Controllable Synthesis and Biological Application of Schiff Bases from d‑Glucosamine and Terephthalaldehyde
Theoretically, the two aldehydes of terephthalaldehyde (TPA) are equivalent, so the single or double Schiff base from TPA and d-glucosamine (Glc) may be formed at the same time. However, it is preferred to produce separately a single Schiff base (L1 ) or double Schiff base (L2 ) for different synthe...
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Published in | ACS omega Vol. 5; no. 38; pp. 24864 - 24870 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
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American Chemical Society
29.09.2020
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Abstract | Theoretically, the two aldehydes of terephthalaldehyde (TPA) are equivalent, so the single or double Schiff base from TPA and d-glucosamine (Glc) may be formed at the same time. However, it is preferred to produce separately a single Schiff base (L1 ) or double Schiff base (L2 ) for different synthesis systems of anhydrous methanol or water–methanol. We calculated the Δr G of the formation of compounds L1 and L2 by density functional theory (DFT). In an anhydrous methanol system, the Δr G values of L1 and L2 are both below zero and L2 is lower, suggesting the spontaneous formation of the two Schiff bases. Though adjusting the molar ratio of Glc to TPA, L1 and L 2 both were separately formed in anhydrous methanol. However, in the water–methanol system, L2 was absent, which is most likely due to higher Δr G (4.95 eV) and better water solubility. The results also exhibits that the positive charge of C in −CHO for TPA is smaller in a mixed solvent than that in methanol, which confirms that the nucleophilic reaction of the Schiff base is more difficult in a mixed solvent. Therefore, we could realize to control the synthesis of a pure single or double Schiff base from Glc and TPA by adjusting the molar ratio and solvent. The as-prepared two kinds of Schiff bases have strong optical properties, high bacteriostatic activity, and can be used as fluorescent probes for tumor cell imaging. |
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AbstractList | Theoretically, the two aldehydes of terephthalaldehyde (TPA) are equivalent, so the single or double Schiff base from TPA and d-glucosamine (Glc) may be formed at the same time. However, it is preferred to produce separately a single Schiff base (L1 ) or double Schiff base (L2 ) for different synthesis systems of anhydrous methanol or water–methanol. We calculated the Δr G of the formation of compounds L1 and L2 by density functional theory (DFT). In an anhydrous methanol system, the Δr G values of L1 and L2 are both below zero and L2 is lower, suggesting the spontaneous formation of the two Schiff bases. Though adjusting the molar ratio of Glc to TPA, L1 and L 2 both were separately formed in anhydrous methanol. However, in the water–methanol system, L2 was absent, which is most likely due to higher Δr G (4.95 eV) and better water solubility. The results also exhibits that the positive charge of C in −CHO for TPA is smaller in a mixed solvent than that in methanol, which confirms that the nucleophilic reaction of the Schiff base is more difficult in a mixed solvent. Therefore, we could realize to control the synthesis of a pure single or double Schiff base from Glc and TPA by adjusting the molar ratio and solvent. The as-prepared two kinds of Schiff bases have strong optical properties, high bacteriostatic activity, and can be used as fluorescent probes for tumor cell imaging. Theoretically, the two aldehydes of terephthalaldehyde (TPA) are equivalent, so the single or double Schiff base from TPA and d -glucosamine (Glc) may be formed at the same time. However, it is preferred to produce separately a single Schiff base ( L 1 ) or double Schiff base ( L 2 ) for different synthesis systems of anhydrous methanol or water–methanol. We calculated the Δ r G of the formation of compounds L 1 and L 2 by density functional theory (DFT). In an anhydrous methanol