Study on the Design, Synthesis, Bioactivity and Translocation of the Conjugates of Phenazine-1-carboxylic Acid and N-Phenyl Alanine Ester
Abstract
:1. Introduction
2. Result and Discussion
2.1. Chemistry
2.2. Antifungal Activity
2.3. Preliminary Analysis of Structure–Activity Relationship (SAR)
2.4. Phloem Mobility
2.5. Predicting Phloem Mobility and Possible Mobility Mechanism of F Series Compounds
2.6. The Phloem Mobility of Compound F2 Up-Taken through Tobacco Seedlings
3. Materials and Methods
3.1. Chemicals and Instruments
3.2. Test Fungus and Plant Materials
3.3. Synthesis
3.3.1. General Procedure for the Preparation of B
3.3.2. General Procedure for the Preparation of Intermediate D
3.3.3. General Procedure for the Preparation of Target Compounds E
3.3.4. General Procedure for the Preparation of Target Compound F
3.4. Antifungal Activity Assay
3.5. Phloem Sap Collection and Analysis
3.5.1. Phloem Sap Collection
3.5.2. Analytical Methods
3.6. Mobile Distribution of Compound F2 in Tobacco
3.6.1. Uptake and Translocation of Compound F2 by Tobacco Seedlings
3.6.2. Extraction and Analysis of Compounds F2
3.6.3. Spike Recovery
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compd. b | Average Inhibition Rate ± SD (%) (n = 3) | |||||||
---|---|---|---|---|---|---|---|---|
S. S a | B. s | P. p | P. c | A. s | P. a | R. s | P. i | |
E1 | <10 | <10 | 13.36 ± 2.13 | <10 | <10 | 16.39 ± 1.27 | <10 | <10 |
E2 | 21.38 ± 3.13 | 14.06 ± 0.08 | <10 | <10 | 22.98 ± 2.76 | <10 | <10 | 10.26 ± 2.16 |
E3 | 17.76 ± 2.88 | 10.63 ± 1.03 | <10 | <10 | 19.09 ± 1.90 | <10 | <10 | <10 |
E4 | <10 | 10.00 ± 0.49 | 19.80 ± 1.26 | <10 | 12.30 ± 3.07 | <10 | <10 | <10 |
E5 | 19.74 ± 4.54 | <10 | <10 | <10 | 21.68 ± 4.28 | <10 | <10 | 12.91 ± 1.85 |
E6 | <10 | <10 | <10 | <10 | <10 | <10 | <10 | <10 |
E7 | <10 | <10 | <10 | <10 | <10 | 11.11 ± 0.48 | <10 | <10 |
E8 | 22.70 ± 3.62 | 14.38 ± 1.37 | <10 | 23.44 ± 1.69 | 15.53 ± 4.77 | <10 | 10.20 ± 5.49 | <10 |
E9 | <10 | <10 | 10.74 ± 3.11 | <10 | 15.86 ± 3.49 | <10 | <10 | <10 |
E10 | 29.35 ± 2.80 | <10 | 22.15 ± 0.82 | <10 | 19.49 ± 1.09 | 22.78 ± 1.92 | <10 | <10 |
E11 | 38.16 ± 1.63 | 45.00 ± 0.74 | 41.61 ± 0.80 | 29.69 ± 1.28 | 44.66 ± 1.43 | 50.90 ± 4.04 | 32.86 ± 2.28 | 24.5 ± 1.79 |
E12 | 16.45 ± 4.33 | 12.19 ± 0.07 | 22.15 ± 0.68 | <10 | 16.18 ± 1.99 | 25.00 ± 1.40 | 10.20 ± 1.53 | <10 |
E13 | 57.89 ± 1.17 | 49.38 ± 0.71 | 59.06 ± 1.19 | 42.81 ± 0.31 | 38.51 ± 2.15 | 57.83 ± 2.16 | 40.23 ± 1.53 | 26.16 ± 0.77 |
E14 | 55.59 ± 0.82 | 33.13 ± 0.48 | 22.15 ± 3.34 | 17.19 ± 4.57 | 23.95 ± 3.89 | 27.41 ± 4.74 | 23.23 ± 1.73 | <10 |
E15 | <10 | <10 | <10 | 12.32 ± 8.89 | 12.64 ± 1.65 | 13.33 ± 1.67 | <10 | <10 |
E16 | <10 | 10.31 ± 0.89 | <10 | <10 | 19.09 ± 3.36 | <10 | <10 | <10 |
