Co-reporter:Yuxia Gao, Jie Hao, Jindan Wu, Xun Zhang, Jun Hu, and Yong Ju
Langmuir 2016 Volume 32(Issue 7) pp:1685-1692
Publication Date(Web):February 1, 2016
DOI:10.1021/acs.langmuir.5b04398
Although a few architectures have been fabricated by the self-assembly of natural triterpenoids, the precise control of shape and size is rarely studied. Herein, a methyl oleanolate-bearing amphiphile, 1-[2-(methyl oleanolate)-2-oxoethyl]pyridinium bromide (MOP), has been designed and its assembly behavior was investigated. It was found that the morphologies of MOP assemblies ranged from nanoparticles to rigid microrods and flexible nanofibers in chloroform/p-xylene and methanol/water, respectively. During the assembly process, the systematical variational solvophobic/solvophilic effect resulted in the formation of spherical nanoparticles with opposite dipoles and converse bilayer structures. Moreover, such opposite molecular orientations lead to the inversion of supramolecular chirality and distinct mechanical properties. The driving forces and packing patterns of MOP in each solvent system were clearly demonstrated by the combination of NMR, UV–vis, Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), theoretical computation, and contact angle experiments, which revealed the roles of triterpenoids and pyridinium cations in the assembly process. This work provides a facile strategy to control the supramolecular structures in triterpenoid-based assemblies by adjusting the solvent polarity and composition.
Co-reporter:Yuxia Gao, Jie Hao, Jindan Wu, Xun Zhang, Jun Hu and Yong Ju
Nanoscale 2015 vol. 7(Issue 32) pp:13568-13575
Publication Date(Web):09 Jul 2015
DOI:10.1039/C5NR03699B
A glycyrrhetate-containing amphiphile, MGP (1-[2-(methyl glycyrrhetate)-2-oxoethyl]pyridinium bromide), has been synthesized, and found to assemble into supramolecular helical nanofibers in chloroform/aromatic solvents, which are primarily driven by π–π stacking, van der Waals forces, and hydrophobic interactions. During the assembly process, MGP stacked into J-aggregates resulting in the sequestration of the hydrophilic pyridinium cation within the interior with the concomitant projection of its hydrophobic skeleton on the outside surface. Ultimately, this protrusion generated a staggered angle due to the steric hindrance between stacked molecules. This staggered angle further led to molecular misalignments and the formation of helical fibrils, which could twist with each other to fabricate larger helical fibers. Consequently, a gel was formed by intertwining these nanofibers into three-dimensional networks. Using this strategy, we found that other triterpenoid-tailored pyridinium amphiphiles are also potential scaffolds for supramolecular helical structures. This work provides a facile approach for the fabrication of supramolecular macroscopic chiral nanostructures that originate from natural products.
Co-reporter:Xun Zhang, Yuxia Gao, Yuan Lin, Jun Hu and Yong Ju
Polymer Chemistry 2015 vol. 6(Issue 22) pp:4162-4166
Publication Date(Web):27 Apr 2015
DOI:10.1039/C5PY00476D
A photosensitive amphiphile 2 was synthesized, in which the anthracene moiety in each arm was connected to a dipyridinium center by an alkyl chain. Using host–guest interactions between γ-CD and the anthracene moiety in 2, a supramolecular polymer was achieved, and such a supramolecular polymer can be further converted into its corresponding covalent polymer upon irradiation at 365 nm via [4 + 4] photocyclodimerization of anthracenes within the cavity of γ-CD. This approach affords a strategy in the transformation from supramolecular to covalently linked polymers.
Co-reporter:Yuxia Gao, Ying Li, Xia Zhao, Jun Hu and Yong Ju
RSC Advances 2015 vol. 5(Issue 123) pp:102097-102100
Publication Date(Web):23 Nov 2015
DOI:10.1039/C5RA22967G
A glycyrrhetinic acid-based (GA, a natural pentacyclic triterpenoid) supramolecular hydrogel was attained in physiological phosphate buffered saline for the first time. Its assembly process and potential applications in drug release were preliminarily explored.
