoresponsive pre-fragrance compound linked to an antimicrobial peptide and its application. Background Technology

[0002] Fragrance molecules are widely used in the textile industry to impart pleasant scents to products. However, traditional fragrances generally suffer from inherent defects such as poor chemical stability and high volatility, resulting in short-lasting fragrance on fabrics and an unsustainable effect. Fragrance sustained-release technology, especially the "pro-fragrance" strategy, achieves controlled release of fragrance molecules triggered by specific environmental stimuli (such as light, temperature, and pH) by linking fragrance molecules to a low-volatility matrix through environmentally responsive, cleavable chemical bonds. This is an effective way to overcome these defects. Among them, light-responsive pro-fragrances have become an ideal choice for achieving intelligent fragrance release due to their significant advantages such as clean and pollution-free triggering methods, precise spatiotemporal control, and the elimination of the need for chemical initiators.

[0003] However, free fragrances and existing photoresponsive pre-fragrances have poor hydrophilicity, making it difficult for them to effectively bind with natural fibers such as cotton, linen, silk, and wool. As a result, they are easily shed under friction, washing, or sweat, making it difficult to achieve long-lasting fragrance. To overcome this bottleneck, it is urgent to develop a new type of pre-fragrance that can simultaneously enhance fabric adhesion and impart additional high-value-added functions.

[0004] Inspired by biomolecular interactions, antimicrobial peptides (AMPs), due to their unique amphiphilic structure and abundant active functional groups (such as amino and carboxyl groups), exhibit the potential to form strong interactions with various fibrous materials (especially fibers with appropriate surface treatments). More importantly, antimicrobial peptides themselves possess broad-spectrum and highly efficient antimicrobial activity. Therefore, research on antimicrobial peptide-fragrance molecule photoresponsive pre-fragrances can significantly improve the overall performance and added value of products. Summary of the Invention

[0005] Technical Problem to be Solved: To address the aforementioned technical problems, the present invention aims to provide a photoresponsive pre-fragrance compound linked to an antimicrobial peptide and its applications. This pre-fragrance compound is prepared by reacting the hydroxyl or carboxyl groups of an alcohol or carboxylic acid fragrance molecule with (5-amino-2-nitrophenyl)methanol and then linking them to an antimicrobial peptide. The photoresponsive pre-fragrance compound prepared by this invention exhibits excellent photoresponsive release performance, prolonging fragrance release time and enhancing fragrance longevity, significantly improving fragrance utilization, and breaking through the traditional passive release mode to achieve active regulation. It also possesses highly efficient broad-spectrum antimicrobial activity; the linked antimicrobial peptide endows the pre-fragrance compound with antimicrobial properties, effectively inhibiting microbial growth. Furthermore, the amino and amide groups of the antimicrobial peptide improve the water solubility of the pre-fragrance compound, further broadening its application range. The preparation process of this invention uses readily available raw materials, involves simple synthesis steps, mild conditions, and high yield. It can be easily synthesized under mild conditions using commercially available raw materials for large-scale production, possessing broad market prospects and economic benefits. In addition, this pre-fragrance enhances the antibacterial properties of the fabric without affecting its breathability and softness, ensuring comfortable wear.

[0006] Technical solution: A photoresponsive pre-fragrance compound linked by an antimicrobial peptide and a fragrance, the molecular structure of which is shown below:

[0007]

[0008] Wherein R is any one or more of C1-C10 alkyl, C1-C10 alkoxy or substituted aryl groups, and n is 1-30; the antimicrobial peptide is polylysine.

[0009] Furthermore, R can be any one of the following molecular formulas:

[0010] , and .

[0011] A method for preparing a photoresponsive pre-fragrance compound linked to an antimicrobial peptide and a fragrance, characterized by comprising the following steps:

[0012] Step 1. Add carboxylic acid fragrance molecules or alcohol fragrance molecules to a solvent, then stir and mix with (5-amino-2-nitrophenyl)methanol, and react at room temperature to obtain an intermediate;

[0013] The intermediate is any one of the following molecular formulas:

[0014]

[0015] Step 2. Add the intermediate to the solvent, then add the condensing agent and catalyst, and then add the antimicrobial peptide and stir for 12-24 hours to obtain the photoresponsive pre-fragrance body linked by the antimicrobial peptide and fragrance; the molar ratio of the intermediate, antimicrobial peptide, condensing agent and catalyst is 1:(1-10):(1-1.5):(0.1-3).

