BNC105 is a potent benzofuran-based tubulin polymerization inhibitor and also a vascular disrupting agent (VDA) prodrug with potential anti-vascular and anticancer activities. In vivo conditions cause a quick conversion of BNC105P to BNC105. By attaching itself to tubulin and preventing its polymerization, BNC105 can disrupt the tumor vasculature, stop the formation of mitotic spindles, and stop the cell cycle. Tumor cells experience apoptosis as a result of the ensuing hypoxic conditions, which starve them of nutrients. By blocking tubulin polymerization, this agent inhibits tumor cells directly in addition to its VDA activity. BNC105 is not a substrate for the multidrug-resistance P-glycoprotein (Pgp) transporter.
Physicochemical Properties
| Molecular Formula | C20H20O7 |
| Molecular Weight | 372.3686 |
| Exact Mass | 372.121 |
| Elemental Analysis | C, 64.51; H, 5.41; O, 30.08 |
| CAS # | 945771-74-4 |
| Related CAS # |
945771-96-0 (sodium); 945772-45-2 (free acid) |
| PubChem CID | 24786555 |
| Appearance | Beige fluffy powder |
| LogP | 3.712 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 27 |
| Complexity | 499 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(C1C2C(=C(C(=CC=2)OC)O)OC=1C)C1C=C(OC)C(OC)=C(OC)C=1 |
| InChi Key | RADMJHVVIZTENA-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C20H20O7/c1-10-16(12-6-7-13(23-2)18(22)19(12)27-10)17(21)11-8-14(24-3)20(26-5)15(9-11)25-4/h6-9,22H,1-5H3 |
| Chemical Name | (7-hydroxy-6-methoxy-2-methyl-1-benzofuran-3-yl)-(3,4,5-trimethoxyphenyl)methanone |
| Synonyms | BCN105; BCN 105; BCN-105 |
| 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 |
| 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]. Discovery of 7-hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan (BNC105), a tubulin polymerization inhibitor with potent antiproliferative and tumor vascular disrupting properties. J Med Chem. 2011 Sep 8;54(17):6014-27. [2]. BNC105: a novel tubulin polymerization inhibitor that selectively disrupts tumor vasculature and displays single-agent antitumor efficacy. Mol Cancer Ther. 2010 Jun;9(6):1562-73. [3]. The vascular disrupting agent BNC105 potentiates the efficacy of VEGF and mTOR inhibitors in renal and breast cancer. Cancer Biol Ther. 2014;15(11):1552-60. |
| Additional Infomation |
Vascular Disrupting Agent BNC105 is a vascular disrupting agent (VDA), with potential anti-vascular and antineoplastic activities. Upon administration, vascular disrupting agent BNC105 binds to tubulin and inhibits its polymerization, which results in a blockage of mitotic spindle formation, cell cycle arrest, and disruption of the tumor vasculature. This deprives tumor cells of nutrients and results in tumor cell apoptosis. In addition to its VDA activity, this agent has a direct cytotoxic effect on tumor cells by inhibiting tubulin polymerization. See also: BNC-105p free acid (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | DMSO: ~25 mg/mL (~67.1 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (6.71 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with heating and sonication. 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 (6.71 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with heating and sonication. 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 (6.71 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 | 2.6855 mL | 13.4275 mL | 26.8550 mL | |
| 5 mM | 0.5371 mL | 2.6855 mL | 5.3710 mL | |
| 10 mM | 0.2686 mL | 1.3428 mL | 2.6855 mL |