Pyrocoll
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| Category | Others |
| Catalog number | BBF-02593 |
| CAS | 484-73-1 |
| Molecular Weight | 186.17 |
| Molecular Formula | C10H6N2O2 |
| Purity | ≥95% |
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Description
Pyrocoll is a compound produced by Streptomyces sp. AK409 with antiparasitic and antitumor effects. It has activity against Arthrobacter bacteria, with an MIC of 1-10 μg/mL. It has a moderate anti-plasmodium effect, and its IC50 for Plasmodium facipaum is 1.19 μg/mL (standard chloroquine is 0.078 μg/mL). It also inhibits the growth of tumor cells. The IC50 pairs of HM02, HepG2 and MCF 7 cells are 0.23, 0.42 and 2.2 μg/mL, respectively.
Specification
| IUPAC Name | 1,7-diazatricyclo[7.3.0.03,7]dodeca-3,5,9,11-tetraene-2,8-dione |
| Canonical SMILES | C1=CN2C(=C1)C(=O)N3C=CC=C3C2=O |
| InChI | InChI=1S/C10H6N2O2/c13-9-7-3-1-5-11(7)10(14)8-4-2-6-12(8)9/h1-6H |
| InChI Key | USCZWOZHDDOBHQ-UHFFFAOYSA-N |
Properties
| Appearance | Solid Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor); parasites |
| Boiling Point | 216.2±36.0°C at 760 mmHg |
| Melting Point | 270°C |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Scents of adolescence: the maturation of the olfactory phenotype in a free-ranging mammal
Stephan Franke, Frank C Schroeder, Barbara A Caspers, Christian C Voigt PLoS One . 2011;6(6):e21162. doi: 10.1371/journal.pone.0021162.
Olfaction is an important sensory modality for mate recognition in many mammal species. Odorants provide information about the health status, genotype, dominance status and/or reproductive status. How and when odor profiles change during sexual maturation is, however often unclear, particularly in free-ranging mammals. Here, we investigated whether the wing sac odorant of male greater sac-winged bats (Saccopteryx bilineata, Emballonuridae) differs between young and adults, and thus offers information about sexual maturity to potential mating partners. Using gas chromatography-mass spectrometry, we found differences in the odorants of young and adult males prior and during, but not after the mating period. The wing sac odorant of adult males consists of several substances, such as Pyrocoll, 2,6,10-trimethyl-3-oxo-6,10-dodecadienolide, and a so far unidentified substance; all being absent in the odor profiles of juveniles prior to the mating season. During the mating season, these substances are present in most of the juvenile odorants, but still at lower quantities compared to the wing sac odorants of adults. These results suggest that the wing sac odorant of males encodes information about age and/or sexual maturity. Although female S. bilineata start to reproduce at the age of half a year, most males of the same age postpone the sexual maturation of their olfactory phenotype until after the first mating season.
2. Streptozotocin-induced diabetes increases disulfide bond formation on cardiac ryanodine receptor (RyR2)
Keshore R Bidasee, Henry R Besch Jr, Karuna Nallani, U Deniz Dincer J Pharmacol Exp Ther . 2003 Jun;305(3):989-98. doi: 10.1124/jpet.102.046201.
In a previous study, we showed that after 6 weeks of streptozotocin-induced diabetes (6D), expression of type 2 ryanodine receptor calcium-release channels (RyR2) did not change significantly in rat hearts. However, the ability of this protein to bind [3H]ryanodine was compromised. Loss in activity therefore resulted from diabetes-induced increases in post-translational modifications on RyR2. In the present study, the effects of diabetes on one type of modification, namely, changes in oxidative state of reactive sulfhydryls was investigated. RyR2 protein from 6D bound 42.3 +/- 7.6 less [3H]ryanodine than RyR2 from controls (6C). The loss in binding was minimized with 2 weeks of insulin treatment initiated after 4 weeks of diabetes (77.8 +/- 5.5% of 6C). Pretreating RyR2 from 6D with 2 mM dithiothreitol in vitro increases [3H]ryanodine binding by 60.8 +/- 5.3%. Dithiothreitol pretreatment of RyR2 from 6C increased [3H]ryanodine binding by 16.8 +/- 4.3%. The reagent pyrocoll interacts with distinct classes of free sulfhydryl groups on 6C RyR2 to induce two major effects. At concentrations < or = 10 microM, it deactivates RyR2 (decreases [3H]ryanodine binding), whereas at higher concentrations it activates them (increases [3H]ryanodine binding). This reagent was unable to activate RyR2 from 6D. Although RyR2 from insulin-treated animals was deactivated by low concentrations of pyrocoll, it was only partially activated at higher concentrations. These data suggest that the dysfunction of RyR2 induced by diabetes may be due in part to formation of disulfide bonds between adjacent sulfhydryl groups and that these changes were attenuated with insulin treatment.
3. Pyrocoll, an antibiotic, antiparasitic and antitumor compound produced by a novel alkaliphilic Streptomyces strain
Winfried Beil, Werner E G Müller, Reto Brun, Hans-Peter Fiedler, Anke Dietera, Gerhard Bringmann, Michael Goodfellow, Andreas Hamm J Antibiot (Tokyo) . 2003 Jul;56(7):639-46. doi: 10.7164/antibiotics.56.639.
A new secondary metabolite was detected in the culture extract of Streptomyces sp. AK 409 by HPLC-diode-array screening. The metabolite was identified as pyrocoll, which is known to be a constituent of cigarette smoke. Pyrocoll is known as a synthetic compound, but until now had not been isolated as a natural product from a microorganism. The compound showed biological activity against various Arthrobacter strains, filamentous fungi, several pathogenic protozoa, and some human tumor cell lines.
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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 ╳