[0016] Further, the solvent is any one or more of dichloromethane, methanol, N,N-dimethylformamide, acetonitrile, tetrahydrofuran, ethyl acetate, acetone, and 1,4-dioxane; the condensing agent is selected from any one or more of N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and N,N'-diisopropylcarbodiimide; the catalyst is selected from any one or more of 4-dimethylaminopyridine, 1-hydroxybenzotriazole, and O-benzotriazole-N,N,N',N'-tetramethylurea hexafluorophosphate.

[0017] Furthermore, the preparation method of intermediate I is as follows: cinnamic acid is added to solvent A, followed by condensing agent B and catalyst C, and then (5-amino-2-nitrophenyl)methanol is added and stirred. The mixture is reacted at room temperature to obtain intermediate I; the molar ratio of cinnamic acid, condensing agent B, catalyst C and (5-amino-2-nitrophenyl)methanol is 1:(1-1.5):(0.1-3):(1-3).

[0018] Further, solvent A is any one or more of dichloromethane, methanol, N,N-dimethylformamide, acetonitrile, tetrahydrofuran, ethyl acetate, acetone, and 1,4-dioxane; condensing agent B is any one or more of N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and N,N'-diisopropylcarbodiimide; catalyst C is any one or more of 4-dimethylaminopyridine, 1-hydroxybenzotriazole, and O-benzotriazole-N,N,N',N'-tetramethylurea hexafluorophosphate.

[0019] Furthermore, the preparation method of intermediate II is as follows: octanoic acid is added to solvent D, followed by condensing agent E and catalyst F, and then (5-amino-2-nitrophenyl)methanol is added and stirred. The mixture is reacted at room temperature to obtain intermediate II; the molar ratio of octanoic acid, condensing agent E, catalyst F and (5-amino-2-nitrophenyl)methanol is 1:(1-1.5):(0.1-3):(1-3).

[0020] Further, the solvent D is any one or more of dichloromethane, methanol, N,N-dimethylformamide, acetonitrile, tetrahydrofuran, ethyl acetate, acetone, and 1,4-dioxane; the condensing agent E is any one or more of N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and N,N'-diisopropylcarbodiimide; and the catalyst F is any one or more of 4-dimethylaminopyridine, 1-hydroxybenzotriazole, and O-benzotriazole-N,N,N',N'-tetramethylurea hexafluorophosphate.

[0021] Furthermore, the preparation method of intermediate III is as follows: leaf alcohol is first subjected to chlorination to generate leaf alcohol chloride; leaf alcohol chloride and acid-binding agent H are added to solvent G, followed by the addition of (5-amino-2-nitrophenyl)methanol and stirring and mixing, and the reaction is carried out at room temperature to obtain intermediate III; the molar ratio of leaf alcohol, acid-binding agent E and (5-amino-2-nitrophenyl)methanol is 1:(1-3):(1-3).

[0022] Furthermore, the solvent G is any one or more of dichloromethane, methanol, N,N-dimethylformamide, acetonitrile, tetrahydrofuran, ethyl acetate, acetone, and 1,4-dioxane; the acid-binding agent H is any one or more of potassium carbonate, sodium carbonate, sodium hydroxide, pyridine, triethylamine, and diisopropylethylamine.

[0023] The above-described application of a photoresponsive pre-fragrance compound linked to an antimicrobial peptide in the fragrance industry.

[0024] Beneficial effects:

[0025] 1. This invention involves reacting a chlorohydrin group (after substitution of the carboxylic acid group or alcohol hydroxyl group in a carboxylic acid or alcohol fragrance molecule) with (5-amino-2-nitrophenyl)methanol to generate an intermediate product. This intermediate product is then linked to an antimicrobial peptide to obtain a photoresponsive pre-fragrance with an antimicrobial peptide-fragrance bond. The photoresponsive group contained in this pre-fragrance is o-nitrobenzyl, which enables photocontrolled release of alcohol / carboxylic acid fragrance molecules through an o-nitrobenzyl phototrigger structure, breaking through the traditional passive release mode of fragrances. Furthermore, the antimicrobial peptide endows the pre-fragrance with antibacterial properties, giving it highly efficient broad-spectrum antibacterial activity and effectively inhibiting microbial growth. In addition, the amino and amide groups of the antimicrobial peptide improve the water solubility of the pre-fragrance, making it more suitable for the field of daily chemical products that require active control of the fragrance release process, thereby broadening the application range of this pre-fragrance.

