A conjugation of stearic acid to apotransferrin, fattigation-platform, as a core to form self-assembled nanoparticles: Encapsulation of a hydrophobic paclitaxel and receptor-driven cancer targeting

Amin, Hardik H.; Meghani, Nilesh M.; Oh, Kyung Taek; Choi, Han‐Gon; Lee, Beom‐Jin

doi:10.1016/j.jddst.2017.07.013

Cited by 15 publications

(7 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Bioconjugation reactions are critical in the modification of peptides. Due to recent advances in the study of biomolecules, peptides can be designed to perform a variety of functions such as cellular monitoring, imaging, and target drug delivery (15)(16)(17)(18)(19)(20).…”

Section: Introductionmentioning

confidence: 99%

Angiotensin(1-7)-Stearic Acid Conjugate: Synthesis and Characterization

Acar¹,

Uçar

2022

Journal of the Turkish Chemical Society Section A: Chemistry

View full text Add to dashboard Cite

The novel coronavirus, SARS-CoV-2, broken out as the COVID-19 epidemic, is transported into the cytoplasm by angiotensin-converting enzyme-2 (ACE2), a key protein of the renin-angiotensin-system (RAS). ACE2 is a protective protein that reduces angiotensin (Ang) II, the bioactive component of RAS, by converting it to its potent antagonist, Ang-(1-7) peptide, in order to provide a pathophysiological response to stimuli. Although ACE-2 is upregulated especially in pulmonary endothelial cells and alveolar epithelial cells, downregulation of ACE-2 in the lung owing to loss of key regulatory factors explains the enzymedependent lethality of SARS-CoV-2. The N-terminal domain (NTD) of S1, one of the protein subunits of coronaviruses, is known to recognize acetylated sialic acids on glycosylated cell surface receptors. In this study, the stearic acid-peptide conjugate mimicking the sialic acid structure was synthesized, which will be able to balance uncontrolled inflammatory response and excessive cytokine production, and depending on these to suppress pneumonia and acute respiratory distress syndrome (ARDS), against SARS-CoV-2. It was expected that fatty acid acylation would greatly enhance cellular internalization and cytosolic distribution of the peptide through the cell membrane. Thus, we synthesized fatty acyl derivative of the N-Ac-Gly4-Ang (1-7) peptide. The peptide was synthesized using Fmoc/tBu solid-phase peptide chemistry and characterized by FT-IR, Zetasizer, and LC-ESI-MS. This study provided more detailed insights into understanding and meeting the basic structural requirements for optimal cellular delivery and formulation of the stearyl Ang (1-7)-peptide conjugate.

show abstract

Section: Introductionmentioning

confidence: 99%

Angiotensin(1-7)-Stearic Acid Conjugate: Synthesis and Characterization

Acar¹,

Uçar

2022

Journal of the Turkish Chemical Society Section A: Chemistry

View full text Add to dashboard Cite

show abstract

“…In contrast, a burst release of free PTX occurred at both pHs, where 50% was released in the first hour at pH 5.0 while at least 40% was released in the subsequent 2 h at pH 7.4 ( Figure 10 A). The sustained release of PTX from NaCNs further supported the notion that NaCNs could limit the exposure of PTX in the blood and to healthy tissues as well, which might enhance the targeting ability of the micelles to cancerous cells while limiting systemic toxicity [ 15 ].…”

Section: Resultsmentioning

confidence: 82%

“…They also tend to confer fewer side-effects as compared to Taxol. However, due to the poor colloidal stability of Abraxane in the blood [ 15 ], as well as minimal improvement of other clinically approved PTX-bound nanoformulations (in terms of response rate and therapeutic efficacy), an improved innovation for the delivery of PTX is required [ 11 ].…”

Section: Introductionmentioning

confidence: 99%

Optimization and Formulation of Nanostructured and Self-Assembled Caseinate Micelles for Enhanced Cytotoxic Effects of Paclitaxel on Breast Cancer Cells

