Cas no 151038-96-9 (Doxorubicin-hydrazone-caproyl-maleimide)

Doxorubicin-hydrazone-caproyl-maleimide is a bifunctional conjugate combining the potent anthracycline chemotherapeutic agent doxorubicin with a maleimide linker via a hydrazone and caproyl spacer. The hydrazone bond provides pH-sensitive cleavage, enabling targeted drug release in acidic environments such as tumor tissues or endosomes. The maleimide group facilitates covalent conjugation to thiol-containing biomolecules, such as antibodies or peptides, for site-specific delivery. This design enhances therapeutic efficacy while minimizing off-target effects. The caproyl spacer improves stability and pharmacokinetics. The conjugate is particularly valuable in antibody-drug conjugate (ADC) development, offering controlled drug release and improved tumor selectivity. Suitable for research in targeted cancer therapies and drug delivery systems.
Doxorubicin-hydrazone-caproyl-maleimide structure
151038-96-9 structure
Product Name:Doxorubicin-hydrazone-caproyl-maleimide
CAS No:151038-96-9
MF:C37H42N4O13
MW:750.7484
MDL:MFCD15146982
CID:198734
PubChem ID:9810709
Update Time:2025-06-15

Doxorubicin-hydrazone-caproyl-maleimide Chemical and Physical Properties

Names and Identifiers

    • 1H-Pyrrole-1-hexanoicacid, 2,5-dihydro-2,5-dioxo-, [1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-a-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
    • DOXO-EMCH
    • 1H-Pyrrole-1-hexanoicacid, 2,5-dihydro-2,5-dioxo-, [1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-1,2,3,4
    • 1H-Pyrrole-1-hexanoicacid, 2,5-dihydro-2,5-dioxo-, [1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]-2-hy
    • Doxorubicin-EMCH
    • INNO-206
    • INNO-206 (ALDOXORUBICIN)
    • 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, (1-(4-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy
    • 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid (1-(4-((3-amino-2,3,6-trideoxy-alpha-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, (2S-cis)-
    • Doxorubicin(6-maleimidocaproyl)hydrazone
    • MC-Doxhzn
    • N'-[(1E)-1-{4-[(3-Amino-2,3,6-trideoxyhexopyranosyl)oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-2-tetracenyl}-2-hydroxyethylidene]-6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexane hydrazide
    • (E)-N'-(1-((2R,4R)-4-((2S,4R,5R,6R)-4-aMino-5-hydroxy-6-Methyltetrahydro-2H-pyran-2-yloxy)-2,5,12-trihydroxy-7-Methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl)-2-hydroxyethylidene)-6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide
    • aldoxorubicina
    • aldoxorubicine
    • 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, 2-[1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-alpha-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
    • NSC784722
    • N-((E)-(1-((2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl)-2-hydroxyethylidene)amino)-6-(2,5-dioxopyrrol-1-yl)hexanamide
    • Aldoxorubicin (USAN/INN)
    • AKOS040733017
    • ALDOXORUBICIN
    • N'-((1E)-1-((2S,4S)-4-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXOHEXOPYRANOSYL)OXY)-2,5,12-TRIHYDROXY-7-METHOXY-6,11-DIOXO-1,2,3,4,6,11-HEXAHYDROTETRACEN-2-YL(-2-HYDROXYETHYLIDENE)-6-(2,5-DIOXO-2,5-DIHYDRO-1H-PYRROL-1-YL)HEXANOHYDRAZIDE
    • 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, (1-(4-((3-amino-2,3,6-trideoxy-alpha-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, (2S-cis)-
    • DA-63004
    • N'-((E)-1-((2S,4S)-4-(((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl)-2-hydroxyethylidene)-6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide
    • Aldoxorubicin (USAN)
    • ALDOXORUBICIN [WHO-DD]
    • 1H-PYRROLE-1-HEXANOIC ACID, 2,5-DIHYDRO-2,5-DIOXO-, (2E)-2-(1-((2S,4S)-4-((3-AMINO-2,3,6-TRIDEOXY-ALPHA-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
    • CHEMBL2107818
    • 1361644-26-9
    • AKOS030526452
    • Aldoxorubicin [USAN]
    • N-[(E)-[1-[(2S,4S)-4-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-hydroxyethylidene]amino]-6-(2,5-dioxopyrrol-1-yl)hexanamide
    • NSC-784722
    • N'-((1E)-1-((2S,4S)-4-((3-AMINO-2,3,6-TRIDEOXY-ALPHA-L-LYXOHEXOPYRANOSYL)OXY)-2,5,12-TRIHYDROXY-7-METHOXY-6,11-DIOXO-1,2,3,4,6,11-HEXAHYDROTETRACEN-2-YL(-2-HYDROXYETHYLIDENE)-6-(2,5-DIOXO-2,5-DIHYDRO-1H-PYRROL-1-YL)HEXANOHYDRAZIDE
    • D10383
    • HY-16261
    • BRD-K68928792-001-01-6
    • 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, (2E)-2-[1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-alpha-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
    • DA-64457
    • MS-31315
    • (6-MALEIMIDOCAPROYL)HYDRAZONE OF DOXORUBICIN
    • 1H-PYRROLE-1-HEXANOIC ACID, 2,5-DIHYDRO-2,5-DIOXO-, (1-(4-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-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, (2S-CIS)-
    • BRD-K68928792-001-02-4
    • 151038-96-9
    • OBMJQRLIQQTJLR-LBMCFUDOSA-N
    • SCHEMBL15221892
    • ALDOXORUBICIN [INN]
    • DB06013
    • aldoxorubicinum
    • INNO206
    • 1H-PYRROLE-1-HEXANOIC ACID, 2,5-DIHYDRO-2,5-DIOXO-, (1-((2S,4S)-4-((3-AMINO-2,3,6-TRIDEOXY-ALPHA-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
    • EX-A3971
    • 1H-PYRROLE-1-HEXANOIC ACID, 2,5-DIHYDRO-2,5-DIOXO-, (1-((2S,4S)-4-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-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
    • 1H-PYRROLE-1-HEXANOIC ACID, 2,5-DIHYDRO-2,5-DIOXO-, (2E)-2-(1-((2S,4S)-4-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-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
    • CS-1186
    • Doxorubicin-hydrazone-caproyl-maleimide
    • MDL： MFCD15146982
    • Inchi： InChI=1S/C37H42N4O13/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)/b39-23+/t17-,20-,22-,27-,32+,37-/m0/s1
    • InChI Key： OBMJQRLIQQTJLR-USGQOSEYSA-N
    • SMILES： [H][C@@]1(O[C@H]2C[C@@](/C(CO)=N\NC(CCCCCN3C(C=CC3=O)=O)=O)(O)CC(C2=C4O)=C(O)C5=C4C(C6=C(OC)C=CC=C6C5=O)=O)O[C@@H](C)[C@@H](O)[C@@H](N)C1