[0026] 2. The photoresponsive pre-fragrance compound linked to antimicrobial peptides prepared in this invention, as a light-controlled release fragrance carrier, exhibits excellent release performance and is particularly suitable for applications requiring extended fragrance release time and improved fragrance longevity, significantly increasing fragrance utilization. Furthermore, leveraging the structural characteristics of the antimicrobial peptides and their strong interaction with fabrics, the adhesion of fragrances or pre-fragrance compounds to the fabric surface can be significantly enhanced, laying the foundation for long-lasting fragrance retention; simultaneously, based on the antibacterial activity of the antimicrobial peptides, it can also provide long-lasting hygienic protection for the fabric.

[0027] 3. The preparation process of the photoresponsive prefragrance with antimicrobial peptide-fragrance linkage in this invention has the characteristics of readily available raw materials, simple synthesis steps, mild conditions, and high yield. It can achieve large-scale production by using commercially available raw materials and simple synthesis steps under mild conditions, which is particularly suitable for industrial fragrance manufacturing scenarios with strict cost control requirements. Attached Figure Description

[0028] Figure 1 The images show the light release effect of the photoresponsive pre-fragrance particles prepared by antimicrobial peptide-fragrance linkage in Examples 4 and 5, where A represents the photoresponsive pre-fragrance particles prepared by antimicrobial peptide-fragrance linkage in Example 4, and B represents the photoresponsive pre-fragrance particles prepared by antimicrobial peptide-fragrance linkage in Example 5.

[0029] Figure 2 The antibacterial effects of photoresponsive prefragrances linked with antimicrobial peptides in Examples 4 and 5 on Escherichia coli and Staphylococcus aureus are shown in the figure.

[0030] Figure 3 The particle size distribution diagrams for the photoresponsive prefragrance particles linked by antimicrobial peptides and fragrances prepared in Examples 4 and 5 are shown below. In these diagrams, A represents the photoresponsive prefragrance particle linked by antimicrobial peptides and fragrances prepared in Example 4, B represents the photoresponsive prefragrance particle linked by antimicrobial peptides and fragrances prepared in Example 5, C represents cinnamic acid, and D represents caprylic acid.

[0031] Figure 4 The stability effect diagrams are shown for the photoresponsive pre-fragrance products prepared by antimicrobial peptide-fragrance linkage in Examples 4 and 5, where A represents the photoresponsive pre-fragrance product prepared by antimicrobial peptide-fragrance linkage in Example 4, and B represents the photoresponsive pre-fragrance product prepared by antimicrobial peptide-fragrance linkage in Example 5. Detailed Implementation

[0032] The present invention will be further described below with reference to the embodiments. The following embodiments are explanations of the present invention and the present invention is not limited to the following embodiments.

[0033] Example 1

[0034] Synthesis of photoresponsive prefragrance intermediate I linked to antimicrobial peptide-fragrance bond

[0035] In a dry reaction flask, 1 mmol of cinnamic acid, 1 mmol of (5-amino-2-nitrophenyl)methanol, 1.2 mmol of 1-ethyl-(3-dimethylaminopropyl)carbodiimide (EDC), 0.1 mmol of 4-dimethylaminopyridine (DMAP), and 10 mL of dichloromethane (DCM) were added sequentially. The mixture was stirred at room temperature for 8 h. After the reaction was complete, the mixture was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography to obtain intermediate I, with a yield of 76%. The reaction process is as follows.

[0036]

[0037] 1H NMR data of photoresponsive pre-fragrance intermediate I linked to antimicrobial peptide-fragrance bond: 1 H NMR (400 MHz, CDCl3)δ 7.74 (d, J = 8.5 Hz, 1H), 7.52 (d, 1H), 7.45-7.38 (m, 2H), 7.30-7.21 (m,3H), 6.85 (s, 1H), 6.54 (d, J = 2.2 Hz, 1H), 6.28 (d, J = 15.9 Hz, 1H), 5.26(s, 2H), 4.13 (s, 2H);

[0038] Carbon spectrum data: 13 C NMR (101 MHz, CDCl3) δ 167.27, 151.97, 145.54, 139.90,134.43, 134.15, 130.06, 129.06, 128.76, 126.18, 116.74, 114.02, 112.11,64.47. Example 2

