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Title: Synthesis and Characterization of Carbon-Based Quantum Dots and Doped Derivatives for Improved Andrographolide’s Hydrophilicity in Drug Delivery Platforms

Journal Article · · ACS Omega

Carbon-based quantum dots (CBQDs), sulfur-doped carbon-based quantum dots (S-CBQDs), and nitrogen-doped carbon-based quantum dots (N-CBQDs) have strong potential for drug delivery platforms. They were conjugated with andrographolide, a well-known hydrophobic drug, to study the concomitant changes in hydrophilicity. The interactions between these nanomaterials and the drug were studied by characterizing the optical and structural properties of the nanoparticles before and after coupling with the drug. It was found that the interaction of the drug with these nanomaterials produced noticeable changes in their optical and structural properties. Moreover, the partition coefficient for the nanocomposites was determined by NMR. The results indicate that conjugating the drug with the nanoparticles significantly enhanced its affinity for the aqueous phase, from 2.632 to 0.1117, thereby opening the possibility of using this approach for developing an effective drug delivery platform for this hydrophobic drug.

Research Organization:
Brookhaven National Laboratory (BNL), Upton, NY (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities (SUF); National Aeronautics and Space Administration (NASA); National Science Foundation (NSF); USDOE
Grant/Contract Number:
SC0012704; 307656; 308523; 80NSSC22M0025; 1626103
OSTI ID:
2320305
Alternate ID(s):
OSTI ID: 2338128
Report Number(s):
BNL-225501-2024-JAAM
Journal Information:
ACS Omega, Vol. 9, Issue 11; ISSN 2470-1343
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
English

References (62)

