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[ CAS No. 25316-40-9 ] {[proInfo.proName]}

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Chemical Structure| 25316-40-9
Chemical Structure| 25316-40-9
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Product Citations

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Magdalena Szota ; Urszula Szwedowicz ; Nina Rembialkowska , et al. DOI:

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? , et al. DOI: PubMed ID:

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 , et al. DOI: PubMed ID:

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

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Kurowska, Izabela ; Markiewicz, Karolina H. ; Niemirowicz-Laskowska, Katarzyna , et al. DOI: PubMed ID:

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 ; DOI: PubMed ID:

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 , et al. DOI: PubMed ID:

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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Product Details of [ 25316-40-9 ]

CAS No. :25316-40-9 MDL No. :MFCD00077757
Formula : C27H30ClNO11 Boiling Point : -
Linear Structure Formula :- InChI Key :MWWSFMDVAYGXBV-RUELKSSGSA-N
M.W : 579.98 Pubchem ID :443939
Synonyms :
Hydroxydaunorubicin hydrochloride;Doxorubicin (hydrochloride);DOX;Hydroxydaunorubicin HCl;NSC 123127;Adriamycin;Doxorubicin HCl
Chemical Name :(8S,10S)-10-(((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride

Calculated chemistry of [ 25316-40-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 40
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.44
Num. rotatable bonds : 5
Num. H-bond acceptors : 12.0
Num. H-bond donors : 6.0
Molar Refractivity : 139.63
TPSA : 206.07 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.07
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : -1.9
Log Po/w (SILICOS-IT) : 1.17
Consensus Log Po/w : 0.36

Druglikeness

Lipinski : 3.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 3.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -4.63
Solubility : 0.0135 mg/ml ; 0.0000233 mol/l
Class : Moderately soluble
Log S (Ali) : -6.03
Solubility : 0.000545 mg/ml ; 0.00000094 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.2 mg/ml ; 0.000344 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 5.88

Safety of [ 25316-40-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335-H351-H361 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 25316-40-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 25316-40-9 ]