[0039] Synthesis of photoresponsive prefragrance intermediate II linked to antimicrobial peptide-fragrance bond

[0040] In a dry reaction flask, 1 mmol of octanoic acid, 1 mmol of (5-amino-2-nitrophenyl)methanol, 1.2 mmol of 1-ethyl-(3-dimethylaminopropyl)carbodiimide (EDC), 0.1 mmol of 4-dimethylaminopyridine (DMAP), and 10 mL of dichloromethane (DCM) were added sequentially. The mixture was stirred at room temperature for 8 h. After the reaction was complete, the mixture was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography to obtain intermediate II, with a yield of 69%. The reaction process is as follows.

[0041]

[0042] 1H NMR data of photoresponsive pre-fragrance intermediate II linked to antimicrobial peptide-fragrance bond: 1 H NMR (400 MHz, CDCl3) δ 7.87 (d, J = 8.5 Hz, 1H), 6.97 (s, 1H), 6.66 (d, J = 2.2 Hz, 1H), 5.37 (d, J = 1.0 Hz, 2H), 4.25 (s, 2H), 2.33 (t, J = 8.5 Hz, 2H), 1.68-1.57(m, 2H), 1.35-1.21 (m, 8H), 0.89 (t, 3H);

[0043] Carbon spectrum data: 13 C NMR (101 MHz, CDCl3) δ 173.19, 151.97, 139.50, 134.13,126.17, 113.95, 112.11, 64.37, 34.21, 31.62, 29.07, 29.06, 25.04, 22.69,14.09. Example 3

[0044] Synthesis of photoresponsive prefragrance intermediate III linked to antimicrobial peptide-fragrance bond

[0045] 1 mmol of leaf alcohol and 0.05 mmol of N,N-dimethylformamide (DMF) were placed in 10 mL of dichloromethane and cooled to 0 °C. Then, 1.2 mmol of dichlorosulfoxide was slowly added over 10 min, and the mixture was stirred at room temperature for 4 h. The mixture was then concentrated under reduced pressure to obtain an orange oil containing intermediate III′ for the next reaction.

[0046] 1.81 mmol (5-amino-2-nitrophenyl)methanol and 3.62 mmol K2CO3 were dispersed in 5 mL DMF, and then heated to 80 °C under nitrogen protection. After the temperature stabilized, 2 mL of DMF solution containing 3.62 mmol intermediate III′ was added. After the addition was complete, the reaction was continued at 80 °C for 2 h. After the reaction was completed, the mixture was cooled to room temperature, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography to obtain intermediate III, and the structure of the product was characterized by nuclear magnetic resonance. The reaction process is as follows.

[0047] 1H NMR data of photoresponsive pre-fragrance intermediate III linked to antimicrobial peptide-fragrance bond: 1 H NMR (400 MHz, CDCl3) δ 7.89 (d, J = 8.5 Hz, 1H), 6.96-6.91 (m, 1H), 6.66 (d, J = 2.2 Hz, 1H), 5.56-5.46 (m, 1H), 5.46-5.37 (m, 1H), 4.65 (d, J = 1.0 Hz, 2H), 3.98 (s,2H), 3.64 (t, J = 0.9 Hz, 2H), 2.30-2.22 (m, 2H), 2.09-1.99 (m, 2H), 0.96 (t,J = 1.0 Hz, 3H);

[0048] Carbon spectrum data: 13 C NMR (101 MHz, CDCl3)δ 152.11, 140.07, 134.72, 134.37,126.31, 126.02, 113.63, 112.02, 70.19, 69.67, 33.10, 22.44, 14.24. Example 4

[0049] A method for preparing a photoresponsive pre-fragrance compound IV linked to an antimicrobial peptide and a fragrance, comprising the following steps:

[0050] In a dry reaction flask, 1 mmol of polylysine, 0.8 mmol of intermediate I prepared in Example 1, 1.5 mmol of HATU, 3 mmol of DIEA, and 48 mL of anhydrous N,N-dimethylformamide (DMF) were added sequentially, and the mixture was stirred at room temperature for 18 h. After the reaction was completed, some of the solvent was removed by rotary evaporation, resulting in a viscous product. The crude product was then purified by dialysis and lyophilized to obtain photoresponsive pre-fragrance IV linked to the antimicrobial peptide-fragrance bond, with a yield of 73%. The reaction process is as follows.

