Prodigiosin hydrochloride
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| Category | Antibiotics |
| Catalog number | BBF-05803 |
| CAS | 56144-17-3 |
| Molecular Weight | 359.89 |
| Molecular Formula | C20H25N3O.HCl |
| Purity | ≥98% |
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Description
Prodigiosin is an antibiotic from Serratia marcescens and other bacteria. It has a wide range of biological activities, including antimalarial, antifungal, anticancer and immunosuppressant properties.
Specification
| Synonyms | 2,2'-Bi-1H-pyrrole, 4-methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-, hydrochloride (1:1); 4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)-1H,1'H-2,2'-bipyrrole hydrochloride; 2H-Pyrrole, 2-[(4-methoxy[2,2'-bi-1H-pyrrol]-5-yl)methylene]-5-methyl-4-pentyl-, (2Z)-, hydrochloride (1:1) |
| Storage | Store at -20°C |
| IUPAC Name | (2Z)-3-methoxy-2-[(5-methyl-4-pentyl-1H-pyrrol-2-yl)methylidene]-5-(1H-pyrrol-2-yl)pyrrole;hydrochloride |
| Canonical SMILES | CCCCCC1=C(NC(=C1)C=C2C(=CC(=N2)C3=CC=CN3)OC)C.Cl |
| InChI | InChI=1S/C20H25N3O.ClH/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17;/h7,9-13,21-22H,4-6,8H2,1-3H3;1H/b19-12-; |
| InChI Key | UQRGJSTXVCWXNU-JHMJKTBASA-N |
Properties
| Appearance | Dark Red Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Fungi |
| Solubility | Soluble in Acetonitrile, Ethanol, Methanol, Chloroform, DMSO, Water (Insoluble) |
Reference Reading
1.Cycloprodigiosin hydrochloride activates the Ras-PI3K-Akt pathway and suppresses protein synthesis inhibition-induced apoptosis in PC12 cells.
Kawauchi K1, Tobiume K, Iwashita K, Inagaki H, Morikawa T, Shibukawa Y, Moriyama Y, Hirata H, Kamata H. Biosci Biotechnol Biochem. 2008 Jun;72(6):1564-70. Epub 2008 Jun 7.
Cycloprodigiosin hydrochloride (cPrG-HCl), a member of the prodigiosin family of compounds, has been reported to act as an H(+)/Cl(-) symporter. This compound induces apoptosis in several cancer cells and acts as an antitumor drug in animal models. In this study, we found a novel function of cPrG-HCl; to suppress cell death in PC12 cells, which is caused by protein synthesis inhibitors cycloheximide and actinomycin D. cPrG-HCl activated Akt and suppressed apoptosis, and this was accompanied by inhibition of caspase-3 activity and DNA fragmentation independently of its H(+)/Cl(-) symporter activity. Wortmannin, a phosphatidylinositol 3-kinase (PI3K) inhibitor, and dominant-negative Ras attenuated the anti-apoptotic activity of cPrG-HCl, which indicates that cPrG-HCl activated the Ras-PI3K-Akt pathway suppressing apoptosis. On the other hand, serum-deprivation-induced apoptosis was not suppressed by cPrG-HCl.
2.A possible immunosuppressant, cycloprodigiosin hydrochloride, obtained from Pseudoalteromonas denitrificans.
Kawauchi K1, Shibutani K, Yagisawa H, Kamata H, Nakatsuji S, Anzai H, Yokoyama Y, Ikegami Y, Moriyama Y, Hirata H. Biochem Biophys Res Commun. 1997 Aug 28;237(3):543-7.
Cycloprodigiosin hydrochloride (cPrG.HCl), a member of the prodigiosin family, is a red pigment obtained from the marine bacterium Pseudoalteromonas denitrificans. cPrG.HCl markedly suppressed 3H-thymidine incorporation by concanavalin A stimulated murine splenocytes but had little effect on lipopolysaccharide dependent 3H-thymidine incorporation, indicating that cPrG.HCl acts as a selective inhibitor of T cell proliferation in the same way as other members of the prodigiosin family. cPrG.HCl inhibited the proliferation of the PMA stimulated Jurkat cells through an apoptotic process. Intriguingly, cPrG.HCl inhibited the H+ translocation by vacuolar type ATPase in chromaffin granule membranes without any effect on either its ATPase activity nor on the membrane conductance of phospholipid bilayers, suggesting that cPrG.HCl selectively uncouples H+ translocation from the ATPase reaction rather than acting as a non-specific ionophore. Since crystalline cPrG.
3.Induction of apoptosis of activated murine splenic T cells by cycloprodigiosin hydrochloride, a novel immunosuppressant.
Azuma T1, Watanabe N, Yagisawa H, Hirata H, Iwamura M, Kobayashi Y. Immunopharmacology. 2000 Jan;46(1):29-37.
Two types of immunosuppressants, cycloprodigiosin hydrochloride (cPrG) and L-leucyl-L-leucine methyl ester (LeuLeuOMe), both have the ability to selectively inhibit the lysosomal function, and a related compound to cPrG, prodigiosin 25-C, and LeuLeuOMe have been reported to selectively inhibit the T cell function in vitro. We therefore examined the cell-type specificity of cPrG and LeuLeuOMe using murine splenocytes. Concanavalin A (Con A)- and lentil lectin-induced proliferation was suppressed by cPrG more profoundly than lipopolysaccharide-induced proliferation. At the optimal concentration, Con A induced the proliferation of both CD4+ and CD8+ cells, whereas at a supra-optimal concentration Con A induced rather selective proliferation of CD8+ cells. Irrespective of the dose of Con A, CD4+ and CD8+ cells were equally affected by cPrG. In contrast, LeuLeuOMe induced the selective loss of CD8+ cells. cPrG enhanced the apoptosis of murine splenocytes and nylon fiber column-purified T cells cultured in the presence of Con A, as shown by the decrease in cell size and/or DNA fragmentation.
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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 ╳
