Metal coordination as a tool for controlling the self-assembling and gelation properties of novel type cholic amide–phenanthroline gelating agent
(3α,7α,12α)-Trihydroxy- N-[1,10-phenanthrolin-5-yl]-5β-cholan-24-amide was found to be a powerful gelating agent for methanol–water in gelator to solvent ratio starting from 0.1% in absence of metal ion. Formation of phenanthroline–zinc (II) 2:1 complex changes dramatically gelating properties; when...
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| Published in | Tetrahedron Vol. 59; no. 23; pp. 4069 - 4076 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
02.06.2003
Elsevier |
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| Abstract | (3α,7α,12α)-Trihydroxy-
N-[1,10-phenanthrolin-5-yl]-5β-cholan-24-amide was found to be a powerful gelating agent for methanol–water in gelator to solvent ratio starting from 0.1% in absence of metal ion. Formation of phenanthroline–zinc (II) 2:1 complex changes dramatically gelating properties; when stored, it dissolves into clear solution without Tyndall effect and this solution, when heated to ca. 70°C reversibly forms a gel again, without chemical change as proven by NMR spectrometry. Structures of the gels of cholic amide–phenanthroline and its Zn
2+ complex were studied by SEM.
Steroid–phenanthroline conjugate was found to be a powerful gelating agent for methanol–water. Formation of phenanthroline–zinc (II) 2:1 complex changes the gelating properties; when stored, it dissolves into solution and this solution, when heated reversibly forms a gel again. Complexes and gels were studied by spectroscopic methods and SEM. |
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| AbstractList | (3alpha,7alpha,12alpha)-Trihydroxy-N-[1,10-phenanthrolin-5-yl]-5beta-cholan-24-amide was found to be a powerful gelating agent for methanol-water in gelator to solvent ratio starting from 0.1% in absence of metal ion. Formation of phenanthroline-zinc (II) 2:1 complex changes dramatically gelating properties; when stored, it dissolves into clear solution without Tyndall effect and this solution, when heated to ca. 70degreesC reversibly forms a gel again, without chemical change as proven by NMR spectrometry. Structures of the gels of cholic amide-phenanthroline and its Zn2+ complex were studied by SEM. (C) 2003 Elsevier Science Ltd. All rights reserved. (3α,7α,12α)-Trihydroxy- N-[1,10-phenanthrolin-5-yl]-5β-cholan-24-amide was found to be a powerful gelating agent for methanol–water in gelator to solvent ratio starting from 0.1% in absence of metal ion. Formation of phenanthroline–zinc (II) 2:1 complex changes dramatically gelating properties; when stored, it dissolves into clear solution without Tyndall effect and this solution, when heated to ca. 70°C reversibly forms a gel again, without chemical change as proven by NMR spectrometry. Structures of the gels of cholic amide–phenanthroline and its Zn 2+ complex were studied by SEM. Steroid–phenanthroline conjugate was found to be a powerful gelating agent for methanol–water. Formation of phenanthroline–zinc (II) 2:1 complex changes the gelating properties; when stored, it dissolves into solution and this solution, when heated reversibly forms a gel again. Complexes and gels were studied by spectroscopic methods and SEM. |
| Author | Kroulı́k, J. Pouzar, V. Drašar, P. Černý, I. Král, V. Šaman, D. Dukh, M. |
| Author_xml | – sequence: 1 givenname: M. surname: Dukh fullname: Dukh, M. organization: Institute of Organic Chemistry and Biochemistry AS CR, 166 10 Prague 6, Czech Republic – sequence: 2 givenname: D. surname: Šaman fullname: Šaman, D. organization: Institute of Organic Chemistry and Biochemistry AS CR, 166 10 Prague 6, Czech Republic – sequence: 3 givenname: J. surname: Kroulı́k fullname: Kroulı́k, J. organization: Department of Analytical Chemistry, Institute of Chemical Technology, Prague, Technicka 5, 166 28 Prague 6, Czech Republic – sequence: 4 givenname: I. surname: Černý fullname: Černý, I. organization: Institute of Organic Chemistry and Biochemistry AS CR, 166 10 Prague 6, Czech Republic – sequence: 5 givenname: V. surname: Pouzar fullname: Pouzar, V. organization: Institute of Organic Chemistry and Biochemistry AS CR, 166 10 Prague 6, Czech Republic – sequence: 6 givenname: V. surname: Král fullname: Král, V. email: vladimir.kral@vscht.cz organization: Institute of Organic Chemistry and Biochemistry AS CR, 166 10 Prague 6, Czech Republic – sequence: 7 givenname: P. surname: Drašar fullname: Drašar, P. email: pavel.drasar@vscht.cz organization: Institute of Organic Chemistry and Biochemistry AS CR, 166 10 Prague 6, Czech Republic |
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| Keywords | cholic acid CD assembling phenanthroline NMR gels GELATORS STEROIDS COMPLEXES ORGANOGELS DYNAMICS COMPONENT CHOLESTEROL-STILBENE |
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| Snippet | (3α,7α,12α)-Trihydroxy-
N-[1,10-phenanthrolin-5-yl]-5β-cholan-24-amide was found to be a powerful gelating agent for methanol–water in gelator to solvent ratio... (3alpha,7alpha,12alpha)-Trihydroxy-N-[1,10-phenanthrolin-5-yl]-5beta-cholan-24-amide was found to be a powerful gelating agent for methanol-water in gelator to... |
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| SubjectTerms | assembling Chemistry Chemistry, Organic cholic acid gels NMR phenanthroline Physical Sciences Science & Technology |
| Title | Metal coordination as a tool for controlling the self-assembling and gelation properties of novel type cholic amide–phenanthroline gelating agent |
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