Co-reporter:Jindan Wu, Xia Zhao, Yuxia Gao, Jun Hu, Yong Ju
Sensors and Actuators B: Chemical 2015 Volume 221() pp:334-340
Publication Date(Web):31 December 2015
DOI:10.1016/j.snb.2015.06.140
A novel Zn2+ ion chemosensor 1 has been developed based on deoxycholic acid and salen motifs, and this chemosensor can be used in test-strips and living cells imaging for Zn2+ ion through a turn-on effect. Moreover, the resulting [1·Zn2+] complex exhibits turn-off response toward H2PO4− ion, thus leading to the fabrication of an INHIBIT (INH) logic gate using Zn2+ ion and H2PO4− ion as inputs and the emission of 1 as outputs, respectively. This line of research not only enriches the library of Zn2+ ion sensors, but also expands the applications of natural products-based chemosensors.A novel Zn2+ ion chemosensor 1 has been developed based on deoxycholic acid and salen motifs, and this chemosensor can be used in test-strips and living cells imaging for Zn2+ ion through a turn-on effect. Moreover, the resulting [1·Zn2+] complex exhibits turn-off response toward H2PO4− ion, leading to the fabrication of an INHIBIT (INH) logic gate using Zn2+ ion and H2PO4− ion as inputs and the emission of 1 as outputs, respectively. This line of research not only enriches the library of Zn2+ ion sensors, but also expands the applications of natural products-based chemosensors.
Co-reporter:Yuxia Gao, Jinrong Lu, Jindan Wu, Jun Hu and Yong Ju
RSC Advances 2014 vol. 4(Issue 108) pp:63539-63543
Publication Date(Web):17 Nov 2014
DOI:10.1039/C4RA12247J
A redox-responsive chiral supramolecular gel based on coumarin-tailed cholesterol linked with disulfide was reported. It was found that the gelation was primarily driven by the combination of hydrogen bonding, π–π stacking, and van der Waals forces. Moreover, its assembled morphology could be regulated from nanofibers to micro flowers and ribbons by water on account of its amphiphilic nature.
Co-reporter:Jinrong Lu, Jindan Wu and Yong Ju
New Journal of Chemistry 2014 vol. 38(Issue 12) pp:6050-6056
Publication Date(Web):15 Sep 2014
DOI:10.1039/C4NJ01146E
New gelators, based on chiral triterpenoids linked with aromatic rings and amide structures, were designed and synthesized. Different chiral properties of assembly of the organogels were observed and these were expressed by different close degrees of molecular packing, which were attributed to the formation of H-type aggregates in the monotriterpenoid and of J-type aggregates in the bis-triterpenoid derivatives. The nanofibers of the organogel in dimethylsulfoxide were used to engineer gold nanoparticles and generate gel–nanoparticle hybrid materials.
Co-reporter:Jun Hu;Jindan Wu
Chinese Journal of Chemistry 2014 Volume 32( Issue 2) pp:133-136
Publication Date(Web):
DOI:10.1002/cjoc.201300758
Abstract
A new oleanolic acid derivative with A-ring lactone, C-ring rearrangement and decarboxylation at C28 was synthesized, which was confirmed by HRMS, NMR and X-ray crystal structure. It is the first report about the methyl rearrangement on C-ring of oleanolic phenylmethyl ester, and the possible mechanism was proposed as the 1,2-methyl shift.
Co-reporter:Jindan Wu, Jinrong Lu, Jun Hu, Yuxia Gao, Qing Ma and Yong Ju
RSC Advances 2013 vol. 3(Issue 47) pp:24906-24909
Publication Date(Web):18 Oct 2013
DOI:10.1039/C3RA43306D
Sodium glycyrrhetinate, a simple triterpenoid derivative, was found to form a hydrogel with dipole–dipole interaction of sodium carboxylates as the main driving force. The hydrogel showed properties in selective dye adsorption and sustainable release.
