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Purity: ≥98%
Mc-MMAE is a novel protective group for MMAE [(maleimidocaproyl)-conjugated monomethyl auristatin E], which is a highly potent mitotic/tubulin inhibitor, and is a toxin payload/warhead in antibody drug conjugate (ADC). Effective antibody-drug conjugates (ADC) combine efficient intratumoral drug release with high drug-linker stability in circulation. Monomethyl auristatin E (MMAE) was conjugated to the anti-CD30 monoclonal antibody (mAb), cAC10, to generate a potent and selective ADC against models of Hodgkin's disease and CD30(+) anaplastic large cell lymphoma.
| Targets |
Auristatin
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|---|---|
| ln Vitro |
Maleimidocaproic acid must be added to a solution of MMAE in methylene chloride in order to synthesize Mc-MMAE. Diethyl cyanophosphate and diisoacetyl amide must then be added [1].
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| Animal Protocol |
The HRP-MMAE reporter enzyme-drug conjugate is created by thiolating horseradish peroxidase (HRP) with 2-iminothiolane and conjugating it to mc-MMAE. Briefly, a thiolation reaction mixture containing 0.2 mM HRP (8 mg/mL) and 50 mM 2-iminothiolane in 25 mM sodium borate decahydrate (Na2B4O7•10H2O) buffer (pH 9.0) is incubated for 1 hour at 37°C. The removal of unreacted 2-iminothiolane is achieved by passing it through a PD-10 desalting column that has been adjusted to pH 7.4. Peak fractions are combined, and a 3:1 molar ratio is used to couple mc-MMAE to thiolated HRP (HRP-SH). The final conjugation reaction mixture contained 80 μM HRP-SH (3.2 mg/mL) in sodium borate buffer [50 mM H3BO3, 50 mM NaCl (pH 8.0); 80% v/v] and 240 μM mc-MMAE in ice-cold CH3CN (20% v/v). After 30 minutes on ice, the reaction is terminated with a 20-fold molar excess of free cysteine (4.8 mM) before PD-10 chromatography. Peak fractions containing HRP-MMAE (exchanged into PBS) are pooled and evaluated for extent of modification using the thiol-reactive dye, Alexa Fluor 594 C5 maleimide[1].
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| References |
[1]. Sanderson RJ, et al. In vivo drug-linker stability of an anti-CD30 dipeptide-linked auristatin immunoconjugate. Clin Cancer Res. 2005 Jan 15;11(2 Pt 1):843-52
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| Molecular Formula |
C49H78N6O10
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|---|---|
| Molecular Weight |
911.17782
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| Exact Mass |
910.58
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| Elemental Analysis |
C, 64.59; H, 8.63; N, 9.22; O, 17.56
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| CAS # |
863971-24-8
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| Related CAS # |
863971-24-8
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| Appearance |
Solid
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| SMILES |
CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@@H]([C@@H](C)C(=O)N[C@H](C)[C@H](C2=CC=CC=C2)O)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N(C)C(=O)CCCCCN3C(=O)C=CC3=O
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| InChi Key |
UGJOTJHSQWBROP-AXJCKIDNSA-N
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| InChi Code |
InChI=1S/C49H78N6O10/c1-13-32(6)44(37(64-11)29-41(59)54-28-20-23-36(54)46(65-12)33(7)47(61)50-34(8)45(60)35-21-16-14-17-22-35)53(10)49(63)42(30(2)3)51-48(62)43(31(4)5)52(9)38(56)24-18-15-19-27-55-39(57)25-26-40(55)58/h14,16-17,21-22,25-26,30-34,36-37,42-46,60H,13,15,18-20,23-24,27-29H2,1-12H3,(H,50,61)(H,51,62)/t32-,33+,34+,36-,37+,42-,43-,44-,45+,46+/m0/s1
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| Chemical Name |
6-(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
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| Synonyms |
Mc-MMAE; Maleimidocaproyl-monomethylauristatin E
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. (2). This product is not stable in solution, please use freshly prepared working solution for optimal results. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ~180 mg/mL (~197.56 mM)
H2O 中的溶解度: < 0.1 mg/mL |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 4.5 mg/mL (4.94 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 45.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 4.5 mg/mL (4.94 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 45.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.0975 mL | 5.4874 mL | 10.9748 mL | |
| 5 mM | 0.2195 mL | 1.0975 mL | 2.1950 mL | |
| 10 mM | 0.1097 mL | 0.5487 mL | 1.0975 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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