F1 | 33.70 ± 3.56 | 11.22 ± 0.48 | 33.33 ± 2.22 | <10 | <10 | <10 | 53.14 ± 2.70 | 22.15 ± 2.49 |
F2 | 44.93 ± 1.33 | 68.98 ± 0.90 | 26.74 ± 1.79 | 10.15 ± 0.20 | 66.08 ± 0.58 | 54.29 ± 0 | 29.04 ± 5.35 | 19.54 ± 1.41 |
F3 | 46.01 ± 0.39 | <10 | 20.83 ± 1.36 | 22.46 ± 2.41 | <10 | 17.73 ± 0.50 | 20.13 ± 1.88 | 14.66 ± 0.70 |
F4 | 78.62 ± 1.57 | <10 | 47.22 ± 0.40 | 28.31 ± 1.63 | <10 | 13.30 ± 1.26 | 20.79 ± 0.90 | 26.38 ± 1.88 |
F5 | 81.16 ± 0.53 | <10 | 40.28 ± 2.44 | 16.92 ± 1.61 | <10 | 13.85 ± 0.58 | 31.35 ± 1.21 | 41.04 ± 1.05 |
F6 | 81.52 ± 1.17 | 11.88 ± 0.87 | 27.78 ± 0.95 | <10 | <10 | 13.57 ± 1.50 | 32.67 ± 0.87 | 28.99 ± 0.79 |
F7 | 81.52 ± 1.03 | <10 | 49.31 ± 2.05 | 12.31 ± 3.29 | <10 | 20.22 ± 1.00 | 22.44 ± 1.84 | 27.69 ± 1.42 |
F8 | 78.99 ± 0.38 | 10.89 ± 1.87 | 25.00 ± 1.16 | <10 | <10 | <10 | 30.36 ± 2.31 | 29.64 ± 2.19 |
F9 | 81.52 ± 0.89 | 62.71 ± 0.31 | 47.22 ± 1.18 | 13.23 ± 1.68 | 47.95 ± 0.29 | 26.32 ± 0.76 | 26.40 ± 2.27 | 34.85 ± 0.68 |
F10 | 71.74 ± 0.50 | 11.22 ± 1.40 | 43.75 ± 1.15 | 11.08 ± 2.25 | <10 | 17.45 ± 0.76 | 42.90 ± 2.37 | 25.73 ± 1.36 |
F11 | 81.16 ± 0.39 | 46.20 ± 0.78 | 35.07 ± 0.26 | 66.77 ± 0.35 | 24.85 ± 0.29 | 22.16 ± 0.58 | 42.57 ± 1.37 | 30.62 ± 1.73 |
F12 | 70.29 ± 0.40 | 13.86 ± 0.85 | 43.40 ± 1.50 | 11.38 ± 1.75 | <10 | <10 | 24.75 ± 1.52 | 57.65 ± 0.80 |
F13 | 80.80 ± 0.78 | 16.17 ± 0.44 | 26.39 ± 1.51 | 20.31 ± 2.07 | <10 | 14.13 ± 1.04 | 36.63 ± 0.63 | 39.41 ± 0.33 |
F14 | 83.70 ± 0.27 | 15.18 ± 1.36 | 37.15 ± 0.26 | 51.38 ± 2.80 | 15.20 ± 1.15 | 21.33 ± 0.76 | 8.58 ± 6.36 | 63.19 ± 0.20 |
F15 | 35.51 ± 1.16 | <10 | 37.50 ± 1.24 | 10.46 ± 0.74 | 11.70 ± 0.29 | 14.13 ± 0.58 | 43.23 ± 5.87 | 19.54 ± 1.17 |
F16 | 19.57 ± 1.16 | 60.40 ± 1.38 | <10 | <10 | 29.24 ± 0.29 | 23.55 ± 0.50 | 19.47 ± 0.42 | 12.38 ± 1.09 |
PCA c | 98.55 ± 0.51 | 100.00 ± 0 | 85.76 ± 0.65 | 68.00 ± 1.06 | 75.73 ± 0.29 | 73.13 ± 0.29 | 93.07 ± 1.66 | 89.25 ± 0.98 |
Metal. d | 15.58 ± 1.80 | <10 | 80.56 ± 0.71 | <10 | 24.56 ± 0 | 16.62 ± 0.29 | 56.11 ± 1.23 | <10 |
Compd. | EC50/(μg/mL) | EC50/(μmol/L) | Regression Equation | 95% Confidence Interval/(μg/mL) | Correlation Coefficient (R2) |
---|---|---|---|---|---|
F5 | 14.57 | 35.98 | y = 3.2851 + 1.4740x | 13.1904–16.0933 | 0.9961 |
F6 | 18.11 | 44.72 | y = 2.6425 + 1.8741x | 15.7107–20.8773 | 0.9924 |
F7 | 6.57 | 16.22 | y = 4.0718 + 1.1352x | 5.5046–7.8456 | 0.9939 |
F9 | 9.92 | 22.09 | y = 3.5751 + 1.4296x | 9.1232–10.7955 | 0.9972 |
F11 | 20.43 | 51.20 | y = 2.5061 + 1.9032x | 16.6768–25.0367 | 0.9742 |
F13 | 16.97 | 41.09 | y = 3.0535 + 1.5830x | 15.5039–18.5692 | 0.9965 |
F14 | 8.02 | 19.42 | y = 3.8083 + 1.3183x | 6.8062–9.4396 | 0.9939 |
PCA | 3.87 | 17.28 | y = 4.1864 + 1.3840x | 3.218–4.6567 | 0.9901 |
Compd. | Regression Equation | Correlation Coefficient (R2) |
