Citreoindole
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| Category | Mycotoxins |
| Catalog number | BBF-04681 |
| CAS | 138655-14-8 |
| Molecular Weight | 496.56 |
| Molecular Formula | C29H28N4O4 |
| Purity | >95% by HPLC |
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Description
Citreoindole is a diketopiperazine metabolite isolated from a hybrid cell fusion of two strains of P. citreovirde that is cytotoxic in vitro against HeLa cells at 8.4 μM.
Specification
| Storage | Store at -20°C |
| IUPAC Name | (3S,6S)-3-benzyl-6-[[(2S,10R)-10-hydroxy-4-oxo-2-phenyl-1,2,3,10a-tetrahydropyrimido[1,2-a]indol-10-yl]methyl]piperazine-2,5-dione |
| Canonical SMILES | C1C(NC2C(C3=CC=CC=C3N2C1=O)(CC4C(=O)NC(C(=O)N4)CC5=CC=CC=C5)O)C6=CC=CC=C6 |
| InChI | InChI=1S/C29H28N4O4/c34-25-16-21(19-11-5-2-6-12-19)32-28-29(37,20-13-7-8-14-24(20)33(25)28)17-23-27(36)30-22(26(35)31-23)15-18-9-3-1-4-10-18/h1-14,21-23,28,32,37H,15-17H2,(H,30,36)(H,31,35)/t21-,22-,23-,28?,29+/m0/s1 |
| InChI Key | PDYXWTDVSYEDKW-WDARXMFGSA-N |
Properties
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. Antibacterial and photocatalytic activities of 5-nitroindole capped bimetal nanoparticles against multidrug resistant bacteria
Ranjith Kumar Manoharan, Shanmugam Mahalingam, Prakash Gangadaran, Young-Ho Ahn Colloids Surf B Biointerfaces. 2020 Apr;188:110825. doi: 10.1016/j.colsurfb.2020.110825. Epub 2020 Jan 24.
The emergence of antibiotic resistance to commercially- available antibiotics is becoming a major health crisis worldwide. Non-antibiotic strategies are needed to combat biofilm-associated infectious diseases caused by multidrug resistant (MDR) bacterial pathogens. In this study, MBR1 was isolated from a membrane bioreactor used in wastewater treatment plants, and the resistance profile was explored. 5-Nitroindole (5 N)-capped CuO/ZnO bimetal nanoparticles (5 NNP) were synthesized using a one pot method to improve the antibacterial and antibiofilm activities of 5 N against Gram-negative (Escherichia coli ATCC700376 and Pseudomonas aeruginosa PA01) and positive (Staphylococcus aureus ATCC6538) human pathogens. 5 NNP containing 1 mM of 5 N exhibited strong antibacterial and antibiofilm properties to most MDR bacteria. In addition, the photocatalytic activity of CuO/ZnO reduced bacterial cell growth by 1.8 log CFU/mL maximum when exposed to visible light. Scanning electron microscopy showed that 5 NNP reduced the cell density and biofilm attachment of MBR1 by >90% under static conditions. In addition to the antimicrobial and antibiofilm activities, 5 NNP inhibited the persister cell formation of MDR bacterial strains P. aeruginosa, MBR1, E. coli and S. aureus. Therefore, it is speculated that 5 NNP potentially inhibits biofilm and persister cells; hence, 5 NNP could be an alternative agent to combat MDR infectious diseases using a non-antibiotic therapeutic approach.
2. Regioselective synthesis of 6-nitroindole derivatives from enaminones and nitroaromatic compounds via transition metal-free C-C and C-N bond formation
Danhua Ge, Li-Wen Sun, Zi-Lun Yu, Xin-Long Luo, Pei Xu, Zhi-Liang Shen Org Biomol Chem. 2022 Feb 16;20(7):1493-1499. doi: 10.1039/d1ob02443d.
Few methods are known for the synthesis of nitroindole derivatives. A simple and practical Cs2CO3-promoted method for the synthesis of 6-nitroindole derivatives from enaminones and nitroaromatic compounds has been developed. Two new C-C and C-N bonds were formed in a highly regioselective manner under transition metal-free conditions.
3. Synthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity
Vijaykumar D Nimbarte, Julia Wirmer-Bartoschek, Santosh L Gande, Islam Alshamleh, Marcel Seibert, Hamid Reza Nasiri, Frank Schnütgen, Hubert Serve, Harald Schwalbe ChemMedChem. 2021 May 18;16(10):1667-1679. doi: 10.1002/cmdc.202000835. Epub 2021 Mar 22.
Lead-optimization strategies for compounds targeting c-Myc G-quadruplex (G4) DNA are being pursued to develop anticancer drugs. Here, we investigate the structure-activity- relationship (SAR) of a newly synthesized series of molecules based on the pyrrolidine-substituted 5-nitro indole scaffold to target G4 DNA. Our synthesized series allows modulation of flexible elements with a structurally preserved scaffold. Biological and biophysical analyses illustrate that substituted 5-nitroindole scaffolds bind to the c-Myc promoter G-quadruplex. These compounds downregulate c-Myc expression and induce cell-cycle arrest in the sub-G1/G1 phase in cancer cells. They further increase the concentration of intracellular reactive oxygen species. NMR spectra show that three of the newly synthesized compounds interact with the terminal G-quartets (5'- and 3'-ends) in a 2 : 1 stoichiometry.
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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 ╳
