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Chemical Structure| 25316-40-9 Chemical Structure| 25316-40-9

Structure of Doxorubicin HCl
CAS No.: 25316-40-9

Chemical Structure| 25316-40-9

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CAS No.: 25316-40-9

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Doxorubicin HCl is an effective inhibitor of DNA topoisomerase I and II, with IC50 values of 0.8 μM and 2.67 μM, respectively. Doxorubicin HCl has cytotoxic properties and induces apoptosis and autophagy, making it a widely used chemotherapeutic agent in cancer treatment.

Synonyms: Hydroxydaunorubicin hydrochloride; Doxorubicin (hydrochloride); DOX

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Magdalena Szota ; Urszula Szwedowicz ; Nina Rembialkowska ; Anna Janicka-Klos ; Daniel Doveiko ; Yu Chen , et al.

Abstract: The unique structure of G4.0 PAMAM allows a drug to be enclosed in internal spaces or immobilized on the surface. In the conducted research, the conditions for the formation of the active G4.0 PAMAM complex with (DOX) were optimized. The physicochemical properties of the system were monitored using dynamic light scattering (DLS), circular dichroism (CD), and fluorescence spectroscopy. The Quartz Crystal Microbalance with Dissipation Monitoring (QCM-D) method was chosen to determine the preferential conditions for the complex formation. The highest binding efficiency of the drug to the cationic was observed under basic conditions when the DOX molecule was deprotonated. The decrease in the zeta potential of the complex confirms that DOX immobilizes through electrostatic interaction with the carrier’s surface groups. The binding constants were determined from the fluorescence quenching of the DOX molecule in the presence of G4.0 PAMAM. The two-fold way of binding doxorubicin in the structure of was visible in the Isothermal calorimetry (ITC) isotherm. Fluorescence spectra and release curves identified the reversible binding of DOX to the nanocarrier. Among the selected cancer cells, the most promising anticancer activity of the G4.0-DOX complex was observed in A375 malignant melanoma cells. Moreover, the preferred intracellular location of the complexes concerning the free drug was found, which is essential from a therapeutic point of view

Keywords: PAMAM dendrimers ; doxorubicin ; dendrimer-doxorubicin interactions ; drug delivery systems ; DDS

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Jachimska, Barbara ; Goncerz, Magdalena ; Wolski, Pawe? ; Meldrum, Callum ; Lustyk, ?ukasz ; Panczyk, Tomasz

Abstract: The work presents correlations between the physicochemical properties of the carrier and the active substance and optimization of the conditions for creating an active system based on PAMAM dendrimers and doxorubicin. The study monitored the influence of the ionized form of the doxorubicin molecule on the efficiency of complex formation. The deprotonated form of doxorubicin occurs under basic conditions in the pH range of 9.0?10.0. In the presence of doxorubicin, changes in the zeta potential of the complex concerning the initial system are observed. These changes result from electrostatic interactions between the drug molecules and external functional groups. Based on changes in the absorbance intensity of UV-vis spectra, the binding of the drug in the polymer structure is observed depending on the pH of the environment and the molar ratio. Optimal conditions for forming complexes occur under alkaline conditions. UV?vis, Fourier transform infrared spectroscopy, and circular dichroism spectroscopy confirmed the stability of the formed dendrimer-DOX complex. Molecular dynamics simulations were conducted to gain a deeper insight into the molecular mechanism of adsorption on and within the G4.0 PAMAM dendrimers. It was observed that the protonation state of both the dendrimer and significantly influences the adsorption stability. The system exhibited high stability at high pH values (～9-10), with molecules strongly adsorbed on the dendrimer surface and partially within its bulk. However, under lower pH conditions, a reduction in adsorption strength was observed, leading to the detachment of clusters from the dendrimer structure.

Keywords: ; doxorubicin ; DDS ; molecular dynamic ; nanotechnology ; dendrimer?drug interactions

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Chen, Jing ; Ji, Peng ; Gnawali, Giri ; Chang, Mengyang ; Gao, Feng ; Xu, Hang , et al.

Abstract: The current targeting drug delivery mainly relies on cancer cell surface receptors. However, in many cases, binding affinities between protein receptors and homing ligands is relatively low and the expression level between cancer and normal cells is not significant. Distinct from conventional targeting strategies, we have developed a general cancer targeting platform by building artificial receptor on cancer cell surface via a chemical remodeling of cell surface glycans. A new tetrazine (Tz) functionalized chemical receptor has been designed and efficiently installed on cancer cell surface as "overexpressed" biomarker through a metabolic glycan engineering. Different from the reported bioconjugation for drug targeting, the tetrazine labeled cancer cells not only locally activate TCO-caged prodrugs but also release active drugs via the unique bioorthogonal Tz-TCO click-release reaction. The studies have demonstrated that the new drug targeting strategy enables local activation of prodrug, which ultimately leads to effective and safe cancer therapy.

Keywords: Artificial receptor ; Click and release ; Local activation ; Protein degradation

Kurowska, Izabela ; Markiewicz, Karolina H. ; Niemirowicz-Laskowska, Katarzyna ; Destarac, Mathias ; Wielgat, Przemyslaw ; Misztalewska-Turkowicz, Iwona , et al.

