82-89-3 Usage
Description
Prodigiosin is a naturally occurring, intensely red, tripyrrole alkaloid compound with antibiotic properties, produced by several bacteria, most notably Serratia marcescens. It possesses a broad biological profile, displaying immunosuppressive and anti-tumor properties, and is capable of inducing apoptosis and cell cycle arrest in tumor cells.
Used in Pharmaceutical Industry:
Prodigiosin is used as an immunosuppressant for its ability to modulate the immune system, as demonstrated in 2007. It acts via caspase inhibition to induce apoptosis in human primary cancer cells and upregulates p21WAF1/CIP1 expression via the transforming growth factor-β receptor pathway, as well as activating NAG-1 via glycogen synthase kinase-3β.
Used in Anticancer Applications:
Prodigiosin is used as an anti-tumor agent for its ability to selectively upregulate p21WAF/CIP1 and NAG-1, downregulate survivin expression levels, and induce mitochondria-mediated apoptosis and cell cycle arrest in tumor cells. It also prevents FADD phosphorylation and augments cisplatin-induced apoptosis, making it a potential candidate for cancer treatment.
Used in Antimicrobial Applications:
Prodigiosin is used as an antibiotic due to its activity against fungi and tumor cell lines, as well as its effectiveness against malaria. Its broad biological profile makes it a valuable compound in the development of new antimicrobial agents.
Used in Research:
Prodigiosin is used as a research tool for studying the mechanisms of apoptosis, cell cycle regulation, and immune system modulation. Its ability to block NF-κB activation and shrink tumor growth in animal models makes it an important compound for understanding the complex interactions between cells and their microenvironment.
Enzyme inhibitor
This red bacterial pigment (FWfree-base = 323.44 g/mol; melting point = 151- 152°C) is an antibiotic produced by Serratia marcescens (formerly Chromobacterium prodigiosum). Prodigiosin is the parent member of a class of pyrrole-containing natural products that exhibit immunosuppressive, cytotoxic, and apoptotic activity and can facilitate copper-promoted oxidative double-strand DNA cleavage through reductive activation of Cu2+. They also uncouple lysosomal vacuolar-type ATPases by promoting H+/Cl– symport activity. The solid pigment is dark red and displays a green reflex. Acidic aqueous solutions are also red, but neutral or alkaline solutions are orange-yellow. Target(s): DNA topoisomerase I; DNA topoisomerase II; FoF1 ATPase, or H+-transporting two-sector ATPase, as an uncoupler; H+/K+-ATPase, as an uncoupler; proton translocation, as an uncoupler; and Serratia marcescens nuclease.
Check Digit Verification of cas no
The CAS Registry Mumber 82-89-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 2 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 82-89:
(4*8)+(3*2)+(2*8)+(1*9)=63
63 % 10 = 3
So 82-89-3 is a valid CAS Registry Number.
82-89-3Relevant articles and documents
Pyrrole-Type compounds, compositions, and methods for treating cancer or viral diseases
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, (2008/06/13)
The present invention relates to novel Pyrrole-Type compounds, compositions comprising Pyrrole-Type compounds, and methods useful for treating or preventing cancer or a neoplastic disorder comprising administering a composition comprising a Pyrrole-Type compound. The compounds, compositions, and methods of the invention are also useful for inhibiting the growth of a cancer cell or neoplastic cell. The present invention also relates to novel Pyrrole-Type compounds, compositions, and methods useful for treating or preventing a viral infection. The compounds, compositions, and methods of the invention are also useful for inhibiting the replication and/or infectivity of a virus.
Process for the preparation of 2,2'-bipyrrolyl-pyrromethene (prodigiosins) derivatives
-
, (2008/06/13)
The present invention is related to a process for the preparation of 5-?2H-pyrrol-2-ylidene)methyl!-2,2'-bi-1H-pyrrole compounds and an intermediate compound.
Total Synthesis of Prodigiosin, Prodigiosene, and Desmethoxyprodigiosin: Diels-Adler Reactions of Heterocyclic Azadienes and Development of an Effective Palladium(II)-Promoted 2,2'-Bipyrrole Coupling Procedure
Boger, Dale L.,Patel, Mona
, p. 1405 - 1415 (2007/10/02)
The total synthesis of prodigiosin (1), a red pigment first isolated from Serratia marcescens, possessing the characteristic pyrrolylpyrromethene skeleton of a class of naturally occurring polypyrroles exhibiting antimicrobial and cytotoxic properties, is detailed.The approach is based application of an inverse electron demand Diels-Adler reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate in a 1,2,4,5-tetrazine--->1,2-diazine--->pyrrole strategy for preparation of prodigiosin pyrrole ring B and the subsequent implementation of an effective intramolecular palladium(II)-promoted 2,2'-diaryl coupling for construction of the prodigiosin 2,2'-bipyrrole AB ring system.In situ generated activated ester derivatives of pyrrole-1-carboxylic acid or the use of pyrrole-1-carboxylic acid anhydride proved suitable for the generation of mixed 1,1'-carbonyldipyrrole compounds for use in the palladium(II)-promoted mixed, 2,2'-bipyrrole coupling.Extensions of this approach to the preparation of the naturally occurring parent pyrrolylpyrromethene, prodigiosene (2a), and 2-methyl-3-pentylprodigiosene (2e, desmethoxyprodigiosin) are detailed.A comparison of the in vitro cytotoxic properties of prodigiosin (1), prodigiosene (2a), and 2-methyl-3-pentylprodigiosene (2e) are reported and reveal exceptional cytotoxic potency (3.7*10-4 μg/mL = 3.7*10-10 g/mL) for prodigiosin against 9PS (P388) mouse leukemia which may be attributed to the presence of the prodigiosin C-6 methoxy substituent.
