Physicochemical Properties
| Molecular Formula | C40H67N5O8 |
| Molecular Weight | 746.003 |
| Exact Mass | 745.498 |
| Elemental Analysis | C, 64.40; H, 9.05; N, 9.39; O, 17.16 |
| CAS # | 163768-50-1 |
| Related CAS # | Auristatin F-d8 |
| PubChem CID | 67472795 |
| Appearance | Off-white to yellow solid powder |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 894.4±65.0 °C at 760 mmHg |
| Flash Point | 494.7±34.3 °C |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| Index of Refraction | 1.523 |
| LogP | 4.99 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 21 |
| Heavy Atom Count | 53 |
| Complexity | 1190 |
| Defined Atom Stereocenter Count | 9 |
| SMILES | CC(C)[C@H](N(C)C)C(N[C@H](C(N([C@@H]([C@@H](C)CC)[C@@H](CC(N1CCC[C@@]1([H])[C@H](OC)[C@@H](C)C(N[C@H](C(O)=O)CC2=CC=CC=C2)=O)=O)OC)C)=O)C(C)C)=O |
| InChi Key | LGNCNVVZCUVPOT-FUVGGWJZSA-N |
| InChi Code | 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 |
| Chemical Name | ((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoyl)-L-phenylalanine |
| Synonyms | Auristatin F |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product is not stable in solution, please use freshly prepared working solution for optimal results. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Microtubule[1] |
| ln Vitro | In antibody-drug conjugates, Auristatin F and Monomethyl Auristatin F (MMAF) are strong ADC cytotoxins[1]. |
| ln Vivo | 8276.76 ng/mL is the Cmax of auristatin F (5 mg/kg; i.v.; male Sprague-Dawley rats). The clearance (CL) is 77.33 mL/min/kg, which is higher than the rat's hepatic blood flow, and the AUClast is 65661.30 min*ng/mL[2]. |
| Animal Protocol |
Animal Model: Male Sprague-Dawley rats[2] Dosage: 5 mg/kg Administration: Intravenous injection |
| References |
[1]. SMI-Ribosome inactivating protein conjugates selectively inhibit tumor cell growth. Chem Commun (Camb). 2017 Apr 11;53(30):4234-4237. [2]. Pharmacokinetic and Metabolism Studies of Monomethyl Auristatin F via Liquid Chromatography-Quadrupole-Time-of-Flight Mass Spectrometry. Molecules. 2019 Jul 29;24(15):2754. [3]. Temming K, et al. Improved efficacy of alphavbeta3-targeted albumin conjugates by conjugation of a novel auristatin derivative. Mol Pharm. 2007 Sep-Oct;4(5):686-94. [3]. Enhanced activity of monomethylauristatin F through monoclonal antibody delivery: effects of linker technology on efficacy and toxicity. Bioconjug Chem. 2006 Jan-Feb;17(1):114-24 |
Solubility Data
| Solubility (In Vitro) | DMSO : ~200 mg/mL (~268.10 mM ) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (6.70 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 5 mg/mL (6.70 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 5 mg/mL (6.70 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.3405 mL | 6.7024 mL | 13.4048 mL | |
| 5 mM | 0.2681 mL | 1.3405 mL | 2.6810 mL | |
| 10 mM | 0.1340 mL | 0.6702 mL | 1.3405 mL |