Daunorubicin EP Impurity D (Doxorubicin)
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| Category | Antibiotics |
| Catalog number | BBF-00550 |
| CAS | 23214-92-8 |
| Molecular Weight | 543.52 |
| Molecular Formula | C27H29NO11 |
| Purity | >98% |
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Description
Doxorubicin is an anthracycline antibiotic produced in Str. peucetius var. caesinus. Doxorubicin has anti-Gram-positive bacteria activity and has a broad anti-tumor spectrum. Doxorubicin is an antibiotic agent that inhibits DNA topoisomerase II and induces DNA damage and apoptosis.
Specification
| Related CAS | 25316-40-9 (Hydrochloride) |
| Synonyms | (8S,10S)-10-[(3-amino-2,3,6-trideoxy-α-L-lyxohexopyranosyl)oxy]-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione; Adriamycin; Doxil; Adriablastin; Doxorubicine; Adriblastina; 14-Hydroxydaunomycin; 14-Hydroxydaunorubicine; Caelyx; Hydroxydaunorubicin; NSC-759155; 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-; NSC-123127; (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside; Epirubicin EP Impurity C |
| Shelf Life | Neutral aq soln are stable at room temp |
| Storage | Store at -20°C |
| IUPAC Name | (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione |
| Canonical SMILES | CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O |
| InChI | InChI=1S/C27H29NO11/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/t10-,13-,15-,17-,22+,27-/m0/s1 |
| InChI Key | AOJJSUZBOXZQNB-TZSSRYMLSA-N |
| Source | Streptomyces peucetius |
Properties
| Appearance | Orange to Red Powder |
| Application | ADCs Cytotoxin |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 810.3±65.0°C at 760 mmHg |
| Melting Point | 204-205 °C |
| Flash Point | 443.8ºC |
| Density | 1.61 g/cm3 |
| Solubility | Soluble in DMF, DMSO, Ethanol, Methanol, Water (Poorly) |
| LogP | 1.27 |
Toxicity
| Carcinogenicity | 2A, probably carcinogenic to humans. |
| Mechanism Of Toxicity | Doxorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Doxorubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes. |
| Toxicity | LD50: 21 800 ug/kg (Subcutaneous, Rat). |
Reference Reading
1. Multiwalled carbon nanotube–doxorubicin supramolecular complexes for cancer therapeutics
Hanene Ali-Boucetta, Khuloud T. Al-Jamal, Kostas Kostarelos*. Chem. Commun., 2008, 459–461
In this communication, we describe a previously unreported non-covalent multiwalled nanotube (MWNT)–doxorubicin supra-molecular complex that can be developed for cancer therapy. We have investigated the ability of doxorubicin to interact non-covalently with very thin, pristine MWNT 1 at various mass ratios and evaluated their capability to kill human breast cancer cells. Doxorubicin belongs to a clinically-used family of anthracyclines, therefore constitutes one of the best candidates to test non-covalent complexation with MWNTs. Moreover, doxorubicin 3 is a fluorescent molecule with a chromophore composed of three planar and aromatic hydroxyanthraquinonic rings that are used to monitor its supramolecular interaction with MWNTs. MWNTs were dispersed in water using the tri-block copolymer.
2. Synthesis, in vitro and in vivo anticancer activity of novel 1-(4-imino-1-substituted-1H-pyrazolo[3,4-d] pyrimidin-5(4H)-yl)urea derivatives
Chandra Bhushan Mishra, Raj Kumar Mongre, Shikha Kumari, Dong Kee Jeong* and Manisha Tiwari*. RSC Adv.,2016, 6, 24491–24500
To study apoptosis by flow cytometer, A549 cells were treated with CBS-1 (5 μM and 10 μM) and doxorubicin (10 μM) for 24 h. In result, CBS-1 at 10 μM concentration showed significant (p <0.05) apoptosis against A549 cells and it was found better than doxorubicin (10 μM) as shown in Fig. 6 and Table 3. Result points out that CBS-1 (10 μM) showed 50.98% apoptosis and while doxorubicin (10 mM) displayed 22.74% apoptosis in 24 h. Thus, Hoechst 33342 staining and flow cytometry studies evidently indicate that CBS-1 (10 mM) showed better apoptosis against A549 cells as compared to doxorubicin.
3. Multifunctional ATRP based pH responsive polymeric nanoparticles for improved doxorubicin chemotherapy in breast cancer by proton sponge effect/endo-lysosomal escape
Shantanu V. Lale, Arun Kumar, Farhat Naz, Alok C. Bharti and Veena Koul*. Polym. Chem.,2015, 6,2115–2132
Polymer nanoparticles (NPs) for doxorubicin delivery in breast cancer have been investigated by many researchers to overcome the cardiotoxicity, non-specificity and acquired resistance of cancer cells to current doxorubicin chemotherapy. Polymeric nanoparticles help to improve the bioavailability of doxorubicin by passive targeting of tumors via an enhanced permeation and retention (EPR) effect, by increasing the circulation half-life of doxorubicin and by overcoming acquired cancer cell resistance. These polymeric nanosystems suffer from few drawbacks, which lead to a decreased antitumor efficacy of doxorubicin. Doxorubicin hydrochloride is a water-soluble drug, which makes it difficult to physically load doxorubicin into nanoparticles in sufficient amounts.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C27H29NO11
Molecular Weight (Monoisotopic Mass): 543.1741 Da
Molecular Weight (Avergae Mass): 543.5193 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C27H29NO11
Molecular Weight (Monoisotopic Mass): 543.1741 Da
Molecular Weight (Avergae Mass): 543.5193 Da
LC-MS/MS Spectrum - LC-ESI-qTof , Positive
Experimental Conditions
Instrument Type: LC-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C27H29NO11
Molecular Weight (Monoisotopic Mass): 543.1741 Da
Molecular Weight (Avergae Mass): 543.5193 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C27H29NO11
Molecular Weight (Monoisotopic Mass): 543.1741 Da
Molecular Weight (Avergae Mass): 543.5193 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
