Boron-containing delocalised lipophilic cations for the selective targeting of cancer cells

Calabrese, Giuseppe; Daou, Anis; Rova, Aikaterini; Tseligka, Eirini D.; Ioannis, Vizirianakis S.; Dimitrios, Fatouros G.; Tsibouklis, John

doi:10.1039/c6md00383d

Cited by 10 publications

(6 citation statements)

References 45 publications

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“…10 B-drugs to tumour cells is followed by irradiation with slow neutrons ( 1 n), leading to tissue repair. (Adapted from Calabrese et al [20]).…”

Section: Boron Neutron Capture Therapymentioning

confidence: 99%

“…The first step is the selective uptake of a therapeutic dose of the drug by the cancer cells; this is critical for the success of the BNCT treatment. The second step involves irradiating the area of interest with a neutron beam to form 11B, which undergoes nuclear fission, releasing the radiating energy that leads to a high probability of local tumour cell death by direct DNA damage [20]. Accordingly, the nuclear reaction of 10 B can be used for the selective destruction of malignant tumour cells without compromising nearby normal and healthy tissues [21].…”

Section: Boron Neutron Capture Therapymentioning

confidence: 99%

“…The yields obtained were around 85%, with the product having a fine texture and dark red in colour. FT-IR: (3-carboranylpropyl) (3,7-diamino-5-phenylphenazin-5-ium bromide): 3226 cm −1 (aromatic C-H, Weak, 3,4,6,10,12,13,20,21,22,23,24), 2924 cm −1 (C-H Stretch, medium, 16, 17), 2522 cm −1 (B-H stretch, medium, 18), 1511 cm −1 (amine stretch, medium, 25), 1000 cm −1 (B-H deformation, medium, 18), 800-900 cm −1 (B-H vibration, medium, 18).…”

Section: Synthesis Of (3-carboranylpropyl) (Triphenyl Phosphonium) Bromide (2)mentioning

confidence: 99%

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Formulation of Boron Encapsulated Smart Nanocapsules for Targeted Drug Delivery to the Brain

2021

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Drug delivery through the Blood–Brain Barrier (BBB) represents a significant challenge. Despite the current strategies to circumvent the BBB, nanotechnology offers unprecedented opportunities for combining selective delivery, improved bioavailability, drug protection, and enhanced pharmacokinetics profiles. Chitosan nanocarriers allow for a more efficacious strategy at the cellular and sub-cellular levels. Boron Neutron Capture Therapy (BNCT) is a targeted chemo-radiotherapeutic technique that allows the selective depletion of cancer cells by means of selective tagging of cancer cells with 10B, followed by irradiation with low-energy neutrons. Consequently, the combination of a polymer-based nanodelivery system enclosing an effective BNCT pharmacophore can potentially lead to the selective delivery of the load to cancer cells beyond the BBB. In this work, synthesized novel boronated agents based on carborane-functionalized Delocalized Lipophilic Cations (DLCs) are assessed for safety and selective targeting of tumour cells. The compounds are then encapsulated in nanocarriers constituted by chitosan to promote permeability through the BBB. Additionally, chitosan was used in combination with polypyrrole to form a smart composite nanocapsule, which is expected to release its drug load with variations in pH. Results indicate the achievement of more selective boron delivery to cells via carboranyl DLCs. Finally, preliminary cell studies indicate no toxicity was detected in chitosan nanocapsules, further enhancing its viability as a potential delivery vehicle in the BNCT of brain tumours.

