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

Zohar Shpilt; Rajesh Manne; Mostofa Ataur Rohman; Sivaprasad Mitra; Edward R.T. Tiekink; Tushar S. Basu Baul; Edit Y. Tshuva

doi:10.1002/aoc.5309

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

Zohar Shpilt, Rajesh Manne, Mostofa Ataur Rohman, Sivaprasad Mitra, Edward R.T. Tiekink^*, Tushar S. Basu Baul, Edit Y. Tshuva

^*Corresponding author for this work

Institute of Chemistry

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Abstract

Six homoleptic Ti (IV) compounds of dianionic tridentate ONO Schiff base ligands with various substitutions were prepared from chiral amino acids, 2-hydroxybenzaldehyde, which were generated in situ, and Ti (OⁱPr)₄. The compounds were spectroscopically characterized and the molecular geometries of five complexes were established by X-ray crystallography; for two structures, two independent molecules compose the asymmetric units. The di-anionic, tridentate ligands coordinate the titanium centers via the carboxylate-O-, imine-N- and phenoxide-O atoms to form five- and six-membered chelate rings. The molecules are based on a trans-N₂O₄ donor with each carboxylate-O atom trans to a phenoxide-O atom. For the smallest derivative with Me substitution, racemization occurs during repeated recrystallization. Photophysical profiles of the titanium compounds in the solid phase and in solution are discussed. 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 of the complexes were studied by NMR in 10% D₂O solutions which provided t_1/2 values of up to 15 ± 2 hr.

Original language	American English
Article number	e5309
Journal	Applied Organometallic Chemistry
Volume	34
Issue number	1
DOIs	https://doi.org/10.1002/aoc.5309
State	Published - 1 Jan 2020

Bibliographical note

Funding Information:
Funding was received from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme (grant agreement 681243). Additionally, financial support from the University Grants Commission, India (Grant No. 42-396/2013 (SR), 2013, TSBB) and the University Grants Commission, India through SAP-CAS, Phase-I (Grant No. F 540/21/CAS/2013 (SAP-I) are gratefully acknowledged. TSBB and RM acknowledge DST-PURSE for the diffractometer facility.

Funding Information:
Funding was received from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme (grant agreement 681243). Additionally, financial support from the University Grants Commission, India (Grant No. 42‐396/2013 (SR), 2013, TSBB) and the University Grants Commission, India through SAP‐CAS, Phase‐I (Grant No. F 540/21/CAS/2013 (SAP‐I) are gratefully acknowledged. TSBB and RM acknowledge DST‐PURSE for the diffractometer facility.

Publisher Copyright:
© 2019 John Wiley & Sons, Ltd.

Keywords

SCXRD structure elucidation
Schiff-base ligands
cytotoxicity
titanium (IV)

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Shpilt, Z., Manne, R., Rohman, M. A., Mitra, S., Tiekink, E. R. T., Basu Baul, T. S., & Tshuva, E. Y. (2020). Homoleptic Ti[ONO]₂ 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), Article e5309. https://doi.org/10.1002/aoc.5309

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

abstract = "Six homoleptic Ti (IV) compounds of dianionic tridentate ONO Schiff base ligands with various substitutions were prepared from chiral amino acids, 2-hydroxybenzaldehyde, which were generated in situ, and Ti (OiPr)4. The compounds were spectroscopically characterized and the molecular geometries of five complexes were established by X-ray crystallography; for two structures, two independent molecules compose the asymmetric units. The di-anionic, tridentate ligands coordinate the titanium centers via the carboxylate-O-, imine-N- and phenoxide-O atoms to form five- and six-membered chelate rings. The molecules are based on a trans-N2O4 donor with each carboxylate-O atom trans to a phenoxide-O atom. For the smallest derivative with Me substitution, racemization occurs during repeated recrystallization. Photophysical profiles of the titanium compounds in the solid phase and in solution are discussed. 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 of the complexes were studied by NMR in 10% D2O solutions which provided t1/2 values of up to 15 ± 2 hr.",

keywords = "SCXRD structure elucidation, Schiff-base ligands, cytotoxicity, titanium (IV)",

author = "Zohar Shpilt and Rajesh Manne and Rohman, {Mostofa Ataur} and Sivaprasad Mitra and Tiekink, {Edward R.T.} and {Basu Baul}, {Tushar S.} and Tshuva, {Edit Y.}",

note = "Funding Information: Funding was received from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme (grant agreement 681243). Additionally, financial support from the University Grants Commission, India (Grant No. 42-396/2013 (SR), 2013, TSBB) and the University Grants Commission, India through SAP-CAS, Phase-I (Grant No. F 540/21/CAS/2013 (SAP-I) are gratefully acknowledged. TSBB and RM acknowledge DST-PURSE for the diffractometer facility. Funding Information: Funding was received from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme (grant agreement 681243). Additionally, financial support from the University Grants Commission, India (Grant No. 42‐396/2013 (SR), 2013, TSBB) and the University Grants Commission, India through SAP‐CAS, Phase‐I (Grant No. F 540/21/CAS/2013 (SAP‐I) are gratefully acknowledged. TSBB and RM acknowledge DST‐PURSE for the diffractometer facility. Publisher Copyright: {\textcopyright} 2019 John Wiley & Sons, Ltd.",

