A prodrug form of doxorubicin
Related Products
Active Metabolite(s)
15007Doxorubicin (hydrochloride)
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Aldoxorubicin (hydrochloride)

Item No. 35311

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,5-dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid, 2-[1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]-2-hydroxyethylidene]hydrazide, hydrochloride
CAS Number
480998-12-7
Synonyms
  • DOXO-EMCH
  • Doxorubicin (6-maleimidocaproyl)hydrazone
  • INNO-206
  • MC-DOXHZN
Molecular Formula
C37H42N4O13 • HCl
Formula Weight
787.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleEthanol: soluble
SMILES
OC1=C(C(C2=CC=CC(OC)=C2C3=O)=O)C3=C(O)C4=C1C[C@](C(CO)=NNC(CCCCCN5C(C=CC5=O)=O)=O)(O)C[C@@H]4O[C@H]6C[C@@H]([C@@H]([C@@H](O6)C)O)N.Cl
InChi Code
InChI=1S/C37H42N4O13.ClH/c1-17-32(46)20(38)13-27(53-17)54-22-15-37(51,23(16-42)39-40-24(43)9-4-3-5-12-41-25(44)10-11-26(41)45)14-19-29(22)36(50)31-30(34(19)48)33(47)18-7-6-8-21(52-2)28(18)35(31)49;/h6-8,10-11,17,20,22,27,32,42,46,48,50-51H,3-5,9,12-16,38H2,1-2H3,(H,40,43);1H/t17-,20-,22-,27-,32+,37-;/m0./s1
InChi Key
NGKHWQPYPXRQTM-USZGXNDZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    5 mg

    $97

    Add

    10 mg

    $174

    Add

    25 mg

    $291

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Aldoxorubicin is a prodrug form of the anthracycline antitumor antibiotic doxorubicin (Item No. 15007).1 Aldoxorubicin selectively binds to serum albumin, which releases doxorubicin in acidic environments, such as the tumor microenvironment. It inhibits the proliferation of RenCa renal cell carcinoma cells as well as MCF-7 breast and LXFL 529 lung cancer cells (IC50s = 1, 1.1, and 0.5 µM, respectively). Aldoxorubicin (39.3 µmol/kg) induces tumor regression in an MDA-MB-435 breast cancer mouse xenograft model. Unlike doxorubicin, aldoxorubicin is not toxic to mice (LD50 = >60 mg/kg).2 It has also been used to conjugate doxorubicin to antibodies.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kratz, F., Warnecke, A., Scheuermann, K., et al. Probing the cysteine-34 position of endogenous serum albumin with thiol-binding doxorubicin derivatives. Improved efficacy of an acid-sensitive doxorubicin derivative with specific albumin-binding properties compared to that of the parent compound. J. Med. Chem. 45(25), 5523-5533 (2002).

    2. Kratz, F., Ehling, G., Kauffmann, H.M., et al. Acute and repeat-dose toxicity studies of the (6-maleimidocaproyl)hydrazone derivative of doxorubicin (DOXO-EMCH), an albumin-binding prodrug of the anticancer agent doxorubicin. Hum. Exp. Toxicol. 26(1), 19-35 (2007).

    3. Willner, D., Trail, P.A., Hofstead, S.J., et al. (6-Maleimidocaproyl)hydrazone of doxorubicin—a new derivative for the preparation of immunoconjugates of doxorubicin. Bioconjug. Chem. 4(6), 521-527 (1993).