177
2 Materials
1. Temozolomide (T2577) and p-sulfonatocalix[4]arene (55523)
were purchased from Sigma-Aldrich.
2. Methanol and water (both LC-MS grade).
2.1 Synthesis
and Characterization
of Encapsulated TMZ
Fig. 1 Reaction scheme for the base-catalyzed decomposition of TMZ to its active metabolite MTIC and then
to 5-amino-imidazole-4-carboxamide (AIC) and methyl diazonium cation
NH
N
N
N
O
NH 2
N
N N
N
N
NH 2
O
O
Temozolomide
N
N
HN
N
N
H
NH 2
O
MTIC
N
N N
N
N
NH 2
O
O
Temozolomide
N
N
HN
N
N
H
NH 2
O
MTIC
NH
N
N
N
O
N
H
A p o p t o s i s
TMZ@PSC4
Scheme 1 Schematic representation of the degradation of TMZ to 5-(3-methyl-triazen-1-yl) imidazole-4-carboxamide (MTIC) outside of the cell and the mechanism of stabilization of TMZ through complexation with
PSC4
Encapsulation of Small Drugs in a Supramolecule Enhances Solubility, Stability…
2 Materials
1. Temozolomide (T2577) and p-sulfonatocalix[4]arene (55523)
were purchased from Sigma-Aldrich.
2. Methanol and water (both LC-MS grade).
2.1 Synthesis
and Characterization
of Encapsulated TMZ
Fig. 1 Reaction scheme for the base-catalyzed decomposition of TMZ to its active metabolite MTIC and then
to 5-amino-imidazole-4-carboxamide (AIC) and methyl diazonium cation
NH
N
N
N
O
NH 2
N
N N
N
N
NH 2
O
O
Temozolomide
N
N
HN
N
N
H
NH 2
O
MTIC
N
N N
N
N
NH 2
O
O
Temozolomide
N
N
HN
N
N
H
NH 2
O
MTIC
NH
N
N
N
O
N
H
A p o p t o s i s
TMZ@PSC4
Scheme 1 Schematic representation of the degradation of TMZ to 5-(3-methyl-triazen-1-yl) imidazole-4-carboxamide (MTIC) outside of the cell and the mechanism of stabilization of TMZ through complexation with
PSC4
Encapsulation of Small Drugs in a Supramolecule Enhances Solubility, Stability…