Fiscalin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00929 |
| CAS | |
| Molecular Weight | 386.45 |
| Molecular Formula | C23H22N4O2 |
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Description
Fiscalin B is a substance P inhibitor produced by Neosartorya fischeri.
Specification
| IUPAC Name | (1S,4R)-4-(1H-indol-3-ylmethyl)-1-propan-2-yl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione |
| Canonical SMILES | CC(C)C1C2=NC3=CC=CC=C3C(=O)N2C(C(=O)N1)CC4=CNC5=CC=CC=C54 |
| InChI | InChI=1S/C23H22N4O2/c1-13(2)20-21-25-18-10-6-4-8-16(18)23(29)27(21)19(22(28)26-20)11-14-12-24-17-9-5-3-7-15(14)17/h3-10,12-13,19-20,24H,11H2,1-2H3,(H,26,28)/t19-,20+/m1/s1 |
| InChI Key | DNPSVQYQTPYSPH-UXHICEINSA-N |
Reference Reading
1. Glucose-6-phosphate dehydrogenase immobilized onto magnetic beads (G6PDH-Mb) as a generator system for production of NADPH: Development and application in metabolism studies
Izadora Liranço Furlani, Regina Vincenzi Oliveira, Quezia Bezerra Cass J Pharm Biomed Anal. 2022 Sep 20;219:114901. doi: 10.1016/j.jpba.2022.114901. Epub 2022 Jun 18.
Reduced nicotinamide adenine dinucleotide phosphate (NADPH) participates in several anabolic and catabolic pathways, being essential in numerous biochemical reactions involving energy release. Most of these reactions require a high amount of NADPH, which can be expensive from an industry point of view. Thus, biotechnology industries developed a great interest in NADPH production. Currently, there are different ways to obtain NADPH in situ, however, the most common is by enzymatic reactions, known as generator systems. Although this approach can be beneficial in terms of cost, the major drawback is the impossibility of reusing the enzyme. To overcome this, enzyme immobilization is a proven alternative. Herein, we report the use of glucose-6-phosphate dehydrogenase immobilized onto magnetic beads (G6PDH-Mb) through glutaraldehyde coupling to produce high amounts of NADPH. The G6PDH-Mbs were kinetically characterized showing a sigmoidal curve. Besides, the stability was evaluated, and their reuse was demonstrated for a period superior to 40 days. The G6PDH-Mb was used to in situ production of the NADPH metabolism experiments, using human liver microsome solutions and either albendazole or fiscalin B as model targets. The production of in vitro metabolites from albendazole and fiscalin B was evaluated by comparing the use of NADPH generated in situ with those obtained by commercial NADPH. Moreover, the activity of the G6PDH-Mb was monitored after using it for five consecutive albendazole metabolism reactions, with only a minor decrease in the enzyme activity (3.58 ± 1.67%) after the fifth time of use. The higher concentration obtained when using the designed G6PDH-Mb generator system demonstrated proof of the concept and its applicability.
2. Synthesis of New Proteomimetic Quinazolinone Alkaloids and Evaluation of Their Neuroprotective and Antitumor Effects
Solida Long, Diana I S P Resende, Anake Kijjoa, Artur M S Silva, Ricardo Fernandes, Cristina P R Xavier, M Helena Vasconcelos, Emília Sousa, Madalena M M Pinto Molecules. 2019 Feb 1;24(3):534. doi: 10.3390/molecules24030534.
New quinazolinone derivatives of the marine-derived alkaloids fiscalin B (3) and fumiquinazoline G (1), with neuroprotective and antitumor effects, were synthesized. Eleven quinazolinone-containing indole alkaloids were synthesized, proceeding the anti analogs via a one-pot method, and the syn analogs by the Mazurkiewicz-Ganesan approach. The neuroprotection capacity of these compounds on the rotenone-damage human neuroblastoma cell SH-SY5y was evaluated using the MTT assay. Compounds 1, 3, 5, and 7 showed more than 25% protection. The antitumor activity was investigated using the sulforhodamine B assay and some compounds were tested on the non-malignant MCF-12A cells. Fumiquinazoline G (1) was the most potent compound, with GI50 values lower than 20 µM. Compounds 5, 7, and 11 were more active in all tumor cell lines when compared to their enantiomers. Compounds 5, 7, 10, and 11 had very little effect in the viability of the non-malignant cells. Differences between enantiomeric pairs were also noted as being essential for these activities the S-configuration at C-4. These results reinforce the previously described activities of the fiscalin B (3) as substance P inhibitor and fumiquinazoline G (1) as antitumor agent showing potential as lead compounds for the development of drugs for treatment of neurodegenerative disorders and cancer, respectively.
3. Determination of the Absolute Configuration of Bioactive Indole-Containing Pyrazino[2,1- b]quinazoline-3,6-diones and Study of Their In Vitro Metabolic Profile
Solida Long, Izadora L Furlani, Juliana M de Oliveira, Diana I S P Resende, Artur M S Silva, Luís Gales, José A Pereira, Anake Kijjoa, Quezia B Cass, Regina V Oliveira, Emília Sousa, Madalena M M Pinto Molecules. 2021 Aug 21;26(16):5070. doi: 10.3390/molecules26165070.
In recent decades, fungi-derived naturally occurring quinazolines have emerged as potential drug candidates. Nevertheless, most studies are conducted for bioactivity assays, and little is known about their absorption, distribution, metabolism, and elimination (ADME) properties. To perform metabolic studies, the synthesis of the naturally occurring quinazolinone, fiscalin B (1), and its chloro derivative, 4-((1H-indol-3-yl)methyl)-8,10-dichloro-1-isobutyl-1,2-dihydro-6H-pyrazino[2,1-b]quinazoline-3,6(4H)-dione (2), disclosed as an antibacterial agent, was performed in a gram scale using a microwave-assisted polycondensation reaction with 22% and 17% yields, respectively. The structure of the non-natural (+)-fiscalin B was established, for the first time, by X-ray crystallography as (1R,4S)-1, and the absolute configuration of the naturally occurring fiscalin B (-)-1 was confirmed by comparison of its calculated and experimental electronic circular dichroism (ECD) spectra as (1S,4R)-1. in vitro metabolic studies were monitored for this class of natural products for the first time by ultra-high-performance liquid chromatography (UHPLC) coupled with high-resolution mass spectrometry (HRMS). The metabolic characteristics of 1 and 2 in human liver microsomes indicated hydration and hydroxylation mass changes introduced to the parent drugs.
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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 ╳
