The influence of charge and lipophilicity of daunorubicin and idarubicin on their penetration of model biological membranes – Langmuir monolayer and electrochemical studies

Matyszewska, Dorota

doi:10.1016/j.bbamem.2019.183104

Cited by 20 publications

(4 citation statements)

References 46 publications

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“…This confirms previous claims that EPI is a derivative of DOX, and shares a similar mechanism with DOX, while IDA is an analog derived from daunorubicin, another ANT (Kuffel et al, 1992;Minotti et al, 2004). The lipophilic ability could be an underlying factor that leads to the differences in protein profiles, in which IDA has higher lipophilicity than its parent molecule, daunorubicin (Matyszewska, 2020), while daunorubicin has higher lipophilicity than DOX (Matyjaszczyk-Gwarda et al, 2019). Specially, a rat cardiomyoblast study showed the inverse correlation between the lipophilicity of ANT analogs and their toxicity (Matyjaszczyk-Gwarda et al, 2019).…”

Section: Discussionsupporting

confidence: 89%

Translational Proteomics Analysis of Anthracycline-Induced Cardiotoxicity From Cardiac Microtissues to Human Heart Biopsies

et al. 2021

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Anthracyclines, including doxorubicin, idarubicin, and epirubicin, are common antitumor drugs as well as well-known cardiotoxic agents. This study analyzed the proteomics alteration in cardiac tissues caused by these 3 anthracyclines analogs. The in vitro human cardiac microtissues were exposed to drugs in 2 weeks; the proteomic data were measured at 7 time points. The heart biopsy data were collected from heart failure patients, in which some patients underwent anthracycline treatment. The anthracyclines-affected proteins were separately identified in the in vitro and in vivo dataset using the WGCNA method. These proteins engage in different cellular pathways including translation, metabolism, mitochondrial function, muscle contraction, and signaling pathways. From proteins detected in 2 datasets, a protein-protein network was established with 4 hub proteins, and 7 weighted proteins from both cardiac microtissue and human biopsies data. These 11 proteins, which involve in mitochondrial functions and the NF-κB signaling pathway, could provide insights into the anthracycline toxic mechanism. Some of them, such as HSPA5, BAG3, and SH3BGRL, are cardiac therapy targets or cardiotoxicity biomarkers. Other proteins, such as ATP5F1B and EEF1D, showed similar responses in both the in vitro and in vivo data. This suggests that the in vitro outcomes could link to clinical phenomena in proteomic analysis.

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Section: Discussionsupporting

confidence: 89%

Translational Proteomics Analysis of Anthracycline-Induced Cardiotoxicity From Cardiac Microtissues to Human Heart Biopsies

et al. 2021

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“…Tamoxifen [204], Cytarabine [205], 5-Fluorouracil [206,207], Daunorubicin [208,209], β-Lapachone [210], Minerval [211], Miltefosine [212], Tofacitinib [213], Edelfosine [214], Miltefosine [214], Perifosine [214], Camptothecin [215,216], Pirarubicin, Ellipticine [217], Perillyl alcohol [218], Cisplatin [219,220], Doxorubicin [179,217,221], 5-fluorouracil [206];…”

Section: Application and Target Drugs And Pharmaceuticsmentioning

confidence: 99%

“…Indocyanine green [144,170] Potential anticancer drug Curcumin [164,[227][228][229], Aplysiatoxin [230], Bryostatin [231], Phorbol [231], 12,13-dibutyrate [231], Prostratin [231] Antibiotics Imipenem [232], Doripenem [232], Ertapenem [232], Meropenem [232], Ciprofloxacin [233,234], Ciprofloxacin ternary copper complex [235], Daunorubicin [209], Idarubicin [209],…”

Section: Application and Target Drugs And Pharmaceuticsmentioning

confidence: 99%

Mechanistic Understanding from Molecular Dynamics in Pharmaceutical Research 2: Lipid Membrane in Drug Design

2021

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We review the use of molecular dynamics (MD) simulation as a drug design tool in the context of the role that the lipid membrane can play in drug action, i.e., the interaction between candidate drug molecules and lipid membranes. In the standard “lock and key” paradigm, only the interaction between the drug and a specific active site of a specific protein is considered; the environment in which the drug acts is, from a biophysical perspective, far more complex than this. The possible mechanisms though which a drug can be designed to tinker with physiological processes are significantly broader than merely fitting to a single active site of a single protein. In this paper, we focus on the role of the lipid membrane, arguably the most important element outside the proteins themselves, as a case study. We discuss work that has been carried out, using MD simulation, concerning the transfection of drugs through membranes that act as biological barriers in the path of the drugs, the behavior of drug molecules within membranes, how their collective behavior can affect the structure and properties of the membrane and, finally, the role lipid membranes, to which the vast majority of drug target proteins are associated, can play in mediating the interaction between drug and target protein. This review paper is the second in a two-part series covering MD simulation as a tool in pharmaceutical research; both are designed as pedagogical review papers aimed at both pharmaceutical scientists interested in exploring how the tool of MD simulation can be applied to their research and computational scientists interested in exploring the possibility of a pharmaceutical context for their research.

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“…This confirms the prior knowledge that EPI is a derivative of DOX, and shares a similar mechanism with DOX, while IDA is an analog derived from daunorubicin, another ANT [3,4]. The lipophilic ability could be an underlying factor that leads to the differences in protein profiles, in which IDA has higher lipophilicity than its parent molecule, daunorubicin [77], while daunorubicin has higher lipophilicity than DOX [78]. Interestingly, a rat cardiomyoblast study showed the inverse correlation between the lipophilicity of ANT analogs and their toxicity [78].…”

Section: Discussionsupporting

confidence: 84%

The way forward in multi-omics data analyses

Nguyen

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The influence of charge and lipophilicity of daunorubicin and idarubicin on their penetration of model biological membranes – Langmuir monolayer and electrochemical studies

Cited by 20 publications

References 46 publications

Translational Proteomics Analysis of Anthracycline-Induced Cardiotoxicity From Cardiac Microtissues to Human Heart Biopsies

Translational Proteomics Analysis of Anthracycline-Induced Cardiotoxicity From Cardiac Microtissues to Human Heart Biopsies

Mechanistic Understanding from Molecular Dynamics in Pharmaceutical Research 2: Lipid Membrane in Drug Design

The way forward in multi-omics data analyses

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