system, the Δ r G values of L 1 and L 2 are both below zero and L 2 is lower, suggesting the spontaneous formation of the two Schiff bases. Though adjusting the molar ratio of Glc to TPA, L 1 and L 2 both were separately formed in anhydrous methanol. However, in the water–methanol system, L 2 was absent, which is most likely due to higher Δ r G (4.95 eV) and better water solubility. The results also exhibits that the positive charge of C in −CHO for TPA is smaller in a mixed solvent than that in methanol, which confirms that the nucleophilic reaction of the Schiff base is more difficult in a mixed solvent. Therefore, we could realize to control the synthesis of a pure single or double Schiff base from Glc and TPA by adjusting the molar ratio and solvent. The as-prepared two kinds of Schiff bases have strong optical properties, high bacteriostatic activity, and can be used as fluorescent probes for tumor cell imaging. |
Author | Weng, Qinghua Wang, Yaduan Sun, Weiming Chen, Xiaoping Kang, Jie Han, Zhizhong Yi, Jinquan Luo, Dengwang |
AuthorAffiliation | School of Pharmacy Fujian Key Laboratory of Drug Target Discovery and Structural and Functional Research |
AuthorAffiliation_xml | – name: School of Pharmacy – name: Fujian Key Laboratory of Drug Target Discovery and Structural and Functional Research |
Author_xml | – sequence: 1 givenname: Qinghua surname: Weng fullname: Weng, Qinghua organization: Fujian Key Laboratory of Drug Target Discovery and Structural and Functional Research – sequence: 2 givenname: Jinquan surname: Yi fullname: Yi, Jinquan organization: Fujian Key Laboratory of Drug Target Discovery and Structural and Functional Research – sequence: 3 givenname: Xiaoping surname: Chen fullname: Chen, Xiaoping organization: Fujian Key Laboratory of Drug Target Discovery and Structural and Functional Research – sequence: 4 givenname: Dengwang surname: Luo fullname: Luo, Dengwang organization: Fujian Key Laboratory of Drug Target Discovery and Structural and Functional Research – sequence: 5 givenname: Yaduan surname: Wang fullname: Wang, Yaduan organization: School of Pharmacy – sequence: 6 givenname: Weiming orcidid: 0000-0002-9882-0511 surname: Sun fullname: Sun, Weiming organization: Fujian Key Laboratory of Drug Target Discovery and Structural and Functional Research – sequence: 7 givenname: Jie surname: Kang fullname: Kang, Jie email: davidkj660825@163.com organization: School of Pharmacy – sequence: 8 givenname: Zhizhong orcidid: 0000-0001-7888-5601 surname: Han fullname: Han, Zhizhong email: zzhan@fjmu.edu.cn organization: Fujian Key Laboratory of Drug Target Discovery and Structural and Functional Research |
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Cites_doi | 10.1002/slct.201803072 10.1016/j.tiv.2018.09.005 10.1016/j.colsurfb.2012.10.023 10.1246/bcsj.40.935 10.1016/j.ccr.2007.09.005 10.1021/cr0683616 10.1021/acsanm.8b01125 10.1016/j.ejmech.2015.04.042 10.1097/01.GME.0000087983.28957.5D 10.1021/jp810292n 10.1016/j.dyepig.2006.07.019 10.1016/S0223-5234(01)01245-4 10.5101/nbe.v8i2.p72-81 10.1021/bm401204n 10.1166/jnn.2019.16367 10.1016/S0968-0896(02)00312-7 10.1080/10610278.2013.833334 10.1016/0144-8617(83)90012-7 10.1021/ja307628w 10.1002/slct.201801936 10.1039/C9SC01615E 10.1021/jo301644w 10.1016/S0008-6215(03)00237-4 10.1016/j.jare.2010.05.004 10.1021/cr400559g 10.1021/ja409097c 10.1159/000226660 10.1021/jm200961q 10.1016/j.ccr.2008.09.011 10.2174/138527209787193774 10.1246/bcsj.57.3182 |
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Snippet | Theoretically, the two aldehydes of terephthalaldehyde (TPA) are equivalent, so the single or double Schiff base from TPA and d-glucosamine (Glc) may be formed... Theoretically, the two aldehydes of terephthalaldehyde (TPA) are equivalent, so the single or double Schiff base from TPA and d -glucosamine (Glc) may be... |
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Title | Controllable Synthesis and Biological Application of Schiff Bases from d‑Glucosamine and Terephthalaldehyde |
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