Chemistry - A European Journal
10.1002/chem.201604182
COMMUNICATION
The above results attracted more interests toward the impact of
the head group on the potential cellular effect of our NHC
derivatives, with the aim to establish the relationship between
their surface activity and their biological properties. Here the
cellular toxicity of 1-3 and 8 was evaluated using a panel of cell
lines including C6 glioma tumor cell line (Table 2). Because of
the poor solubility in DMSO the Au-NHC complex 7 could not be
investigated. A lower EC50 value corresponds to a higher
potency to induce the cells death.
opening the pathway for
organometallic drugs. For
a
a
novel and simple class of
specific set of two times a
pentadecyl chain, the elaboration of the imidazolium core with
sterically hindered and hydrophobic substituents considerably
improves both the surface activity and anti-tumor activity. Thus,
in conclusion we showed that the steric effect and the
hydrophobicity of the head group of our NHC derivatives
modulate both their surface properties and cellular effect.
Keywords: NHC salts • lipids • surface activity • cytotoxicity •
antitumor reagents
6
Table 2: Cytotoxicity comparison and the selectivity against C glioma
tumor cell line.
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EC50 ± SD/μM
Compound
C6 glioma
MDCK II
NIH3T3
11.3 ± 2.0[a]
20.6 ± 4.2[a]
8.7 ± 0.7[a]
1
2
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16.3 ± 0.6
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N/A
23.6 ± 1.1
32.2 ± 3.3
N/A
3.5 ± 0.9
12.2 ± 1.7
N/A
28.1 ± 0.7[a]
15.9 ± 0.5[a]
7.7 ± 0.2[a]
EC50(MDCK ΙΙ)
EC50(C6)
EC (NIH3T3)
50
EC (C6)
50
1
2
3
7
8
1.82
1.45
0.48
N/A
0.77
0.21
0.18
N/A
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