Name: Auristatin E
Brand: BOC Sciences
Price: 939 USD
Availability: MadeToOrder

Size

Price

Stock

Quantity

5 mg

$939

In stock

Synonyms

Auristatin E

IUPAC Name

(2S)-2-[[(2S)-2-(dimethylamino)-3-methylbutanoyl]amino]-N-[(3R,4S,5S)-1-[(2S)-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]-N,3-dimethylbutanamide

Canonical SMILES

CCC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NC(C)C(C2=CC=CC=C2)O)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)N(C)C

InChI

InChI=1S/C40H69N5O7/c1-14-26(6)35(44(11)40(50)33(24(2)3)42-39(49)34(25(4)5)43(9)10)31(51-12)23-32(46)45-22-18-21-30(45)37(52-13)27(7)38(48)41-28(8)36(47)29-19-16-15-17-20-29/h15-17,19-20,24-28,30-31,33-37,47H,14,18,21-23H2,1-13H3,(H,41,48)(H,42,49)/t26-,27+,28+,30-,31+,33-,34-,35-,36+,37+/m0/s1

InChIKey

WOWDZACBATWTAU-FEFUEGSOSA-N

Density

1.1±0.1 g/cm3

Solubility

Soluble in DMSO, not in water

Flash Point

480.6±34.3 °C

Index Of Refraction

1.519

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, or blue ice upon request.

Storage

Dry, dark and at 0 - 4 °C for short term (days to weeks) or -20 °C for long term (months to years).

Pictograms

Health Hazard

Signal Word

Danger

Boiling Point

871.0±65.0 °C at 760 mmHg

In Vivo

Two auristatin E-based albumin-binding drugs, AE-Keto-Sulf07 and AE-Ester-Sulf07 was describeed, which were designed to release the active compound at the tumor site in a pH-dependent manner. A panel of patient- and cell-derived human tumor xenograft models (melanoma A375, ovarian carcinoma A2780, non-small-cell lung cancer LXFA737 and LXFE937, and head and neck squamous cell carcinomas) were screened with starting tumor volumes in the range of either 130-150 mm3 (small tumors) or 270-380 mm3 (large tumors). Both albumin-binding prodrugs showed compelling anticancer efficacy compared to the parent drug auristatin E, inducing statistically significant long-term partial and/or complete tumor regressions. AE-Keto-Sulf07 displayed very good antitumor response over a wide dose range, 3.0-6.5 mg/kg (5-8 injections, biweekly). AE-Ester-Sulf07 was highly efficacious between 1.9 and 2.4 mg/kg (8 injections, biweekly) or at 3.8 mg/kg (4 injections, weekly), but caused cumulative skin irritation due to scratching and biting. In contrast at its MTD, auristatin E (0.3 mg/kg, 8 injections, biweekly) was only marginally active.

NCT Number	Condition Or Disease	Phase	Start Date	Sponsor	Status
NCT00649584	Disease, Hodgkin	Phase 1	2014-12-18	Seagen Inc.	Terminated (Sponsor decision not to enroll cohorts of combined SGN-35 and gemcitabine therapy.)
NCT01925612	Lymphoma, B-cell	Phase 2	2018-06-21	Seagen Inc.	Terminated (Sponsor decision based on portfolio prioritization and changing treatment landscape in frontline DLBCL)
NCT01990534	Hodgkin Lymphoma	Phase 4	2021-04-09	Millennium Pharmaceuticals, Inc.	Completed
NCT01777152	Anaplastic Large-Cell Lymphoma	Phase 3	2021-03-22	Seagen Inc.	Completed
NCT01461538	Acute Lymphoid Leukemia	Phase 2	2016-03-04	Seagen Inc.	Completed

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.

Catalog	Product Name	CAS
BADC-00045	Auristatin F	163768-50-1
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