Auristatin F
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| Category | Mycotoxins |
| Catalog number | BBF-05829 |
| CAS | 163768-50-1 |
| Molecular Weight | 745.99 |
| Molecular Formula | C40H67N5O8 |
| Purity | ≥97% by HPLC |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-05829 | 25 mg | $1099 | In stock |
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Add to cartDescription
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.
Specification
| 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 |
| Shelf Life | ≥360 days if stored properly |
| Storage | Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years) |
| 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 |
| InChI Key | LGNCNVVZCUVPOT-FUVGGWJZSA-N |
Properties
| Appearance | White to off-white solid |
| Application | ADCs Cytotoxin |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 894.4±65.0 °C at 760 mmHg |
| Melting Point | >140°C (dec.) |
| Flash Point | 494.7±34.3 °C |
| Density | 1.112±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in DMSO (Slightly), Methanol (Slightly, Heated) |
| LogP | 4.99 |
Reference Reading
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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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