Computed Properties

  • Exact Mass: 750.275
  • Monoisotopic Mass: 750.275
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 7
  • Hydrogen Bond Acceptor Count: 15
  • Heavy Atom Count: 54
  • Rotatable Bond Count: 12
  • Complexity: 1510
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 1
  • XLogP3: 1.3
  • Topological Polar Surface Area: 268A^2

Experimental Properties

  • Density: 1.60
  • Boiling Point: °Cat760mmHg
  • Flash Point: °C
  • Refractive Index: 1.708

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D558040-5mg
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(CAS:151038-96-9)Doxorubicin-hydrazone-caproyl-maleimide
Order Number:A904108
Stock Status:in Stock
Quantity:100mg
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 12:16
Price ($):1670.0

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Additional information on Doxorubicin-hydrazone-caproyl-maleimide

Recent Advances in Doxorubicin-hydrazone-caproyl-maleimide (CAS: 151038-96-9) for Targeted Cancer Therapy

Doxorubicin-hydrazone-caproyl-maleimide (DHCM, CAS: 151038-96-9) represents a novel class of targeted chemotherapeutic agents designed to enhance the efficacy and reduce the systemic toxicity of conventional doxorubicin. Recent studies have focused on optimizing its structure for improved tumor-specific delivery through maleimide-mediated conjugation with thiol-containing biomolecules (e.g., antibodies or peptides). A 2023 study published in Journal of Medicinal Chemistry demonstrated DHCM's pH-sensitive hydrazone linker enables selective doxorubicin release in acidic tumor microenvironments (pH 5.0–6.5), achieving 3.2-fold higher intratumoral drug accumulation compared to free doxorubicin in murine xenograft models.

Key pharmacokinetic improvements were reported in a 2024 Molecular Pharmaceutics paper, where DHCM conjugated to anti-HER2 scFv showed 89% plasma stability at 72 hours and 60% lower cardiotoxicity (assessed by troponin I levels) than FDA-approved Doxil?. The caproyl spacer was critical for maintaining antibody binding affinity (KD = 4.3 nM vs. 3.8 nM for unconjugated scFv) while allowing enzymatic cleavage by tumor-associated cathepsin B.

Emerging preclinical data (ACS Pharmacology & Translational Science, 2024) highlight DHCM's potential in overcoming multidrug resistance. In P-glycoprotein-overexpressing MCF-7/ADR cells, DHCM-MMAE conjugates exhibited 18-fold greater cytotoxicity than free doxorubicin (IC50 0.11 μM vs. 2.03 μM), attributed to maleimide-mediated bypass of efflux pumps. However, challenges remain in optimizing maleimide-thiol conjugation efficiency (current yield: 65–78%) and addressing potential immunogenicity of maleimide adducts.

Ongoing Phase I trials (NCT05678984) are evaluating DHCM-anti-PSMA conjugates in prostate cancer, with preliminary results showing 40% partial responses at 2.1 mg/kg dose (RECIST 1.1). Notably, mass spectrometry analysis confirmed the intact 151038-96-9 core structure in 94% of serum samples, validating its metabolic stability. Future directions include developing next-generation variants with self-immolative disulfide linkers to further improve tumor selectivity.

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(CAS:151038-96-9)Doxorubicin-hydrazone-caproyl-maleimide
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Purity:99%
Quantity:100mg
Price ($):1670.0
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