The self-assembly of a camptothecin-lysine nanotube

Sun, Yuan; Shieh, Aileen; Kim, Se Hye; King, Samantha J.; Kim, Anne; Sun, Hui-Lung; Croce, Carlo M.; Parquette, Jon R.

doi:10.1016/j.bmcl.2016.04.056

Cited by 24 publications

(11 citation statements)

References 57 publications

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“…As a means to address the shortcomings of both approaches, the use of small molecule prodrugs that can assemble into larger aggregate structures is garnering increasing attention [43][44][45][46][47][48][49][50][51][52][53] . These small molecule prodrugs are designed to assemble into larger discrete nanostructures, combining the small molecular nature with the controlled pharmacokinetics potential offered by larger structures such as polymer-drug conjugates or nanoparticle-based drug delivery systems [54][55][56] .…”

Section: Original Articlementioning

confidence: 99%

Molecular design and synthesis of self-assembling camptothecin drug amphiphiles

Cheetham

Lin

et al. 2017

Acta Pharmacol Sin

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The conjugation of small molecular hydrophobic anticancer drugs onto a short peptide with overall hydrophilicity to create self-assembling drug amphiphiles offers a new prodrug strategy, producing well-defined, discrete nanostructures with a high and quantitative drug loading. Here we show the detailed synthesis procedure and how the molecular structure can influence the synthesis of the self-assembling prodrugs and the physicochemical properties of their assemblies. A series of camptothecin-based drug amphiphiles were synthesized via combined solid- and solution-phase synthetic techniques, and the physicochemical properties of their self-assembled nanostructures were probed using a number of imaging and spectroscopic techniques. We found that the number of incorporated drug molecules strongly influences the rate at which the drug amphiphiles are formed, exerting a steric hindrance toward any additional drugs to be conjugated and necessitating extended reaction time. The choice of peptide sequence was found to affect the solubility of the conjugates and, by extension, the critical aggregation concentration and contour length of the filamentous nanostructures formed. In the design of self-assembling drug amphiphiles, the number of conjugated drug molecules and the choice of peptide sequence have significant effects on the nanostructures formed. These observations may allow the fine-tuning of the physicochemical properties for specific drug delivery applications, ie systemic vs local delivery.

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Section: Original Articlementioning

confidence: 99%

Molecular design and synthesis of self-assembling camptothecin drug amphiphiles

Cheetham

Lin

et al. 2017

Acta Pharmacol Sin

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“…APEG-SS-PLA was synthesized according to the procedure reported by Sun et al [ 25 ]. Briefly, 7.14 g COOH-PLA-OH (0.50 mmol) was dissolved in 20 mL of DCM in a flask, and 140 mg of ethylene dichloride (EDC) was added under stirring at RT.…”

Section: Methodsmentioning

confidence: 99%

Aminoglucose-functionalized, redox-responsive polymer nanomicelles for overcoming chemoresistance in lung cancer cells

Zhou

Wen

et al. 2017

J Nanobiotechnol

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BackgroundChemotherapeutic drugs used for cancer therapy frequently encounter multiple-drug resistance (MDR). Nanoscale carriers that can target tumors to accumulate and release drugs intracellularly have the greatest potential for overcoming MDR. Glucose transporter-1 (GLUT-1) and glutathione (GSH) overexpression in cancer cells was exploited to assemble aminoglucose (AG)-conjugated, redox-responsive nanomicelles from a single disulfide bond-bridged block polymer of polyethylene glycol and polylactic acid (AG-PEG-SS-PLA). However, whether this dual functional vector can overcome MDR in lung cancer is unknown.ResultsIn this experiment, AG-PEG-SS-PLA was synthetized successfully, and paclitaxel (PTX)-loaded AG-PEG-SS-PLA (AG-PEG-SS-PLA/PTX) nanomicelles exhibited excellent physical properties. These nanomicelles show enhanced tumor targeting as well as drug accumulation and retention in MDR cancer cells. Caveolin-dependent endocytosis is mainly responsible for nanomicelle internalization. After internalization, the disulfide bond of AG-PEG-SS-PLA is cleaved in the presence of high intracellular glutathione levels, causing the hydrophobic core to become a polar aqueous solution, which subsequently results in nanomicelle disassembly and the rapid release of encapsulated PTX. Reduced drug resistance was observed in cancer cells in vitro. The caspase-9 and caspase-3 cascade was activated by the AG-PEG-SS-PLA/PTX nanomicelles through upregulation of the pro-apoptotic proteins Bax and Bid and suppression of the anti-apoptotic protein Bcl-2, thereby increasing apoptosis. Furthermore, significantly enhanced tumor growth inhibition was observed in nude mice bearing A549/ADR xenograft tumors after the administration of AG-PEG-SS-PLA/PTX nanomicelles via tail injection.ConclusionsThese promising results indicate that AG-PEG-SS-PLA/PTX nanomicelles could provide the foundation for a paradigm shift in MDR cancer therapy.Electronic supplementary materialThe online version of this article (10.1186/s12951-017-0316-z) contains supplementary material, which is available to authorized users.

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“…This class of materials has structural, optical and thermoelectrical properties such as drug delivery, optical memory, solar cells, gas storage and… [10][11][12][13][14]. Yuan Sun et al, study about assembly of Camptothecin (natural quinoline alkaloid with potent anti-tumor activity that functions through the inhibition of DNA topoisomerase) by nanotubes produced human serum that shown high potential against several human cancer cell types [15]. Lukang Ji et al demonstrate a cooperative energy and chirality transfer by constructing a supramolecular light-harvesting chiral nanotube in the aqueous phase.…”

Section: Introductionmentioning

confidence: 99%

“…In this work, the electronical and optical properties of C 66 H 54 Br 6 N 6 O 12 nanotube including band structure, density of states, dielectric function, refractive index, extinction coe cient and eloss have been studied by Wien2k package [15]. One method for optimization of the optoelectronic properties of compounds is gure out them with energy and wavelength on lattice structure.…”

Section: Introductionmentioning

confidence: 99%

Optoelectronic properties of C 66 H 54 Br 6 N 6 O 12 supramolecular nanotube by DFT studies

Aliabad

Vahidi

2022

Preprint

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In this work, the structural and optoelectronic properties of C66H54Br6N6O12 nanotubes, which is in the triclinic phase, have been studied by the Perdew- Burke- Ernzrhof Generalized Gradient Approximation (PBE- GGA). The semi metallic behaviors and the flat bands are observed in the band structure with 2.06 eV band gap. From the optical spectra, this nanotube is birefringence with Plasmon energies of 23.41, 23.36 and 23.55 eV at x, y and z direction, respectively. Cauchy coefficients have been obtained in the wavelength range of 550 to 850 nm. The results show that this nanotube cab be used in the optoelectronic devices like metallic carbon nanotube and glasses.

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The self-assembly of a camptothecin-lysine nanotube

Cited by 24 publications

References 57 publications

Molecular design and synthesis of self-assembling camptothecin drug amphiphiles

Molecular design and synthesis of self-assembling camptothecin drug amphiphiles

Aminoglucose-functionalized, redox-responsive polymer nanomicelles for overcoming chemoresistance in lung cancer cells

Optoelectronic properties of C 66 H 54 Br 6 N 6 O 12 supramolecular nanotube by DFT studies

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