et al. 2020

View full text Add to dashboard Cite

Background: Paclitaxel (PTX) is a widely used anti-cancer drug for treating various types of solid malignant tumors including breast, ovarian and lung cancers. However, PTX has a low therapeutic response and is linked with acquired resistance, as well as a high incidence of adverse events, such as allergic reactions, neurotoxicity and myelosuppression. The situation is compounded when its complex chemical structure contributes towards hydrophobicity, shortening its circulation time in blood, causing off-target effects and limiting its therapeutic activity against cancer cells. Formulating a smart nano-carrier may overcome the solubility and toxicity issues of the drug and enable its more selective delivery to the cancerous cells. Among the nano-carriers, natural polymers are of great importance due to their excellent biodegradability, non-toxicity and good accessibility. The aim of the present research is to develop self-assembled sodium caseinate nanomicelles (NaCNs) with PTX loaded into the hydrophobic core of NaCNs for effective uptake of the drug in cancer cells and its subsequent intracellular release. Methods: The PTX-loaded micelle was characterized with high-performance liquid chromatography (HPLC), Fourier Transform Infrared Spectra (FTIR), High Resolution-Transmission Electron Microscope (HR-TEM), Field Emission Scanning Electron Microscope (FESEM) and Energy Dispersive X-Ray (EDX). Following treatment with PTX-loaded NaCNs, cell viability, cellular uptake and morphological changes were analyzed using MCF-7 and MDA-MB 231 human breast cancer cell lines. Results: We found that PTX-loaded NaCNs efficiently released PTX in an acidic tumor environment, while showing an enhanced cytotoxicity, cellular uptake and in-vivo anti-tumor efficacy in a mouse model of breast cancer when compared to free drug and blank micelles. Additionally, the nanomicelles also presented improved colloidal stability for three months at 4 °C and −20 °C and when placed at a temperature of 37 °C. Conclusions: We conclude that the newly developed NaCNs is a promising carrier of PTX to enhance tumor accumulation of the drug while addressing its toxicity issues as well.

show abstract

“…The formation mechanism and identification of AOC have been well recognized in our fattigation researches. 9,[11][12][13] Albumin is an endogenous protein of human blood and is safely used…”

Section: Synthesis and Characterization Of Aoc Nanonization Identification Of Aocsmentioning

confidence: 99%

“…9,10 It is a very promising technique because biodegradable and biocompatible materials such as albumin, gelatin, and transferrin have been utilized to solubilize poorly water-soluble drugs and aid in the cancer treatment. 9,[11][12][13] The aim of this study was to investigate the feasibility of employing an amphiphilic albumin-oleic acid conjugate (AOC) for ISFI capability and solubilization of poorly water-soluble drug in a solvent system using solvent exchange mechanisms. Injectable solvents used in ISFI systems must have low viscosity, high water affinity, polymer dissolving ability and non-toxic properties.…”

Section: Introductionmentioning

confidence: 99%

Double-Controlled Release of Poorly Water-Soluble Paliperidone Palmitate from Self-Assembled Albumin-Oleic Acid Nanoparticles in PLGA in situ Forming Implant

Ngo

Jin

et al. 2021

IJN

Self Cite

View full text Add to dashboard Cite

Purpose: To investigate the effects of solvents on the formation of self-assembled nanonization of albumin-oleic acid conjugates (AOCs) using a solvent exchange mechanism for the construction of in situ forming implants (ISFI). Methods: A poorly water-soluble drug, paliperidone palmitate (PPP), was chosen as the model drug. AOC was synthesized with the 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) reaction. Dichloromethane, tetrahydrofuran, ethanol, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and deionized water were selected to investigate the formation of selfassembled AOC nanoparticles (AONs). The volume ratios of organic solvents against water could determine the miscibility, injectability, and in situ nanonizing capability without aggregation. Results: As the polarity of the organic solvents increased, the AONs exhibited a spherical shape, and the larger the volume of the solvent, the smaller the size of the AONs. To use AOC in ISFI for controlled release of PPP, poly(d,l-lactide-co-glycolide) (PLGA) was combined with the AOC in 2 mL of N-methyl-2-pyrrolidone and water solution (1.8/0.2 ratio). The release rates of all formulations exhibited similar curve patterns overall but were more controlled in decreasing order as follows: AOC, PLGA, and AOC/PLGA for 14 days. Conclusion:A combined formulation of AOC and PLGA was found to effectively control the initial burst release of the drug.

show abstract

A conjugation of stearic acid to apotransferrin, fattigation-platform, as a core to form self-assembled nanoparticles: Encapsulation of a hydrophobic paclitaxel and receptor-driven cancer targeting

Cited by 15 publications

References 40 publications

Angiotensin(1-7)-Stearic Acid Conjugate: Synthesis and Characterization

Angiotensin(1-7)-Stearic Acid Conjugate: Synthesis and Characterization

Optimization and Formulation of Nanostructured and Self-Assembled Caseinate Micelles for Enhanced Cytotoxic Effects of Paclitaxel on Breast Cancer Cells

Double-Controlled Release of Poorly Water-Soluble Paliperidone Palmitate from Self-Assembled Albumin-Oleic Acid Nanoparticles in PLGA in situ Forming Implant

Contact Info

Product

Resources

About