Synthesis, Experimental and Density Functional Theory (DFT) Studies on Solubility of Camptothecin Derivatives

Lai, Chin‐Hung; Chang, Chia-Chin; Weng, Yi-Lin; Chuang, Ta-Hsien

doi:10.3390/molecules23123170

Cited by 9 publications

(2 citation statements)

References 28 publications

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“…It has been demonstrated to have remarkable antitumor effects against liver, gastrointestinal, bladder, and prostate cancers as well as certain types of leukemia by blocking the synthesis of the DNA enzyme topo-isomerase [2,3]. Semi-synthetic derivatives of CPT, such as topotecan (hycamtin) and irinotecan (CPT-11), have been employed as anticancer therapeutic agents and approved by Food and Drug Administration (FDA) [4,5]. However, the systemic toxicity of CPT, low aqueous solubility, low bioavailability, and inappropriate drug-targeting remain the major challenges associated with chemotherapeutic results [6,7].…”

Section: Introductionmentioning

confidence: 99%

Dextran-coated superparamagnetic nanoparticles modified with folate for targeted drug delivery of camptothecin

Al-Musawi¹,

Albukhaty

Al-Karagoly

et al. 2020

Adv. Nat. Sci: Nanosci. Nanotechnol.

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Drug delivery vehicles based on magnetic nanoparticles present a promising strategy for cancer treatment, due to controlled targeted treatment, high loading efficiency, and biosafety as compared to traditional drug delivery approaches. In the present study, superparamagnetic iron oxide (Fe3O4) nanoparticles (SPIONs) were synthesised by a co-precipitation approach, stabilised with dextran (DEX), and successfully conjugated with folate (FA) for delivery of camptothecin (CPT) in prostate cancer cells. Size and other characteristics of the modified nanoparticles were measured using scanning electron microscopy (SEM), transmission electron microscopy (TEM), dynamic light scattering (DLS), and zeta-potential. The results demonstrated that the prepared FA-DEX-SPIONs were spherical in shape with an average diameter of 63.31 nm. They had anticancer activity with high CPT loading efficiency in AT3B-1cancer cells, enabling the therapeutic activity of the drug via its active delivery and release at 37 °C in phosphate and citrate buffer solutions. MTT results exhibited no cytotoxicity on rat androgen independent prostate cancer (AT3B-1) and normal human prostate (RWPE-1) cells. In conclusion, FA-DEX-SPION composite is a promising candidate that could be used for the targeted release of CPT anti-cancer drug.

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Section: Introductionmentioning

confidence: 99%

Dextran-coated superparamagnetic nanoparticles modified with folate for targeted drug delivery of camptothecin

Al-Musawi¹,

Albukhaty

Al-Karagoly

et al. 2020

Adv. Nat. Sci: Nanosci. Nanotechnol.

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“…Qualitatively, the fluorescence emitted by the additional CPT in solution could be readily visualized by simply illuminating the sample with a hand-held lamp (Figure 8c). Quantitative measurements found the drug loading efficiency to be 0.22% with a 10-fold improvement in aqueous solubility from 8.4 ng/mL, 59 to 75 ng/mL (see Supporting Information). The next step was to determine if a formulation of HBPn• CPT enhanced delivery of CPT into cells and induced a higher toxic effect.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Supramolecular Loading of a Broad Spectrum of Molecular Guests In Hyperbranched Polytriazole Nanoparticles with Cores Containing Multiple Functional Groups

Padilla‐Coley

Morsby

et al. 2020

Biomacromolecules

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This study evaluated the supramolecular properties of a new family of water-soluble hyperbranched polytriazoles that have a unimolecular micelle structure. Two new, structurally related hyperbranched polymers (HBPa and HBPn), with the same size (D h = 11 nm) and core−shell architecture, were prepared and found to act as nanoscale hosts for a broad spectrum of molecular guests. The globular-shaped hyperbranched polymers were synthesized by a straightforward one-pot polymerization method that permits easy synthetic control of the multiple functional groups within the core. Surrounding the core is a shell of polyethylene glycol chains that promotes solubility in pH 7.4 buffer solution and inhibits self-aggregation of the nanoparticles. The core of HBPa, containing a mixture of anionic carboxylate groups and 1,2,3-triazole rings, could be loaded with cationic hydrophilic (i.e., propidium iodide) or partially hydrophobic (i.e., Hoechst 33342) dyes or drugs, including a binary dye/drug pair (i.e., indocyanine green/mitoxantrone). The core of HBPn, containing a mixture of uncharged 2-pentanone chains and 1,2,3-triazole rings, could be loaded with uncharged and very hydrophobic dyes (i.e., Nile Red) or drugs. Improved aqueous solubility of camptothecin was achieved 10-fold from 8.4 to 75 ng/mL. Additionally, cell toxicity studies showed that HBPn was able to release the camptothecin drug inside A549 cancer cells resulting in increased cell death. Taken together, the results suggest that this new family of water-soluble hyperbranched polytriazoles could be broadly useful as nanocarriers for various applications in therapy, imaging, or a combination of the two (theranostics).

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Camptothecin: chemistry, biosynthesis, analogs, and chemical synthesis

Pullaiah

Raveendran

2020

Camptothecin and Camptothecin Producing Plants

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Synthesis, Experimental and Density Functional Theory (DFT) Studies on Solubility of Camptothecin Derivatives

Cited by 9 publications

References 28 publications

Dextran-coated superparamagnetic nanoparticles modified with folate for targeted drug delivery of camptothecin

Dextran-coated superparamagnetic nanoparticles modified with folate for targeted drug delivery of camptothecin

Supramolecular Loading of a Broad Spectrum of Molecular Guests In Hyperbranched Polytriazole Nanoparticles with Cores Containing Multiple Functional Groups

Camptothecin: chemistry, biosynthesis, analogs, and chemical synthesis

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