Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading Mechanism
To develop a new pesticide with phloem mobility, a series of new amino acid–fipronil conjugates were designed and synthesized based on derivatization at the 3-position of the pyrazole ring of fipronil. Experiments using a Ricinus communis seedling system showed that all tested conjugates were phloem...
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MDPI AG
2018-03-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/4/778 |
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| author | Qingqing Sheng Xinxin Liu Yun Xie Fei Lin Zhixiang Zhang Chen Zhao Hanhong Xu |
| author_facet | Qingqing Sheng Xinxin Liu Yun Xie Fei Lin Zhixiang Zhang Chen Zhao Hanhong Xu |
| author_sort | Qingqing Sheng |
| collection | DOAJ |
| description | To develop a new pesticide with phloem mobility, a series of new amino acid–fipronil conjugates were designed and synthesized based on derivatization at the 3-position of the pyrazole ring of fipronil. Experiments using a Ricinus communis seedling system showed that all tested conjugates were phloem mobile except for the isoleucine–fipronil conjugate, and that the serine–fipronil conjugate (4g) exhibited the highest concentration in phloem sap (52.00 ± 5.80 μM). According to prediction with log Cf values and uptake experiments with Xenopus oocytes, the phloem loading process of conjugate 4g involved both passive diffusion and an active carrier system (RcANT15). In particular, compared with for a previously reported glycinergic–fipronil conjugate (GlyF), passive diffusion played a more important role for conjugate 4g in the enhancement of phloem mobility. This study suggests that associating a nutrient at a different position of an existing pesticide structure could still be effective in obtaining phloem-mobile derivatives, but the distinct physicochemical properties of resultant conjugates may lead to different phloem loading mechanisms. |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T21:33:55Z |
| publishDate | 2018-03-01 |
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| spelling | doaj.art-f8d9b48cd98c42af856ee0e9765322172022-12-22T02:29:04ZengMDPI AGMolecules1420-30492018-03-0123477810.3390/molecules23040778molecules23040778Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading MechanismQingqing Sheng0Xinxin Liu1Yun Xie2Fei Lin3Zhixiang Zhang4Chen Zhao5Hanhong Xu6State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, South China Agricultural University, Guangzhou 510642, ChinaState Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, South China Agricultural University, Guangzhou 510642, ChinaState Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, South China Agricultural University, Guangzhou 510642, ChinaState Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, South China Agricultural University, Guangzhou 510642, ChinaState Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, South China Agricultural University, Guangzhou 510642, ChinaState Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, South China Agricultural University, Guangzhou 510642, ChinaState Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, South China Agricultural University, Guangzhou 510642, ChinaTo develop a new pesticide with phloem mobility, a series of new amino acid–fipronil conjugates were designed and synthesized based on derivatization at the 3-position of the pyrazole ring of fipronil. Experiments using a Ricinus communis seedling system showed that all tested conjugates were phloem mobile except for the isoleucine–fipronil conjugate, and that the serine–fipronil conjugate (4g) exhibited the highest concentration in phloem sap (52.00 ± 5.80 μM). According to prediction with log Cf values and uptake experiments with Xenopus oocytes, the phloem loading process of conjugate 4g involved both passive diffusion and an active carrier system (RcANT15). In particular, compared with for a previously reported glycinergic–fipronil conjugate (GlyF), passive diffusion played a more important role for conjugate 4g in the enhancement of phloem mobility. This study suggests that associating a nutrient at a different position of an existing pesticide structure could still be effective in obtaining phloem-mobile derivatives, but the distinct physicochemical properties of resultant conjugates may lead to different phloem loading mechanisms.http://www.mdpi.com/1420-3049/23/4/778phloem-mobile pesticidesfipronilpassive diffusionamino acid transporter |
| spellingShingle | Qingqing Sheng Xinxin Liu Yun Xie Fei Lin Zhixiang Zhang Chen Zhao Hanhong Xu Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading Mechanism Molecules phloem-mobile pesticides fipronil passive diffusion amino acid transporter |
| title | Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading Mechanism |
| title_full | Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading Mechanism |
| title_fullStr | Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading Mechanism |
| title_full_unstemmed | Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading Mechanism |
| title_short | Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading Mechanism |
| title_sort | synthesis of novel amino acid fipronil conjugates and study on their phloem loading mechanism |
| topic | phloem-mobile pesticides fipronil passive diffusion amino acid transporter |
| url | http://www.mdpi.com/1420-3049/23/4/778 |
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