Auristatin F

Alias: Auristatin F

Cat No.:V11901 Purity: ≥98%

COA Product Data Instructions for use SDS

Auristatin F is anMMAF analogused as a cytotoxin in ADC (Antibody-drug conjugates) synthesis, acting as highlypotent antimitotic agent/tubulin inhibitor and anticancer agent thatinhibits tubulin polymerization.

Auristatin F Chemical Structure CAS No.: 163768-50-1
Product category: ADC Cytotoxin

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

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1g
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Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

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J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

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Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Analogous to MMAF, auristatin F is a strong cytotoxin found in antibo-conjugated agents. Vascular damaging agent (VDA) and strong microtubule inhibitor is auristatin F. Auristatin F stops tubulin from aggregating, which stops cell division. One application for auristatin F is in antibody-drug conjugates (ADC).

Biological Activity I Assay Protocols (From Reference)

Targets	Microtubule[1]
ln Vitro	In antibody-drug conjugates, Auristatin F and Monomethyl Auristatin F (MMAF) are strong ADC cytotoxins[1].
ln Vivo	8276.76 ng/mL is the Cmax of auristatin F (5 mg/kg; i.v.; male Sprague-Dawley rats). The clearance (CL) is 77.33 mL/min/kg, which is higher than the rat's hepatic blood flow, and the AUClast is 65661.30 min*ng/mL[2].
Animal Protocol	Animal Model: Male Sprague-Dawley rats[2] Dosage: 5 mg/kg Administration: Intravenous injection
References	[1]. SMI-Ribosome inactivating protein conjugates selectively inhibit tumor cell growth. Chem Commun (Camb). 2017 Apr 11;53(30):4234-4237. [2]. Pharmacokinetic and Metabolism Studies of Monomethyl Auristatin F via Liquid Chromatography-Quadrupole-Time-of-Flight Mass Spectrometry. Molecules. 2019 Jul 29;24(15):2754. [3]. Temming K, et al. Improved efficacy of alphavbeta3-targeted albumin conjugates by conjugation of a novel auristatin derivative. Mol Pharm. 2007 Sep-Oct;4(5):686-94. [3]. 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	C40H67N5O8
Molecular Weight	746.003
Exact Mass	745.50
Elemental Analysis	C, 64.40; H, 9.05; N, 9.39; O, 17.16
CAS #	163768-50-1
Related CAS #	Auristatin F-d8
Appearance	Solid powder
SMILES	CC[C@@H]([C@H](N(C([C@@H](NC([C@@H](N(C)C)C(C)C)=O)C(C)C)=O)C)[C@H](OC)CC(N1CCC[C@H]1[C@H](OC)[C@H](C(N[C@H](C(O)=O)CC2=CC=CC=C2)=O)C)=O)C
InChi Key	LGNCNVVZCUVPOT-FUVGGWJZSA-N
InChi Code	InChI=1S/C40H67N5O8/c1-13-26(6)35(44(10)39(49)33(24(2)3)42-38(48)34(25(4)5)43(8)9)31(52-11)23-32(46)45-21-17-20-30(45)36(53-12)27(7)37(47)41-29(40(50)51)22-28-18-15-14-16-19-28/h14-16,18-19,24-27,29-31,33-36H,13,17,20-23H2,1-12H3,(H,41,47)(H,42,48)(H,50,51)/t26-,27+,29-,30-,31+,33-,34-,35-,36+/m0/s1
Chemical Name	((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoyl)-L-phenylalanine
Synonyms	Auristatin F
Storage	Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
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 : ~200 mg/mL (~268.10 mM )
Solubility (In Vivo)	Solubility in Formulation 1: ≥ 5 mg/mL (6.70 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 50.0 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: ≥ 5 mg/mL (6.70 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 50.0 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: ≥ 5 mg/mL (6.70 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 50.0 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 : ~200 mg/mL (~268.10 mM )

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 5 mg/mL (6.70 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 50.0 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: ≥ 5 mg/mL (6.70 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 50.0 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: ≥ 5 mg/mL (6.70 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 50.0 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	1.3405 mL	6.7024 mL	13.4048 mL
	5 mM	0.2681 mL	1.3405 mL	2.6810 mL
	10 mM	0.1340 mL	0.6702 mL	1.3405 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:

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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?

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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:

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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
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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)
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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)

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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.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT05755048	Recruiting	Investigational drug: Recombinant Anti-HER2 Humanized Monoclonal Antibody Monomethyl Auristatin F Conjugates for Injection	Breast Cancer	Shanghai Fosun Pharmaceutical Industrial Development Co	March 28, 2023	Phase 3

Biological Data

Effect of the SMI-Sap and SMI(AF)-Sap conjugates on cell viability and proliferation. [1].Chem Commun (Camb). 2017 Apr 11;53(30):4234-4237.

Structure of a RIP1 mutant, Saporin 6 alanine 157 cysteine (A157C), and small the molecule inhibitor of integrins αvβ3 and αvβ5, as well as the potent cytotoxin, Auristatin F used here. [1].Chem Commun (Camb). 2017 Apr 11;53(30):4234-4237.

Flow cytometry analysis showing (a) the αvβ3/αvβ5 integrin expression level in M21 cells, and (b) binding of cpAb 38C2-1, prepared by chemical programming of aldolase Ab 38C2 using a diketone derivative, 1a, of a potent αvβ3/αvβ5 integrin SMI, 1, to M21 and UCLA-P3 tumor cells expressing the target integrins. [1].Chem Commun (Camb). 2017 Apr 11;53(30):4234-4237.