Doxorubicinol hydrochloride
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04065 |
| CAS | 63950-05-0 |
| Molecular Weight | 582.00 |
| Molecular Formula | C27H32ClNO11 |
| Purity | ≥90% |
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Description
Doxorubicinol is the major metabolite of doxorubicin, which inhibits DNA topoisomerase II by inducing double-stranded DNA breaks.
Specification
| Related CAS | 54193-28-1 (free base) |
| Synonyms | (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-[(1S)-1,2-dihydroxyethyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione Hydrochloride; Adriamycinol Hydrochloride; 13-Dihydrodoxorubicin Hydrochloride; (1S,3S)-3-[(1S)-1,2-Dihydroxyethyl]-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside hydrochloride (1:1); 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-[(1S)-1,2-dihydroxyethyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-, hydrochloride (1:1) |
| Storage | Store at -20°C, Under Inert Atmosphere |
| IUPAC Name | (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-9-[(1S)-1,2-dihydroxyethyl]-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride |
| Canonical SMILES | CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(CO)O)O)N)O.Cl |
| InChI | InChI=1S/C27H31NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15-17,22,29-31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,16-,17-,22+,27-;/m0./s1 |
| InChI Key | ORLHIGGRLIJIIM-PNOIAXSSSA-N |
Properties
| Appearance | Red to Dark Red Solid |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 188-192°C |
| Solubility | Soluble in DMSO (Slightly), Methanol (Slightly) |
Reference Reading
1. Development of doxorubicin hydrochloride-loaded whey protein nanoparticles and its surface modification with N-acetyl cysteine for triple-negative breast cancer
Samipta Singh, Priyanka Maurya, Soniya Rani, Nidhi Mishra, Raquibun Nisha, Priya Singh, Shubhini A Saraf Drug Deliv Transl Res. 2022 Dec;12(12):3047-3062. doi: 10.1007/s13346-022-01169-8. Epub 2022 Apr 30.
Limited targeted therapies are available for triple-negative breast cancer (TNBC). Thus, the current research focused on developing a targeted protein nanoparticle for TNBC. First, the doxorubicin hydrochloride (Dox)-loaded genipin-crosslinked whey protein nanoparticles (WD) were prepared and optimised by the QbD method using BBD. The hydrodynamic diameter of WD was found to be 364.38 ± 49.23 nm, zeta potential -27.59 ± 1.038 mV, entrapment 63.03 ± 3.625% and Dox loading was found to be 1.419 ± 0.422%. The drug recovery after 18 months of storage was 69%. Then, it was incubated with NAC to obtain modified WD (CyWD). WD followed first-order release kinetics, whereas CyWD followed the Higuchi model. Hemagglutination and hemolysis were not found qualitatively in WD and CyWD. Upon injecting the nanoformulations to 4T1-induced mice, the highest efficacy was found to be in CyWD followed by WD and Dox injection. Upon histopathological observance, it was found that the CyWD group gave the most significant damage to the 4T1 tumour tissue. Thus, NAC-modified protein nanoparticles carrying chemotherapeutic agents can be an excellent targeted therapeutic system against TNBC.
2. Absorption behavior of doxorubicin hydrochloride in visible region in different environments: a combined experimental and computational study
Cheng Giuseppe Chen, Alessandro Nicola Nardi, Mauro Giustini, Marco D'Abramo Phys Chem Chem Phys. 2022 May 18;24(19):12027-12035. doi: 10.1039/d1cp05182b.
The experimental absorption measurements in the interval 350-600 nm (Vis), molecular dynamics simulations, quantum-mechanics calculations and an advanced molecular treatment of simulation data are here combined to provide a complete picture of the absorption behavior in the visible portion of the electromagnetic spectrum of the doxorubicin hydrochloride (DX) molecule in different environments. By such an approach, we have shown that it is possible to characterize the effect of the environment on the DX absorption behavior - including the vibronic contributions - as well as to interpret such differences in terms of molecular electronic excited states, which are found to be strongly influenced by the environment.
3. Highly Efficient Encapsulation of Doxorubicin Hydrochloride in Metal-Organic Frameworks for Synergistic Chemotherapy and Chemodynamic Therapy
Lijia Yao, Ying Tang, Wenqian Cao, Yuanjing Cui, Guodong Qian ACS Biomater Sci Eng. 2021 Oct 11;7(10):4999-5006. doi: 10.1021/acsbiomaterials.1c00874. Epub 2021 Sep 22.
Iron-based metal-organic frameworks (MOFs) have been reported to have great potential for encapsulating doxorubicin hydrochloride (DOX), which is a frequently used anthracycline anticancer drug. However, developing a facile approach to realize high loading capacity and efficiency as well as controlled release of DOX in MOFs remains a huge challenge. Herein, we synthesized water-stable MIL-101(Fe)-C4H4 through a microwave-assisted method. It was found the nano-MOFs acted as nanosponges when soaked in a DOX alkaline aqueous solution with a loading capacity experimentally up to 24.5 wt %, while maintaininga loading efficiency as high as 98%. The mechanism of the interaction between DOX and nanoMOFs was investigated by absorption spectra and density functional theory (DFT) calculations, which revealed that the deprotonated DOX was electrostatically adsorbed to the unsaturated Fe3OCl(COO)6·H2O (named Fe3 trimers). In addition, the as-designed poly(ethylene glycol-co-propylene glycol) (F127) modified nanoparticles (F127-DOX-MIL) could be decomposed under the stimulation of glutathione (GSH) and ATP. As a result, DOX and Fe(III) ions were released, and they could undergo a Fenton-like reaction with the endogenous H2O2 to generate the highly toxic hydroxyl radical (·OH). The in vitro experiments indicated that F127-DOX-MIL could cause remarkable Hela cells inhibition through chemotherapy and chemodynamic therapy. Our study provides a new strategy to design a GSH/ATP-responsive drug-delivery nanosystem for chemo/chemodynamic therapy.
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Bio Calculators
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