Abstract: Herein, we report the formation of drug delivery systems from original thermoresponsive block copolymers containing lipid-based segments. Two acrylate monomers derived from palmitic- or oleic-acid-based diacylglycerols (DAGs) were synthesized and polymerized by the reversible addition-fragmentation chain transfer (RAFT) method. Well-defined DAG-based polymers with targeted molar masses and narrow molar mass distributions were next used as macro-chain transfer agents (macro-CTAs) for the polymerization of N-isopropylacrylamide (NIPAAm) or N-vinylcaprolactam (NVCL). The obtained amphiphilic block copolymers were formed into polymeric nanoparticles (PNPs) with and without encapsulated doxorubicin and characterized. Their biol. assessment indicated appropriate cytocompatibility with the representatives of normal cells. Furthermore, compared to the free drug, increased cytotoxicity and apoptosis or necrosis induction in breast cancer cells was documented, including a highly aggressive and invasive triple-neg. MDA-MB-231 cell line.

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Szota, Magdalena ; Jachimska, Barbara ;

Abstract: In this study, special attention was paid to the correlation between the degree of ionization of the components and the effective formation of the complex under alk. conditions. Using UV-Vis, 1H NMR, and CD, structural changes of the drug depending on the pH were monitored. In the pH range of 9.0 to 10.0, the G4.0 PAMAM dendrimer can bind 1 to 10 DOX mols., while the efficiency increases with the concentration of the drug relative to the carrier. The binding efficiency was described by the parameters of loading content (LC = 4.80-39.20%) and encapsulation efficiency (EE = 17.21-40.16%), whose values increased twofold or even fourfold depending on the conditions. The highest efficiency was obtained for G4.0PAMAM-DOX at a molar ratio of 1:24. Nevertheless, regardless of the conditions, the DLS study indicates system aggregation. Changes in the zeta potential confirm the immobilization of an average of two drug mols. on the dendrimer's surface. CD spectra anal. shows a stable dendrimer-drug complex for all the systems obtained. Since the doxorubicin mol. can simultaneously act as a therapeutic and an imaging agent, the theranostic properties of the PAMAM-DOX system have been demonstrated by the high fluorescence intensity observable on fluorescence microscopy.

Keywords: PAMAM dendrimers ; doxorubicin ; drug delivery systems ; nanotechnology ; PAMAM-DOX complex

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Misiak, Pawel ; Niemirowicz-Laskowska, Katarzyna ; Misztalewska-Turkowicz, Iwona ; Markiewicz, Karolina H. ; Wielgat, Przemyslaw ; Car, Halina , et al.

Abstract: The study presents the synthesis of original cholesterol-terminated copolymers comprising acetylacetone-based (AcacI) and N-isopropylacrylamide (NIPAAm) units with a varied arrangement (block and random copolymers). The nanopptn. method was used to form empty and doxorubicin-loaded polymeric nanoparticles (PNPs) from these copolymers, which were further studied in terms of their physicochem. and biol. properties. Unexpectedly, it was revealed that even empty PNPs are effective against breast cancer cells, specifically towards estrogen-dependent MCF-7 cell line. The anti-cancer efficacy was further improved when a low dose of doxorubicin was introduced to the tested systems. It was shown that the proposed carriers modulate doxorubicin (DOX) compatibility with representatives of normal cells, including immune cells, cardiomyocyte cells, and fibroblasts, and reduce side effects associated with standard chemotherapy. The use of these carriers might be a strategy leading to enhancement of DOX activity in cancer cells which develop resistance through decreased drug penetration or drug efflux.

Keywords: Smart drug delivery systems ; Acetylacetone derivative ; Drug carriers ; Cholesterol-end capped poly(N-isopropylacrylamide) ; Cell-penetrating molecules ; Anti-cancer ; Doxorubicin ; Thermoresponsive polymers

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Alternative Products

Product Details of Doxorubicin HCl

CAS No. :25316-40-9
Formula : C27H30ClNO11
M.W : 579.98
SMILES Code : COC1=CC=CC2=C1C(C3=C(C(O)=C4C[C@](O)(C[C@@H](C4=C3O)O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O)N)C(CO)=O)C2=O)=O.[H]Cl
Synonyms :
Hydroxydaunorubicin hydrochloride; Doxorubicin (hydrochloride); DOX
MDL No. :MFCD00077757
InChI Key :MWWSFMDVAYGXBV-RUELKSSGSA-N
Pubchem ID :443939

Safety of Doxorubicin HCl

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335-H351-H361
Precautionary Statements:P261-P305+P351+P338

Related Pathways of Doxorubicin HCl

DNA

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Human Umbilical Vein Endothelial Cells (HUVECs) 1 μM 24 h To evaluate the protective effect of MGN on DOX-induced cytotoxicity in HUVECs, results showed that MGN significantly increased cell viability and reduced DNA fragmentation. PMC8073066
CHO-pAcGFP1-Mem cells 2 μM 2 h and 24 h Measure changes in cell-substrate distances, results showed significant increases in cell-substrate distances after 2 and 24 h. PMC9181088
MCF-7 breast cancer cells 2 μM 2 h Measure changes in cell-substrate distances, results showed significant increases in cell-substrate distances after 2 h. PMC9181088

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1.72mL

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