---|---|---|
F1 | y = 11034099x − 10368260 | 0.9927 |
F2 | y = 10613651x − 650875 | 0.9990 |
F3 | y = 1202838x − 5885 | 0.9997 |
F4 | y = 2065740x − 44534 | 0.9962 |
F5 | y = 2234165x − 1020903 | 0.9992 |
F6 | y = 6126714x − 6610569 | 0.9972 |
F7 | y = 6695972x − 3185573 | 0.9952 |
F8 | y = 5314495x − 2033452 | 0.9994 |
F9 | y = 1173264x − 85687 | 0.9980 |
F10 | y = 7134918x − 6908171 | 0.9983 |
F11 | y = 12128866x + 5301627 | 0.9998 |
F12 | y = 6795334x − 1939715 | 0.9991 |
F13 | y = 11573595x − 985307 | 1.0000 |
F14 | y = 2148578x − 669546 | 0.9992 |
F15 | y = 14370508x + 103540 | 0.9998 |
F16 | y = 3231821x − 2254916 | 0.9991 |
Metal. | y = 922409x + 211247 | 0.9995 |
PCA | y = 27002x − 2443 | 0.9971 |
Compd. | Molecular Weight (g/mol) | LogKow | pKa |
---|---|---|---|
F1 | 371.40 | 2.74 | 3.447 |
F2 | 389.39 | 3.38 | 3.322 |
F3 | 389.39 | 3.30 | 3.374 |
F4 | 389.39 | 3.38 | 3.239 |
F5 | 405.84 | 3.70 | 3.299 |
F6 | 405.84 | 3.67 | 3.365 |
F7 | 405.84 | 3.64 | 3.285 |
F8 | 450.29 | 3.99 | 3.363 |
F9 | 450.29 | 3.97 | 3.303 |
F10 | 385.42 | 3.13 | 3.481 |
F11 | 399.45 | 3.82 | 3.461 |
F12 | 399.45 | 3.87 | 3.415 |
F13 | 413.48 | 3.98 | 3.442 |
F14 | 413.48 | 4.05 | 3.408 |
F15 | 399.45 | 3.37 | 3.396 |
F16 | 415.39 | 3.09 | 3.156 |
PCA | 224.22 | 2.34 | 1.59 |
Metal. | 279.34 | -- | -- |
Detected Organs of Seeding | Added Content (μmol/L) | Detected Content (μmol/L) | Average Recoveries (%) | Coefficient of Variation (%) |
---|---|---|---|---|
Foliage | 400 | 301.21 | 75.30 ± 1.54 | 2.05 |
100 | 87.65 | 87.65 ± 3.62 | 3.85 | |
40 | 42.40 | 106.00 ± 2.26 | 2.13 | |
Stem | 400 | 335.75 | 83.94 ± 4.26 | 5.07 |
100 | 104.16 | 104.16 ± 2.59 | 2.49 | |
40 | 43.93 | 109.83 ± 1.39 | 1.27 | |
Root | 400 | 309.31 | 77.33 ± 1.44 | 1.86 |
100 | 70.67 | 70.67 ± 5.10 | 7.22 | |
40 | 29.22 | 73.04 ± 3.27 | 4.48 |
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Wu, Y.; Mao, G.; Xing, G.; Tian, Y.; Hu, Y.; Liao, C.; Li, L.; Zhu, X.; Li, J. Study on the Design, Synthesis, Bioactivity and Translocation of the Conjugates of Phenazine-1-carboxylic Acid and N-Phenyl Alanine Ester. Molecules 2024, 29, 1780. https://doi.org/10.3390/molecules29081780
Wu Y, Mao G, Xing G, Tian Y, Hu Y, Liao C, Li L, Zhu X, Li J. Study on the Design, Synthesis, Bioactivity and Translocation of the Conjugates of Phenazine-1-carboxylic Acid and N-Phenyl Alanine Ester. Molecules. 2024; 29(8):1780. https://doi.org/10.3390/molecules29081780
Chicago/Turabian StyleWu, Yiran, Guoqing Mao, Gaoshan Xing, Yao Tian, Yong Hu, Changzhou Liao, Li Li, Xiang Zhu, and Junkai Li. 2024. "Study on the Design, Synthesis, Bioactivity and Translocation of the Conjugates of Phenazine-1-carboxylic Acid and N-Phenyl Alanine Ester" Molecules 29, no. 8: 1780. https://doi.org/10.3390/molecules29081780