Co-reporter:Jinrong Lu, Chulong Liu, Jun Hu, Yong Ju
Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 5) pp:1302-1305
Publication Date(Web):1 March 2013
DOI:10.1016/j.bmcl.2012.12.102
Two fan-shaped bile acid trimers have been synthesized via CuI-catalyzed azide–alkyne cycloaddition (CuAAC) ‘click chemistry’, and their extraction experiments of cresol red sodium (CR) and pyrene were investigated in the polar and non-polar solvents, respectively. The transmission electron microscopy (TEM) results showed that the homogenous hollow capsules formed with the diameter size range of 40–70 nm in a solution of water and acetone. Thus the amphiphilicity of fan-shaped bile acid trimers might be used as the promising candidate in biological and drug delivery applications.
Co-reporter:Jinrong Lu, Jun Hu, Chulong Liu, Hongxin Gao and Yong Ju
Soft Matter 2012 vol. 8(Issue 37) pp:9576-9580
Publication Date(Web):07 Aug 2012
DOI:10.1039/C2SM26085A
The conjugate of oleanlic acid with adenine was synthesized and it could be gelled in mixed solvents of THF and water, but no gel was formed in the single organic solvent. The self-aggregation behaviour and physical properties of the organogel were characterized by 1H NMR, FT-IR, and scanning electron microscopy. The morphology and the stability of the gel were remarkably affected by the uracil derivative through destroying hydrogen-bonding.
Co-reporter:Jun Hu, Jindan Wu, Jinrong Lu, Yong Ju
Tetrahedron Letters 2012 Volume 53(Issue 49) pp:6705-6709
Publication Date(Web):5 December 2012
DOI:10.1016/j.tetlet.2012.09.118
A glycyrrhetinic acid-based macrocycle was synthesized using CuAAC ‘click chemistry’ and it showed remarkable selectivity and affinity for F− ions, as well as Hg2+ ions. During the dual-responsive recognition process, 1,2,3-triazole ring, carbonyl group, and glycyrrhetinic acid rigid skeleton play the significant roles in the ion binding.
Co-reporter:Jinrong Lu, Jun Hu, Yang Song, and Yong Ju
Organic Letters 2011 Volume 13(Issue 13) pp:3372-3375
Publication Date(Web):June 9, 2011
DOI:10.1021/ol201129y
A novel functional tweezer based on uracil-appended glycyrrhetinic acid with excellent gelation ability was synthesized, and the gel could transform to sol by F– and Hg2+.
Co-reporter:Jun Hu, Jinrong Lu, Ruofan Li and Yong Ju
Soft Matter 2011 vol. 7(Issue 3) pp:891-894
Publication Date(Web):06 Jan 2011
DOI:10.1039/C0SM01392G
A novel glycyrrhetinic acid conjugate containing uracil and 2,6-diaminopyridine units was synthesized and the exclusive supramolecular dimeric structure through six intermolecular hydrogen bonds was characterized by NMR spectroscopy and ESI-MS. The supramolecular dimeric structure could recognize the polar molecule in aprotic polar solvents.
Co-reporter:Jun Hu, Ruofan Li, Jinrong Lu, Yong Ju
Tetrahedron Letters 2011 Volume 52(Issue 32) pp:4211-4214
Publication Date(Web):10 August 2011
DOI:10.1016/j.tetlet.2011.06.022
A novel cyclic dimer based on oleanolic acid was synthesized using click chemistry and it showed remarkable selectivity and affinity to bind fluoride ion through C–H⋯F hydrogen bond interactions which involved the delocalization of proton in methylene.
Co-reporter:Jun Hu;Libing Yu;Meng Zhang
Chinese Journal of Chemistry 2011 Volume 29( Issue 6) pp:1139-1142
Publication Date(Web):
DOI:10.1002/cjoc.201190213
Abstract
A novel fan-shaped C3 molecule with three glycyrrhetinic acid units was synthesized via "click chemistry" in high yield and the self-assembly characteristics were studied in different mixed solvents.
Co-reporter:J. Hu;J. R. Lu; Y. Ju
Chemistry – An Asian Journal 2011 Volume 6( Issue 10) pp:2636-2647
Publication Date(Web):
DOI:10.1002/asia.201100378
Abstract
This Focus Review highlights the design and synthesis of various functional molecules based on steroid/triterpenoid as building blocks through the copper-catalyzed azide–alkyne cycloaddition (CuAAC) “click” reaction, as well as their applications in bioactivity, recognition, and assembly. This method shows great promise to allow us to develop novel molecules with characteristic functions using the CuAAC “click” reaction.
