Structure and Location of Protein Sites Binding Self-Associated Congo Red Molecules with Intercalated Drugs as Compact Ligands—Theoretical Studies

Ptak-Kaczor, Magdalena; Kwiecińska, Klaudia; Korchowiec, Jacek; Chłopaś, Katarzyna; Banach, Mateusz; Roterman, Irena; Jagusiak, Anna

doi:10.3390/biom11040501

Cited by 4 publications

(3 citation statements)

References 22 publications

(30 reference statements)

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“…Additionally, theoretical analyses showed that CR-Dox complexes are bound by BSA. Albumin is negatively charged, but inside the large cleft, it has short basic helices responsible for binding the negatively charged CR and the CR-Dox complex [28]. The results obtained in this study confirm the binding of the model drug (Dox) to CR and the formation of a large complex binding to albumin.…”

Section: Discussionsupporting

confidence: 75%

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Albumin Binds Doxorubicin via Self–Assembling Dyes as Specific Polymolecular Ligands

Jagusiak

Chłopaś

Zemanek

et al. 2022

IJMS

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Congo red (CR) type self−assembled ribbon−like structures (SRLS) were previously shown to interact with some proteins, including albumin. SRLS also complex with some drugs with a flat, ring−shaped structure with aromatic characteristics, intercalating them into their ribbon structure. The combination of interaction with proteins and drug binding by SRLS enables the use of such systems for immunotargeting. It is especially interesting in the case of chemotherapeutic agents. The present experiments aimed to show that the model carrier system composed of supramolecular albumin and Congo red efficiently binds doxorubicin (Dox) and that the drug can be released at reduced pH. The presented results come from the studies on such complexes differing in the molar ratio of CR to Dox. The following methods were used for the analysis: electrophoresis, dialysis, gel filtration, spectral analysis, and analysis of the size of the hydrodynamic radius using the dynamic light scattering method (DLS). The applied methods confirmed the formation of the CR−Dox complex, with large dimensions and changed properties compared with free CR. The presented results show that albumin binds both CR and its complex with Dox. Various CR−Dox molar ratios, 5:1, 2:1, and 1:1, were analyzed. The confirmation of the possibility of releasing the drug from the carriers thus formed was also obtained. The presented research is important due to the search for optimal solutions for the use of SRLS in drug immunotargeting, with particular emphasis on chemotherapeutic agents.

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Section: Discussionsupporting

confidence: 75%

“…Ribbon-like supramolecular systems (SRLS), of which the representative is Congo red, are an example of such systems. Congo red type self-assembled ribbon-like structures (SRLS) were previously shown to interact with some proteins, including albumin [27][28][29]. CR also binds Dox by intercalation.…”

Section: Introductionmentioning

confidence: 99%

Albumin Binds Doxorubicin via Self–Assembling Dyes as Specific Polymolecular Ligands

Jagusiak

Chłopaś

Zemanek

et al. 2022

IJMS

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“…It was also shown that planar DOX molecules can be incorporated into CR aggregates by intercalating the anthraquinone part between CR molecules [ 25 , 26 ]. What is more, CR has the ability to selectively bind to immune complexes and proteins [ 27 , 28 ]. This feature can be used to load supramolecular DOX/CR complexes on drug-carrying proteins, e.g., albumin [ 29 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

Insights into Transfer of Supramolecular Doxorubicin/Congo Red Aggregates through Phospholipid Membranes

Stachowicz-Kuśnierz,

Rychlik,

Korchowiec

et al. 2024

Molecules

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Doxorubicin (DOX) is a commonly used chemotherapeutic drug, from the anthracycline class, which is genotoxic to neoplastic cells via a DNA intercalation mechanism. It is effective and universal; however, it also causes numerous side effects. The most serious of them are cardiotoxicity and a decrease in the number of myeloid cells. For this reason, targeted DOX delivery systems are desirable, since they would allow lowering the drug dose and therefore limiting systemic side effects. Recently, synthetic dyes, in particular Congo red (CR), have been proposed as possible DOX carriers. CR is a planar molecule, built of a central biphenyl moiety and two substituted naphthalene rings, connected with diazo bonds. In water, it forms elongated ribbon-shaped supramolecular structures, which are able to selectively interact with immune complexes. In our previous studies, we have shown that CR aggregates can intercalate DOX molecules. In this way, they preclude DOX precipitation in water solutions and increase its uptake by MCF7 breast cancer cells. In the present work, we further explore the interactions between DOX, CR, and their aggregates (CR/DOX) with phospholipid membranes. In addition to neutral molecules, the protonated doxorubicin form, DXP, is also studied. Molecular dynamics simulations are employed to study the transfer of CR, DOX, DXP, and their aggregates through POPC bilayers. Interactions of CR, DOX, and CR/DOX with model monolayers are studied with Langmuir trough measurements. This study shows that CR may support the transfer of doxorubicin molecules into the bilayer. Both electrostatic and van der Waals interactions with lipids are important in this respect. The former promote the initial stages of the insertion process, the latter keep guest molecules inside the bilayer.

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Congo Red as a Supramolecular Carrier System for Doxorubicin: An Approach to Understanding the Mechanism of Action

Kwiecińska

Stachowicz‐Kuśnierz

Korchowiec

et al. 2022

IJMS

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The uptake and distribution of doxorubicin in the MCF7 line of breast-cancer cells were monitored by Raman measurements. It was demonstrated that bioavailability of doxorubicin can be significantly enhanced by applying Congo red. To understand the mechanism of doxorubicin delivery by Congo red supramolecular carriers, additional monolayer measurements and molecular dynamics simulations on model membranes were undertaken. Acting as molecular scissors, Congo red particles cut doxorubicin aggregates and incorporated them into small-sized Congo red clusters. The mixed doxorubicin/Congo red clusters were adsorbed to the hydrophilic part of the model membrane. Such behavior promoted transfer through the membrane.

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Structure and Location of Protein Sites Binding Self-Associated Congo Red Molecules with Intercalated Drugs as Compact Ligands—Theoretical Studies

Cited by 4 publications

References 22 publications

Albumin Binds Doxorubicin via Self–Assembling Dyes as Specific Polymolecular Ligands

Albumin Binds Doxorubicin via Self–Assembling Dyes as Specific Polymolecular Ligands

Insights into Transfer of Supramolecular Doxorubicin/Congo Red Aggregates through Phospholipid Membranes

Congo Red as a Supramolecular Carrier System for Doxorubicin: An Approach to Understanding the Mechanism of Action

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