Chlorambucil labelled with the phenosafranin scaffold as a new chemotherapeutic for imaging and cancer treatment

Miksa, Beata; Sierant, Małgorzata; Skorupska, Ewa; Michalski, Adam; Kaźmierski, Sławomir; Steinke, Urszula; Różański, Artur; Uznański, Paweł

doi:10.1016/j.colsurfb.2017.08.045

Cited by 10 publications

(12 citation statements)

References 53 publications

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“…The sharp absorption at 1575 cm −1 is attributed to the CC stretching vibration of the Py ring. The band at 1539 cm −1 is assigned to CC asymmetric phenazine ring stretching and the CN stretching vibration in a PSF unit in the PPy structure [ 63,64 ] and describes the CC, CC in‐ring Py stretch mode. [ 61 ] The band at 1456 cm −1 corresponded to the CN and CC asymmetric stretch in Py rings indicated the large number of conjugated monomer units.…”

Section: Resultsmentioning

confidence: 99%

Thermostable Fluorescent Capsules with the Cross‐Linked Heterocyclic Polymer Shell from Poly(pyrrole‐phenosafranin)

Miksa

Steinke

Trzeciak

et al. 2021

Macro Chemistry & Physics

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The present investigation describes the synthesis of capsules with a poly(pyrrole‐phenosafranin) cross‐linked shell. The capsules are prepared in a water solution by the facile single‐step chemical oxidative polymerization of monomers within hydrophobic interior of lipid bilayers that act as temporary scaffolds created by liposomes from 1,2‐dilauroyl‐sn‐glycero‐3‐phosphatidylcholine. The polypyrrole links phenosafranin units via amino groups, thus new thermostable nanocapsules are obtained without additional cross‐linking agents. Their spherical shape is confirmed by electron microscopy. Wide spectral characteristics of capsules by using different analytical methods provide detailed information about their structures.

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Section: Resultsmentioning

confidence: 99%

Thermostable Fluorescent Capsules with the Cross‐Linked Heterocyclic Polymer Shell from Poly(pyrrole‐phenosafranin)

Miksa

Steinke

Trzeciak

et al. 2021

Macro Chemistry & Physics

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“…The PSF-Chl conjugate ( 69) is a new nitrogen mustard alkylating agent due to the chloroethylamine functional group of Chl and can be used for future progress in the area of electron-deficient DNA-intercalating ligands with potent anticancer activity. [267] The properties of a cationic phenazine core would provide an innovative method to transport a Chl drug into cells. The in vitro assay revealed that cytotoxic activity of PSF-Chl was two-fold higher in comparison to a parent Chl drug evaluated against the HeLa cell line.…”

Section: Phenosafranin Hybrid Conjugatesmentioning

confidence: 99%

“…The in vitro assay revealed that cytotoxic activity of PSF-Chl was two-fold higher in comparison to a parent Chl drug evaluated against the HeLa cell line. [267] Thus, the conjugate has chemotherapeutic potency. Moreover, Chl labeled with a photosensitive PSF molecule can be more convenient for monitoring the course and efficacy of anticancer therapy at the same time, because PSF-Chl works as a theranostic compound (a fluorescent marker that can provide a closer relationship between diagnostics and therapy).…”

Section: Phenosafranin Hybrid Conjugatesmentioning

confidence: 99%

“…The flat, cationic PSF molecule was covalently linked with chlorambucil (Chl) usually applied in leukemia treatments. The PSF‐Chl conjugate ( 69 ) is a new nitrogen mustard alkylating agent due to the chloroethylamine functional group of Chl and can be used for future progress in the area of electron‐deficient DNA‐intercalating ligands with potent anticancer activity [267] . The properties of a cationic phenazine core would provide an innovative method to transport a Chl drug into cells.…”

Section: Phenosafranin Hybrid Conjugatesmentioning

confidence: 99%

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The Phenazine Scaffold Used as Cytotoxic Pharmacophore Applied in Bactericidal, Antiparasitic and Antitumor Agents

Miksa

2022

Helvetica Chimica Acta

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Phenazine derivatives are important bactericidal antibiotics and antiparasitic compounds which can be used in synergistic combinations with anticancer drugs in chemotherapy treatments. The development of synthetic phenazines with anticancer activity improves the effectiveness of chemotherapy. Chemical variations introduced at the phenazine core which is known as a chromophore with fluorescent properties provide advanced theranostic agents useful in optical bioimaging techniques and photodynamic anticancer therapy. This review summarizes the field of structural modifications of phenazine derivatives which have been tested against different parasitic and bacterial infections. The report highlights advances in design and biological evaluations of phenazines as anticancer drugs for the development of new chemotherapeutic as well as bio‐imaging reagents.

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“…Generally, such effects have been ascribed to the polarity sensed by the dye in the confined surroundings, which usually differs from that of the bulk solvent. This has led to use dyes as fluorescent probes for imaging and disease treatment and for characterizing micro and nanoenvironments , which can be used as models of biological media. Another relevant application of confined dyes is as photoinitiating system of vinyl polymerization, in the presence of an electron donor.…”

Section: Introductionmentioning

confidence: 99%

A Comparative Study on the Photophysical and Photochemical Properties of Dyes in the Presence of Low Generation Amino‐terminated Polyamidoamine Dendrimers

Grassano

Altamirano

Militello

et al. 2018

Photochem & Photobiology

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The photophysical and photochemical properties of the xanthene dyes mercurochrome (MCr) and eosin-Y (Eos); and the phenazine dye safranine-O (SF) are evaluated in the presence of amino-terminated polyamidoamine (PAMAM) dendrimers of low generations. The dendrimers produce a red shift in the UV-vis absorption spectra of the dyes, which increases with concentration and the size of the PAMAM molecule. The Stern-Volmer plots of fluorescence quenching for xanthenic dyes present a downward curvature. It is ascribed to a static mechanism involving a dye-dendrimer binding. A nonlinear fitting of the SV plots allows the calculation of the binding constants. For SF, the fluorescence is only slightly quenched by PAMAMs and the SV plots are linear. The binding constants are in the order K bind (SF) ( K bind (Eos) < K bind (MCr). The difference must be due to important specific structural effects. A decrease in the triplet lifetime and an increase in the absorption of the semireduced form of the dyes are observed in the presence of dendrimers. While for the two xanthene dyes, the rate constants reach the diffusional limit for G2 and G3, for SF they are one order of magnitude lower. This is explained by a different quenching mechanism of the two types of dyes.

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Chlorambucil labelled with the phenosafranin scaffold as a new chemotherapeutic for imaging and cancer treatment

Cited by 10 publications

References 53 publications

Thermostable Fluorescent Capsules with the Cross‐Linked Heterocyclic Polymer Shell from Poly(pyrrole‐phenosafranin)

Thermostable Fluorescent Capsules with the Cross‐Linked Heterocyclic Polymer Shell from Poly(pyrrole‐phenosafranin)

The Phenazine Scaffold Used as Cytotoxic Pharmacophore Applied in Bactericidal, Antiparasitic and Antitumor Agents

A Comparative Study on the Photophysical and Photochemical Properties of Dyes in the Presence of Low Generation Amino‐terminated Polyamidoamine Dendrimers

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