Spectroelectrochemistry of the redox activation of anti-cancer drug mitoxantrone

Enache, Mirela; Bendic, Cezar; Volanschi, Elena

doi:10.1016/j.bioelechem.2007.10.001

Cited by 20 publications

(22 citation statements)

References 22 publications

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“…It may be inferred that the carbonyl group of a phenyl ketone [(5-ethoxycarbonylmethylidene-4-oxothiazolidine-2-ylidene)-N-phenylethanone] seems to be better in stabilizing the conjugate base than that of N-phenylacetamide and consequently, compound 1 should be more acidic than the related phenylacetamide previously investigated [13]. These results are in line with literature data [42] on the pKa values in DMSO for 4-oxothiazolidine (18.3) and related 6-membered cyclic or acyclic amides (in the range [21][22][23][24]. It was shown that if the increase of acidity of 4-oxothiazolidine is mainly due to the sulphur substitution, the lower acidity of acyclic amide may be due to the steric bulk of the substituted nitrogen, when it is not part of a ring like the lactam substrate.…”

Section: Radicalsupporting

confidence: 92%

“…Therefore a better knowledge of the behaviour of these compounds in electron transfer (ET) reactions in both, protic and aprotic media, as well as the identification and reactivity of the intermediate species involved, is of great importance. Electrochemical methods are best suited for this type of investigation and in conjunction with spectral (UV-Vis and EPR in situ techniques) and solvent dependent theoretical modeling, provide better insight and understanding at molecular level of the reactivity of heterocyclic compounds in redox processes in different media and conditions [20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

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Electrochemical reduction of (5-etoxycarbonylmethylidene-4-oxothiazolidine-2-ylidene)-N-phenylethanone in aprotic medium: A spectroelectrochemical approach

Cekic‐Laskovic

Marković

Minić

et al. 2011

Journal of Electroanalytical Chemistry

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Section: Radicalsupporting

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Electrochemical reduction of (5-etoxycarbonylmethylidene-4-oxothiazolidine-2-ylidene)-N-phenylethanone in aprotic medium: A spectroelectrochemical approach

Cekic‐Laskovic

Marković

Minić

et al. 2011

Journal of Electroanalytical Chemistry

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“…Hayakawa and coworkers have also reported the formation of doxorubicin-based hydrogels through the use of high NaCl concentrations [36], which induce further self-association via π–π stacking of the aggregates. Similar dimerization behavior was also found for the anthracycline-alternative mitoxantrone [37], and for the water-soluble camptothecin derivative irinotecan (CPT-11) [38]. …”

Section: Nanostructure Formed By Free Drugssupporting

confidence: 60%

Building nanostructures with drugs

2016

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The convergence of nanoscience and drug delivery has prompted the formation of the field of nanomedicine, one that exploits the novel physicochemical and biological properties of nanostructures for improved medical treatments and reduced side effects. Until recently, this nanostructure-mediated strategy considered the drug to be solely a biologically active compound to be delivered, and its potential as a molecular building unit remained largely unexplored. A growing trend within nanomedicine has been the use of drug molecules to build well-defined nanostructures of various sizes and shapes. This strategy allows for the creation of self-delivering supramolecular nanomedicines containing a high and fixed drug content. Through rational design of the number and type of the drug incorporated, the resulting nanostructures can be tailored to assume various morphologies (e.g. nanospheres, rods, nanofibers, or nanotubes) for a particular mode of administration such as systemic, topical, and local delivery. This review covers the recent advances in this rapidly developing field, with the aim of providing an in-depth evaluation of the exciting opportunities that this new field could create to improve the current clinical practice of nanomedicine.

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“…It blocks both DNA and RNA expression, and as a consequence protein synthesis, by inhibition of RNA polymerase and transcription in nucleoli and therefore induces cellular p53‐independant apoptosis . It intercalates preferentially between guanine (G) and cytosine (C) base pairs in DNA via the phenoxazone ring and forms strong hydrogen bonds in the minor groove between the 2 pentapeptide side chains and the guanine 2 amino groups, blocking the subsequent chain elongation . ACT is also able to bind externally to DNA, to the terminal GC base pairs, and to interact with double‐ and single‐stranded DNA and some DNA sequences containing no GC binding site .…”

Section: Introductionmentioning

confidence: 99%

An in vitro study of the interaction of the chemotherapeutic drug Actinomycin D with lung cancer cell lines using Raman micro‐spectroscopy

Farhane¹,

Bonnier

Byrne³

2017

Journal of Biophotonics

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The applications of Raman microspectroscopy have been extended in recent years into the field of clinical medicine, and specifically in cancer research, as a non-invasive diagnostic method in vivo and ex vivo, and the field of pharmaceutical development as a label-free predictive technique for new drug mechanisms of action in vitro. To further illustrate its potential for such applications, it is important to establish its capability to fingerprint drug mechanisms of action and different cellular reactions. In this study, cytotoxicity assays were employed to establish the toxicity profiles for 48 and 72 hours exposure of lung cancer cell lines, A549 and Calu-1, after exposure to Actinomycin D (ACT) and Raman micro-spectroscopy was used to track its mechanism of action at subcellular level and subsequent cellular responses. Multivariate data analysis was used to elucidate the spectroscopic signatures associated with ACT chemical binding and cellular resistances. Results show that the ACT uptake and mechanism of action are similar in the 2 cell lines, while A549 cells exhibits spectral signatures of resistance to apoptosis related to its higher chemoresistance to the anticancer drug ACT. The observations are discussed in comparison to previous studies of the similar anthracyclic chemotherapeutic agent Doxorubicin. A, Preprocessed Raman spectrum of ACT stock solution dissolved in sterile water and mean spectrum with SD of (B) nucleolus, (C) nucleus and (D) cytoplasm of A549 cell lines after 48 hours exposure to the corresponding IC 50 . K E Y W O R D SA549, Actinomycin D, binding signature, Calu-1, Raman micro-spectroscopy | INTRODUCTIONRaman micro-spectroscopy is a non-invasive analytical tool, whose potential in clinical applications to distinguish between normal and cancer cells and monitoring drug mechanisms of action has already been demonstrated [1][2][3][4][5]. Therefore, it can potentially be used in preclinical development for the prediction of chemotherapeutic efficacy and potentially ultimately as a companion diagnostic tool. In order to assure its application as a predictive tool, Raman spectroscopy should provide information about drug mechanisms of action and cellular reactions or resistance. Previous studies were made using Raman microspectroscopy and chemotherapeutic drugs such as Cisplatin [6], Vincristine [6], Erlotinib [7], Panitumumab [8] and Doxorubicin (DOX) [9] showing the potential of this

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Spectroelectrochemistry of the redox activation of anti-cancer drug mitoxantrone

Cited by 20 publications

References 22 publications

Electrochemical reduction of (5-etoxycarbonylmethylidene-4-oxothiazolidine-2-ylidene)-N-phenylethanone in aprotic medium: A spectroelectrochemical approach

Electrochemical reduction of (5-etoxycarbonylmethylidene-4-oxothiazolidine-2-ylidene)-N-phenylethanone in aprotic medium: A spectroelectrochemical approach

Building nanostructures with drugs

An in vitro study of the interaction of the chemotherapeutic drug Actinomycin D with lung cancer cell lines using Raman micro‐spectroscopy

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