Photoresponsive Coumarin‐Stabilized Polymeric Nanoparticles as a Detectable Drug Carrier

Chung, J. W.; Lee, KangAe; Neikirk, Colin; Nelson, Celeste M.; Priestley, Rodney D.

doi:10.1002/smll.201102263

Cited by 76 publications

(41 citation statements)

References 27 publications

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“…Alkylation reactions were done according to procedures previously described with small modifications [23,24], using different alkyl halides; (allyl bromide, geranyl bromide, prenyl bromide and ethyl chloro-acetate) which gave coumarin derivatives: 11 [25], 13 [26], 16 [26], 17 [27], 18 [28], 19 [29], 20 [30] and 21 [31] in satisfactory yields (45.5%–98%, except 18 ). Acetylation was carried out under ultrasonic irradiation (which increases the rate, speed and yield of chemical reactions, by liquids emulsification [32]), using an acetic anhydride and pyridine mixture afforded derivatives 15 [33], 14 [17], and 12 [34], in good yields (77%–90%).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity

Araújo

Guerra

Lima

et al. 2013

IJMS

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The increased incidence of opportunistic fungal infections, associated with greater resistance to the antifungal drugs currently in use has highlighted the need for new solutions. In this study twenty four coumarin derivatives were screened in vitro for antifungal activity against strains of Aspergillus. Some of the compounds exhibited significant antifungal activity with MICs values ranging between 16 and 32 μg/mL. The structure-activity relationships (SAR) study demonstrated that O-substitutions are essential for antifungal activity. It also showed that the presence of a short aliphatic chain and/or electron withdrawing groups (NO2 and/or acetate) favor activity. These findings were confirmed using density functional theory (DFT), when calculating the LUMO density. In Principal Component Analysis (PCA), two significant principal components (PCs) explained more than 60% of the total variance. The best Partial Least Squares Regression (PLS) model showed an r2 of 0.86 and q2cv of 0.64 corroborating the SAR observations as well as demonstrating a greater probe N1 interaction for active compounds. Descriptors generated by TIP correlogram demonstrated the importance of the molecular shape for antifungal activity.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity

Araújo

Guerra

Lima

et al. 2013

IJMS

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“…Photo-cleavage reactions occur in o -nitrobenzyl 165,166 and coumarin 167,168 containing molecules. In this regard, Dong et al 169 designed an s -( o -nitrobenzyl)- l -cysteine N -carboxyanhydride monomer and synthesized a novel block copolymer derivative for controlled release of DOX via photo-cleavage in the core of the NPs.…”

Section: Different Stimuli-responsive Mnpsmentioning

confidence: 99%

Smart micro/nanoparticles in stimulus-responsive drug/gene delivery systems

et al. 2016

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New achievements in the realm of nanoscience and innovative techniques of nanomedicine have moved micro/nanoparticles (MNPs) to the point of becoming actually useful for practical applications in the near future. Various differences between the extracellular and intracellular environments of cancerous and normal cells and the particular characteristics of tumors such as physicochemical properties, neovasculature, elasticity, surface electrical charge, and pH have motivated the design and fabrication of inventive “smart” MNPs for stimulus-responsive controlled drug release. These novel MNPs can be tailored to be responsive to pH variations, redox potential, enzymatic activation, thermal gradients, magnetic fields, light, and ultrasound (US), or can even be responsive to dual or multi-combinations of different stimuli. This unparalleled capability has increased their importance as site-specific controlled drug delivery systems (DDSs) and has encouraged their rapid development in recent years. An in-depth understanding of the underlying mechanisms of these DDS approaches is expected to further contribute to this groundbreaking field of nanomedicine. Smart nanocarriers in the form of MNPs that can be triggered by internal or external stimulus are summarized and discussed in the present review, including pH-sensitive peptides and polymers, redox-responsive micelles and nanogels, thermo- or magnetic-responsive nanoparticles (NPs), mechanical- or electrical-responsive MNPs, light or ultrasound-sensitive particles, and multi-responsive MNPs including dual stimuli-sensitive nanosheets of graphene. This review highlights the recent advances of smart MNPs categorized according to their activation stimulus (physical, chemical, or biological) and looks forward to future pharmaceutical applications.

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“…Polymer films comprising photoresponsive molecules such as 2-nitrobenzyl [260,261], spiropyran [262][263][264], azobenzene [265], cinnamoyl [266], and coumarin [267] represent other attractive candidates for controlling protein and cell adhesion on surfaces. Ober et al [261] studied polyelectrolyte brushes with side groups containing photocleavable, cationic nitrobenzyl moieties to control the electrostatic adsorption of proteins.…”

Section: Polymer Filmsmentioning

confidence: 99%

Stimuli‐Responsive Surfaces in Biomedical Applications

Pranzetti¹,

Preece²,

Mendes³

2013

Intelligent Stimuli‐Responsive Materials

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Nature provides mechanisms that are able to dynamically control specific and nonspecific interactions between cells and biological surfaces [1,2]. Scientists have long tried to reproduce these dynamic biological events and have recently made an important step in that direction by creating artificial stimuli-responsive surfaces [3][4][5][6][7]. These smart substrates present modulatory surface properties that are able to respond to external chemical/biochemical [8][9][10][11][12], thermal [13][14][15], electrical [16][17][18][19][20], and optical stimuli [21][22][23][24][25][26][27][28][29][30][31]. Due to their dynamic nature such substrates are very appealing for applications in the biomedical field [32]. Progress to date has led to control over biomolecule activity [33] and immobilization of a diverse array of proteins, including enzymes [34] and antibodies [35]. These prior achievements have encouraged researchers to take the challenge of using dynamic surfaces to modulate larger and more complex systems, such as bacteria [36] and mammalian cells [37].Achieving control over surface properties could provide new insights in the understanding of cell behavior and can offer distinct benefits with regard to the development of medical devices. For instance, the modulation of cell attachment and detachment could lead to the prevention of unwanted bacteria fouling on implants, reducing the risk of infections and rejection [38][39][40][41][42]. Furthermore, dynamic surfaces able to present on demand regulatory signals to a cell could provide unprecedented opportunities in studies of cell responses in real-time. Cells in tissues adhere to and interact with their extracellular environment via specialized cell-cell and cell-extracellular

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Photoresponsive Coumarin‐Stabilized Polymeric Nanoparticles as a Detectable Drug Carrier

Cited by 76 publications

References 27 publications

Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity

Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity

Smart micro/nanoparticles in stimulus-responsive drug/gene delivery systems

Stimuli‐Responsive Surfaces in Biomedical Applications

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