MonoMethylauristatin F

in vivo

Product Name: MonoMethylauristatin F
CAS No.: 745017-94-1
Chemical Name: MonoMethylauristatin F
Synonyms: MMAF;MonoMethylauristatin;F(MMAF);Tacrinum;745017-97-1;Methyloratatin F;MMAF, 10 mM in DMSO;MonoMethylauristatin F;Thiazole,2-bromo-6-methyl-;MMAF (MonoMethylauristatin F)
CBNumber: CB62667922
Molecular Formula: C39H65N5O8
Formula Weight: 731.96
MOL File: 745017-94-1.mol

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MonoMethylauristatin F Property

Boiling point:: 896.8±65.0 °C(Predicted)
Density: 1.116±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: Soluble in DMSO
form: A solid
pka: 3.56±0.10(Predicted)
color: White to off-white
Stability:: Hygroscopic
InChIKey: MFRNYXJJRJQHNW-UQVYMQKONA-N

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 30197
Product name: MMAF
Packaging: 25mg
Price: $606
Updated: 2024/03/01

Cayman Chemical

Product number: 30197
Product name: MMAF
Packaging: 50mg
Price: $1062
Updated: 2024/03/01

Cayman Chemical

Product number: 30197
Product name: MMAF
Packaging: 5mg
Price: $153
Updated: 2024/03/01

Cayman Chemical

Product number: 30197
Product name: MMAF
Packaging: 10mg
Price: $275
Updated: 2024/03/01

TRC

Product number: M564805
Product name: MonomethylAuristatinF
Packaging: 25mg
Price: $745
Updated: 2021/12/16

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MonoMethylauristatin F Chemical Properties,Usage,Production

in vivo

The maximum tolerated dose in mice of MMAF (Monomethylauristatin F) (>16 mg/kg) is much higher than MMAF (Monomethylauristatin F) (1 mg/kg). cAC10-L1-MMAF4 has an MTD of 50 mg/kg in mice and 15 mg/kg in rats. The corresponding cAC10-L4-MMAF4 ADC was much less toxic, having MTDs in mice and rats of >150 mg/ kg and 90 mg/kg in rats, respectively.

Description

MMAF (Monomethylauristatin F) is an effective tubulin polymerization inhibitor, used as an anti-tumor drug. MMAF (Monomethylauristatin F) is widely used as the cytotoxic component of antibody-conjugated drugs (ADCs), such as Vorsetuzumab mafodotin and SGN-CD19A.

Uses

Monomethyl Auristatin F is an antimicrotubule agent. A potent mitotic inhibitor.

Biological Activity

MMAF (Monomethylauristatin F) is a potent tubulin polymerization inhibitor and is used as a antitumor agent. MMAF (Monomethylauristatin F) is widely used as a cytotoxic component of antibody-drug conjugates (ADCs) such as vorsetuzumab mafodotin and SGN-CD19A.

Biotechnological Applications

MMAF is a new auristatin derivative with a charged C-terminal phenylalanine that attenuates its cytotoxic activity compared to its uncharged counterpart, Monomethyl auristatin E (MMAE). Because of MMAF is highly toxic, it cannot be used as a drug itself. MMAF induces potent antitumor effects when conjugated via protease cleavable linkers to a monoclonal antibody targeting internalizing, tumor-specific cell surface antigens. The linker to the monoclonal antibody is stable in extracellular fluid, but is cleaved by cathepsin once the conjugate has entered a tumor cell, thus activating the anti-mitotic mechanism.

Synthesis

1369427-27-9

745017-94-1

The synthesis of (S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-dimethyl-2-((S)-3-methyl-2-(methylaminopropionamido)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl) was carried out using the compound (CAS: 1369427-27-9) as starting material. (methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid was prepared in the following general steps: (S)-2-((2R,3R)-3-((S)-1-((6S,9S,12S,13R)-12-((S)-sec-butyl)-6,9-diisopropyl-13-methoxy-2,2,5,11-tetramethyl-4,7,10-trioxo-3- oxa-5,8,11-triazatetradecan-15-yl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid (25 mg, 0.030 mmol) was dissolved in a mixture of 0.3 ml of HCl and 0.9 ml of 1,4-dioxane and stirred at room temperature for 35 min. The reaction mixture was diluted with 1.0 ml of ethanol and 1.0 ml of toluene, subsequently concentrated and evaporated again with ethanol/toluene (2:1) to afford the target product (S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butyramido)butanamide (S)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid as a white solid (22 mg, about 400% yield), which can be used in the next reaction without further purification.LC-MS (ESI) m/z calculated value: C39H66N5O8 [M + H]+: 732.48, measured value: 732.60.

in vitro

MMAF inhibits anaplastic large cell lymphoma Karpas 299, breast carcinoma H3396, renal cell carcinoma 786-O and Caki-1 cells with IC50s of 119, 105, 257 and 200 nM in vitro cytotoxicity assay.

