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Daunorubicin hydrochloride

  CAS No.: 23541-50-6   Cat No.: BADC-00041   Purity: >98% HNMR HPLC MS 4.5  

Daunorubicin hydrochloride is a classic ADC payload intercalating DNA and inhibiting topoisomerase II, inducing apoptosis. It remains a valuable ADC cytotoxin for targeted hematologic and solid tumor therapies.

Daunorubicin hydrochloride

Structure of 23541-50-6

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Category
ADC Cytotoxin
Molecular Formula
C27H30ClNO10
Molecular Weight
563.98
Target
DNA Topoisomerase II
Shipping
Room temperature
Storage
Store at -20°C

* For research and manufacturing use only. We do not sell to patients.

Size Price Stock Quantity
1 g $439 In stock

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Popular Publications Citing BOC Sciences Products
Synonyms
RP 13057 Hydrochloride; Daunomycin; RP13057 Hydrochloride; RP-13057 Hydrochloride; Rubidomycin hydrochloride
IUPAC Name
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
Canonical SMILES
CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)C)O)N)O.Cl
InChI
InChI=1S/C27H29NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,14-,16-,17-,22+,27-;/m0./s1
InChIKey
GUGHGUXZJWAIAS-QQYBVWGSSA-N
Solubility
Soluble in DMSO
Melting Point
166-170°C (dec.)
Flash Point
419.5°C
PSA
185.84000
Vapor Pressure
6.99E-26mmHg at 25°C
Appearance
Red to Dark Red Solid
Quantity
Milligrams-Grams
Shelf Life
≥360 days if stored properly
Shipping
Room temperature
Storage
Store at -20°C
Pictograms
Health Hazard; Acute Toxic
Signal Word
Danger
Boiling Point
770°C at 760 mmHg
In Vitro
The mean IC50 value is 0.04 μM for Daunorubicin (Dnr) in Molt-4 cells. Daunorubicin belongs to the anthracyclines, a group of cytotoxic chemotherapeutics. The cytotoxic effects of anthracyclines are caused by DNA intercalation and the ability to interfere with DNA transcription and replication by inhibiting Topoisomerase II as well as by producing reactive oxygen species Daunorubicin inhibits of both DNA and RNA syntheses in HeLa cells over a concentration range of 0.2 through 2 μM. The IC50 value is 0.4 μM for Daunorubicin (Dnr) in human pancreatic cell line L3.6.
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT01802333Acute Myeloid LeukemiaPhase 32018-12-19National Cancer Institute (NCI)Completed
NCT00085124Adult Acute Myeloid Leukemia With 11q23 (MLL) AbnormalitiesPhase 32013-06-05National Cancer Institute (NCI)Completed
NCT00474006ACUTE MYELOGENOUS LEUKEMIAPhase 32011-06-10Cooperative Study Group A for HematologyCompleted
NCT01806571Untreated Adult Acute Myeloid LeukemiaPhase 22020-08-18Mayo ClinicCompleted
NCT02971397Acute Myeloid LeukemiaPhase 22018-11-02Wake Forest University Health SciencesUnknown Verified November 2018 by Wake Forest University Health Sciences. Recruitment status was Active, not recruiting

Daunorubicin hydrochloride is an anthracycline antibiotic and a potent ADC cytotoxin used as an ADC payload in antibody-drug conjugates. Its cytotoxic mechanism involves intercalation into DNA, inhibition of topoisomerase II, and generation of reactive oxygen species (ROS), resulting in DNA strand breaks, replication arrest, and induction of apoptosis in proliferating tumor cells. The hydrochloride salt form enhances solubility and chemical stability, allowing efficient conjugation to monoclonal antibodies through cleavable or non-cleavable linker chemistries. This enables controlled intracellular delivery in targeted ADC applications.

In antibody-drug conjugates, Daunorubicin hydrochloride is covalently linked to antibodies using linker strategies designed to maintain stability in systemic circulation while enabling selective payload release inside target cells. The ADC remains inactive during circulation, reducing off-target cytotoxicity. Upon internalization via receptor-mediated endocytosis, enzymatic or chemical cleavage of the linker releases the active daunorubicin payload. The released compound intercalates into nuclear DNA, inhibits topoisomerase II activity, and induces apoptosis, providing site-specific cytotoxic activity in antigen-expressing tumor cells.