Synthesis of graphene quantum dots and their applications in drug delivery journal October 2020
Andrographolide sensitizes prostate cancer cells to TRAIL-induced apoptosis journal January 2018
Graphene quantum dots synthesis and energy application: a review journal June 2020
Approaches to Improve Solubility, Stability and the Clinical Potential of Andrographolide: A Review journal February 2022
Facile synthesis and photoluminescence characteristics of blue-emitting nitrogen-doped graphene quantum dots journal March 2016
One-Step Synthesis of Size-Tunable Gold@Sulfur-Doped Graphene Quantum Dot Nanocomposites for Highly Selective and Sensitive Detection of Nanomolar 4-Nitrophenol in Aqueous Solutions with Complex Matrix journal April 2018
Nitrogen-doped graphene quantum dots prepared by electrolysis of nitrogen-doped nanomesh graphene for the fluorometric determination of ferric ions journal May 2020
Insights of doxorubicin loaded graphene quantum dots: Synthesis, DFT drug interactions, and cytotoxicity journal March 2021
Synthesis, Separation, and Characterization of Small and Highly Fluorescent Nitrogen-Doped Carbon NanoDots journal January 2016
Graphene Quantum Dots: Syntheses, Properties, and Biological Applications book January 2016
Enhancing oral bioavailability of andrographolide via sodium dodecyl sulfate and D-α-Tocopherol polyethylene glycol 1000 succinate copolymer modified nanocrystals journal January 2023
Anomalous Behaviors of Visible Luminescence from Graphene Quantum Dots: Interplay between Size and Shape journal August 2012
Highly stable yellow-emitting fluorescent film based on graphene quantum dots for white laser-emitting devices journal October 2021
Preparation and Characterization of PEG4000 Palmitate/PEG8000 Palmitate-Solid Dispersion Containing the Poorly Water-Soluble Drug Andrographolide journal March 2020
Drug delivery systems book June 2015
Poor oral bioavailability of a promising anticancer agent andrographolide is due to extensive metabolism and efflux by P‐glycoprotein journal November 2011
Apoptosis Induction and Antimigratory Activity of Andrographolide Analog (3A.1)-Incorporated Self-Assembled Nanoparticles in Cancer Cells journal August 2018
Fluorescent graphene quantum dots as traceable, pH-sensitive drug delivery systems journal October 2015
Andrographolide‐loaded solid lipid nanoparticles enhance anti‐cancer activity against head and neck cancer and precancerous cells journal December 2020
13C NMR of organosulphur compounds: I—the effects of sulphur substituents on the 13C chemical shifts of alkyl chains and of S‐heterocycles journal February 1976
Blue luminescent graphene quantum dots and graphene oxide prepared by tuning the carbonization degree of citric acid journal October 2012
Octanol-Water Partition Constant book August 2019
DNA–Carbon Dots Function as Fluorescent Vehicles for Drug Delivery journal March 2015
Determination of Association Constants (Ka) from Solution NMR Data journal August 2000
Size-dependence of the skin penetration of andrographolide nanosuspensions: In vitro release-ex vivo permeation correlation and visualization of the delivery pathway journal June 2023
Graphene quantum dot assisted translocation of drugs into a cell membrane journal January 2019
Bioavailability of andrographolide and protection against carbon tetrachloride-induced oxidative damage in rats journal October 2014
Review of performance improvement strategies for doped graphene quantum dots for fluorescence-based sensing journal June 2021
Sulfur doped graphene quantum dots as a potential sensitive fluorescent probe for the detection of quercetin journal July 2020
Biocompatibility and toxicity of graphene quantum dots for potential application in photodynamic therapy journal August 2018
Andrographolide: its pharmacology, natural bioavailability and current approaches to increase its content in andrographispaniculata journal January 2018
Enhanced low-temperature lithium storage performance of multilayer graphene made through an improved ionic liquid-assisted synthesis journal May 2015
Nanoemulsion as a strategy for improving the oral bioavailability and anti-inflammatory activity of andrographolide journal January 2018
Graphene quantum dots from chemistry to applications journal December 2018
Dual-Responsive Carbon Dots for Tumor Extracellular Microenvironment Triggered Targeting and Enhanced Anticancer Drug Delivery journal July 2016
Preparation and evaluation of andrographolide-loaded microemulsion journal April 2012
Andrographolide-Soya-L-α-Phosphatidyl Choline Complex Augmented Solubility and Drug Delivery in Leishmania donovani, a Causative Agent for Cutaneous and Visceral Leishmaniasis journal January 2023
Advances and challenges in developing andrographolide and its analogues as cancer therapeutic agents journal September 2019
Improved bioavailability of orally administered andrographolide from pH-sensitive nanoparticles journal December 2010
Large scale preparation of graphene quantum dots from graphite with tunable fluorescence properties journal January 2013
Preparation of Excitation‐Independent Photoluminescent Graphene Quantum Dots with Visible‐Light Excitation/Emission for Cell Imaging journal October 2013
Estimation of aqueous solubility of organic compounds by using the general solubility equation journal August 2002
From One Electron to One Hole: Quasiparticle Counting in Graphene Quantum Dots Determined by Electrochemical and Plasma Etching journal July 2010
Recent Advances in the Cancer Bioimaging with Graphene Quantum Dots journal August 2018
Synthesis of fluorescent nitrogen-doped carbon dots from dried shrimps for cell imaging and boldine drug delivery system journal January 2016
Molecular scale rapid synthesis of graphene quantum dots (GQDs) journal February 2017
LogD: Lipophilicity for ionisable compounds journal August 2008
Andrographolide-loaded nanoparticles for brain delivery: Formulation, characterisation and in vitro permeability using hCMEC/D3 cell line journal October 2017
N-doped graphene quantum dots as a novel highly-efficient matrix for the analysis of perfluoroalkyl sulfonates and other small molecules by MALDI-TOF MS journal January 2017
Sulfur-doped graphene quantum dot-based paper sensor for highly sensitive and selective detection of 4-nitrophenol in contaminated water and wastewater journal January 2019
Physicochemical characteristics and oral bioavailability of andrographolide complexed with hydroxypropyl-β-cyclodextrin journal August 2009
Possible 3D Carbon Structures as Progressive Intermediates in Graphite to Diamond Phase Transition journal December 1999
Nitrogen doped graphene quantum dots as a cocatalyst of SrTiO3(Al)/CoOx for photocatalytic overall water splitting journal January 2021
An easy‐to‐use and general nuclear magnetic resonance method for the determination of partition coefficients of drugs and natural products journal April 2021
Andrographolide Derivatives Target the KEAP1/NRF2 Axis and Possess Potent Anti‐SARS‐CoV‐2 Activity journal January 2022
Carbon-13 nuclear magnetic resonance spectra of organic sulfur compounds. Comparison of chemical shifts for carbonyl and thiocarbonyl compounds in the pyrone, thiopyrone, and pyridone series journal January 1976
A review: recent advances in preparations and applications of heteroatom-doped carbon quantum dots journal January 2020
Charge-Convertible Carbon Dots for Imaging-Guided Drug Delivery with Enhanced in Vivo Cancer Therapeutic Efficiency journal March 2016
Octanol–Water Partition Coefficient Measurement by a Simple 1H NMR Method journal September 2017
Getting physical in drug discovery: a contemporary perspective on solubility and hydrophobicity journal August 2010
Targeting TNF-related apoptosis-inducing ligand (TRAIL) receptor by natural products as a potential therapeutic approach for cancer therapy journal April 2015
Nanoparticle-Based Drug Delivery in Cancer Therapy and Its Role in Overcoming Drug Resistance journal August 2020

Figures / Tables (10)