Development of the poly(l-histidine) grafted carbon nanotube as a possible smart drug delivery vehicle

Haghi, Ahmad; Raissi, Heidar; Farzad, Farzaneh

doi:10.1016/j.compbiomed.2022.105336

Cited by 17 publications

(6 citation statements)

References 44 publications

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“…In the case of DOX-loaded micelles, the STEM images displayed uniform spherical assemblies with much higher contrast due to the successful DOX incorporation ( Figure 5 ). Interestingly, all samples in STEM images ( Figure 5 a–c) revealed a gradual decrease in average diameters compared with the unloaded micelles ( Figure 5 d–f, PEG2K-PHis20 + DOX with an average diameter of 109 ± 17 nm, PEG2K-PHis26 + DOX with an average diameter of 105 ± 19 nm, and PEG2K-PHis32 + DOX with an average diameter of 71 ± 13 nm), indicating strong unspecific hydrophobic interactions of PHis with the DOX molecules [ 56 ]. Additionally, DOX may form compact nanocrystals inside the PHis moiety, where this phenomenon is observed with drugs in a similar environment [ 57 ], all leading to compaction of the inner core.…”

Section: Resultsmentioning

confidence: 99%

Solid-Phase Synthesized Copolymers for the Assembly of pH-Sensitive Micelles Suitable for Drug Delivery Applications

Ghiarasim¹,

Tiron

et al. 2022

Nanomaterials

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Diblock copolymers of polyhistidine are known for their self-assembly into micelles and their pH-dependent disassembly due to the amphiphilic character of the copolymer and the unsaturated imidazole groups that undergo a hydrophobic-to-hydrophilic transition in an acidic pH. This property has been largely utilized for the design of drug delivery systems that target a tumor environment possessing a slightly lower extracellular pH (6.8–7.2). The main purpose of this study was to investigate the possibility of designed poly(ethylene glycol)-polyhistidine sequences synthesized using solid-phase peptide synthesis (SPPS), to self-assemble into micelles, to assess the ability of the corresponding micelles to be loaded with doxorubicin (DOX), and to investigate the drug release profile at pH values similar to a malignant extracellular environment. The designed and assembled free and DOX-loaded micelles were characterized from a physico-chemical point of view, their cytotoxicity was evaluated on a human breast cancer cell line (MDA-MB-231), while the cellular areas where micelles disassembled and released DOX were assessed using immunofluorescence. We concluded that the utilization of SPPS for the synthesis of the polyhistidine diblock copolymers yielded sequences that behaved similarly to the copolymeric sequences synthesized using ring-opening polymerization, while the advantages of SPPS may offer facile tuning of the histidine site or the attachment of a large variety of functional molecules.

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Section: Resultsmentioning

confidence: 99%

Solid-Phase Synthesized Copolymers for the Assembly of pH-Sensitive Micelles Suitable for Drug Delivery Applications

Ghiarasim¹,

Tiron

et al. 2022

Nanomaterials

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“…The protonation of the imidazole ring in 2-methylimidazole helps pDNA@ZIF to escape endosomal attack [ 67 ]. Functionalization with His enhances the therapeutic delivery of nucleic acid due to the presence of imidazole rings that influence the disruption and destabilization of cell and endosomal membranes, thereby enhancing therapeutic nucleic acid delivery [ 56 , 68 ]. The pDNA@ZIF Arg biocomposites have the potential to enter cells very effectively due to less negative zeta potentials.…”

Section: Resultsmentioning

confidence: 99%

Amino Acid-Coated Zeolitic Imidazolate Framework for Delivery of Genetic Material in Prostate Cancer Cell

