Metal–Organic Polyhedron Capped with Cucurbit[8]uril Delivers Doxorubicin to Cancer Cells

Samanta, Soumen K.; Moncelet, Damien; Briken, Volker; Isaacs, Lyle

doi:10.1021/jacs.6b09504

Cited by 167 publications

(122 citation statements)

References 94 publications

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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%

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Synthetic mimics of biotin/(strept)avidin

et al. 2017

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Biotin/(strept)avidin self-assembly is a powerful platform for nanoscale fabrication and capture with many different applications in science, medicine, and nanotechnology. However, biotin/(strept)avidin self-assembly has several well-recognized drawbacks that limit performance in certain technical areas and there is a need for synthetic mimics that can either become superior replacements or operational partners with bio-orthogonal recognition properties. The goal of this tutorial review is to describe the recent progress in making high affinity synthetic association partners that operate in water or biological media. The review starts with a background summary of biotin/(strept)avidin self-assembly and the current design rules for creating synthetic mimics. A series of case studies are presented that describe recent success using synthetic derivatives of cyclodextrins, cucurbiturils, and various organic cyclophanes such as calixarenes, deep cavitands, pillararenes, and tetralactams. In some cases, two complementary partners associate to produce a nanoscale complex and in other cases a ditopic host molecule is used to link two partners. The article concludes with a short discussion of future directions and likely challenges.

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Section: Host•guest Mimics Of Biotin/(strept)avidinmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Synthetic mimics of biotin/(strept)avidin

et al. 2017

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“…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%

Cucurbit[7]uril Enables Multi-Stimuli-Responsive Release from the Self-Assembled Hydrophobic Phase of a Metal Organic Polyhedron

et al. 2017

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Mixed self-assembly of ligand 1, 2, 1,6-hexanediamine (HDA) and Pd(NO3)2 afforded Fujita-type metal organic polyhedron MOP1 (diameter ≈ 8.2 nm) which is covalently functionalized with an average of 18 cucurbit[7]uril (CB[7]) units as evidenced by 1H NMR, diffusion ordered spectroscopy NMR and transmission electron microscopy measurements. By virtue of the host-guest properties of CB[7], the inner cavity of MOP can be rendered hydrophobic by using octadecyl HDA (3) as guest during the self-assembly process. The hydrophobic cavity was successfully utilized to trap the hydrophobic dye Nile Red (NR) and the anticancer drug Doxorubicin (DOX). The stimuli responsive release of encapsulated NR or DOX occurs: 1) upon addition of a competitive binder (e.g. adamantane ammonium (ADA)) for CB[7], 2) by a dual pH-chemical stimulus involving the protonation state change of adamantane carboxylate at pH 5.8, and 3) a dual pH-photochemical stimulus involving photoisomerization of trans-6 to cis-6 at pH 5.8. NR is released from NR@MOP2 within HeLa cancer cells. This body of work suggests that the covalent attachment of cucurbit[n]uril to metal organic polyhedra constitutes a promising vehicle for the development of both diagnostic and therapeutic nanoparticles.

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“…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%

Investigating Subcellular Compartment Targeting Effect of Porous Coordination Cages for Enhancing Cancer Nanotherapy

Fang

Lian

et al. 2018

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Understanding the key factors for successful subcellular compartment targeting for cargo delivery systems is of great interest in a variety of fields such as bionanotechnology, cell biology, and nanotherapies. However, the fundamental basis for intracellular transportation with these systems has thus far rarely been discussed. As a cargo vector, porous coordination cages (PCCs) have great potential for use in cancer nanotherapy and to elucidate fundamental insight regarding subcellular compartment targeting. Herein, it is shown that the transportation of PCC cargo vectors though various subcellular barriers of the mammalian cell can be manipulated by tuning the vector's electronic property and surface affinity. It is found that the PCCs become selectively aggregated at the cell membrane, the cytoplasm, or the nucleus, respectively. When a DNA topoisomerase inhibitor is delivered into the nucleus by a neutral and lipophilic PCC, the anticancer efficacy is dramatically improved. The findings shed light to tune the interactions at the "bio-nano" interface. This study provides a key strategy for future work in targeting specific cell organelles for cell imaging, cargo delivery, and therapy. This research also offers key insight into the engineering of nanoscopic materials for furnishing cell organelle-specificity.

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Metal–Organic Polyhedron Capped with Cucurbit[8]uril Delivers Doxorubicin to Cancer Cells

Cited by 167 publications

References 94 publications

Synthetic mimics of biotin/(strept)avidin

Synthetic mimics of biotin/(strept)avidin

Cucurbit[7]uril Enables Multi-Stimuli-Responsive Release from the Self-Assembled Hydrophobic Phase of a Metal Organic Polyhedron

Investigating Subcellular Compartment Targeting Effect of Porous Coordination Cages for Enhancing Cancer Nanotherapy

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