(S)-10,11-Dehydrocurvularin
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| Category | Mycotoxins |
| Catalog number | BBF-05797 |
| CAS | 21178-57-4 |
| Molecular Weight | 290.31 |
| Molecular Formula | C16H18O5 |
| Purity | ≥98% |
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Description
It is a natural mycotoxin that has cytotoxic activity against select cancer cell lines. It has been shown to activate the heat shock response, block TGF-β signaling, and scavenge superoxide anions.
Specification
| Related CAS | 1095588-70-7 (R-isomer) |
| Synonyms | alpha,beta-Dehydrocurvularin; Trans-Dehydrocurvularin; (S)-10,11-dehydrocurvularin; (10E,15S)-10,11-Dehydrocurvularin; (4S,8E)-4,5,6,7-tetrahydro-11,13-dihydroxy-4-methyl-2H-3-benzoxacyclododecin-2,10(1H)-dione; (4S,8E)-4beta-Methyl-11,13-dihydroxy-1,4,5,6,7,10-hexahydro-2H-3-benzoxacyclododecin-2,10-dione; α,β-dehydro Curvularin |
| Storage | Store at -20°C |
| IUPAC Name | (5S,9E)-13,15-dihydroxy-5-methyl-4-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraene-3,11-dione |
| Canonical SMILES | CC1CCCC=CC(=O)C2=C(CC(=O)O1)C=C(C=C2O)O |
| InChI | InChI=1S/C16H18O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h4,6-7,9-10,17,19H,2-3,5,8H2,1H3/b6-4+/t10-/m0/s1 |
| InChI Key | AVIRMQMUBGNCKS-RWCYGVJQSA-N |
Properties
| Appearance | White to Off-white Powder |
| Antibiotic Activity Spectrum | Bacterial |
| Boiling Point | 576.3±50.0 °C at 760 mmHg |
| Melting Point | 223-224°C |
| Density | 1.225±0.06 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1.NPY1-36 and PYY1-36 activate cardiac fibroblasts: an effect enhanced by genetic hypertension and inhibition of dipeptidyl peptidase 4.
Zhu X1, Gillespie DG1, Jackson EK2. Am J Physiol Heart Circ Physiol. 2015 Nov;309(9):H1528-42. doi: 10.1152/ajpheart.00070.2015. Epub 2015 Sep 14.
Cardiac sympathetic nerves release neuropeptide Y (NPY)1-36, and peptide YY (PYY)1-36 is a circulating peptide; therefore, these PP-fold peptides could affect cardiac fibroblasts (CFs). We examined the effects of NPY1-36 and PYY1-36 on the proliferation of and collagen production ([(3)H]proline incorporation) by CFs isolated from Wistar-Kyoto (WKY) normotensive rats and spontaneously hypertensive rats (SHRs). Experiments were performed with and without sitagliptin, an inhibitor of dipeptidyl peptidase 4 [DPP4; an ectoenzyme that metabolizes NPY1-36 and PYY1-36 (Y1 receptor agonists) to NPY3-36 and PYY3-36 (inactive at Y1 receptors), respectively]. NPY1-36 and PYY1-36, but not NPY3-36 or PYY3-36, stimulated proliferation of CFs, and these effects were more potent than ANG II, enhanced by sitagliptin, blocked by BIBP3226 (Y1 receptor antagonist), and greater in SHR CFs. SHR CF membranes expressed more receptor for activated C kinase (RACK)1 [which scaffolds the Gi/phospholipase C (PLC)/PKC pathway] compared with WKY CF membranes.
2.The Influence of the 1-(3-Trifluoromethyl-Benzyl)-1H-Pyrazole-4-yl Moiety on the Adenosine Receptors Affinity Profile of Pyrazolo[4,3-e][1,2,4]Triazolo[1,5-c]Pyrimidine Derivatives.
Federico S1, Redenti S1, Sturlese M2, Ciancetta A2, Kachler S3, Klotz KN3, Cacciari B4, Moro S2, Spalluto G1. PLoS One. 2015 Dec 1;10(12):e0143504. doi: 10.1371/journal.pone.0143504. eCollection 2015.
A new series of pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine (PTP) derivatives has been developed in order to explore their affinity and selectivity profile at the four adenosine receptor subtypes. In particular, the PTP scaffold was conjugated at the C2 position with the 1-(3-trifluoromethyl-benzyl)-1H-pyrazole, a group believed to confer potency and selectivity toward the human (h) A2B adenosine receptor (AR) to the xanthine ligand 8-(1-(3-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione (CVT 6975). Interestingly, the synthesized compounds turned out to be inactive at the hA2B AR but they displayed affinity at the hA3 AR in the nanomolar range. The best compound of the series (6) shows both high affinity (hA3 AR Ki = 11 nM) and selectivity (A1/A3 and A2A/A3 > 9090; A2B/A3 > 909) at the hA3 AR. To better rationalize these results, a molecular docking study on the four AR subtypes was performed for all the synthesized compounds.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