[0051]

[0052] 1H NMR data of photoresponsive pre-fragrance group IV linked to antimicrobial peptide-fragrance bond: 1 H NMR (400 MHz, CDCl3) δ9.41 (s, 1H), 8.07 (d, J = 8.7 Hz, 1H), 7.81 (d, J= 2.1 Hz, 1H), 7.78-7.72(m, 1H), 7.64 (d, 1H), 7.57-7.51 (m, 2H), 7.42-7.34 (m, 3H), 6.80 (t, J = 5.3Hz, 26H), 6.40 (d, J = 15.9 Hz, 1H), 5.50 (s, 2H), 4.91 (d, J = 5.9 Hz, 2H), 4.31 (d, J = 0.7 Hz, 52H), 3.81-3.73 (m, 1H), 3.68-3.59 (m, 26H), 3.19-3.03(m, 52H), 2.71-2.57 (m, 2H), 1.93-1.66 (m, 29H), 1.67-1.17 (m, 135H). Example 5

[0053] A method for preparing a photoresponsive pre-fragrance V linked by an antimicrobial peptide and a fragrance, comprising the following steps:

[0054] In a dry reaction flask, 1 mmol of polylysine, 0.8 mmol of intermediate II prepared in Example 2, 1.5 mmol of HATU, 3 mmol of DIEA, and 48 mL of anhydrous N,N-dimethylformamide (DMF) were added sequentially, and the mixture was stirred at room temperature for 18 h. After the reaction was completed, some of the solvent was removed by rotary evaporation, resulting in a viscous product. The crude product was then purified by dialysis and lyophilized to obtain photoresponsive prefragrance V linked to the antimicrobial peptide and fragrance, with a yield of 63%. The reaction process is as follows.

[0055]

[0056] 1H NMR data of photoresponsive prefragrant body V linked to antimicrobial peptide-fragrance bond: 1 H NMR (400 MHz, CDCl3) δ9.41 (s, 1H), 8.07 (d, J = 8.7 Hz, 1H), 7.81 (d, J = 2.1 Hz, 1H), 7.77-7.72(m, 1H), 6.80 (t, J = 5.3 Hz, 26H), 5.48 (d, J = 0.7 Hz, 2H), 4.91 (d, J =5.9 Hz, 2H), 4.31 (d,J = 0.7 Hz, 52H), 3.81-3.71 (m, 1H), 3.69-3.58 (m,26H), 3.23-3.08 (m, 52H), 2.71-2.55 (m, 2H), 2.33 (t, J = 8.5 Hz, 2H), 1.89-1.73 (m, 27H), 1.73 (t, 2H), 1.67-1.24 (m, 145H), 0.92-0.86 (m, 3H). Example 6

[0057] A method for preparing a photoresponsive pre-fragrance VI linked to an antimicrobial peptide and a fragrance, comprising the following steps:

[0058] In a dry reaction flask, 1 mmol of polylysine, 0.8 mmol of intermediate III prepared in Example 3, 1.5 mmol of HATU, 3 mmol of DIEA, and 48 mL of anhydrous N,N-dimethylformamide (DMF) were added sequentially, and the mixture was stirred at room temperature for 18 h. After the reaction was completed, some of the solvent was removed by rotary evaporation, resulting in a viscous product. The crude product was then purified by dialysis and lyophilized to obtain photoresponsive prefragrance VI linked to the antimicrobial peptide and fragrance, with a yield of 72%. The reaction process is as follows.

[0059]

[0060] 1H NMR data of photoresponsive pre-fragrance VI linked to antimicrobial peptide-fragrance bond: 1H NMR (400 MHz, CDCl3) δ9.46 (s, 1H), 8.08 (d, J = 8.8 Hz, 1H), 7.82 (d, J = 2.2 Hz, 1H), 7.75-7.65(m, 1H), 6.80 (t, J = 5.3 Hz, 26H), 5.55-5.47 (m, 1H), 5.46-5.38 (m, 1H),4.91 (d, J = 5.9 Hz, 2H), 4.78 (d, J = 1.0 Hz, 2H), 4.31 (d, J = 0.7 Hz,52H), 3.88-3.70 (m, 1H), 3.70-3.57 (m, 28H), 3.21-3.02 (m, 52H), 2.73-2.52(m, 2H), 2.30-2.22 (m, 2H), 2.111.99 (m, 2H), 1.91-1.73 (m, 27H), 1.71 (t, J= 6.5 Hz, 2H), 1.64-1.24 (m, 135H), 0.96 (t, J = 0.9 Hz, 3H). Example 7

