TY - JOUR
T1 - Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone
AU - Peixoto, Daniela
AU - Figueiredo, Margarida
AU - Malta, Gabriela
AU - Roma-Rodrigues, Catarina
AU - Baptista, Pedro V.
AU - Fernandes, Alexandra R.
AU - Barroso, Sónia
AU - Carvalho, Ana Luísa
AU - Afonso, Carlos A. M.
AU - Ferreira, Luisa M.
AU - Branco, Paula S.
N1 - info:eu-repo/grantAgreement/FCT/5876/147218/PT#
info:eu-repo/grantAgreement/FCT/5876/147258/PT#
info:eu-repo/grantAgreement/FCT/3599-PPCDT/127013/PT#
info:eu-repo/grantAgreement/FCT/3599-PPCDT/125363/PT#
POCI-01-0145- 710-FEDER-007265
POCI-01-0145-FEDER-007728
PY - 2018/1/31
Y1 - 2018/1/31
N2 - A new and never before reported hetero-arylidene-9(10H)-anthrone structure (4) was unexpectedly isolated on reaction of 1,2-dimethyl-3-ethylimidazolium iodide (2) and 9-anthracenecarboxaldehyde (3) under basic conditions. Its structure was unequivocally confirmed by X-ray crystallography. No cytotoxicity in human healthy fibroblasts and in two different cancer cell lines was observed, indicating its applicability in biological systems. Compound 4 interacts with CT-DNA by intercalation between the adjacent base pairs of DNA with a high binding affinity [Kb = 2.0 (±0.20) × 105 m–1], which is 10 × higher than that described for doxorubicin [Kb = 3.2 (±0.23) × 104 m–1]. Furthermore, compound 4 quenches the fluorescence emission of a GelRed–CT-DNA system with a quenching constant (KSV) of 3.3 (±0.3) × 103 m–1 calculated by the Stern–Volmer equation.
AB - A new and never before reported hetero-arylidene-9(10H)-anthrone structure (4) was unexpectedly isolated on reaction of 1,2-dimethyl-3-ethylimidazolium iodide (2) and 9-anthracenecarboxaldehyde (3) under basic conditions. Its structure was unequivocally confirmed by X-ray crystallography. No cytotoxicity in human healthy fibroblasts and in two different cancer cell lines was observed, indicating its applicability in biological systems. Compound 4 interacts with CT-DNA by intercalation between the adjacent base pairs of DNA with a high binding affinity [Kb = 2.0 (±0.20) × 105 m–1], which is 10 × higher than that described for doxorubicin [Kb = 3.2 (±0.23) × 104 m–1]. Furthermore, compound 4 quenches the fluorescence emission of a GelRed–CT-DNA system with a quenching constant (KSV) of 3.3 (±0.3) × 103 m–1 calculated by the Stern–Volmer equation.
KW - Anthracenecarboxaldehyde
KW - Anthrone
KW - Decarbonylation
KW - DNA intercalation
KW - Imidazolium salt
UR - http://www.scopus.com/inward/record.url?scp=85041287294&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201701500
DO - 10.1002/ejoc.201701500
M3 - Article
AN - SCOPUS:85041287294
SN - 1434-193X
VL - 2018
SP - 545
EP - 549
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 4
ER -