<sup>1</sup>H NMR and IR spectra of antitumour anthracyclines: Effect of the substitution pattern on the chemical shift values of the phenolic protons and on IR absorptions of the quinone system

Vigevani, A.; Ballabio, Marzia; Gandini, E.; Penco, Sergio

doi:10.1002/mrc.1260230513

Cited by 13 publications

(3 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…After the EDC mediated reaction, two absorption bands associated with the formation of amide bonds at 1645 cm –1 (CO, Amide I) and 1565 cm –1 (NH and CN, Amide II) appeared . In addition, the presence of vibration bands related to DOX at 1710 cm –1 , 1617 cm –1 , 1585 cm –1 , and 1540 cm –1 indicated the incorporation of the anticancer drug in the macromolecular structure. − These FTIR results demonstrated the formation of the amide linkage between the COO – group of CMC and amino group (NH 2 ) of the drug. The FTIR analysis of bioconjugates of CMC-DOX modified with RGD sequence (Arg-Gly-Asp) and l -arginine are less evident, because the peptides exhibit characteristic vibrations of asymmetric carboxylate and primary amine (−NH 3 + antisymmetric and symmetric stretching modes and N–H bending) in the range of 1500 cm –1 up to 1640 cm –1 , which are overlapped with CMC, DOX, and amide bonds in FTIR spectra (Figure c and d).…”

Section: Results and Discussionmentioning

confidence: 86%

Design and Development of Polysaccharide-Doxorubicin-Peptide Bioconjugates for Dual Synergistic Effects of Integrin-Targeted and Cell-Penetrating Peptides for Cancer Chemotherapy

et al. 2018

View full text Add to dashboard Cite

Polymer-drug conjugation is an attractive approach for target delivering insoluble and highly toxic drugs to tumor sites to overcome the side-effects caused by cancer chemotherapy. In this study we designed and synthesized novel polymer-drug-peptide conjugates for improved specificity on targeting cancer cells. Chemically modified polysaccharide, carboxymethylcellulose (CMC), was conjugated with doxorubicin (DOX) anticancer drug by amide bonds and dually biofunctionalized with integrin-target receptor tripeptide (RGD) and l-arginine (R) as cell-penetrating amino acid for synergistic targeting and enhancing internalization by cancer cells. These bioconjugates were tested as prodrugs against bone, breast, and brain cancer cell lines (SAOS, MCF7, and U87) and a normal cell line (HEK 293T, reference). The physicochemical characterization showed the formation of amide bonds between carboxylates (-RCOO) from CMC biopolymer and amino groups (-NH) from DOX and peptides (RGD or R). Moreover, these polymer-drug-peptide bioconjugates formed nanoparticulate colloidal structures and behaved as "smart" drug delivery systems (DDS) promoting remarkable reduction of the cytotoxicity toward normal cells (HEK 293T) while retaining high killing activity against cancer cells. Based on cell viability bioassays, DNA-staining, and confocal laser microscopy, this effect was assigned to the association of physicochemical aspects with the difference of the endocytic pathways and the drug release rates in live cells caused by the biofunctionalization of the macromolecule-drug systems with RGD and l-arginine. In addition, chick chorioallantoic membrane (CAM) assay was performed as an in vivo xenograft model test, which endorsed the in vitro results of anticancer activities of these polymer-drug systems. Thus, prodrug nanocarriers based on CMC-DOX-peptide bioconjugates were developed for simultaneously integrin-targeting and high killing efficacy against cancer cells, while preserving healthy cells with promising perspectives in cancer chemotherapy.

show abstract

Section: Results and Discussionmentioning

confidence: 86%

Design and Development of Polysaccharide-Doxorubicin-Peptide Bioconjugates for Dual Synergistic Effects of Integrin-Targeted and Cell-Penetrating Peptides for Cancer Chemotherapy

et al. 2018

View full text Add to dashboard Cite

show abstract

“…To enlighten the interaction between the doxorubicin and the copolymer chains, FT-IR experiments were conducted, and Figure shows that the FTIR-ATR spectra of DOX, MNPs, and NP-DOX recorded in DMEM medium. The assignments were performed according to the literature. − The spectrum of DOX (Figure a) shows well-defined bands at 1582, 1285, 1269, 1211, 1013, and 990 cm –1 assigned to the aromatic moieties of DOX. In addition, the bands at 1724 and 1624 cm –1 were assigned to the CO stretching band and the NH 2 bending band, respectively, which clearly differ from the core/shell MNPs as described above.…”

Section: Resultsmentioning

confidence: 99%

Doxorubicin-Loaded Thermoresponsive Superparamagnetic Nanocarriers for Controlled Drug Delivery and Magnetic Hyperthermia Applications

