MMAF Hydrochloride

Alias: Monomethylauristatin F hydrochloride; MMAF hydrochloride

Cat No.:V32943 Purity: ≥98%

COA Product Data Instructions for use SDS

Monomethyl auristatin F (MMAF) HCl is a highly potent tubulin inhibitor and an antineoplastic agent used as a warhead in ADCs (antibody-drug conjugates) such as vorsetuzumab mafodotin and SGN-CD19A.

MMAF Hydrochloride Chemical Structure CAS No.: 1415246-68-2
Product category: Microtubule(Tubulin)

This product is for research use only, not for human use. We do not sell to patients.

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Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Biological Data

Product Description

Monomethyl auristatin F (MMAF) HCl is a highly potent tubulin inhibitor and an antineoplastic agent used as a warhead in ADCs (antibody-drug conjugates) such as vorsetuzumab mafodotin and SGN-CD19A. Mafodotin is the term used in International Nonproprietary Names for MMAF-antibody-conjugates to describe MMAF along with its antibody-binding structure. As opposed to auristatin F, which has two methyl substituents in its N-terminal amino group, MMAF is actually desmethyl-auristatin F.

Biological Activity I Assay Protocols (From Reference)

Targets	Auristatin
ln Vitro	MMAF prevents the growth of anaplastic large cell lymphoma. In vitro cytotoxicity assays yielded IC50 values of 119, 105, 257, and 200 nM for Karpas 299, breast carcinoma H3396, renal cell carcinoma 786-O, and Caki-1 cells[4].
ln Vivo	MMAF has a much higher maximum tolerated dose in mice (>16 mg/kg) than MMAE (1 mg/kg). The MTD of cAC10-L1-MMAF₄ is 15 mg/kg in rats and 50 mg/kg in mice. With MTDs in mice and rats of >150 mg/kg and 90 mg/kg in rats, respectively, the corresponding cAC10-L4-MMAF₄ ADC was significantly less toxic[4].
Cell Assay	Depending on the cell line, cells are treated with serial dilutions of test molecules and incubated for four to six days. The Alamar Blue dye reduction assay is used to evaluate cellular growth and reduce data in order to produce IC50 values[1].
Animal Protocol	Mice: The size of the subcutaneous Karpas 299 tumor is 300 mm³, and three animals per group are given one intravenous injection of either cAC10-L1-MMAF₄ or cBR96-L1-MMAF₄ (10 mg antibody component/kg body weight). Immunohistochemistry evaluation is used to stain 5 μm-thin frozen tissue sections after the tumors have been removed and placed in an optimal cutting temperature compound[1].
References	[1]. EphA2 targeted chemotherapy using an antibody drug conjugate in endometrial carcinoma. Clin Cancer Res. 2010 May 1;16(9):2562-70. [2]. Enzymatic prenylation and oxime ligation for the synthesis of stable and homogeneous protein-drug conjugates for targeted therapy. Angew Chem Int Ed Engl. 2015 Oct 5;54(41):12020-4. [3]. Strategies and Advancement in Antibody-Drug Conjugate Optimization for Targeted CancerTherapeutics. [4]. Enhanced activity of monomethylauristatin F through monoclonal antibody delivery: effects of linker technology on efficacy and toxicity. Bioconjug Chem. 2006 Jan-Feb;17(1):114-24.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C39H66CLN5O8
Molecular Weight	768.4231
Exact Mass	767.4599918
CAS #	1415246-68-2
Related CAS #	MMAF;745017-94-1;MMAF-d8 hydrochloride;MMAF sodium;1799706-65-2;MMAF-OMe;863971-12-4;MMAF-d8
Appearance	Solid
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](CC2=CC=CC=C2)C(=O)O)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC.Cl
InChi Key	BUPKFQQDMNUXOY-KMYLZLQDSA-N
InChi Code	InChI=1S/C39H65N5O8.ClH/c1-12-25(6)34(43(9)38(48)33(24(4)5)42-37(47)32(40-8)23(2)3)30(51-10)22-31(45)44-20-16-19-29(44)35(52-11)26(7)36(46)41-28(39(49)50)21-27-17-14-13-15-18-27;/h13-15,17-18,23-26,28-30,32-35,40H,12,16,19-22H2,1-11H3,(H,41,46)(H,42,47)(H,49,50);1H/t25-,26+,28-,29-,30+,32-,33-,34-,35+;/m0./s1
Chemical Name	(2S)-2-[[(2R,3R)-3-methoxy-3-[(2S)-1-[(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl-[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(methylamino)butanoyl]amino]butanoyl]amino]heptanoyl]pyrrolidin-2-yl]-2-methylpropanoyl]amino]-3-phenylpropanoic acid;hydrochloride
Synonyms	Monomethylauristatin F hydrochloride; MMAF hydrochloride
Storage	Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product is not stable in solution, please use freshly prepared working solution for optimal results. (2). Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)	DMSO: ~27 mg/mL (~35.1 mM) H2O: < 0.1 mg/mL
Solubility (In Vivo)	Solubility in Formulation 1: ≥ 2.5 mg/mL (3.25 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (3.25 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 25.0 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. View More Solubility in Formulation 3: ≥ 2.5 mg/mL (3.25 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 25.0 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.)

Solubility (In Vitro)

DMSO: ~27 mg/mL (~35.1 mM)
H2O: < 0.1 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (3.25 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (3.25 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 25.0 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.

View More

Solubility in Formulation 3: ≥ 2.5 mg/mL (3.25 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 25.0 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	1.3014 mL	6.5069 mL	13.0137 mL
	5 mM	0.2603 mL	1.3014 mL	2.6027 mL
	10 mM	0.1301 mL	0.6507 mL	1.3014 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.

Calculator

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
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See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
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The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
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The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

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Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

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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.

Note： (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.

Biological Data

Effect of MEDI-547 on in vitro tumor cell viability. A, Viability of cultured Hec-1A cells after treatment with 1C1 or antibody drug conjugates (IgG-mcMMAF or MEDI-547). Clin Cancer Res . 2010 May 1;16(9):2562-70.

Effect of MEDI-547 therapy on endometrial cancer growth. Mice inoculated with Hec-1A A, Ishikawa B, or SPEC-2 C, received PBS (control), 1C1, control IgG-mcMMAF, or MEDI-547 (each at 3 mg/kg) after 2 weeks following cell line injection. Clin Cancer Res . 2010 May 1;16(9):2562-70.