Co-reporter:Jun Hu, Meng Zhang, Li B. Yu, Yong Ju
Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 15) pp:4342-4345
Publication Date(Web):1 August 2010
DOI:10.1016/j.bmcl.2010.06.079
A novel type of receptors based on 1,2,3-triazole glycyrrhetinic acid derived from natural triterpenoid molecules has been synthesized via click chemistry and they showed high selectivity and affinity for Hg2+ ion by both the 1,2,3-triazole rings and aldehyde groups.A novel type of receptors based on 1,2,3-triazole glycyrrhetinic acid derived from natural triterpenoid molecules has been synthesized via click chemistry and they showed high selectivity and affinity for Hg2+ ion by both the 1,2,3-triazole rings and aldehyde groups.
Co-reporter:Jun Hu, Meng Zhang and Yong Ju
Soft Matter 2009 vol. 5(Issue 24) pp:4971-4974
Publication Date(Web):08 Oct 2009
DOI:10.1039/B916427H
The organogel formation of 2,3-dihydroxyimino-oleanic acid in different organic solvents was reported for the first time. The structure and physical properties of the organogel were studied by scanning electron microscopy, circular dichromism spectroscopy and differential scanning calorimetry. The intermolecular hydrogen bonding was considered as the primary driving force for gel formation, which was confirmed by infrared spectroscopy and variable temperature 1H NMR.
Co-reporter:Yan Li;Weijun Chu
Heteroatom Chemistry 2008 Volume 19( Issue 4) pp:402-407
Publication Date(Web):
DOI:10.1002/hc.20447
Abstract
The H-phosphonate bioconjugates of bile acids, conjugated with various alcohols and nucleosides, were obtained in one pot by a tandem transesterification with diphenyl phosphite (DPP). The synthesis of cholic acid derived phosphoramide from the corresponding H-phosphonate was also demonstrated. The structures of these novel conjugates were confirmed on the basis of IR,31P NMR, 1H NMR, and mass spectra. The synthesized bile acid conjugates were mixtures of diastereoisomers due to the chirality of the phosphorus. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:402–407, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20447
Co-reporter:Dimao Wu, Sanhao Ji, Yan Wu, Yong Ju, Yufen Zhao
Bioorganic & Medicinal Chemistry Letters 2007 Volume 17(Issue 11) pp:2983-2986
Publication Date(Web):1 June 2007
DOI:10.1016/j.bmcl.2007.03.067
A series of bile acid–polyamine amides conjugated with 3′-azido-3′-deoxythymidine (AZT) as potential antitumor prodrugs in the form of phosphoramidates were synthesized in good yields and their antitumor activities were assayed against two human cancer cells in vitro: cervix cancer HeLa cells and renal cancer 7860 cells. The improved antitumor activity probably derived from the enhanced delivery efficiency of AZT due to bile acid–polyamine conjugates.Design, synthesis, and antitumor evaluation of a series of bile acid–polyamine–AZT phosphoramidate conjugates are reported.
Co-reporter:Qiang Xiao;Yufen Zhao
Heteroatom Chemistry 2003 Volume 14(Issue 3) pp:208-210
Publication Date(Web):24 APR 2003
DOI:10.1002/hc.10130
The symmetric H-phosphonates of carbohydrate and other compounds were conveniently prepared by direct transesterification of the corresponding monohydroxylic compounds with diphenyl phosphite. The approach has the merits of mild reaction conditions and high yields. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:208–210, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10130
Co-reporter:Jun Hu, Jindan Wu, Jinrong Lu, Yong Ju
Tetrahedron Letters (5 December 2012) Volume 53(Issue 49) pp:6705-6709
Publication Date(Web):5 December 2012
DOI:10.1016/j.tetlet.2012.09.118
A glycyrrhetinic acid-based macrocycle was synthesized using CuAAC ‘click chemistry’ and it showed remarkable selectivity and affinity for F− ions, as well as Hg2+ ions. During the dual-responsive recognition process, 1,2,3-triazole ring, carbonyl group, and glycyrrhetinic acid rigid skeleton play the significant roles in the ion binding.Download full-size image
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