Ferjaoui

Dine

Kulmukhamedova

et al. 2019

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

This study reports on the development of thermoresponsive core/shell magnetic nanoparticles (MNPs) based on an iron oxide core and a thermoresponsive copolymer shell composed of 2-(2-methoxy)ethyl methacrylate (MEO2MA) and oligo(ethylene glycol)methacrylate (OEGMA) moieties. These smart nano-objects combine the magnetic properties of the core and the drug carrier properties of the polymeric shell. Loading the anticancer drug doxorubicin (DOX) in the thermoresponsive MNPs via supramolecular interactions provides advanced features to the delivery of DOX with spatial and temporal controls. The so coated iron oxide MNPs exhibit superparamagnetic behavior with a saturation magnetization of around 30 emu g–1. Drug release experiments confirmed that only a small amount of DOX was released at room temperature, while almost 100% drug release was achieved after 52 h at 42 °C with Fe3−δO4@P(MEO2MA60OEGMA40), which grafted polymer chains displaying a low critical solution temperature of 41 °C. Moreover, the MNPs exhibit magnetic hyperthermia properties as shown by specific absorption rate measurements. Finally, the cytotoxicity of the core/shell MNPs toward human ovary cancer SKOV-3 cells was tested. The results showed that the polymer-capped MNPs exhibited almost no toxicity at concentrations up to 12 μg mL–1, whereas when loaded with DOX, an increase in cytotoxicity and a decrease of SKOV-3 cell viability were observed. From these results, we conclude that these smart superparamagnetic nanocarriers with stealth properties are able to deliver drugs to tumor and are promising for applications in multimodal cancer therapy.

show abstract

“…These data enabled the assignment of the phenolic hydroxyl groups in the 11-O-methyl compound 11 (6-OH:13.93 ppm; 4-OH: 13.08 ppm). The data are in accordance with the published values for phenolic hydroxy groups in anthracyclines 7. The TMS protective groups in 10 were cleaved quantitatively with O.lN HC1 inCH 2 Cl 2 /methanol at 0 °C.…”

mentioning

confidence: 81%

Semisynthetic 4-O-Methyl-ß-Rhodomycins: Synthesis and Structure-Activity Relationships

Kolář¹,

Gerken²,

Kraemer³

et al. 1990

Journal of Carbohydrate Chemistry

View full text Add to dashboard Cite

The synthesis of 7-0-a-L-daunosaminyl-4-0-methyl-P-rhodomycinone (3) and the determination of its cytotoxic potency compared to that of the natural 7-<9-cc-L-daunosaminyl-p-rhodomycinone (4) are described. Starting with natural P-rhodomycinone (7), trimethylsilyl protecting groups were attached to the hydroxy groups at position 7 and 10, and the 4-OH group was subsequently methylated (MeVCs 2 CO3), thus providing the 4-0-methyl-7,lO-bis-0-trimethylsilyl-p-rhodomycinone (10). The two TMS groups were then deblocked to give 4-0-methyl-P-rhodomycinone (12). In a 3-stage synthesis 12 was converted into 4-O-methyl-10-d-trifluoroacetyl-B-rhodomycinone (15) to which l,4-bis-O-p-nitrobenzoyl-3-A'-trifluoroacetyl-L-daunosamine 16 was selectively linked to afford the 7-O-a-glycoside 17. The acyl protective groups are removed by treatment with lNNaOHtogive3. 223 Copyright© 1990 by Marcel Dekker, Inc. Downloaded by [McMaster University] at 10:22 22 December 2014 224 KOLAR ET AL.

show abstract

¹H NMR and IR spectra of antitumour anthracyclines: Effect of the substitution pattern on the chemical shift values of the phenolic protons and on IR absorptions of the quinone system

Cited by 13 publications

References 29 publications

Design and Development of Polysaccharide-Doxorubicin-Peptide Bioconjugates for Dual Synergistic Effects of Integrin-Targeted and Cell-Penetrating Peptides for Cancer Chemotherapy

Design and Development of Polysaccharide-Doxorubicin-Peptide Bioconjugates for Dual Synergistic Effects of Integrin-Targeted and Cell-Penetrating Peptides for Cancer Chemotherapy

Doxorubicin-Loaded Thermoresponsive Superparamagnetic Nanocarriers for Controlled Drug Delivery and Magnetic Hyperthermia Applications

Semisynthetic 4-O-Methyl-ß-Rhodomycins: Synthesis and Structure-Activity Relationships

Contact Info

Product

Resources

About

1H NMR and IR spectra of antitumour anthracyclines: Effect of the substitution pattern on the chemical shift values of the phenolic protons and on IR absorptions of the quinone system

Cited by 13 publications

References 29 publications

Design and Development of Polysaccharide-Doxorubicin-Peptide Bioconjugates for Dual Synergistic Effects of Integrin-Targeted and Cell-Penetrating Peptides for Cancer Chemotherapy

Design and Development of Polysaccharide-Doxorubicin-Peptide Bioconjugates for Dual Synergistic Effects of Integrin-Targeted and Cell-Penetrating Peptides for Cancer Chemotherapy

Doxorubicin-Loaded Thermoresponsive Superparamagnetic Nanocarriers for Controlled Drug Delivery and Magnetic Hyperthermia Applications

Semisynthetic 4-O-Methyl-ß-Rhodomycins: Synthesis and Structure-Activity Relationships

Contact Info

Product

Resources

About

¹H NMR and IR spectra of antitumour anthracyclines: Effect of the substitution pattern on the chemical shift values of the phenolic protons and on IR absorptions of the quinone system