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DBM-MMAE

  CAS No.: 1912408-87-7   Cat No.: BADC-01413 4.5  

DBM-MMAE is a thiol-reactive drug-linker conjugate used in the synthesis of antibody-drug conjugates (ADCs).

DBM-MMAE

Structure of 1912408-87-7

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Category
ADC Cytotoxin with Linker
Molecular Formula
C49H76Br2N6O10
Molecular Weight
1068.99

* For research and manufacturing use only. We do not sell to patients.

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Synonyms
6-(3,4-dibromo-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-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)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)-N-methylhexanamide; L-Valinamide, N-[6-(3,4-dibromo-2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-N-methyl-L-valyl-N-[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]amino]-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl]-2-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-; N-[6-(3,4-Dibromo-2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-N-methyl-L-valyl-N-[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]amino]-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl]-2-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-L-valinamide
IUPAC Name
6-(3,4-dibromo-2,5-dioxopyrrol-1-yl)-N-[(2S)-1-[[(2S)-1-[[(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]-methylamino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]-N-methylhexanamide
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)N(C)C(=O)CCCCCN3C(=O)C(=C(C3=O)Br)Br
InChI
InChI=1S/C49H76Br2N6O10/c1-13-30(6)42(35(66-11)27-37(59)56-26-20-23-34(56)44(67-12)31(7)45(61)52-32(8)43(60)33-21-16-14-17-22-33)55(10)49(65)40(28(2)3)53-46(62)41(29(4)5)54(9)36(58)24-18-15-19-25-57-47(63)38(50)39(51)48(57)64/h14,16-17,21-22,28-32,34-35,40-44,60H,13,15,18-20,23-27H2,1-12H3,(H,52,61)(H,53,62)/t30-,31+,32+,34-,35+,40-,41-,42-,43+,44+/m0/s1
InChIKey
LCCOGRCIWHHOIG-SWBKYIDTSA-N
Density
1.302±0.06 g/cm3
Boiling Point
1053.5±65.0°C at 760 mmHg

DBM-MMAE, comprising a designed drug-linker conjugate, plays a pivotal role in the innovative field of antibody-drug conjugates (ADCs). ADCs are a significant advancement in targeted cancer therapies, as they combine the high specificity of monoclonal antibodies with the potent cytotoxic effects of chemotherapy agents. This dual ability enables ADCs to selectively target and kill cancer cells while minimizing impact on healthy tissues. As part of this sophisticated system, DBM-MMAE acts as an intermediate that facilitates the effective binding of cytotoxic drugs to monoclonal antibodies. This is especially important in ensuring that the therapeutic agents are released only within or near target cancer cells, thereby maximizing efficacy and reducing systemic side effects.

The core of DBM-MMAE’s functionality is its thiol-reactive maleimide group, which allows it to form stable linkages with cysteine residues on antibodies. This reactivity ensures that the drug-linker can be attached to antibodies with precision, forming a crucial component of ADCs. Once attached, the linker remains stable in the bloodstream but is cleaved once it enters the tumor cells, releasing the cytotoxic payload exactly where it is needed. The most common payload used in combination with DBM for ADCs is Monomethyl Auristatin E (MMAE), a synthetic anti-neoplastic agent that disrupts microtubule formation, leading to cell cycle arrest and apoptosis of cancer cells. This synergy enhances the therapeutic window of cytotoxic drugs, which are otherwise too toxic for systemic administration.

DBM-MMAE has revolutionized drug discovery processes by serving as a prototype for designing new ADC therapeutics. Researchers utilize DBM-MMAE to test and develop novel ADCs that can be tailored to treat specific types of cancer. Its implementation has demonstrated significant improvements in preclinical models, showing increased tumor cell eradication with reduced collateral damage to normal tissues. Furthermore, the ongoing research in modifying and optimizing linkers like DBM enhances the ADC stability and release mechanisms, offering further refinements in therapeutic index. As more monoclonal antibodies against various cancer markers are developed, DBM-MMAE continues to be an invaluable tool in exploratory and translational research phases in oncology.

The specificity of DBM-MMAE also allows for the exploration of personalized medicine approaches. By selecting antibodies that target unique antigens expressed by an individual’s tumor profile, ADCs constructed using DBM-MMAE can provide customized treatment regimens that are far more effective than conventional therapies. Moreover, this capability aligns well with growing clinical demands for precision oncology, paving the way for treatments that are not only effective but also adaptable to individual patient needs. As a result, DBM-MMAE is not just a reactive compound in laboratory settings but a foundational piece in the broader context of cancer treatment innovations, significantly influencing the direction of future therapeutic strategies.

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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