Polash,

Garlick-Trease,

Pyreddy

et al. 2023

Molecules

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Metal–organic frameworks (MOFs) are currently under progressive development as a tool for non-viral biomolecule delivery. Biomolecules such as proteins, lipids, carbohydrates, and nucleic acids can be encapsulated in MOFs for therapeutic purposes. The favorable physicochemical properties of MOFs make them an attractive choice for delivering a wide range of biomolecules including nucleic acids. Herein, a green fluorescence protein (GFP)-expressing plasmid DNA (pDNA) is used as a representative of a biomolecule to encapsulate within a Zn-based metal–organic framework (MOF) called a zeolitic imidazolate framework (ZIF). The synthesized biocomposites are coated with positively charged amino acids (AA) to understand the effect of surface functionalization on the delivery of pDNA to prostate cancer (PC-3) cells. FTIR and zeta potential confirm the successful preparation of positively charged amino acid-functionalized derivatives of pDNA@ZIF (i.e., pDNA@ZIFAA). Moreover, XRD and SEM data show that the functionalized derivates retain the pristine crystallinity and morphology of pDNA@ZIF. The coated biocomposites provide enhanced uptake of genetic material by PC-3 human prostate cancer cells. The AA-modulated fine-tuning of the surface charge of biocomposites results in better interaction with the cell membrane and enhances cellular uptake. These results suggest that pDNA@ZIFAA can be a promising alternative tool for non-viral gene delivery.

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“…ules 2024, 29, x FOR PEER REVIEW 2 of 24 [12], functional carbon nanomaterials [13,14], covalent organics frameworks [15], boron nitrides [16], smart polymers [17] and polypeptides [18], or combined smart carriers [19,20]. In addition to the carrier systems listed above, synthetic dye molecules have been proposed as promising candidates for supramolecular drug carriers [21][22][23].…”

Section: Introductionmentioning

confidence: 99%

“…Doxorubicin’s low toxicity index [ 10 ] prompted the search for targeted drug delivery systems, which would allow the lowering of the systemic DOX dose by selectively releasing the drug at its action site [ 11 ]. In the past few decades, many carrier systems have been proposed, e.g., liposomal formulations [ 12 ], functional carbon nanomaterials [ 13 , 14 ], covalent organics frameworks [ 15 ], boron nitrides [ 16 ], smart polymers [ 17 ] and polypeptides [ 18 ], or combined smart carriers [ 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Insights into Transfer of Supramolecular Doxorubicin/Congo Red Aggregates through Phospholipid Membranes

Stachowicz-Kuśnierz,

Rychlik,

Korchowiec

et al. 2024

Molecules

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Doxorubicin (DOX) is a commonly used chemotherapeutic drug, from the anthracycline class, which is genotoxic to neoplastic cells via a DNA intercalation mechanism. It is effective and universal; however, it also causes numerous side effects. The most serious of them are cardiotoxicity and a decrease in the number of myeloid cells. For this reason, targeted DOX delivery systems are desirable, since they would allow lowering the drug dose and therefore limiting systemic side effects. Recently, synthetic dyes, in particular Congo red (CR), have been proposed as possible DOX carriers. CR is a planar molecule, built of a central biphenyl moiety and two substituted naphthalene rings, connected with diazo bonds. In water, it forms elongated ribbon-shaped supramolecular structures, which are able to selectively interact with immune complexes. In our previous studies, we have shown that CR aggregates can intercalate DOX molecules. In this way, they preclude DOX precipitation in water solutions and increase its uptake by MCF7 breast cancer cells. In the present work, we further explore the interactions between DOX, CR, and their aggregates (CR/DOX) with phospholipid membranes. In addition to neutral molecules, the protonated doxorubicin form, DXP, is also studied. Molecular dynamics simulations are employed to study the transfer of CR, DOX, DXP, and their aggregates through POPC bilayers. Interactions of CR, DOX, and CR/DOX with model monolayers are studied with Langmuir trough measurements. This study shows that CR may support the transfer of doxorubicin molecules into the bilayer. Both electrostatic and van der Waals interactions with lipids are important in this respect. The former promote the initial stages of the insertion process, the latter keep guest molecules inside the bilayer.

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Development of the poly(l-histidine) grafted carbon nanotube as a possible smart drug delivery vehicle

Cited by 17 publications

References 44 publications

Solid-Phase Synthesized Copolymers for the Assembly of pH-Sensitive Micelles Suitable for Drug Delivery Applications

Solid-Phase Synthesized Copolymers for the Assembly of pH-Sensitive Micelles Suitable for Drug Delivery Applications

Amino Acid-Coated Zeolitic Imidazolate Framework for Delivery of Genetic Material in Prostate Cancer Cell

Insights into Transfer of Supramolecular Doxorubicin/Congo Red Aggregates through Phospholipid Membranes

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