MedKoo Cat#: 572946 | Name: Auristatin E
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Auristatin E is a cytotoxic tubulin modifier with potent and selective antitumor activity; it is a synthetic analog of dolastatin 10. Auristatin E is a highly potent antimitotic agent that inhibits tubulin polymerization. Auristatin E-antibody conjugates have proven to be successful anticancer agents.

Chemical Structure

Auristatin E
Auristatin E
CAS#160800-57-7

Theoretical Analysis

MedKoo Cat#: 572946

Name: Auristatin E

CAS#: 160800-57-7

Chemical Formula: C40H69N5O7

Exact Mass: 731.5197

Molecular Weight: 732.02

Elemental Analysis: C, 65.63; H, 9.50; N, 9.57; O, 15.30

Price and Availability

Size Price Availability Quantity
100mg USD 550.00 2 Weeks
250mg USD 1,050.00 2 Weeks
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Synonym
Auristatin E
IUPAC/Chemical Name
(S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N-((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)-N,3-dimethylbutanamide
InChi Key
WOWDZACBATWTAU-FEFUEGSOSA-N
InChi Code
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
SMILES Code
O[C@H]([C@@H](C)NC([C@H](C)[C@@H](OC)[C@H]1N(C(C[C@@H](OC)[C@H]([C@@H](C)CC)N(C)C([C@H](C(C)C)NC([C@H](C(C)C)N(C)C)=O)=O)=O)CCC1)=O)C2=CC=CC=C2
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 732.02 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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Drugs. 2021 Nov;81(16):1929-1935. doi: 10.1007/s40265-021-01614-x. PMID: 34661865. 5: Shi F, Liu Y, Zhou X, Shen P, Xue R, Zhang M. Disitamab vedotin: a novel antibody-drug conjugates for cancer therapy. Drug Deliv. 2022 Dec;29(1):1335-1344. doi: 10.1080/10717544.2022.2069883. PMID: 35506447; PMCID: PMC9090390. 6: Abawi A, Wang X, Bompard J, Bérot A, Andretto V, Gudimard L, Devillard C, Petiot E, Joseph B, Lollo G, Granjon T, Girard-Egrot A, Maniti O. Monomethyl Auristatin E Grafted-Liposomes to Target Prostate Tumor Cell Lines. Int J Mol Sci. 2021 Apr 15;22(8):4103. doi: 10.3390/ijms22084103. PMID: 33921088; PMCID: PMC8071391. 7: Cabaud O, Berger L, Crompot E, Adélaide J, Finetti P, Garnier S, Guille A, Carbuccia N, Farina A, Agavnian E, Chaffanet M, Gonçalves A, Charafe-Jauffret E, Mamessier E, Birnbaum D, Bertucci F, Lopez M. Overcoming Resistance to Anti- Nectin-4 Antibody-Drug Conjugate. Mol Cancer Ther. 2022 Jul 5;21(7):1227-1235. doi: 10.1158/1535-7163.MCT-22-0013. PMID: 35534238. 8: Heath EI, Rosenberg JE. The biology and rationale of targeting nectin-4 in urothelial carcinoma. Nat Rev Urol. 2021 Feb;18(2):93-103. doi: 10.1038/s41585-020-00394-5. Epub 2020 Nov 25. PMID: 33239713. 9: Purcell JW, Tanlimco SG, Hickson J, Fox M, Sho M, Durkin L, Uziel T, Powers R, Foster K, McGonigal T, Kumar S, Samayoa J, Zhang D, Palma JP, Mishra S, Hollenbaugh D, Gish K, Morgan-Lappe SE, Hsi ED, Chao DT. LRRC15 Is a Novel Mesenchymal Protein and Stromal Target for Antibody-Drug Conjugates. Cancer Res. 2018 Jul 15;78(14):4059-4072. doi: 10.1158/0008-5472.CAN-18-0327. Epub 2018 May 15. PMID: 29764866. 