Applications of Daunorubicin hydrochloride include its integration into ADCs targeting hematologic malignancies such as leukemia and lymphoma, as well as solid tumors expressing specific antigens. Its chemical compatibility with diverse linker systems allows optimization of conjugation efficiency, intracellular release kinetics, and pharmacokinetic behavior. Daunorubicin hydrochloride exhibits defined cytotoxic activity in target-expressing tumor cells and supports the development of ADCs with precise mechanisms of DNA damage and apoptosis induction, providing a controlled approach for tumor-targeted therapy in antibody-drug conjugate development.

1.Stability of [(N-pyrrolidine)metylene]daunorubicin in aqueous solutions
Anna Jeli ska, Justyna Uszak. React Kinet Catal Lett (2009) 98:69–75
The hydrolysis of [(N-Pyrrolidine)metylene]daunorubicin hydrochloride (PMD) involves: hydrolysis of protonated molecules of [(N-Pyrrolidine)metylene]daunorubicin hydrochloride (PMD) depending on hydrogen ions and spontaneous hydrolysis of zwitter, unprotonated and monoanions of [(N-Pyrrolidine)metylene]daunorubicin hydrochloride (PMD) under the influence of water. The components of phosphate, acetate and borate buffers do not demonstrate any catalytic effect. [(N-Pyrrolidine)metylene]daunorubicin hydrochloride (PMD) is the most stable at pH 2-4.
2.Administration of Chromium(III) and Manganese(II) as a Potential Protective Approach Against Daunorubicin-Induced Cardiotoxicity: in vitro and in vivo Experimental Evidence
Yang Liu & Debin Wang. Biol Trace Elem Res (2013) 156:253–261
Daunorubicin hydrochloride for injection was supplied by Pfizer Italia S.r.1. Cardiac myosin, prepared and determined according to the protocols of our previous study, was diluted to 0.4 μM with 0.01M Tris–HCl buffer saline (pH 7.4) containing 0.6 M KCl. CrCl3•6H2O and MnCl2•4H2O were purchased from Chinese Medicine (Group) Shanghai Chemical Reagent Company. Other chemical reagents weremade in China and were of analytical grades, and ultrapure water was used throughout the studies.

What is Daunorubicin hydrochloride?

Daunorubicin hydrochloride is an anthracycline cytotoxin that intercalates DNA and inhibits topoisomerase II. It is widely used as an ADC payload for targeted cancer therapy due to its potent DNA-damaging activity when delivered via antibody conjugates.

16/2/2020

Dear BOC Sciences, how does Daunorubicin hydrochloride contribute to ADC therapeutic effects?

Daunorubicin hydrochloride exerts cytotoxic effects selectively in target cells when conjugated to antibodies. This targeted delivery reduces systemic toxicity while maintaining strong DNA-damaging activity to induce apoptosis in tumor cells.

12/5/2018

Dear BOC Sciences, which linkers are suitable for Daunorubicin hydrochloride conjugation?

Daunorubicin hydrochloride can be conjugated via cleavable linkers, including hydrazone or peptide-based linkers. These linkers ensure stable circulation and controlled intracellular release, optimizing ADC stability and efficacy.

8/8/2019

Is Daunorubicin hydrochloride applicable in preclinical ADC studies?

Yes, it is extensively used in preclinical ADC research to study cytotoxicity, pharmacokinetics, and antitumor efficacy. These studies inform ADC design and optimize therapeutic outcomes before clinical development.

25/9/2017

Dear BOC Sciences, what safety precautions should be followed for Daunorubicin hydrochloride?

Handling Daunorubicin hydrochloride requires strict laboratory safety, including PPE, fume hoods, and proper waste disposal, due to its potent DNA-damaging properties and potential systemic toxicity.

15/6/2019

— Dr. David Miller, Senior ADC Researcher (USA)

Daunorubicin hydrochloride from BOC Sciences exhibited outstanding purity, which was critical for our ADC conjugation studies.

8/8/2019

— Dr. John Miller, Principal Investigator (USA)

Daunorubicin hydrochloride from BOC Sciences maintained the highest level of purity across multiple deliveries.

15/6/2019

— Ms. Claudia Fischer, ADC Development Scientist (Germany)

The compound’s reproducibility in our ADC assays highlighted the reliability of BOC Sciences’ production.

25/9/2017

— Dr. Simon Turner, Research Manager (UK)

We were impressed with the comprehensive CoA and timely delivery of Daunorubicin hydrochloride.

16/2/2020

— Mr. Marco Bianchi, Biotech Specialist (Italy)

Daunorubicin hydrochloride performed exceptionally well in conjugation experiments, supporting our pipeline development.

— Dr. Isabelle Laurent, Medicinal Chemist (France)

Working with BOC Sciences for Daunorubicin hydrochloride sourcing has been seamless and professional.

12/5/2018

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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