References

[1] Patent: WO2015/155753, 2015, A2. Location in patent: Page/Page column 101
[2] Patent: WO2018/86139, 2018, A1. Location in patent: Page/Page column 192; 193
[3] Patent: WO2012/166560, 2012, A1. Location in patent: Page/Page column 165
[4] Patent: WO2013/185117, 2013, A1. Location in patent: Paragraph 00453
[5] Patent: WO2016/59622, 2016, A2. Location in patent: Page/Page column 130

MonoMethylauristatin F Preparation Products And Raw materials

Raw materials

Preparation Products

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MonoMethylauristatin F Suppliers

China 218 Japan 1 United States 15 Global 234

Shanghai ruichang pharmaceutical technology co., LTD

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View Lastest Price from MonoMethylauristatin F manufacturers

Wuhan Topule Biopharmaceutical Co., Ltd

Product: Monomethyl auristatin F 745017-94-1
Price: US $20.00/g
Min. Order: 1g
Purity: 98%
Supply Ability: 5KG
Release date: 2023-06-13

Zhuozhou Wenxi import and Export Co., Ltd

Product: MMAF; Monomethylauristatin F 745017-94-1
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-11

Hebei shuoxi biotechnology co. LTD

Product: Monomethyl auristatin F MMAF 745017-94-1
Price: US $56.00/Kg/Bag
Min. Order: 10g
Purity: 99%
Supply Ability: 20tons
Release date: 2019-10-22

745017-94-1, MonoMethylauristatin FRelated Search:

L-Phenylalanine Fr 1,1,1-Trichlorotrifluoroethane 2,6-Di-tert-butyl-4-(dimethylaminomethyl)phenol F4 (2R,3R)-N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)-3-Methoxy-2-Methyl-3-((S)-pyrrolidin-2-yl)propanaMide (hydrochloride) VcMMAE N-Boc-(2R,3R,4S)-dolaproine (9H-fluoren-9-yl)Methyl ((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-Met MonoMethyl auristatin E (3R,4S,5S)-tert-butyl 3-Methoxy-5-Methyl-4-(MethylaMino)heptanoate hydroc hloride VcMMAD McMMAE MC-MMAF McMMAD MonoMethyl Dolastatin 10

MMAF

MonoMethylauristatin F

MonoMethyl Auristatin F | MMAF

MMAF (MonoMethylauristatin F)

Monomethyl auristatin phenylalanine

MONOMETHYLAURISTATIN F; MMAF; MONOMETHYL AURISTATIN PHENYLALANINE; 745017-94-1

(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

(2S)-2-[[(2R,3R)-3-methoxy-3-[(2S)-1-[(3R,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

L-Phenylalanine, N-methyl-L-valyl-L-valyl-(3R,4S,5S)-3-methoxy-5-methyl-4-(methylamino)heptanoyl-(αR,βR,2S)-β-methoxy-α-methyl-2-pyrrolidinepropanoyl-

F(MMAF)

MonoMethylauristatin

745017-94-1 MonoMethylauristatin F

Tacrinum

Methyloratatin F

Thiazole,2-bromo-6-methyl-

MMAF (Synonyms: Monomethylauristatin F)

745017-97-1

(S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-Dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid[Monomethylauristatin F

(S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-Dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid

(2S)-2-[(2R)-2-[(R)-[(2S)-1-[(3R,4S,5S)-4-[(2S)-N,3-dimethyl-2-[(2S)-3-methyl-2-(methylamino)butanamido]butanamido]-3-methoxy-5-methylheptanoyl]-2-hydrogeniopyrrolidin-2-yl](methoxy)methyl]propanamido]-3-phenylpropanoic acid

(2S)-2-[[(2R,3R)-3-methoxy-3-[(2S)-1-[(3R,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]am

MMAF, 10 mM in DMSO

Abmole M5041-2mg MMAF 745017-94-1

((2r,3r)-3-((s)-1-((3r,4s,5s)-4-((s)-n,3-dimethyl-2-((s)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoyl)-l-phenylalanine

745017-94-1

75017-94-1

745017-97-1

ADCs