Acyl-homoserine lactone compound and application thereof in environmental protection
A technology for acylation of homoserine and ester compounds, applied in the field of environmental microorganisms, can solve problems such as biological toxicity, secondary pollution, and drug resistance of acidophilic Thiobacillus ferrooxidans in mining areas, and achieve the purpose of inhibiting the production of acidic heavy metal mine water , no secondary pollution, good inhibitory effect
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Embodiment 1
[0031] Synthesis of embodiment 1 Thiobacillus ferrooxidans biofilm inhibitor
[0032]
[0033] In the formula,
[0034] No.1: R 1 =Br,R 2 = H, R 3 = H, n = 2;
[0035] No.2: R 1 =Br,R 2 = H, R 3 =H,n=0;
[0036] No. 3: R 1 = H, R 2 = H, R 3 =Br,n=0;
[0037] No. 4: R 1 = H, R 2 =Br,R 3 =H,n=0;
[0038] No.5: R 1 = Cl, R 2 = H, R 3 =H,n=0;
[0039] No. 6: R 1 = H, R 2 = F, R 3 =H,n=0;
[0040] No. 7: R 1 = F, R 2 = H, R 3 =H,n=0;
[0041] No. 8: R 1 = NO 2 , R 2 = H, R 3 =H,n=0;
[0042] No. 9: R 1 = CF 3 , R 2 = H, R 3 =H,n=0;
[0043] No. 10: R 1 =Br,R 2 = H, R 3 = H, n = 1;
[0044] Among them, No.1, No.2, No.3, No.4, No.5, No.6, No.7, No.8, No.9, and No.10 are respectively a kind of acylated homoserine lactone Compound analogues.
[0045] Concrete synthetic steps are:
[0046] (1) Place 169 mg (0.93 mM) of (R)-(+)-α-amino-γ-butyrolactone hydrochloride and the corresponding 0.93 mM organic acid in 10 mL of dry CH 2 Cl 2Mix well...
Embodiment 2
[0048] The influence of embodiment 2 compound on the normal growth of Thiobacillus ferrooxidans
[0049] Experimental materials: A. ferrooxidans ATCC23270 was purchased from American Type Culture Collection (ATCC).
[0050] Acidophilus ferrooxidans converts Fe 2+ Oxidized to Fe 3+ Gain energy to grow. Detection of Fe in Solution by Potassium Dichromate Titration 3+ content, reflecting the effect of compounds on bacterial Fe 2+ Oxidation ability, so as to ensure that the drug concentration will not affect the normal growth of bacteria. The experimental method is as follows:
[0051] (1) Add 100mL of 9K medium with pH 1.8 into a 250mL Erlenmeyer flask (9K medium preparation method: mix 3.0g (NH 4 ) SO 4 , 0.1g KCl, 0.5g K 2 HPO 4 , 0.5g MgSO 4 ·7H 2 O, 0.01g Ca(NO 3 ) 2 , 44.67g FeSO 4 ·7H 2 O was dissolved in 1000mL distilled water, and the pH was adjusted to 2.0 with dilute sulfuric acid, and sterilized by filtration), and then the experiment was divided into th...
Embodiment 3
[0055] Example 3 Biofilm Inhibitor Inhibition Activity Detection
[0056] (1) Collect A.ferrooxidans ATCC23270 cells by centrifuging at 10°C for 15 min at 9000 r / min, wash the cells twice with dilute sulfuric acid solution with pH 2.0, and finally resuspend them in a solution containing 2 g / L Fe 2+ , pH 2.0 basic salt solution (without FeSO 4 9K medium), and the bacterial density of the bacterial suspension was adjusted to 1.0×10 8 cells / mL;
[0057] (2) Divide the above-mentioned bacterial suspension into three groups, the first group uses no compound as the blank control group; compound. The bacterial suspension was added to a 96-well cell culture plate, 150 μL / well, and 8 parallels were made for each experimental group. Then put the 96-well cell culture plate into a constant temperature incubator, and culture it at 30°C for 48 hours to form a biofilm;
[0058] (3) After 48 hours, discard the bacteria solution in the wells, and wash each well twice with sterile deionize...
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