aldoxorubicin-hcl

InvivoChem Cat #:V4149CAS #:480998-12-7Purity >=98%

Description: Aldoxorubicin HCl (also known as MC-DOXHZN; INNO-206, Doxo-EMCH, INNO-206) is a prodrug of doxorubicin and 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-epsilon-maleimidocaproic acid hydrazide, or EMCH). After administration, aldoxorubicin rapidly binds endogenous circulating albumin through the EMCH linker. Circulating albumin preferentially accumulates in tumors, bypassing uptake by other non-specific sites including heart, bone marrow and gastrointestinal tract. Once albumin-bound aldoxorubicin reaches the tumor, the acidic environment of the tumor causes cleavage of the acid sensitive linker.Free doxorubicin is released at the site of the tumor.

Description:

References: The Open Drug Delivery Journal, 2008, 2, 77-85.

References:

Related CAS#: 1361644-26-9 (free base) or 151038-96-9

-20C for 3 years in powder form

Synonym: MC-DOXHZN hydrochloride; Doxorubicin(6-maleimidocaproyl)hydrazone hydrochloride; DOXO-EMCH; EMCH-Doxo; EMCH-doxorubicin; INNO206; INNO-206; INNO 206; INNO-206 HCl; Aldoxorubicin.
IUPAC/Chemical Name: (E)-N'-(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 hydrochloride
InChi Key: NGKHWQPYPXRQTM-UKFSEGPMSA-N
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/b39-23+; /t17-, 20-, 22-, 27-, 32+, 37-; /m0./s1
SMILES Code: O=C(CCCCCN1C(C=CC1=O)=O)N/N=C(CO)/[C]2(O)CC3=C(C4=C(C(O)=C3[CH](C2)O[CH]5O[CH]([CH]([CH](C5)N)O)C)C(C6=C(C=CC=C6C4=O)OC)=O)O.[H]Cl