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month = jan,

day = "1",

doi = "10.1002/aoc.5309",

language = "American English",

volume = "34",

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Shpilt, Z, Manne, R, Rohman, MA, Mitra, S, Tiekink, ERT, Basu Baul, TS & Tshuva, EY 2020, 'Homoleptic Ti[ONO]₂ 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, vol. 34, no. 1, e5309. https://doi.org/10.1002/aoc.5309

Homoleptic Ti[ONO]₂ 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; Rohman, Mostofa Ataur et al.
In: Applied Organometallic Chemistry, Vol. 34, No. 1, e5309, 01.01.2020.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Homoleptic Ti[ONO]2 type complexes of amino-acid-tethered phenolato Schiff-base ligands

T2 - Synthesis, characterization, time-resolved fluorescence spectroscopy, and cytotoxicity against ovarian and colon cancer cells

AU - Shpilt, Zohar

AU - Manne, Rajesh

AU - Rohman, Mostofa Ataur

AU - Mitra, Sivaprasad

AU - Tiekink, Edward R.T.

AU - Basu Baul, Tushar S.

AU - Tshuva, Edit Y.

N1 - Funding Information: Funding was received from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme (grant agreement 681243). Additionally, financial support from the University Grants Commission, India (Grant No. 42-396/2013 (SR), 2013, TSBB) and the University Grants Commission, India through SAP-CAS, Phase-I (Grant No. F 540/21/CAS/2013 (SAP-I) are gratefully acknowledged. TSBB and RM acknowledge DST-PURSE for the diffractometer facility. Funding Information: Funding was received from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme (grant agreement 681243). Additionally, financial support from the University Grants Commission, India (Grant No. 42‐396/2013 (SR), 2013, TSBB) and the University Grants Commission, India through SAP‐CAS, Phase‐I (Grant No. F 540/21/CAS/2013 (SAP‐I) are gratefully acknowledged. TSBB and RM acknowledge DST‐PURSE for the diffractometer facility. Publisher Copyright: © 2019 John Wiley & Sons, Ltd.

PY - 2020/1/1

Y1 - 2020/1/1

N2 - Six homoleptic Ti (IV) compounds of dianionic tridentate ONO Schiff base ligands with various substitutions were prepared from chiral amino acids, 2-hydroxybenzaldehyde, which were generated in situ, and Ti (OiPr)4. The compounds were spectroscopically characterized and the molecular geometries of five complexes were established by X-ray crystallography; for two structures, two independent molecules compose the asymmetric units. The di-anionic, tridentate ligands coordinate the titanium centers via the carboxylate-O-, imine-N- and phenoxide-O atoms to form five- and six-membered chelate rings. The molecules are based on a trans-N2O4 donor with each carboxylate-O atom trans to a phenoxide-O atom. For the smallest derivative with Me substitution, racemization occurs during repeated recrystallization. Photophysical profiles of the titanium compounds in the solid phase and in solution are discussed. 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 of the complexes were studied by NMR in 10% D2O solutions which provided t1/2 values of up to 15 ± 2 hr.

AB - Six homoleptic Ti (IV) compounds of dianionic tridentate ONO Schiff base ligands with various substitutions were prepared from chiral amino acids, 2-hydroxybenzaldehyde, which were generated in situ, and Ti (OiPr)4. The compounds were spectroscopically characterized and the molecular geometries of five complexes were established by X-ray crystallography; for two structures, two independent molecules compose the asymmetric units. The di-anionic, tridentate ligands coordinate the titanium centers via the carboxylate-O-, imine-N- and phenoxide-O atoms to form five- and six-membered chelate rings. The molecules are based on a trans-N2O4 donor with each carboxylate-O atom trans to a phenoxide-O atom. For the smallest derivative with Me substitution, racemization occurs during repeated recrystallization. Photophysical profiles of the titanium compounds in the solid phase and in solution are discussed. 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 of the complexes were studied by NMR in 10% D2O solutions which provided t1/2 values of up to 15 ± 2 hr.

KW - SCXRD structure elucidation

KW - Schiff-base ligands

KW - cytotoxicity

KW - titanium (IV)

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U2 - 10.1002/aoc.5309

DO - 10.1002/aoc.5309

M3 - Article

AN - SCOPUS:85075024121

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JF - Applied Organometallic Chemistry

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