10: Alt M, Stecca C, Tobin S, Jiang DM, Sridhar SS. Enfortumab Vedotin in urothelial cancer. Ther Adv Urol. 2020 Dec 27;12:1756287220980192. doi: 10.1177/1756287220980192. PMID: 33447264; PMCID: PMC7780177. 11: Doronina SO, Toki BE, Torgov MY, Mendelsohn BA, Cerveny CG, Chace DF, DeBlanc RL, Gearing RP, Bovee TD, Siegall CB, Francisco JA, Wahl AF, Meyer DL, Senter PD. Development of potent monoclonal antibody auristatin conjugates for cancer therapy. Nat Biotechnol. 2003 Jul;21(7):778-84. doi: 10.1038/nbt832. Epub 2003 Jun 1. PMID: 12778055. 12: Cho H, Shim MK, Moon Y, Song S, Kim J, Choi J, Kim J, Lee Y, Park JY, Kim Y, Ahn CH, Kim MR, Yoon HY, Kim K. Tumor-Specific Monomethyl Auristatin E (MMAE) Prodrug Nanoparticles for Safe and Effective Chemotherapy. Pharmaceutics. 2022 Oct 7;14(10):2131. doi: 10.3390/pharmaceutics14102131. PMID: 36297566; PMCID: PMC9609178. 13: Li L, Xu MZ, Wang L, Jiang J, Dong LH, Chen F, Dong K, Song HF. Conjugating MMAE to a novel anti-HER2 antibody for selective targeted delivery. Eur Rev Med Pharmacol Sci. 2020 Dec;24(24):12929-12937. doi: 10.26355/eurrev_202012_24196. PMID: 33378043. 14: Cho IK, Shim MK, Um W, Kim JH, Kim K. Light-Activated Monomethyl Auristatin E Prodrug Nanoparticles for Combinational Photo-Chemotherapy of Pancreatic Cancer. Molecules. 2022 Apr 14;27(8):2529. doi: 10.3390/molecules27082529. PMID: 35458727; PMCID: PMC9032578. 15: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Gemtuzumab Ozogamicin. 2022 May 15. PMID: 32697461. 16: Challita-Eid PM, Satpayev D, Yang P, An Z, Morrison K, Shostak Y, Raitano A, Nadell R, Liu W, Lortie DR, Capo L, Verlinsky A, Leavitt M, Malik F, Aviña H, Guevara CI, Dinh N, Karki S, Anand BS, Pereira DS, Joseph IB, Doñate F, Morrison K, Stover DR. Enfortumab Vedotin Antibody-Drug Conjugate Targeting Nectin-4 Is a Highly Potent Therapeutic Agent in Multiple Preclinical Cancer Models. Cancer Res. 2016 May 15;76(10):3003-13. doi: 10.1158/0008-5472.CAN-15-1313. Epub 2016 Mar 24. PMID: 27013195. 17: McGregor BA, Sonpavde G. Enfortumab Vedotin, a fully human monoclonal antibody against Nectin 4 conjugated to monomethyl auristatin E for metastatic urothelial Carcinoma. Expert Opin Investig Drugs. 2019 Oct;28(10):821-826. doi: 10.1080/13543784.2019.1667332. Epub 2019 Sep 17. PMID: 31526130. 18: Hu X, Jiang H, Bai W, Liu X, Miao Q, Wang L, Jin J, Cui A, Liu R, Li Z. Synthesis, characterization, and targeted chemotherapy of SCT200-linker- monomethyl auristatin E conjugates. Eur J Med Chem. 2021 Apr 15;216:113297. doi: 10.1016/j.ejmech.2021.113297. Epub 2021 Feb 24. PMID: 33677351. 19: Cunningham D, Parajuli KR, Zhang C, Wang G, Mei J, Zhang Q, Liu S, You Z. Monomethyl Auristatin E Phosphate Inhibits Human Prostate Cancer Growth. Prostate. 2016 Nov;76(15):1420-30. doi: 10.1002/pros.23226. Epub 2016 Jun 21. PMID: 27325602; PMCID: PMC5033698. 20: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Polatuzumab Vedotin. 2023 May 15. PMID: 37247366.