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“…10 B-drugs to tumour cells is followed by irradiation with slow neutrons ( 1 n), leading to tissue repair. (Adapted from Calabrese et al [20]).…”

Section: Boron Neutron Capture Therapymentioning

confidence: 99%

Section: Boron Neutron Capture Therapymentioning

confidence: 99%

Section: Synthesis Of (3-carboranylpropyl) (Triphenyl Phosphonium) Bromide (2)mentioning

confidence: 99%

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Formulation of Boron Encapsulated Smart Nanocapsules for Targeted Drug Delivery to the Brain

2021

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“…Many other targeting sites have been explored, often focusing on cancer therapies and receptors overexpressed on malignant cells . Promising new ligands are identified regularly, and their discussion goes well beyond the scope of this review (see Table , highlighted in green).…”

Section: Active Targetingmentioning

confidence: 99%

Internal Targeting and External Control: Phototriggered Targeting in Nanomedicine

Arrué

Ratjen

2017

ChemMedChem

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The photochemical control of structure and reactivity bears great potential for chemistry, biology, and life sciences. A key feature of photochemistry is the spatiotemporal control over secondary events. Well‐established applications of photochemistry in medicine are photodynamic therapy (PDT) and photopharmacology (PP). However, although both are highly localizable through the application of light, they lack cell‐ and tissue‐specificity. The combination of nanomaterial‐based drug delivery and targeting has the potential to overcome limitations for many established therapy concepts. Even more privileged seems the merger of nanomedicine and cell‐specific targeting (internal targeting) controlled by light (external control), as it can potentially be applied to many different areas of medicine and pharmaceutical research, including the aforementioned PDT and PP. In this review a survey of the interface of photochemistry, medicine and targeted drug delivery is given, especially focusing on phototriggered targeting in nanomedicine.

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“…Nevertheless, relevant structure‐related properties such as subcellular biodistribution and dynamic of fluorescent‐derived carboranes are still an unmet need. To move towards this goal, several chemical architectures containing carborane fragments have been synthetized by our group, [14] however their molecular structures cannot be easily related to their subcellular distribution and function, even though some correlation of general physicochemical observables has been reported to be helpful on achieving specific biological properties for a great variety of compounds [1b, 10d, 15] …”

Section: Introductionmentioning

confidence: 99%

Tuning the Cell Uptake and Subcellular Distribution in BODIPY–Carboranyl Dyads: An Experimental and Theoretical Study

Labra‐Vázquez

Flores‐Cruz

Galindo‐Hernández

et al. 2020

Chemistry A European J

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As et of BODIPY-carboranyl dyads synthesizedb ya Sonogashira cross-coupling reaction, where different C-substituted ortho-a nd meta-carboranyl fragments have been linked to aB ODIPY fluorophore is described. Chemical, photophysical and physicochemical analyses are presented, in-cludingN MR and singleX RD experiments, optical absorption/emission studies and partition coefficient(log P)m easurements. These studies, supported by DFT computations (M06-2X/6-31G**), provide an explanation to the largely divergentc ell income that thesef luorescent carboranyl-based fluorophores display,f or which as tructural or physicochemi-cal explanation remainse lusive. By studying the cell uptake efficiency and subcellular localization for our set of dyads on living HeLa cells, we trackedt he origins of these differences to significant variations in their static dipolem oments and partitionc oefficients,w hich tune their ability to interactw ith lipophilic microenvironments in cells. Remarkably, m-carboranyl-BODIPY derivativesw ith ah igherl ipophilicity are much betteri nternalisedb yc ells than their homologous with ocarborane, suggestingt hat m-isomers are potentially better theranostic agents for in vitro bioimaging and boron carriers for boron neutron capture therapy.

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Boron-containing delocalised lipophilic cations for the selective targeting of cancer cells

Abstract: To limit the incidence of relapse, cancer treatments must not promote the emergence of drug resistance in tumour and cancer stem cells.

Cited by 10 publications

References 45 publications

Formulation of Boron Encapsulated Smart Nanocapsules for Targeted Drug Delivery to the Brain

Formulation of Boron Encapsulated Smart Nanocapsules for Targeted Drug Delivery to the Brain

Internal Targeting and External Control: Phototriggered Targeting in Nanomedicine

Tuning the Cell Uptake and Subcellular Distribution in BODIPY–Carboranyl Dyads: An Experimental and Theoretical Study

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