Tubulysin A (also called TubA) is a naturally occurring cytotoxic peptide isolated from a strain of myxobacteria with various bioactivity such as antiangiogenic, anticancer, anti-mitotic, anti-microtubule, apoptosis inducing,anti-angiogenic, and antiproliferative activity.
Physicochemical Properties
| Molecular Formula | C43H65N5O10S |
| Molecular Weight | 844.068700000001 |
| Exact Mass | 843.445 |
| CAS # | 205304-86-5 |
| PubChem CID | 12134544 |
| Appearance | White to light yellow solid powder |
| LogP | 7.063 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 13 |
| Rotatable Bond Count | 24 |
| Heavy Atom Count | 59 |
| Complexity | 1390 |
| Defined Atom Stereocenter Count | 7 |
| SMILES | CC[C@H](C)[C@@H](C(=O)N(COC(=O)CC(C)C)[C@H](C[C@H](C1=NC(=CS1)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C[C@H](C)C(=O)O)OC(=O)C)C(C)C)NC(=O)[C@H]3CCCCN3C |
| InChi Key | IBEDDHUHZBDXGB-OEJISELMSA-N |
| InChi Code | InChI=1S/C43H65N5O10S/c1-10-27(6)38(46-40(53)34-13-11-12-18-47(34)9)42(54)48(24-57-37(51)19-25(2)3)35(26(4)5)22-36(58-29(8)49)41-45-33(23-59-41)39(52)44-31(20-28(7)43(55)56)21-30-14-16-32(50)17-15-30/h14-17,23,25-28,31,34-36,38,50H,10-13,18-22,24H2,1-9H3,(H,44,52)(H,46,53)(H,55,56)/t27-,28-,31+,34+,35+,36+,38-/m0/s1 |
| Chemical Name | (2S,4R)-4-[[2-[(1R,3R)-1-acetyloxy-4-methyl-3-[3-methylbutanoyloxymethyl-[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]amino]pentyl]-1,3-thiazole-4-carbonyl]amino]-5-(4-hydroxyphenyl)-2-methylpentanoic acid |
| 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: (1). This product requires protection from light (avoid light exposure) during transportation and storage.(2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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
| References |
[1]. Biological evaluation of tubulysin A: a potential anticancer and antiangiogenic natural product. Biochem J. 2006 Jun 1;396(2):235-42. [2]. Tubulysins, new cytostatic peptides from myxobacteria acting on microtubuli. Production, isolation, physico-chemical and biological properties. J Antibiot (Tokyo). 2000 Sep;53(9):879-85. [3]. Mechanism of action of tubulysin, an antimitotic peptide from myxobacteria. Chembiochem. 2006 Apr;7(4):678-83. [4]. Polymeric tubulysin-peptide nanoparticles with potent antitumor activity. Clin Cancer Res. 2009 Jan 1;15(1):181-9. |
| Additional Infomation |
Tubulysin A is a diester and a carboxylic acid. Tubulysin A has been reported in Archangium gephyra with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~118.47 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.96 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 25.0 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: ≥ 2.5 mg/mL (2.96 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 25.0 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: ≥ 2.5 mg/mL (2.96 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 25.0 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 | 1.1847 mL | 5.9237 mL | 11.8474 mL | |
| 5 mM | 0.2369 mL | 1.1847 mL | 2.3695 mL | |
| 10 mM | 0.1185 mL | 0.5924 mL | 1.1847 mL |