Aldoxorubicin

Aldoxorubicin (INNO-206) is a tumor-targeted doxorubicin conjugate in development by CytRx. Specifically, it is the (6-maleimidocaproyl) hydrazone of doxorubicin. Essentially, this chemical name describes doxorubicin attached to an acid-sensitive linker (N-ε-maleimidocaproic acid hydrazide, or EMCH).

CAS Number

• 1361644-26-9

PubChem CID

• 71300693

ChemSpider

• 7986464

UNII

• C28MV4IM0B

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Aldoxorubicin

Identifiers
IUPAC name N-[[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
CAS Number	1361644-26-9
PubChem CID	71300693
ChemSpider	7986464
UNII	C28MV4IM0B
KEGG	D10383
ECHA InfoCard	100.244.879
Chemical and physical data
Formula	C37H42N4O13
Molar mass	750.758 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=NNC(=O)CCCCCN6C(=O)C=CC6=O)CO)O)N)O
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)/t17-,20-,22-,27-,32+,37-/m0/s1 Key:OBMJQRLIQQTJLR-FRTGXRTISA-N

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The proposed mechanism of action is as follows:

1. After administration, aldoxorubicin rapidly binds endogenous circulating albumin through the EMCH linker.
2. Circulating albumin preferentially accumulates in tumors, bypassing uptake by other non-specific sites including heart, bone marrow and gastrointestinal tract.
3. Once albumin-bound aldoxorubicin reaches the tumor, the acidic environment of the tumor causes cleavage of the acid sensitive linker.
4. Free doxorubicin is released at the site of the tumor.