[ 25316-40-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 64987-85-5 ]
  • [ 25316-40-9 ]
  • [ 400647-59-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 20℃;pH Ca. 8;Darkness; To produce the maleimide-functionalized doxorubicin, SMCC was dissolved in DMF with the addition of triethylamine (TEA) to adjust the solution pH to approximately 8, measured roughly with pH paper. To this, 1.1 equivalents of doxorubicin HC1 was added. The mixture was allowed to mix in the dark overnight at room temperature before purification by HPLC using a gradient of 30-90% acetonitrile against 0.1% trifluoroacetic acid over 40 minutes. Retention time for unreacted doxorubicin was 13 minutes, unreacted SMCC was 23.5 minutes, and the product SMCC-Dox was 24.5 minutes.
  • 2
  • [ 64987-85-5 ]
  • [ 25316-40-9 ]
  • C39H44N2O14 [ No CAS ]
  • 3
  • [ 25316-40-9 ]
  • [ 546-43-0 ]
  • C42H49NO13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With sodium hydrogencarbonate; In methanol; water; at 20℃; for 144h; Doxorubicin hydrochloride (250 mg, 0.431 mmol), <strong>[546-43-0]alantolactone</strong> (2, 100.1 mg, 0.431 mmol), andNaHCO3 (72 mg, 0.862 mmol) were dissolved in MeOH (3 mL) and H2O (0.1 mL) and left for 6 d at room temperature. Thecourse of the reaction was monitored by TLC on Silufol plates using CHCl3-MeOH (4:1, Rf of 3b, 0.75). The mixture wasevaporated at reduced pressure and purified by column chromatography over silica gel (20 g) with elution first by CHCl3 andthen by mixtures with added MeOH (10% and 20%). Evaporation afforded the product (144 mg, 43%, 0.186 mmol) as redplate-like crystals, mp 214-220, found: m/z 776.3244 [ + H]+. C42H49NO13. Calcd: 776.3277 [M + H]+. 1 NMR spectrum(CDCl3, , ppm, J/Hz): 0.90 (3H, d, J = 7.4, H-42), 0.9 (1, m, H-34), 1.00 (3H, s, H-41), 1.15 (3H, d, J = 6.5, H-27), 1.21 (1H,m, H-35), 1.32 (2H, m, H-32 + H-36), 1.40 (1H, m, H-34), 1.63 (3H, m, H-23 + H-35), 1.89 (1H, dd, J1 = 14.8, J2 = 2.9,H-32), 1.98 (1H, dd, J1 = 14.9, J2 = 4.2, H-12), 2.20 (1H, d, J = 14.9, H-12), 2.24 (1H, m, H-37), 2.54 (1H, m, H-28), 2.69(1H, m, H-24), 2.79 (3H, m, H-10 + H-28 + H-29), 2.96 (1H, m, H-30), 3.02 (1H, d, J = 18.0, H-10), 3.52 (1H, br.s, H-25),3.89 (4H, m, H-21 + H-26), 4.59 (3H, m, H-20 + H-31), 4.89 (1H, d, J = 2.5, H-39), 5.07 (1H, br.s, H-13), 5.32 (1H, br.s,H-22), 7.26 (1H, m, H-2), 7.62 (1H, t, J = 8.2, H-3), 7.80 (1H, d, J = 8.2, H-4). 13C NMR spectrum (CDCl3, , ppm): 16.5(C-35), 16.6 (C-27), 22.6 (C-42), 28.3 (C-41), 30.0 (C-23), 32.6 (C-36), 32.8 (C-33), 33.4 (C-10), 35.4 (C-12), 37.5 (C-30),38.3 (C-37), 42.0 (C-34), 42.1 (C-28), 42.4 (C-32), 45.7 (C-29), 52.7 (C-24), 56.4 (C-21), 64.9 (C-20), 66.8 (C-25), 67.3(C-26), 69.5 (C-13), 77.3 (C-31), 100.9 (C-22), 114.4 (C-39), 118.6 (C-2), 119.6 (C-4), 135.8 (C-3).
43% With triethylamine; In methanol; chloroform; at 20℃; for 168h; General procedure: The corresponding lactone (I)-(VI)(0.431 mmol) was dissolved in the mixture of methanol(1.5 mL) and chloroform (1.5 mL). Doxorubicinhydrochloride (250 mg) and triethylamine (120 muL,2 equivalents) were added. The reaction mixture waskept seven days at room temperature. The reaction wasmonitored by TLC in the CHCl3-MeOH chromatographicsystem (9 : 1). The product Rf ? 0.5. The reactionmixture was evaporated at a reduced pressure andpurified by column chromatography on silica gel. Thecolumn was eluted with CHCl3 and then with 20%MeOH in chloroform. The product was eluted fromthe column as a narrow zone.
  • 4
  • [ 1151989-04-6 ]
  • [ 25316-40-9 ]
  • C51H51N3O14S2 [ No CAS ]
  • 5
  • [ 1151989-04-6 ]
  • [ 25316-40-9 ]
  • C40H38N2O13S2 [ No CAS ]
  • 6
  • [ 1426827-79-3 ]
  • [ 25316-40-9 ]
  • (1R,8S,9R)-bicyclo[6.1.0]non-4-yn-9-ylmethyl ((2S,3S,4S,6R)-3-hydroxy-2-methyl-6-(((1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl)oxy)tetrahydro-2H-pyran-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;Inert atmosphere; Doxorubicin hydrochloride (DOX, 6.0 mg, 10 μιηο), BCN-OSu (Method S22, 6.0 mg, 21 μπιο, 2x), and DIEA (5.3 mg, 41 μιηο, 4x) were dissolved in minimal DMF and reacted overnight to functionalize doxorubicin with BCN. Complete functionalization of doxorubicin was confirmed via HPLC. The product (DOX-BCN) was used without any further purification.
  • 7
  • [ 1151989-04-6 ]
  • [ 25316-40-9 ]
  • C40H38N2O13S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% Synthesis of Compound 9:Doxorubicin hydrochloride in the dark at room temperature (DOX·HCl, 127 mg, 0.22 mmol, 1 eq)Dissolved into dry dimethylformamide (4 mL),Triethylamine (34 mg, 46 muL, 0.33 mmol, 1.5 eq) was added slowly.The reaction solution was stirred at room temperature for 0.5 hour.Compound 8 (95 mg, 0.23 mmol, 1.05 eq) was added slowly,A solution of traces of 4-dimethylaminopyridine in dimethylformamide (2 mL).The reaction was carried out in the dark at room temperature and poured directly into water. The precipitated solid was filtered, washed with purified water and dried under vacuum.The crude product was further purified by rapid preparative column chromatography (methanol: dichloromethane, 1:50 to 1:10 v/v)Obtained as a dark red solid (61 mg, 34%).
  • 8
  • [ 1151989-04-6 ]
  • [ 25316-40-9 ]
  • doxorubicin [ No CAS ]
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