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 - 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)
UR - http://www.scopus.com/inward/record.url?scp=85075024121&partnerID=8YFLogxK
U2 - 10.1002/aoc.5309
DO - 10.1002/aoc.5309
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AN - SCOPUS:85075024121
SN - 0268-2605
VL - 34
JO - Applied Organometallic Chemistry
JF - Applied Organometallic Chemistry
IS - 1
M1 - e5309
ER -
