Prodigiosin

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Prodigiosin
Category Antibiotics
Catalog number BBF-02587
CAS 82-89-3
Molecular Weight 323.43
Molecular Formula C20H25N3O
Purity >95% by HPLC

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Description

It is an antibiotic produced by Serratia marcescens HY-3 and Ser. marinorubra. It has a broad biological profile with activity against fungi, tumour cell lines and malaria. It also acts as an inducer of p21WAF1/CIP1 expression via transforming growth factor-β receptor pathway, and activates NAG-1 via glycogen synthase kinase-3β.

Specification

Synonyms (2Z,5Z)-4-methoxy-5-((5-methyl-4-pentyl-1H-pyrrol-2-yl)methylene)-1,5-dihydro-2,2'-bipyrrolylidene
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
Canonical SMILES CCCCCC1=C(NC(=C1)C=C2C(=CC(=N2)C3=CC=CN3)OC)C
InChI InChI=1S/C20H25N3O/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/b19-12-
InChI Key SHUNBVWMKSXXOM-UNOMPAQXSA-N
Source Serratia marcescens

Properties

Appearance Dark Red Crystal
Antibiotic Activity Spectrum fungi; neoplastics (Tumor)
Boiling Point 542.4°C at 760 mmHg
Melting Point 152-153°C (dec.)
Density 1.12 g/cm3
Solubility Soluble in DMSO, ethanol, methanol, DMF

Reference Reading

1. Recent Advances in Prodigiosin as a Bioactive Compound in Nanocomposite Applications
Mario E Barocio, Damià Barceló, Hafiz M N Iqbal, Natalia Rodríguez Zavala, Enrique Hidalgo-Vázquez, Roberto Parra-Saldívar, Juan Eduardo Sosa-Hernández, Carlos Castillo-Zacarías, Lizeth Parra-Arroyo, Manuel Martínez-Ruiz, Jesús Alfredo Rodríguez-Hernández, Wei Ning Chen, Rafael G Araújo, María Adriana Martínez-Prado Molecules . 2022 Aug 5;27(15):4982. doi: 10.3390/molecules27154982.
Bionanocomposites based on natural bioactive entities have gained importance due to their abundance; renewable and environmentally benign nature; and outstanding properties with applied perspective. Additionally, their formulation with biological molecules with antimicrobial, antioxidant, and anticancer activities has been produced nowadays. The present review details the state of the art and the importance of this pyrrolic compound produced by microorganisms, with interest towardsSerratia marcescens, including production strategies at a laboratory level and scale-up to bioreactors. Promising results of its biological activity have been reported to date, and the advances and applications in bionanocomposites are the most recent strategy to potentiate and to obtain new carriers for the transport and controlled release of prodigiosin. Prodigiosin, a bioactive secondary metabolite, produced bySerratia marcescens, is an effective proapoptotic agent against bacterial and fungal strains as well as cancer cell lines. Furthermore, this molecule presents antioxidant activity, which makes it ideal for treating wounds and promoting the general improvement of the immune system. Likewise, some of the characteristics of prodigiosin, such as hydrophobicity, limit its use for medical and biotechnological applications; however, this can be overcome by using it as a component of a bionanocomposite. This review focuses on the chemistry and the structure of the bionanocomposites currently developed using biorenewable resources. Moreover, the work illuminates recent developments in pyrrole-based bionanocomposites, with special insight to its application in the medical area.
2. Prodigiosin of Serratia marcescens ZPG19 Alters the Gut Microbiota Composition of Kunming Mice
Xue Li, Jie Zhang, Xinfeng Tan, Baolei Jia, Xiaoling Zhu, Jing Zhang, Qingshuang Chen Molecules . 2021 Apr 9;26(8):2156. doi: 10.3390/molecules26082156.
Prodigiosin is a red pigment produced bySerratia marcescenswith anticancer, antimalarial, and antibacterial effects. In this study, we extracted and identified a red pigment from a culture ofS. marcescensstrain ZPG19 and investigated its effect on the growth performance and intestinal microbiota of Kunming mice. High-performance liquid chromatography/mass spectrometry revealed that the pigment had a mass-to-charge ratio (m/z) of 324.2160, and thus it was identified as prodigiosin. To investigate the effect of prodigiosin on the intestinal microbiota, mice (n = 5) were administered 150 μg/kg/d prodigiosin (crude extract, 95% purity) via the drinking water for 18 days. Administration of prodigiosin did not cause toxicity in mice. High-throughput sequencing analysis revealed that prodigiosin altered the cecum microbiota abundance and diversity; the relative abundance ofDesulfovibriosignificantly decreased, whereasLactobacillus reuterisignificantly increased. This finding indicates that oral administration of prodigiosin has a beneficial effect on the intestinal microbiota of mice. As prodigiosin is non-toxic to mouse internal organs and improves the mouse intestinal microbiota, we suggest that it is a promising candidate drug to treat intestinal inflammation.
3. The production and bioactivity of prodigiosin: quo vadis?
Yu-Hsin Chen, Ching-Feng Weng, Feng-Jen Tseng, Shian-Ren Lin Drug Discov Today . 2020 May;25(5):828-836. doi: 10.1016/j.drudis.2020.03.017.
Prodigiosin (PG), a red tripyrrole pigment, belongs to a member of the prodiginine family and is normally secreted by various sources including Serratia marcescens and other Gram-negative bacteria. The studies of PG have received innovative devotion as a result of reported antimicrobial, larvicidal and anti-nematoid immunomodulation and antitumor properties, owing to its antibiotic and cytotoxic activities. This review provides a comprehensive summary of research undertaken toward the isolation and structural elucidation of the prodiginine family of natural products. Additionally, the current evidence-based understanding of the biological activities and medicinal potential of PG is employed to determine the efficacy, with some reports of information related to pharmacokinetics, pharmacodynamics and toxicology.

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