[0061] Responsive release assay of photoresponsive pre-fragrance compounds linked to antimicrobial peptides and fragrances

[0062] Weigh 2.10 g of cinnamic acid, 42.40 g of antimicrobial peptide-fragrance bonded photoresponsive prefragrance compound IV, 2.04 g of caprylic acid and 42.34 g of antimicrobial peptide-fragrance bonded photoresponsive prefragrance compound V, and place them in 20 mL headspace vials respectively. The release of fragrance under light and dark conditions was monitored by solid phase microextraction combined with GC-MS.

[0063] like Figure 1 As shown, under light conditions, the photoresponsive pre-fragrance compound IV prepared in Example 4 and the photoresponsive pre-fragrance compound V prepared in Example 5 gradually released fragrance over time, with the release concentration continuously increasing and eventually reaching a stable level. In contrast, cinnamic acid and caprylic acid initially maintained a high concentration but later showed a decreasing trend. This indicates that the photoresponsive pre-fragrance compound connected to the antimicrobial peptide-fragrance can delay the release of fragrance to achieve a long-lasting fragrance effect. Example 8

[0064] Antimicrobial test of photoresponsive prefragrances linked to antimicrobial peptides and fragrances

[0065] Take 20 μL of 1×10 -420 μL of mol / L photoresponsive pre-fragrance body IV aqueous solution linked to antimicrobial peptide-fragrance, 1×10 -4 mol / L antimicrobial peptide-fragrance bonded photoresponsive pre-fragrance body V aqueous solution, 20 μL 1×10 -4 mol / L cinnamic acid solution and 20 μL 1×10 -4 mol / L octanoic acid solution was co-cultured with Escherichia coli and Staphylococcus aureus solutions at 37°C for 24 h; a parallel experiment was set up with 20 μL of pure water instead of the sample solution as a negative control.

[0066] like Figure 2 As shown, compared with the negative control, the photoresponsive pre-fragrance compound IV with antimicrobial peptide-fragrance bond prepared in Example 4 and the photoresponsive pre-fragrance compound V with antimicrobial peptide-fragrance bond prepared in Example 5 both showed significant antibacterial effects against Escherichia coli and Staphylococcus aureus. Example 9

[0067] Dynamic light scattering (DLS) test of photoresponsive pre-fragrance compounds linked to antimicrobial peptides and fragrances

[0068] Dynamic light scattering (DLS) was used to test 1×10 -4 mol / L antimicrobial peptide-fragrance bonded photoresponsive pre-fragrance body IV aqueous solution, 1×10 -4 mol / L antimicrobial peptide-fragrance bonded photoresponsive prefragrance body V aqueous solution, 1×10 -4 mol / L cinnamic acid solution and 1×10 -4 Particle size and distribution of mol / L octanoic acid solution.

[0069] like Figure 3 As shown, the average particle size of the antimicrobial peptide-fragrance-linked photoresponsive prefragrance compound IV prepared in Example 4 and the antimicrobial peptide-fragrance-linked photoresponsive prefragrance compound V prepared in Example 5 is significantly smaller than that of the corresponding fragrance monomer solution, and they exhibit higher dispersibility (smaller PDI dispersion index). This indicates that the antimicrobial peptide-fragrance-linked photoresponsive prefragrance compound prepared in this invention can form smaller and more uniform dispersed particles in an aqueous system, and has better colloidal stability and solubility. Example 10

[0070] Photoresponsive pre-fragrance stability test of antimicrobial peptide-fragrance linkage

[0071] 1×10 was tested using high performance liquid chromatography (HPLC). -4 mol / L antimicrobial peptide-fragrance bonded photoresponsive pre-fragrance body IV aqueous solution, 1×10 -4 Stability of mol / L antimicrobial peptide-fragrance bonded photoresponsive prefragrance body V aqueous solution over time under dark conditions.

[0072] like Figure 4 As shown, after 14 days of storage, the retention time characteristic peaks of the antimicrobial peptide-fragrance bonded photoresponsive pre-fragrance compound IV prepared in Example 4 and the antimicrobial peptide-fragrance bonded photoresponsive pre-fragrance compound V prepared in Example 5 remained stable, indicating that the antimicrobial peptide-fragrance bonded photoresponsive pre-fragrance compound prepared in this invention can achieve a stable and long-lasting fragrance effect.

