WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 510351
CAS#: 71751-77-4
Description: Meleagrin is a new FabI inhibitor from Penicillium chryosogenum. Bacterial enoyl-acyl carrier protein reductase (FabI) is a promising novel antibacterial target. Meleagrin inhibited intracellular fatty acid biosynthesis and growth of S. aureus, and increased the minimum inhibitory concentration for fabI-overexpressing S. aureus.
MedKoo Cat#: 510351
Name: Meleagrin
CAS#: 71751-77-4
Chemical Formula: C23H23N5O4
Exact Mass: 433.175
Molecular Weight: 433.47
Elemental Analysis: C, 63.73; H, 5.35; N, 16.16; O, 14.76
Synonym: Meleagrin, 6-O-Methyloxaline.
IUPAC/Chemical Name: (7aR,12aS,E)-3-((1H-imidazol-5-yl)methylene)-6-hydroxy-12-methoxy-7a-(2-methylbut-3-en-2-yl)-7a,12-dihydro-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5(3H)-dione
InChi Key: JTJJJLSLKZFEPJ-ZAYCRUKZSA-N
InChi Code: InChI=1S/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m0/s1
SMILES Code: CC(C=C)([C@@]12C=C(O)C(N3[C@@]1(N(OC)C4=CC=CC=C24)NC(/C3=C\C5=CN=CN5)=O)=O)C
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 433.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Zheng CJ, Sohn MJ, Lee S, Kim WG. Meleagrin, a new FabI inhibitor from Penicillium chryosogenum with at least one additional mode of action. PLoS One. 2013 Nov 28;8(11):e78922. doi: 10.1371/journal.pone.0078922. eCollection 2013. PubMed PMID: 24312171; PubMed Central PMCID: PMC3842914.
2: Ries MI, Ali H, Lankhorst PP, Hankemeier T, Bovenberg RA, Driessen AJ, Vreeken RJ. Novel key metabolites reveal further branching of the roquefortine/meleagrin biosynthetic pathway. J Biol Chem. 2013 Dec 27;288(52):37289-95. doi: 10.1074/jbc.M113.512665. Epub 2013 Nov 13. PubMed PMID: 24225953; PubMed Central PMCID: PMC3873581.
3: Qin Y, Bao L, Gao M, Chen M, Lei Y, Liu G, Qu Y. Penicillium decumbens BrlA extensively regulates secondary metabolism and functionally associates with the expression of cellulase genes. Appl Microbiol Biotechnol. 2013 Dec;97(24):10453-67. doi: 10.1007/s00253-013-5273-3. Epub 2013 Oct 10. PubMed PMID: 24113825.
4: Ali H, Ries MI, Nijland JG, Lankhorst PP, Hankemeier T, Bovenberg RA, Vreeken RJ, Driessen AJ. A branched biosynthetic pathway is involved in production of roquefortine and related compounds in Penicillium chrysogenum. PLoS One. 2013 Jun 12;8(6):e65328. doi: 10.1371/journal.pone.0065328. Print 2013. PubMed PMID: 23776469; PubMed Central PMCID: PMC3680398.
5: Han Z, Sun J, Zhang Y, He F, Xu Y, Matsumura K, He LS, Qiu JW, Qi SH, Qian PY. iTRAQ-based proteomic profiling of the barnacle Balanus amphitrite in response to the antifouling compound meleagrin. J Proteome Res. 2013 May 3;12(5):2090-100. doi: 10.1021/pr301083e. Epub 2013 Apr 24. PubMed PMID: 23540395.
6: Kim HY, Park HM, Lee CH. Mass spectrometry-based chemotaxonomic classification of Penicillium species (P. echinulatum, P. expansum, P. solitum, and P. oxalicum) and its correlation with antioxidant activity. J Microbiol Methods. 2012 Sep;90(3):327-35. doi: 10.1016/j.mimet.2012.06.006. Epub 2012 Jun 23. PubMed PMID: 22732319.
7: GarcÃa-Estrada C, Ullán RV, Albillos SM, Fernández-Bodega MÃ
