Spiropyran-Based Drug Delivery Systems

Fagan, Andrew; Bartkowski, Michał; Giordani, Silvia

doi:10.3389/fchem.2021.720087

Cited by 38 publications

(31 citation statements)

References 112 publications

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“…MC can isomerise back to the SP form in the presence of VIS light or through spontaneous relaxation over time. This easily-accessible reversible nature of the SP highlights its viability as a reversible photochromic switch for drug-delivery purposes ( Cardano et al, 2019 ; Fagan et al, 2021 ).…”

Section: Ddss With Switches—controlled By Lightmentioning

confidence: 99%

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Molecular Switches—Tools for Imparting Control in Drug Delivery Systems

2022

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Cancer is a globally prevalent cause of premature mortality. Of growing interest is the development of novel anticancer therapies and the optimisation of associated risks. Major issues presently facing conventional anticancer therapies include systemic toxicity, poor solubility, membrane permeability, and multidrug resistance Nanocarriers have been employed to address these issues. Nanocarriers encapsulate anticancer drugs, enabling them to bypass biological barriers and minimise their adverse side effects. These drug delivery systems offer extensive benefits as they can be modified to gravitate towards specific environmental conditions. To further enhance the safety and efficacy of these drug carriers, modern developments have included incorporating a molecular switching mechanism into their structure. These molecular switches are responsive to endogenous and exogenous stimuli and may undergo reversible and repeatable conformational changes when activated. The incorporation of molecular switches can, therefore, impart stimuli-responsive drug-release control on a DDS. These stimuli can then be manipulated to offer precise dosage control over the drug release at a specific target site. This review discusses recent developments in the design of DDSs incorporating light and pH-responsive molecular switches as drug release controllers.

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Section: Ddss With Switches—controlled By Lightmentioning

confidence: 99%

“… The four micellar and polymeric NPs assembled from the PMMA (blue) and PDMAEMA (green) block copolymers, with terminal SP (purple) groups ( Razavi et al, 2020 ). Figure adapted with permission from Frontiers under a CC BY 4.0 license ( Fagan et al, 2021 ). …”

Section: Ddss With Switches—controlled By Light and Phmentioning

confidence: 99%

Molecular Switches—Tools for Imparting Control in Drug Delivery Systems

2022

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“…When irradiated with UV light (200–400 nm), closed-neutral SP converts, by ring-opening through a cis-trans isomerization, to zwitterionic merocyanine (MC), which is hydrophilic and colorful. The isomerization can be reversed thermally or by visible light irradiation (500–600 nm), as shown in Figure 3 [ 25 , 26 ]. The MC molecule has high hydrophilicity; it dissolves in aqueous solutions.…”

Section: Mechanisms Of Photo-induced Drug Release From Nanocarriersmentioning

confidence: 99%

Photo-Induced Drug Release from Polymeric Micelles and Liposomes: Phototriggering Mechanisms in Drug Delivery Systems

et al. 2022

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Chemotherapeutic drugs are highly effective in treating cancer. However, the side effects associated with this treatment lower the quality of life of cancer patients. Smart nanocarriers are able to encapsulate these drugs to deliver them to tumors while reducing their contact with the healthy cells and the subsequent side effects. Upon reaching their target, the release of the encapsulated drugs should be carefully controlled to achieve therapeutic levels at the required time. Light is one of the promising triggering mechanisms used as external stimuli to trigger drug release from the light-responsive nanocarriers. Photo-induced drug release can be achieved at a wide range of wavelengths: UV, visible, and NIR depending on many factors. In this review, photo-induced release mechanisms were summarized, focusing on liposomes and micelles. In general, light-triggering mechanisms are based on one of the following: changing the hydrophobicity of a nanocarrier constituent(s) to make it more soluble, introducing local defects within a nanocarrier (by conformational transformation or photo-cleavage of its lipids/polymers chains) to make it more porous or concentrating heat for thermo-sensitive nanocarriers to release their payload. Several research studies were also presented to explore the potentials and limitations of this promising drug release triggering mechanism.

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“…Spiropyrans are considered as a good candidate for application in drug delivery systems in which they are used for incorporation with different polymeric micelles, polymersomes and polymeric nanoparticles (NPs), etc. [17]. Spiropyrans represent an important class of spiro-heterocycles in which an equilibrium exists between the colourless spiro-heterocyclic (SP) form and the coloured open merocyanine (MC) form through the cleavage of the C-O bond [15,18] as shown in figure 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel silica encapsulated spiropyran-based thermochromic materials

Iqbal

Umar

et al. 2022

R. Soc. open sci.

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A series of novel spiropyrans were synthesized through the condensation of substituted 3,3-dimethyl-2-methyleneindoline with different nitro-substituted o -hydroxy aromatic aldehydes. Indoles were initially substituted with a variety of alkanes and esters moieties. The substituted 3,3-dimethyl-2-methyleneindoline was then reacted with nitro-substituted o -hydroxy aromatic aldehydes to yield the respective spiropyrans. The synthesized novel spiropyrans were encapsulated in silica nano-shells to protect them from the effect of moisture and pH. The thermochromic behaviour of novel spiropyrans was studied by UV-visible spectroscopy. The thermally induced isomerization of spiropyran derivatives was carried out in a water/ethanol mixture. The thermal isomerization of spiro-heterocyclic (colourless form) to merocyanine (MC) (coloured form) was a discontinuous process and was observed in a temperature range of 5–60°C via UV-visible spectrometer. The absorption process occurs reversibly regardless of the heating/cooling sequence. The spiropyran derivatives, therefore, have a potential application for colorimetric temperature indication.

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Spiropyran-Based Drug Delivery Systems

Cited by 38 publications

References 112 publications

Molecular Switches—Tools for Imparting Control in Drug Delivery Systems

Molecular Switches—Tools for Imparting Control in Drug Delivery Systems

Photo-Induced Drug Release from Polymeric Micelles and Liposomes: Phototriggering Mechanisms in Drug Delivery Systems

Synthesis of novel silica encapsulated spiropyran-based thermochromic materials

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