[0073] The above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention in any way. Any person skilled in the art can make many possible variations and modifications to the technical solutions of the present invention, or modify them into equivalent embodiments, without departing from the spirit and technical essence of the present invention. Therefore, any simple modifications, equivalent substitutions, equivalent changes, and modifications made to the above embodiments based on the technical essence of the present invention, without departing from the content of the technical solutions of the present invention, shall still fall within the scope of protection of the present invention.

Claims

1. A photoresponsive pre-fragrance compound linked to an antimicrobial peptide and a fragrance, characterized in that, The molecular structure of the photoresponsive prefragrance compound linked by the antimicrobial peptide and fragrance is shown below: ， R can be any one of the following molecular formulas: n is 1-30 and n is not 1; the antimicrobial peptide is polylysine.

2. The method for preparing a photoresponsive pre-fragrance compound linked with an antimicrobial peptide-fragrance bond according to claim 1, characterized in that, Includes the following steps: Step 1. Add carboxylic acid fragrance molecules or alcohol fragrance molecules to a solvent, then stir and mix with (5-amino-2-nitrophenyl)methanol, and react at room temperature to obtain an intermediate; The intermediate is any one of the following molecular formulas: ； Step 2. Add the intermediate to the solvent, then add the condensing agent and catalyst, followed by the addition of the antimicrobial peptide and stirring for 12-24 hours to obtain a photoresponsive pre-fragrance linked to the antimicrobial peptide and fragrance; the molar ratio of the intermediate, antimicrobial peptide, condensing agent and catalyst is 1:(1-10):(1-1.5):(0.1-3); the condensing agent is selected from any one or more of N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and N,N'-diisopropylcarbodiimide; the catalyst in Step 2 is selected from any one or more of 4-dimethylaminopyridine, 1-hydroxybenzotriazole, and O-benzotriazole-N,N,N',N'-tetramethylurea hexafluorophosphate.

3. The method for preparing a photoresponsive pre-fragrance compound linked with an antimicrobial peptide-fragrance bond according to claim 2, characterized in that: The solvent is any one or more of dichloromethane, methanol, N,N-dimethylformamide, acetonitrile, tetrahydrofuran, ethyl acetate, acetone, and 1,4-dioxane.

4. The method for preparing a photoresponsive pre-fragrance compound linked with an antimicrobial peptide-fragrance bond according to claim 2, characterized in that, The preparation method of intermediate I is as follows: cinnamic acid is added to solvent A, followed by condensing agent B and catalyst C, and then (5-amino-2-nitrophenyl)methanol is added and stirred. The mixture is reacted at room temperature to obtain intermediate I. The molar ratio of cinnamic acid, condensing agent B, catalyst C and (5-amino-2-nitrophenyl)methanol is 1:(1-1.5):(0.1-3):(1-3).

5. The method for preparing a photoresponsive pre-fragrance compound linked to an antimicrobial peptide-fragrance bond according to claim 2, characterized in that, The preparation method of intermediate II is as follows: octanoic acid is added to solvent D, followed by condensing agent E and catalyst F, and then (5-amino-2-nitrophenyl)methanol is added and stirred. The mixture is reacted at room temperature to obtain intermediate II. The molar ratio of octanoic acid, condensing agent E, catalyst F and (5-amino-2-nitrophenyl)methanol is 1:(1-1.5):(0.1-3):(1-3).

6. The method for preparing a photoresponsive pre-fragrance compound linked with an antimicrobial peptide-fragrance bond according to claim 2, characterized in that, The preparation method of intermediate III is as follows: leaf alcohol is first subjected to chlorination to generate leaf alcohol chloride; leaf alcohol chloride and acid-binding agent H are added to solvent G, followed by the addition of (5-amino-2-nitrophenyl)methanol and stirring and mixing, and the reaction is carried out at room temperature to obtain intermediate III; the molar ratio of leaf alcohol, acid-binding agent E and (5-amino-2-nitrophenyl)methanol is 1:(1-3):(1-3).

7. The application of the antimicrobial peptide-fragrance bonded photoresponsive prefragrance according to claim 1 in the fragrance industry.

Images