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Homoleptic [ONO]2Ti(IV) type complexes of amino-acid-tethered phenolato, Schiff-base ligands: Synthesis, characterization, time-resolved fluorescence spectroscopy, and cytotoxicity against ovarian and colon cancer cells

Six homoleptic Ti(IV) compounds of dianionic tridentate Schiff base ligands were synthesized from chiral amino acids, 2-hydroxybenzaldehyde and Ti(OiPr)4. The compounds were spectroscopically characterized and the molecular geometries were established by X-ray crystallography. The ligands coordinat...

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Main Authors: Shpilt, Zohar, Manne, Rajesh, Rahman, M. A., Mitra, Sivaprasad, Tiekink, Edward R. T. *, Baul, T. S. B., Tshuva, E. Y.
Format: Article
Language:English
Published: Wiley 2019
Subjects:
QD Chemistry
Online Access:http://eprints.sunway.edu.my/1229/1/Tiekink%20AOC%202020%2034%20e5309.pdf
http://eprints.sunway.edu.my/1229/
https://doi.org/10.1002/aoc.5309
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spelling my.sunway.eprints.12292020-10-07T07:55:15Z http://eprints.sunway.edu.my/1229/ Homoleptic [ONO]2Ti(IV) type complexes of amino-acid-tethered phenolato, Schiff-base ligands: Synthesis, characterization, time-resolved fluorescence spectroscopy, and cytotoxicity against ovarian and colon cancer cells Shpilt, Zohar Manne, Rajesh Rahman, M. A. Mitra, Sivaprasad Tiekink, Edward R. T. * Baul, T. S. B. Tshuva, E. Y. QD Chemistry Six homoleptic Ti(IV) compounds of dianionic tridentate Schiff base ligands were synthesized from chiral amino acids, 2-hydroxybenzaldehyde and Ti(OiPr)4. The compounds were spectroscopically characterized and the molecular geometries were established by X-ray crystallography. The ligands coordinated the titanium via carboxylate-O-, imine-N-, and phenoxide-O atoms. Two isomers were identified; each based on a trans-N2O4 donor set, but one with trans carboxylate-O atoms and another with each carboxylate-O atom trans to a phenoxide-O atom. Photophysical profiles exhibited faster excited-state relaxation in the solid phase than in solution. Marked cytotoxicities were recorded toward human ovarian A2780 and colon HT-29 cancer cells with IC50 values ranging between 23±2 and 103±3 µM. Comparative hydrolytic stability studies by NMR in 10% D2O solutions provided t1/2 values of up to 15±2 h, with little correlation to cytotoxicity implying a role of hydrolysis products in the reactivity and identifying steric bulk as a contributor to stability and solubility. Wiley 2019-12-13 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1229/1/Tiekink%20AOC%202020%2034%20e5309.pdf Shpilt, Zohar and Manne, Rajesh and Rahman, M. A. and Mitra, Sivaprasad and Tiekink, Edward R. T. * and Baul, T. S. B. and Tshuva, E. Y. (2019) Homoleptic [ONO]2Ti(IV) type complexes of amino-acid-tethered phenolato, Schiff-base ligands: Synthesis, characterization, time-resolved fluorescence spectroscopy, and cytotoxicity against ovarian and colon cancer cells. Applied Organometallic Chemistry, 34 (1). e5309. ISSN 0268-2605 https://doi.org/10.1002/aoc.5309
institution Sunway University
building Sunway Campus Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Sunway University
content_source Sunway Institutional Repository
url_provider http://eprints.sunway.edu.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Shpilt, Zohar
Manne, Rajesh
Rahman, M. A.
Mitra, Sivaprasad
Tiekink, Edward R. T. *
Baul, T. S. B.
Tshuva, E. Y.
Homoleptic [ONO]2Ti(IV) type complexes of amino-acid-tethered phenolato, Schiff-base ligands: Synthesis, characterization, time-resolved fluorescence spectroscopy, and cytotoxicity against ovarian and colon cancer cells
description Six homoleptic Ti(IV) compounds of dianionic tridentate Schiff base ligands were synthesized from chiral amino acids, 2-hydroxybenzaldehyde and Ti(OiPr)4. The compounds were spectroscopically characterized and the molecular geometries were established by X-ray crystallography. The ligands coordinated the titanium via carboxylate-O-, imine-N-, and phenoxide-O atoms. Two isomers were identified; each based on a trans-N2O4 donor set, but one with trans carboxylate-O atoms and another with each carboxylate-O atom trans to a phenoxide-O atom. Photophysical profiles exhibited faster excited-state relaxation in the solid phase than in solution. Marked cytotoxicities were recorded toward human ovarian A2780 and colon HT-29 cancer cells with IC50 values ranging between 23±2 and 103±3 µM. Comparative hydrolytic stability studies by NMR in 10% D2O solutions provided t1/2 values of up to 15±2 h, with little correlation to cytotoxicity implying a role of hydrolysis products in the reactivity and identifying steric bulk as a contributor to stability and solubility.
format Article
author Shpilt, Zohar
Manne, Rajesh
Rahman, M. A.
Mitra, Sivaprasad
Tiekink, Edward R. T. *
Baul, T. S. B.
Tshuva, E. Y.
author_facet Shpilt, Zohar
Manne, Rajesh
Rahman, M. A.
Mitra, Sivaprasad
Tiekink, Edward R. T. *
Baul, T. S. B.
Tshuva, E. Y.
author_sort Shpilt, Zohar
title Homoleptic [ONO]2Ti(IV) type complexes of amino-acid-tethered phenolato, Schiff-base ligands: Synthesis, characterization, time-resolved fluorescence spectroscopy, and cytotoxicity against ovarian and colon cancer cells
title_short Homoleptic [ONO]2Ti(IV) type complexes of amino-acid-tethered phenolato, Schiff-base ligands: Synthesis, characterization, time-resolved fluorescence spectroscopy, and cytotoxicity against ovarian and colon cancer cells
title_full Homoleptic [ONO]2Ti(IV) type complexes of amino-acid-tethered phenolato, Schiff-base ligands: Synthesis, characterization, time-resolved fluorescence spectroscopy, and cytotoxicity against ovarian and colon cancer cells
title_fullStr Homoleptic [ONO]2Ti(IV) type complexes of amino-acid-tethered phenolato, Schiff-base ligands: Synthesis, characterization, time-resolved fluorescence spectroscopy, and cytotoxicity against ovarian and colon cancer cells
title_full_unstemmed Homoleptic [ONO]2Ti(IV) type complexes of amino-acid-tethered phenolato, Schiff-base ligands: Synthesis, characterization, time-resolved fluorescence spectroscopy, and cytotoxicity against ovarian and colon cancer cells
title_sort homoleptic [ono]2ti(iv) type complexes of amino-acid-tethered phenolato, schiff-base ligands: synthesis, characterization, time-resolved fluorescence spectroscopy, and cytotoxicity against ovarian and colon cancer cells
publisher Wiley
publishDate 2019
url http://eprints.sunway.edu.my/1229/1/Tiekink%20AOC%202020%2034%20e5309.pdf
http://eprints.sunway.edu.my/1229/
https://doi.org/10.1002/aoc.5309
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score 13.223943

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