Photophysical Studies of a New Water Soluble Indocarbocyanine Dye Adsorbed onto Microcrystalline Cellulose and beta-Cyclodextrin

El‐Shishtawy, Reda M.; Oliveira, Anabela S.; Almeida, Paulo; Ferreira, Diana P.; Conceição, D.S.; Ferreira, L.F. Vieira

doi:10.3390/molecules18055648

Cited by 7 publications

(5 citation statements)

References 49 publications

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“… 11 , 14 In addition, CD can affect the photochemical and photophysical properties of guest molecules due to the limitation of the shape and size of the inner cavity. 15 , 16 Coumarin compounds have better optical characteristics and quantum yields, and have been widely developed as fluorescent probes. 17 – 19 The electron-donating group at the 7-position of AUR contributes to increased photostability.…”

Section: Introductionmentioning

confidence: 99%

<p>pH-Responsive Fluorescence Enhanced Nanogel for Targeted Delivery of AUR and CDDP Against Breast Cancer</p>

Cao¹,

Li²,

Li³

et al. 2020

IJN

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Introduction Auraptene (AUR), a natural bioactive prenyloxy coumarin, is a highly pleiotropic molecule that can bind to the MT1 receptor and can effectively reduce the proliferation and migration of breast cancer cells. Cisplatin (CDDP), as the first synthetic platinum-based anticancer drug, is widely used in the clinic due to its definite mechanism and therapeutic effect on diverse tumors. However, both of AUR and CDDP exhibit some disadvantages when used alone, including poor solubility, low bioavailability, lack of selectivity and systemic toxicity when they are used singly. Methods Therefore, the biodegradable materials hyaluronic acid (HA) and β-cyclodextrin derivative (mono-(6-amino-mono-6-deoxy)-β-CD, CD) were employed as carriers to load AUR and CDDP to form nanogel ( CDDP HA-CD@AUR) capable of dual-targeted delivery and synergistic therapy for breast cancer and cell imaging. Results With the help of the CDDP-crosslinked CD-loaded structure, the newly synthesized nanogel exhibited excellent physiological stability and fluorescence effects. The release of AUR and CDDP was affected by the pH value, which was beneficial to the selective release in the tumor microenvironment. Cell experiments in vitro demonstrated that the nanogel could be selectively internalized by MCF-7 cells and exhibited low cytotoxicity to HK-2 cells. Antitumor experiments in vivo showed that the nanogel have better antitumor effects and lower systemic toxicity. Conclusion Based on these, the nanogel loaded with AUR and CDDP have the potential for targeted delivery against breast cancer.

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Section: Introductionmentioning

confidence: 99%

<p>pH-Responsive Fluorescence Enhanced Nanogel for Targeted Delivery of AUR and CDDP Against Breast Cancer</p>

Cao¹,

Li²,

Li³

et al. 2020

IJN

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“…In addition to chemical stability and intense absorption in the visible region, desirable properties of functional dyes include any change of the chromophoric properties, such as photochromism or solvatochromism, that is associated with a modification of the external parameters or aggregation state [ 18 , 19 , 20 , 21 , 22 ].…”

Section: Introductionmentioning

confidence: 99%

Bioinspired Heterocyclic Partnership in a Cyanine-Type Acidichromic Chromophore

et al. 2020

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A new red hair-inspired 1,4-benzothiazine-based scaffold is disclosed herein, built upon a modular D-π-A architecture via condensation of the easily accessible 3-phenyl-2H-1,4-benzothiazine with indole-3-carboxaldehyde. The compound was obtained in around 50% yields and was characterized by complete spectroscopic analysis. The new benzothiazine-based cyanine displayed a characteristic reversible acidichromic behavior with a marked bathochromic shift upon acidification. The chromophore resisted at least fifteen hydrochloric acid/sodium hydroxide cycles without appreciable alterations. The expedient and scalable synthetic procedure together with the pH sensitive chromophoric properties would make the new compound an attractive prototype for novel modular chromophore for pH-sensing and other applications.

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“…Cyanine dyes and their derivatives have been the foremost to show propensity to form aggregates in aqueous solution − and in other media, such as, surfactants, cyclodextrins, etc. That the cyanine dyes can be forced to aggregate by changing the ionic strength of the medium to form higher order aggregates was reported by Mooi et al The asymmetric cyanine dye, TO, is under attention of many workers due to its special properties.…”

Section: Introductionmentioning

confidence: 99%

Modulating Thiazole Orange Aggregation in Giant Lipid Vesicles: Photophysical Study Associated with FLIM and FCS

Das

Purkayastha

2017

ACS Omega

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Thiazole orange (TO) exists mainly as a monomer in aqueous medium, where its fluorescence is negligibly small due to intramolecular movements. In the present study, it has been shown that in presence of giant unilamellar vesicles, produced from anionic lipid molecules, TO prefers to form H-dimer and H-aggregates at low lipid concentrations. The nonfluorescent form of TO (monomer) starts fluorescing in the aggregated or dimeric forms. At higher 1,2-dimyristoyl- sn -glycero-3-phospho-(1′-rac-glycerol) concentration, the TO aggregates disintegrate to the monomeric variants. This is principally due to generation of more surface of residence for the TO molecules. The dye molecules/aggregates reside on the outer surface as well as percolate inside the lipid vesicles toward the inner water pool due to the presence of anionic charges at the interface. We adopted fluorescence lifetime imaging to find out the heterogeneity in photophysics of the different forms of TO inside the lipid vesicles supported by fluorescence correlation spectroscopy to characterize the formation or disintegration of the TO aggregates.

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Photophysical Studies of a New Water Soluble Indocarbocyanine Dye Adsorbed onto Microcrystalline Cellulose and beta-Cyclodextrin

Cited by 7 publications

References 49 publications

<p>pH-Responsive Fluorescence Enhanced Nanogel for Targeted Delivery of AUR and CDDP Against Breast Cancer</p>

<p>pH-Responsive Fluorescence Enhanced Nanogel for Targeted Delivery of AUR and CDDP Against Breast Cancer</p>

Bioinspired Heterocyclic Partnership in a Cyanine-Type Acidichromic Chromophore

Modulating Thiazole Orange Aggregation in Giant Lipid Vesicles: Photophysical Study Associated with FLIM and FCS

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