Physicochemical Properties
| Molecular Formula | C38H58O11 |
| Molecular Weight | 690.86 |
| Exact Mass | 690.398 |
| CAS # | 83329-73-1 |
| PubChem CID | 155859147 |
| Appearance | Typically exists as solid at room temperature |
| LogP | 5.054 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 10 |
| Heavy Atom Count | 49 |
| Complexity | 1300 |
| Defined Atom Stereocenter Count | 12 |
| SMILES | CCC1OC(O)(CC(OC(=O)\C=C/C(O)=O)C1C)C(C)C(O)C(C)C1OC(=O)\C(C)=C\C(\C)=C\C(C)C(O)C(C)C\C(C)=C/C=C/C1OC |c:43,t:30,33,45| |
| InChi Key | UGIOXKVQFJIRMZ-AEZCHWMWSA-N |
| InChi Code | InChI=1S/C38H58O11/c1-11-29-26(7)31(47-33(41)16-15-32(39)40)20-38(45,49-29)28(9)35(43)27(8)36-30(46-10)14-12-13-21(2)17-23(4)34(42)24(5)18-22(3)19-25(6)37(44)48-36/h12-16,18-19,23-24,26-31,34-36,42-43,45H,11,17,20H2,1-10H3,(H,39,40)/b14-12+,16-15+,21-13+,22-18+,25-19+/t23-,24+,26-,27-,28-,29+,30-,31+,34-,35+,36+,38+/m0/s1 |
| Chemical Name | (E)-4-[(2R,4R,5S,6R)-6-ethyl-2-hydroxy-2-[(2S,3R,4S)-3-hydroxy-4-[(2R,3S,4E,6E,9S,10S,11R,12E,14E)-10-hydroxy-3-methoxy-7,9,11,13,15-pentamethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl]-5-methyloxan-4-yl]oxy-4-oxobut-2-enoic 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 |
| 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 | Macrolide |
| ln Vitro | Hygrolidin (0.1, 1 μg/ml) over 24 hours boosts the populations in the G1 and S phases while decreasing the M phases[1]. Cyclolidin (0.1, 1, 10 μg/ml; for 24 hours) raises cyclin E and p21 and lowers cdk4, cyclin D, and cyclin B. The cyclin A-cdk2 complex is preferentially paired with and inhibited by p21 that is produced by hygrolidin[1]. In DLD-1 cells, hygrolidin (0.1, 1 μg/ml) selectively increases p21 at the mRNA level; however, it does not affect WI-38 fibroblasts[1]. Hygrolidin (IC50s = 1.0-33 ng/ml, respectively) suppresses the proliferation of multiple cell lines for three days, including DLD-1 colon cancer, LNCaP prostate cancer, K562 leukemia cells, and EL-4 lymphoma[1]. Trypanosoma cruzi (IC50=1.1 nM), Trypanosoma brucei brucei (IC50=77 nM), and Leishmania donovani (IC50 = 72.5 nM) are the three parasite species on which hygrolidin inhibits growth[3]. |
| Cell Assay |
Cell Cycle Analysis[1] Cell Types: DLD-1 cells Tested Concentrations: 0.1, 1 μg/ml Incubation Duration: For 24 hrs (hours) Experimental Results: Increased both G1 and S phase populations and diminished M phase population. Western Blot Analysis[1] Cell Types: DLD-1 cells Tested Concentrations: 0.1, 1, 10 μg/ml Incubation Duration: For 24 hrs (hours) Experimental Results: diminished the amounts of cdk4, cyclin D, cyclin B and increased the amounts of cyclin E and p21. RT-PCR[1] Cell Types: DLD-1 or WI-38 cells Tested Concentrations: 0.1, 1 μg/ml Incubation Duration: For 24 hrs (hours) Experimental Results: Selectively induced p21 in DLD-1 cells at mRNA level, but not in WI-38 fibroblasts. |
| References |
[1]. Hygrolidin induces p21 expression and abrogates cell cycle progression at G1 and S phases. Biochem Biophys Res Commun. 2002 Oct 18;298(1):178-83. [2]. The isolation and structures of hygrolidin amide and defumarylhygrolidin. J Antibiot (Tokyo). 1984 May;37(5):610-3. [3]. High-throughput screening platform for natural product-based drug discovery against 3 neglected tropical diseases: human African trypanosomiasis, leishmaniasis, and Chagas disease. J Biomol Screen. 2015 Jan;20(1):82-91. |
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 | 1.4475 mL | 7.2374 mL | 14.4747 mL | |
| 5 mM | 0.2895 mL | 1.4475 mL | 2.8949 mL | |
| 10 mM | 0.1447 mL | 0.7237 mL | 1.4475 mL |