Physicochemical Properties
| Molecular Formula | C65H110N10O16 |
| Molecular Weight | 1287.62631845474 |
| Exact Mass | 1286.81 |
| CAS # | 1029227-48-2 |
| PubChem CID | 24881184 |
| Appearance | Typically exists as solid at room temperature |
| LogP | 6.2 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 17 |
| Rotatable Bond Count | 25 |
| Heavy Atom Count | 91 |
| Complexity | 2450 |
| Defined Atom Stereocenter Count | 13 |
| SMILES | CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)O[C@@H]([C@@H](C(=O)N([C@H](C(=O)N1C)COC)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](COC)N(C)C(=O)[C@H](C(C)C)OC(=O)[C@H](C(C)C)N(C)C)C)C)C)CC2=CC=C(C=C2)OC)CC(C)C)C)C |
| InChi Key | LVHKHLZPRPTQJG-BNLDXBMISA-N |
| InChi Code | InChI=1S/C65H110N10O16/c1-26-40(10)52-56(77)66-41(11)57(78)70(17)47(31-36(2)3)55(76)67-46(33-44-27-29-45(89-25)30-28-44)58(79)69(16)42(12)64(85)90-43(13)53(62(83)72(19)50(35-88-24)61(82)74(52)21)75(22)59(80)48(32-37(4)5)71(18)60(81)49(34-87-23)73(20)63(84)54(39(8)9)91-65(86)51(38(6)7)68(14)15/h27-30,36-43,46-54H,26,31-35H2,1-25H3,(H,66,77)(H,67,76)/t40-,41-,42-,43+,46-,47-,48-,49-,50-,51-,52-,53-,54-/m0/s1 |
| Chemical Name | [(2S)-1-[[(2S)-1-[[(2S)-1-[[(3S,6S,9S,12S,15S,18S,21S,22R)-15-[(2S)-butan-2-yl]-18-(methoxymethyl)-6-[(4-methoxyphenyl)methyl]-3,4,10,12,16,19,22-heptamethyl-9-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1-oxa-4,7,10,13,16,19-hexazacyclodocos-21-yl]-methylamino]-4-methyl-1-oxopentan-2-yl]-methylamino]-3-methoxy-1-oxopropan-2-yl]-methylamino]-3-methyl-1-oxobutan-2-yl] (2S)-2-(dimethylamino)-3-methylbutanoate |
| 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
| Targets | VEGFR2 |
| ln Vitro | MDA-MB-231 breast cancer cells are inhibited from proliferating by coibamide A (0.3-1 nM; 3-60 hours) [1]. Human U87-MG and SF-295 glioblastoma cells undergo concentration- and time-dependent cytotoxic mortality in response to coibamide A (2.3-230 nM; 3 days) [2]. Cell type-specific apoptosis and caspase-3/7 activation are induced by coibamide A (10-300 nM; 72 hours) [2]. In anti-apoptotic U87-MG cells, coibamide A (20 nM; 48 hours) causes autophagosome accumulation [2]. |
| ln Vivo | In a subcutaneous mouse model of glioblastoma, coibamide A (300 μg/kg; intratumoral injection; first two days, then every 48 hours for 35 days) inhibits tumor growth [1]. |
| Cell Assay |
Cell Proliferation Assay[1] Cell Types: MDA-MB-231 breast cancer cells Tested Concentrations: 0.3, 1 nM Incubation Duration: 3- 60 hrs (hours) Experimental Results: demonstrated a steady concentration-dependent decrease in proliferative activity relative to vehicle-treated cells Cell Cytotoxicity Assay[2] Cell Types: U87-MG and SF-295 cells Tested Concentrations: 2.3 to 230 nM Incubation Duration: 3 days Experimental Results: Induced concentration-dependent cytotoxicity with EC50 values of 28.8 nM and 96.2 nM for U87-MG and SF-295 cells, respectively. Apoptosis Analysis[2] Cell Types: U87-MG and SF-295 cells Tested Concentrations: 10-300 nM Incubation Duration: 72 h Experimental Results: An 89 kDa band corresponding to the caspase 3-cleaved form of PARP1 was readily detected by 48 h indicative of apoptotic cell death in SF-295 cells, whereas only trace levels of this fragment were observed in late, detaching U87 -MG cell lysates Cell Autophagy Assay[2] Cell Types: U87-MG cell Tested Concentrations: 20 nM Incubation Duration: 48 h Experimental Results: Caused a clear increase in LC3-II expression by 1 h, |
| Animal Protocol |
Animal/Disease Models: 8-week old female nude athymic mice with U87-MG cells[1] Doses: 300 μg/kg Route of Administration: Intratumoral injections; for the first two days, and then every 48 h afterward for 35 days Experimental Results: Remained stable at 200-300 mm3 without significant growth over 4 weeks of treatment, whereas the tumors of vehicle-treated animals continued to grow at a steady rate consistent with this aggressive cancer cell type |
| References |
[1]. Jeffrey D Serrill, et al. Coibamide A, a natural lariat depsipeptide, inhibits VEGFA/VEGFR2 expression and suppresses tumor growth in glioblastoma xenografts. Invest New Drugs. 2016 Feb;34(1):24-40. [2]. Andrew M Hau, et al. Coibamide A induces mTOR-independent autophagy and cell death in human glioblastoma cells. PLoS One. 2013 Jun 6;8(6):e65250. |
| Additional Infomation |
Coibamide A is a cyclodepsipeptide. Coibamide A has been reported in Leptolyngbya with data available. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.7766 mL | 3.8831 mL | 7.7662 mL | |
| 5 mM | 0.1553 mL | 0.7766 mL | 1.5532 mL | |
| 10 mM | 0.0777 mL | 0.3883 mL | 0.7766 mL |