2016
DOI: 10.1021/jacs.6b09504
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Metal–Organic Polyhedron Capped with Cucurbit[8]uril Delivers Doxorubicin to Cancer Cells

Abstract: Self-assembly of ligand 1 and Pd(NO3)2 delivers Fujita-type metal organic polyhedron (MOP) 3 which bears 24 covalently attached methyl viologen units on its external surface as evidenced by 1H NMR, DOSY NMR, electrospray mass spectrometry, TEM, and AFM measurements. MOP 3 undergoes non-covalent complexation with cucurbit[n]urils to yield MOPs 4 – 6 with diameter ≈ 5–6 nm. MOP 5 can be fully loaded with doxorubicin prodrug 2 via hetero ternary complex formation to yield 7. The MOPs exhibit excellent stability t… Show more

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Cited by 169 publications
(122 citation statements)
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“…This CB[8] capped MOP was further able to form heteroternary complexes with a naphthol derivatized doxorubicin prodrug (dox prodrug) to give the drug loaded MOP2. 41 By virtue of its acid labile hydrazone linkage dox prodrug was expected to exhibit pH responsive behavior at the acidic pH of cancer cells. Metabolic assays show that MOP2 is 10-fold more cytotoxic toward HeLa cells than equimolar quantities of doxorubicin prodrug.…”
Section: Host•guest Mimics Of Biotin/(strept)avidinmentioning
confidence: 99%
See 1 more Smart Citation
“…This CB[8] capped MOP was further able to form heteroternary complexes with a naphthol derivatized doxorubicin prodrug (dox prodrug) to give the drug loaded MOP2. 41 By virtue of its acid labile hydrazone linkage dox prodrug was expected to exhibit pH responsive behavior at the acidic pH of cancer cells. Metabolic assays show that MOP2 is 10-fold more cytotoxic toward HeLa cells than equimolar quantities of doxorubicin prodrug.…”
Section: Host•guest Mimics Of Biotin/(strept)avidinmentioning
confidence: 99%
“…b) Metabolic assay showing the 10-fold enhanced cytotoxicity of MOP2 (⑤) compared to dox prodrug (o). (Reprinted by permission from ref 41. Copyright 2016, American Chemical Society).…”
Section: Figurementioning
confidence: 99%
“…18 Recently, we reported a Fujita-type cubooctahedral MOP studded with 24 methyl viologen groups which non-covalently recruited CB[8] and doxorubicin prodrugs by heteroternary complexation and its ability to deliver doxorubicin to HeLa cells. 19 These MOPs which are non-covalently functionalized with CB[n] are less robust and less attractive for in vivo application due to their potential for dissociation which lead us to consider more robust analogues based on a non-covalent but mechanically interlocked architecture. 20 In this paper, we explore a covalently functionalized architecture featuring a cubooctahedral MOP functionalized with CB[7] units.…”
Section: Introductionmentioning
confidence: 99%
“…These features are highly desired for photodynamic therapy and chemotherapy applications. 33-36 Their structural diversity and modulated functionality make PCCs potential candidates for enhancing cellular uptake and directing organelle targeting. An additional benefit to using PCCs is that the cytotoxicity of PCC carrier themselves can be minimized by careful selection of biocompatible components.…”
Section: Introductionmentioning
confidence: 99%