Li Man-Ping, Yang Nan, Xu Wen-Rong
Key Laboratory of Advanced Materials of Tropical Island Resources of Ministry of Education, Department of Chemistry, School of Science or School of Chemical Engineering and Technology, Hainan University, Haikou, 570228, China.
Beilstein J Org Chem. 2022 May 12;18:539-548. doi: 10.3762/bjoc.18.56. eCollection 2022.
A new water-soluble hexacarboxylated tribenzotriquinacene derivative () was synthesized and used as a supramolecular drug carrier to load the model anticancer drugs dimethyl viologen () and doxorubicin () via host-guest interactions. The drugs could be effectively released by spermine (), a molecule overexpressed in cancer cells, through host-guest competitive substitution since has a stronger binding affinity toward than and . The host-guest interactions of the complexes of with , and were investigated by NMR spectroscopy and fluorescence spectroscopy. The association stoichiometry of the complexes of with , , and was found to be 1:1 with association constants of = (7.67 ± 0.34) × 10 M, = (6.81 ± 0.33) × 10 M, and = (5.09 ± 0.98) × 10 M, respectively. The competitive substitution process was visualized by NMR titration. This novel TBTQ-based host-guest drug delivery system may have potential use in supramolecular chemotherapy.
合成了一种新型水溶性六羧基化三亚苯并三萘衍生物（），并将其用作超分子药物载体，通过主客体相互作用负载模型抗癌药物二甲基紫精（）和阿霉素（）。由于精胺（）对该衍生物的结合亲和力强于二甲基紫精和阿霉素，癌细胞中过表达的精胺可通过主客体竞争取代作用有效地释放药物。通过核磁共振光谱和荧光光谱研究了该衍生物与二甲基紫精、阿霉素和精胺形成的配合物的主客体相互作用。发现该衍生物与二甲基紫精、阿霉素和精胺形成的配合物的缔合化学计量比均为1:1，缔合常数分别为 = (7.67 ± 0.34) × 10 M、 = (6.81 ± 0.33) × 10 M和 = (5.09 ± 0.98) × 10 M。通过核磁共振滴定观察了竞争取代过程。这种基于三亚苯并三萘的新型主客体药物递送系统可能在超分子化疗中具有潜在应用。
