Adriamycin - CAS 23214-92-8

Adriamycin - CAS 23214-92-8 Catalog number: BADC-00039

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Adriamycin is an anthracycline antibiotic produced in Str. peucetius var. caesinus . Adriamycin has anti-Gram-positive bacteria activity and has a broad anti-tumor spectrum. Doxorubicin(Adriamycin) is an antibiotic agent that inhibits DNA topoisomerase II and induces DNA damage and apoptosis.

Category
ADCs Cytotoxin
Product Name
Adriamycin
CAS
23214-92-8
Catalog Number
BADC-00039
Molecular Formula
C27H29NO11
Molecular Weight
543.52
Adriamycin

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Description
Adriamycin is an anthracycline antibiotic produced in Str. peucetius var. caesinus . Adriamycin has anti-Gram-positive bacteria activity and has a broad anti-tumor spectrum. Doxorubicin(Adriamycin) is an antibiotic agent that inhibits DNA topoisomerase II and induces DNA damage and apoptosis.
Synonyms
doxorubicin; Doxil; Adriablastin
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-d
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
InChIKey
AOJJSUZBOXZQNB-TZSSRYMLSA-N
Density
1.61 g/cm3
Solubility
Soluble in ethanol, methanol, DMF or DMSO poor water solubility
Melting Point
204-205 °C
Flash Point
443.8ºC
Index Of Refraction
1.709
Optical Rotation
Specific optical rotation: +248 deg at 20 °C/D (0.1% in methanol)
LogP
1.50360
PSA
206.07000
Vapour Pressure
9.64E-28mmHg at 25°C
UV Spectra
Max absorption (methanol at 56 °C): 290 nm (epsilon = 145, 1%, 1 cm); 477 nm (epsilon = 225, 1%, 1 cm); 495 nm (epsilon = 223, 1%, 1 cm); 530 nm (epsilon = 124, 1%, 1 cm); 233 nm (epsilon = 658, 1%, 1 cm); 253 nm (epsilon = 440, 1%, 1 cm)
Mechanism Of Action
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.
Pharmacology
Doxorubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Doxorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Doxorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
Toxicity (LD50)
LD50=21800 ug/kg (rat, subcutaneous).
In Vitro
Peritoneal macrophages from BD IX rats collected 24 hr after an i.p. injection of Adriamycin (10 mg/kg) were cytotoxic to syngeneic cancer cells in culture. In contrast, incubation in vitro in Adriamycin solutions did not evoke tumoricidal activity in peritoneal macrophages, whatever the incubation time (from 1 to 24 hr) and the Adriamycin concentration (from 1 ng to 100 micrograms/ml).
In Vivo
Macrophages incubated with Adriamycin in vitro accumulated the drug in their nuclei, whereas macrophages from animals receiving Adriamycin in vivo accumulated it is cytoplasmic vacuoles. Early observation of peritoneal cells after in vivo exposure to Adriamycin shows that Adriamycin is concentrated in mast cell granules which are released and then phagocytosed by peritoneal macrophages. Adriamycin fluorescence appears in nuclei of cancer cells incubated with in vivo-labeled macrophages, suggesting that macrophages can directly transfer the drug into cancer cells and therefore play a role in the Adriamycin antitumor effect.
Clinical Trial Information
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT03023124Solitary Fibrous TumorsPhase 22021-11-01Italian Sarcoma GroupRecruiting
NCT01404936LymphomaPhase 22013-02-01M.D. Anderson Cancer CenterCompleted
NCT00107094Breast CancerPhase 12007-07-20Celgene CorporationCompleted
NCT03505164Doxorubicin Adverse Reaction2021-04-27Rush University Medical CenterCompleted
NCT03027063Breast Cancer FemaleNot Applicable2021-01-05Johns Hopkins UniversityCompleted
Application
ADCs Cytotoxin
Source
Streptomyces peucetius
Appearance
Orange to Red Powder
Purity
>98%
Shelf Life
Neutral aq soln are stable at room temp
Shipping
-20°C (International: -20°C)
Storage
Store at -20°C
Pictograms
Irritant; Health Hazard
Signal Word
Danger
Current Developer
Janssen Pharmaceutical K.K.
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.

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