Seco-Duocarmycin MA - CAS 1613286-57-9
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Seco-Duocarmycin MA - CAS 1613286-57-9 Catalog number: BADC-00342

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Seco-Duocarmycin MA is a cytotoxic agent, used as the cytotoxic component in antibody-drug conjugates.

Category
ADCs Cytotoxin
Product Name
Seco-Duocarmycin MA
CAS
1613286-57-9
Catalog Number
BADC-00342
Molecular Formula
C34H31ClN4O5
Molecular Weight
611.09
Purity
≥95%
Target
DNA
Seco-Duocarmycin MA

Ordering Information

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BADC-00342 -- $-- Inquiry

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Description
Seco-Duocarmycin MA is a cytotoxic agent, used as the cytotoxic component in antibody-drug conjugates.
Synonyms
Carbamic acid, N-​[4-​[[[2-​[[(1S)​-​1-​(chloromethyl)​-​1,​2-​dihydro-​5-​hydroxy-​3H-​benz[e]​indol-​3-​yl]​carbonyl]​-​1H-​indol-​6-​yl]​amino]​carbonyl]​phenyl]​-​, 1,​1-​dimethylethyl ester;
IUPAC Name
tert-butyl N-[4-[[2-[(1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydrobenzo[e]indole-3-carbonyl]-1H-indol-6-yl]carbamoyl]phenyl]carbamate
Canonical SMILES
CC(C)(C)OC(=O)NC1=CC=C(C=C1)C(=O)NC2=CC3=C(C=C2)C=C(N3)C(=O)N4CC(C5=C4C=C(C6=CC=CC=C65)O)CCl
InChI
InChI=1S/C34H31ClN4O5/c1-34(2,3)44-33(43)37-22-11-8-19(9-12-22)31(41)36-23-13-10-20-14-27(38-26(20)15-23)32(42)39-18-21(17-35)30-25-7-5-4-6-24(25)29(40)16-28(30)39/h4-16,21,38,40H,17-18H2,1-3H3,(H,36,41)(H,37,43)/t21-/m1/s1
InChIKey
MZXQBIDDBQCHFP-OAQYLSRUSA-N
Appearance
Soild powder
Shipping
Room temperature, or blue ice upon request.
1. Structural necessity of indole C5-O-substitution of seco-duocarmycin analogs for their cytotoxic activity
Eunsook Ma, Taeyoung Choi Molecules . 2010 Nov 8;15(11):7971-84. doi: 10.3390/molecules15117971.
A series of racemic indole C5-O-substituted seco-cyclopropylindole (seco-CI) compounds 1-5 were prepared by coupling in the presence of EDCI of 1-(tert-butyloxycarbonyl)-3-(chloromethyl)indoline (seg-A) with 5-hydroxy-, 5-O-methylsulfonyl, 5-O-aminosulfonyl, 5-O-(N,N-dimethylaminosulfonyl)- and 5-O-benzyl-1H-indole-2-carboxylic acid as seg-B. Compounds 1-5 were tested for cytotoxic activity against four human cancer cell lines (COLO 205, SK-MEL-2, A549, and JEG-3) using a MTT assay. Compounds 2 and 3 with small sized sulfonyl substituents like 5-O-methylsulfonyl and 5-O-aminosulfonyl exhibit a similar level of activity as doxorubicin against all cell lines tested.
2. Structural influence of indole C5-N-substitutents on the cytotoxicity of seco-duocarmycin analogs
Eunsook Ma, Taeyoung Choi Arch Pharm Res . 2011 Mar;34(3):357-67. doi: 10.1007/s12272-011-0302-1.
A series of racemic indole C5-substituted seco-cyclopropylindoline compounds (2,3 and 5-7) were prepared by coupling 1-(tert-butyloxycarbonyl)-3-(chlorocarbonyl)indoline (seg-A) with 5,6,7-trimethoxy-, 5,6-dimethoxy-, 5-amino-, 5-methylsulfonylamino- and 5-(N,N-dimethylaminosulfonylamino) indole-2-carboxylic acid as seg-B in the presence of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide. The synthetic compounds (2,3 and 5-7) were tested for cytotoxic activity against human cancer cell lines (COLO 205, SK-MEL-2, A549, and JEG-3) using the MTT assay.
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