Auristatin F - CAS 163768-50-1
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Auristatin F - CAS 163768-50-1 Catalog number: BADC-00045

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Auristatin F, a synthetic analog of dolastatin 10, is a cytotoxic tubulin modifier with potent and selective antitumor activity. It is an MMAF analog and cytotoxin in Antibody-drug conjugates.

Category
ADCs Cytotoxin
Product Name
Auristatin F
CAS
163768-50-1
Catalog Number
BADC-00045
Molecular Formula
C40H67N5O8
Molecular Weight
745.99
Purity
≥97% by HPLC
Auristatin F

Ordering Information

Catalog Number Size Price Quantity
BADC-00045 25 mg $1099 Inquiry

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Description
Auristatin F, a synthetic analog of dolastatin 10, is a cytotoxic tubulin modifier with potent and selective antitumor activity. It is an MMAF analog and cytotoxin in Antibody-drug conjugates.
Synonyms
N,N-Dimethyl-L-valyl-L-valyl-(3R,4S,5S)-3-methoxy-5-methyl-4-(methylamino)heptanoyl-(αR,βR,2S)-β-methoxy-α-methyl-2-pyrrolidinepropanoyl-L-phenylalanine; L-Valinamide, N,N-dimethyl-L-valyl-N-[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1S)-1-carboxy-2-phenylethyl]amino]-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl]-2-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-; N,N-Dimethyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(1S)-1-carboxy-2-phenylethyl]amino}-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl}-3-methoxy-5-methyl-1-oxo-4-heptanyl]-N-methyl-L-valinamide
IUPAC Name
(2S)-2-[[(2R,3R)-3-[(2S)-1-[(3R,4S,5S)-4-[[(2S)-2-[[(2S)-2-(dimethylamino)-3-methylbutanoyl]amino]-3-methylbutanoyl]-methylamino]-3-methoxy-5-methylheptanoyl]pyrrolidin-2-yl]-3-methoxy-2-methylpropanoyl]amino]-3-phenylpropanoic acid
Canonical SMILES
CCC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NC(CC2=CC=CC=C2)C(=O)O)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)N(C)C
InChI
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
InChIKey
LGNCNVVZCUVPOT-FUVGGWJZSA-N
Density
1.112±0.06 g/cm3 (Predicted)
Solubility
Soluble in DMSO (Slightly), Methanol (Slightly, Heated)
Melting Point
>140°C (dec.)
Flash Point
494.7±34.3 °C
Index Of Refraction
1.523
LogP
4.99
PSA
157.82000
Vapor Pressure
0.0±0.3 mmHg at 25°C
Appearance
White to off-white solid
Shelf Life
≥360 days if stored properly
Shipping
Room temperature
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Boiling Point
894.4±65.0 °C at 760 mmHg
In Vitro
When SNAP-tagged single chain antibody fragments (scFvs) are conjugated with a BG-modified version of auristatin F (AURIF), two homogenous ADCs are obtained: 425(scFv)-SNAPAURIF and αHER2(scFv)-SNAP-AURIF, targeting the important solid tumor markers EGFR and HER2. The recombinant ADCs were stable in human serum, internalized rapidly by breast cancer cells and demonstrated potent inhibitory and pro-apoptotic effects against them in vitro at nanomolar concentrations.
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT02855359Diffuse, Large B-Cell, LymphomaPhase 22019-03-11Seagen Inc.Terminated (Sponsor decision based on portfolio prioritization)
1.An anti-HER2 antibody conjugated with monomethyl auristatin E is highly effective in HER2-positive human gastric cancer.
Li H1, Yu C2, Jiang J3, Huang C2, Yao X1, Xu Q2, Yu F2, Lou L4, Fang J1,5,6. Cancer Biol Ther. 2016 Apr 2;17(4):346-54. doi: 10.1080/15384047.2016.1139248. Epub 2016 Feb 6.
Antibody-drug conjugate (ADC) is a novel class of therapeutics for cancer target therapy. This study assessed antitumor activity of ADC with an antimitotic agent, monomethyl auristatin E (MMAE) and a humanized monoclonal anti-HER2 antibody, hertuzumab, in gastric cancer. The efficacy of hertuzumab-MC-Val-Cit-PAB-MMAE (hertuzumab-vcMMAE) on human epidermal growth factor receptor 2 (HER2) positive human gastric cancer cells, NCI-N87, was evaluated in vitro and in vivo. The cytotoxicity of hertuzumab was significantly enhanced after conjugation with MMAE. Compared to trastuzumab, hertuzumab had a higher affinity to HER2 and had more potent antibody-dependent cell-mediated cytotoxicity (ADCC) activity in vitro. After conjugation with MMAE, the binding specificity for HER2 was not affected. Furthermore, the internalization of hertuzumab-vcMMAE in HER2 positive gastric cancer cells was verified. Although the conjugation of hertuzumab and MMAE decreased the ADCC effect, the overall cytotoxicity was dramatically increased in HER2 positive gastric cancer cells.
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