MMAE-[d8] - CAS 2070009-72-0

MMAE-[d8] - CAS 2070009-72-0 Catalog number: BADC-00635

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MMAE-[d8] is a labelled analogue of MMAE, which is a potent mitotic inhibitor and a tubulin inhibitor.

Category
ADCs Cytotoxin
Product Name
MMAE-[d8]
CAS
2070009-72-0
Catalog Number
BADC-00635
Molecular Formula
C39H59D8N5O7
Molecular Weight
726.03
MMAE-[d8]

Ordering Information

Catalog Number Size Price Quantity
BADC-00635 10 mg $5990
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Description
MMAE-[d8] is a labelled analogue of MMAE, which is a potent mitotic inhibitor and a tubulin inhibitor.
Synonyms
D8-MMAE; D8-Monomethyl auristatin E
IUPAC Name
(2S)-2,3,4,4,4-pentadeuterio-N-[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-2-[[(2S)-3-methyl-2-(methylamino)butanoyl]amino]-3-(trideuteriomethyl)butanamide
Canonical SMILES
CCC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NC(C)C(C2=CC=CC=C2)O)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)NC
InChI
InChI=1S/C39H67N5O7/c1-13-25(6)34(43(10)39(49)33(24(4)5)42-38(48)32(40-9)23(2)3)30(50-11)22-31(45)44-21-17-20-29(44)36(51-12)26(7)37(47)41-27(8)35(46)28-18-15-14-16-19-28/h14-16,18-19,23-27,29-30,32-36,40,46H,13,17,20-22H2,1-12H3,(H,41,47)(H,42,48)/t25-,26+,27+,29-,30+,32-,33-,34-,35+,36+/m0/s1/i4D3,5D3,24D,33D
InChIKey
DASWEROEPLKSEI-CMHCZSPYSA-N
Density
1.1±0.1 g/cm3
Solubility
Soluble to 100 mg/ml (13774 mm, need ultrasonic) in DMSO
Appearance
Solid Power
Purity
98% by HPLC; 98% atom D
Shelf Life
≥12 months if stored properly
Shipping
Room temperature
Storage
Store at -20°C
Boiling Point
873.5±65.0 °C at 760 mmHg
1.Intracellular Released Payload Influences Potency and Bystander-Killing Effects of Antibody-Drug Conjugates in Preclinical Models
Li F, Emmerton KK, Jonas M, Zhang X, Miyamoto JB, Setter JR, Nicholas ND, Okeley NM, Lyon RP, Benjamin DR, Law CL
Antibody-drug conjugates (ADC) comprise targeting antibodies armed with potent small-molecule payloads. ADCs demonstrate specific cell killing in clinic, but the basis of their antitumor activity is not fully understood. In this study, we investigated the degree to which payload release predicts ADC activity in vitro and in vivo ADCs were generated to target different receptors on the anaplastic large cell lymphoma line L-82, but delivered the same cytotoxic payload (monomethyl auristatin E, MMAE), and we found that the intracellular concentration of released MMAE correlated with in vitro ADC-mediated cytotoxicity independent of target expression or drug:antibody ratios. Intratumoral MMAE concentrations consistently correlated with the extent of tumor growth inhibition in tumor xenograft models. In addition, we developed a robust admixed tumor model consisting of CD30(+) and CD30(-) cancer cells to study how heterogeneity of target antigen expression, a phenomenon often observed in cancer specimens, affects the treatment response. CD30-targeting ADC delivering membrane permeable MMAE or pyrrolobenzodiazepine dimers demonstrated potent bystander killing of neighboring CD30(-) cells. In contrast, a less membrane permeable payload, MMAF, failed to mediate bystander killing in vivo, suggesting local diffusion and distribution of released payloads represents a potential mechanism of ADC-mediated bystander killing. Collectively, our findings establish that the biophysical properties and amount of released payloads are chief factors determining the overall ADC potency and bystander killing. Cancer Res; 76(9); 2710-9.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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