Name: Auristatin F
Brand: BOC Sciences
Price: 1099 USD
Availability: MadeToOrder

Size

Price

Stock

Quantity

25 mg

$1099

In stock

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

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 Number	Condition Or Disease	Phase	Start Date	Sponsor	Status
NCT02855359	Diffuse, Large B-Cell, Lymphoma	Phase 2	2019-03-11	Seagen 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.

HNMR

HPLC

Catalog	Product Name	CAS
BADC-00188	Auristatin E	160800-57-7
BADC-00338	Auristatin T	1799603-53-4
BADC-00629	MC-Val-Cit-PAB-Auristatin E	2055896-77-8
BADC-00740	MC-vc-PAB-Auristatin 0101