Physicochemical Properties
| Molecular Formula | C71H81N19O18S5 |
| Exact Mass | 1647.461 |
| CAS # | 12656-09-6 |
| PubChem CID | 16130049 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.7±0.1 g/cm3 |
| Index of Refraction | 1.773 |
| LogP | -8.95 |
| Hydrogen Bond Donor Count | 17 |
| Hydrogen Bond Acceptor Count | 31 |
| Rotatable Bond Count | 11 |
| Heavy Atom Count | 113 |
| Complexity | 3970 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C/C=C\1/C2=NC(C(N[C@@H]([C@@]([C@H](O)C)(O)C)C3=NC(C(N[C@H]4[C@H](OC(C5=NC6=C(C([C@@H](O)C)=C5)C=CC(N[C@H](C(NC(C(NC(C(N[C@H](C(N[C@]7(C8=NC(C(NC(C(N1)=O)[C@H](O)C)=O)=CS8)CCC(C9=NC(C(NC(C(NC(C(N)=O)=C)=O)=C)=O)=CS9)=N[C@@H]7C%10=CSC4=N%10)=O)C)=O)=C)=O)=C)=O)C(C)C)C6O)=O)C)=O)=CS3)=O)CS2 |
| InChi Key | AKFVOKPQHFBYCA-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C71H81N19O18S5/c1-14-37-64-83-44(22-109-64)61(103)89-52(70(13,107)34(12)93)67-85-43(23-112-67)59(101)88-48-33(11)108-68(106)40-19-36(31(9)91)35-15-16-38(50(94)49(35)79-40)78-46(25(2)3)62(104)77-29(7)56(98)74-27(5)55(97)75-30(8)57(99)90-71(69-86-45(24-113-69)60(102)87-47(32(10)92)63(105)81-37)18-17-39(80-51(71)41-20-111-66(48)82-41)65-84-42(21-110-65)58(100)76-28(6)54(96)73-26(4)53(72)95/h14-16,19-21,23-25,30-34,38,44,46-48,50-52,78,91-94,107H,4-7,17-18,22H2,1-3,8-13H3,(H2,72,95)(H,73,96)(H,74,98)(H,75,97)(H,76,100)(H,77,104)(H,81,105)(H,87,102)(H,88,101)(H,89,103)(H,90,99) |
| Chemical Name | N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-2-[18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-59-hydroxy-8,31-bis(1-hydroxyethyl)-26,46-dimethyl-40,43-dimethylidene-6,9,16,23,28,38,41,44,47-nonaoxo-37-propan-2-yl-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecazanonacyclo[23.23.9.329,35.12,5.112,15.119,22.154,57.01,53.032,60]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazole-4-carboxamide |
| 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
| ln Vitro | In a dose- and time-dependent way, siomycin A (0-10 µM; 24-72 hours; K562, MCF7, and MiaPaCa-2 cells) therapy markedly decreased cell viability. Human pancreatic cancer MiaPaCa-2 cells showed an IC50 of 6.38 µM, while human leukemia K562 cells had the lowest IC50 of 6.25 µM after 24 hours. Among the three cell lines, the human pancreatic cancer MiaPaCa-2 cells had the lowest IC50 at 48 and 72 hours, measuring 0.76 and 0.54 µM, respectively [1]. Treatment with Siomycin A (0-10 µM) exerts a strong pro-apoptotic effect on MiaPaCa-2 cells [1]. The expression levels of MMP-2, MMP-9, and α-tubulin in MiaPaCa-2 cells were considerably lowered after treatment with siomycin A (0-10 µM) for 24 hours [1]. |
| ln Vivo | Pretreatment with Siomycin A (1 µM; subcutaneous injection; 4 weeks; male Balb/c nude mice) inhibits tumor growth in in vivo mouse models [2]. |
| Cell Assay |
Cell Viability Assay[1] Cell Types: K562, MCF7 and MiaPaCa-2 Cell Tested Concentrations: 0 µM, 0.625 µM, 1.25 µM, 2.5 µM, 5 µM or 10 µM Incubation Duration: 24, 48 and 72 hrs (hours) Experimental Results: Cell viability was Dose- and time-dependent associations were Dramatically diminished. Apoptosis analysis [1] Cell Types: MiaPaCa-2 Cell Tested Concentrations: 0 µM, 0.625 µM, 1.25 µM, 2.5 µM, 5 µM or 10 µM Incubation Duration: Experimental Results: Promotes apoptosis of MiaPaCa-2 cells. Western Blot Analysis[1] Cell Types: MiaPaCa-2 Cell Tested Concentrations: 0 µM, 0.625 µM, 1.25 µM, 2.5 µM, 5 µM or 10 µM Incubation Duration: 24 hrs (hours) Experimental Results: Expression levels of MMP-2 and MMP-9 2.5 The protein in MiaPaCa-2 cells in the , 5 and 10 µM groups was Dramatically diminished. |
| Animal Protocol |
Animal/Disease Models: 4 to 5 weeks old male Balb/c nude mice with IOMM-LEE cells [2] Doses: 1 µM pretreated IOMM-Lee cells Route of Administration: subcutaneous injection; Route of Administration: subcutaneous injection. Results lasting 4 weeks: diminished tumor growth in in vivo mouse model. |
| References |
[1]. Wang B, et al. Effects and mechanism of siomycin A on the growth and apoptosis of MiaPaCa-2 cancer cells. Oncol Lett. 2019 Sep;18(3):2869-2876. [2]. Kim H, et al. Forkhead box M1 (FOXM1) transcription factor is a key oncogenic driver of aggressive human meningioma progression. Neuropathol Appl Neurobiol. 2019 Jun 9. |
| Additional Infomation |
Siomycin A is an oligopeptide. Siomycin has been reported in Streptomyces sioyaensis 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.) |