Page last updated: 2024-10-15

prodigiosin

Description

Prodigiosin: 4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)- 2,2'-bi-1H-pyrrole. A toxic, bright red tripyrrole pigment from Serratia marcescens and others. It has antibacterial, anticoccidial, antimalarial, and antifungal activities, but is used mainly as a biochemical tool. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

prodigiosin : A member of the class of tripyrroles that is a red-coloured pigment with antibiotic properties produced by Serratia marcescens. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID135455579
CHEMBL ID275787
CHEMBL ID5095533
CHEBI ID82758
SCHEMBL ID147408
SCHEMBL ID1388956
SCHEMBL ID19452932
MeSH IDM0017640

Synonyms (22)

Synonym
prodigiosin
mls000736622 ,
NCI60_004112
82-89-3
prodigiosine
smr000446746
CHEMBL275787
chebi:82758 ,
(2z,5z)-3-methoxy-2-[(5-methyl-4-pentyl-1h-pyrrol-2-yl)methylidene]-5-pyrrol-2-ylidenepyrrole
CCG-35303
SCHEMBL147408
4-methoxy-5-[(z)-(5-methyl-4-pentyl-2h-pyrrol-2-ylidene)methyl]-1h,1'h-2,2'-bipyrrole
SCHEMBL1388956
SCHEMBL19452932
Q415663
prodigiosin serratia marcescens - cas 82-89-3
DTXSID001018969
4-methoxy-5-((5-methyl-4-pentyl-2h-pyrrol-2-ylidene)methyl)-1h,1'h-2,2'-bipyrrole
4-methoxy-5-[(5-methyl-4-pentyl-2h-pyrrol-2-ylidene)methyl]-2,2'-bi[1h-pyrrole]
(2z)-3-methoxy-2-[(5-methyl-4-pentyl-1h-pyrrol-2-yl)methylidene]-5-(1h-pyrrol-2-yl)pyrrole
CHEMBL5095533
AKOS040742451

Toxicity

Benznidazole was less toxic (IC(50)=2000 microM) than prodigiosin. It was found to be less toxic in V79 cells based on MTT and NAC assays.

ExcerptReference
" Benznidazole was less toxic (IC(50)=2000 microM) than prodigiosin (IC(50)=1-20 microM) in V79 cells based on the MTT and NAC assays."( Cytotoxicity of prodigiosin and benznidazole on V79 cells.
da Silva Melo, P; Durán, N; Haun, M, 2000
)
" Originally, the specific features of the toxic and genotoxic effects of prodigiosin and the possibility of induction of mutations by pigment in the cells of Salmonella typhimurium TA 100 (Ames test) and chromosome damage of mammalian erythroblasts have been determined."( [Bacterial pigment prodigiosin and its genotoxic effects].
Gnezdilov, OI; Gur'ianov, ID; Iusupova, DV; Karamova, NS; Koshkarova, LA,
)
" PG could slightly significant increase Dox cytotoxicity in all tested normal cells whose toxic alteration was less than that of oral squamous carcinoma cells."( Doxorubicin metabolism moderately attributes to putative toxicity in prodigiosin/doxorubicin synergism in vitro cells.
Chen, CC; Lin, CS; Lin, SR; Tseng, FJ; Weng, CF; Weng, L; Wu, TJ, 2020
)

Pharmacokinetics

ExcerptReference
" After testing the differences in pharmacokinetic parameters of the different formulations using ANOVA, the results showed insignificant differences among the tested parameters."( HPLC with fluorescence detection for the bioanalysis and pharmacokinetic study of Doxorubicin and Prodigiosin loaded on eco-friendly casein nanomicelles in rat plasma.
Abdine, HH; Aboras, SI; Agwa, MM; El Diwany, A; Korany, MA; Ragab, MAA, 2021
)

Compound-Compound Interactions

ExcerptReference
" The therapeutic effect of carbenicillin increased when it was used in combination with prodigiozan and especially in combination with prodigiozan and lysozyme."( [Effect of carbenicillin and its combination with prodigiozan and lysozyme on the course of an experimental inflammatory process of Proteus etiology].
Dikiĭ, BN, 1975
)
" Prednisolone in combination with asathioprin (imuran) administered to CBA mice inhibited the GVHR."( [Effect of prodigiosin and its combination with immunodepressants on the graft versus host reaction in mice].
Alekhin, EK; Shigaev, NI, 1983
)
" In this study, we used prodigiosin, a bacterial pigment endowed with magnificent biological properties, in combination with six antibiotics to study its effect on Pseudomonas aeruginosa, Staphylococcus aureus and Chromobacterium violaceum."( Synergistic bactericidal profiling of prodigiosin extracted from Serratia marcescens in combination with antibiotics against pathogenic bacteria.
Bhattacharjee, G; Gohil, N; Singh, V, 2020
)

Bioavailability

ExcerptReference
" However, PG vehiculation into different delivery systems has been proposed since possesses low bioavailability because of its high hydrophobic character (XLogP3-AA = 4."( Prodigiosin: a promising biomolecule with many potential biomedical applications.
Castro, GR; Duran, N; Islan, GA; Noacco, N; Rodenak-Kladniew, B, 2022
)

Dosage Studied

ExcerptReference
" We examined the activation of caspases-9, -8, and -3 in PG-treated Jurkat cells in a dose-response study."( Prodigiosin induces caspase-9 and caspase-8 activation and cytochrome C release in Jurkat T cells.
Montaner, B; Perez-Tomas, R, 2002
)
" The dose-response for the cytotoxic effect of prodigiosin was analyzed in cells from 12 patients showing an IC(50) of 116+/-25 nM."( Prodigiosin induces apoptosis of B and T cells from B-cell chronic lymphocytic leukemia.
Barragán, M; Bellosillo, B; Campàs, C; Colomer, D; Dalmau, M; Gil, J; Montaner, B; Pérez-Tomás, R; Pons, G, 2003
)
" We observed through Western blot that PG mediated cytochrome c release, caspase cascade activation and PARP cleavage, thereby leading to apoptosis in a dose-response manner."( High cytotoxic sensitivity of the human small cell lung doxorubicin-resistant carcinoma (GLC4/ADR) cell line to prodigiosin through apoptosis activation.
Gimenez-Bonafé, P; Joshi, R; Llagostera, E; Montaner, B; Pérez-Tomás, R; Soto-Cerrato, V, 2005
)
" Each analogue reduced parasitemia by more than 90% after 25 (mg/kg)/day dosing and in some cases provided a cure."( Antimalarial activity of natural and synthetic prodiginines.
Alhamadsheh, M; Challis, GL; Haynes, SW; Kelly, JX; Papireddy, K; Reynolds, KA; Salem, SM; Smilkstein, M, 2011
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Low molecular weight protein-tyrosine phosphatase AMycobacterium tuberculosis H37RvIC50 (µMol)8.80002.74005.39678.8000AID643693
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (1)

Processvia Protein(s)Taxonomy
symbiont-mediated suppression of host apoptosisLow molecular weight protein-tyrosine phosphatase AMycobacterium tuberculosis H37Rv
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (1)

Processvia Protein(s)Taxonomy
protein tyrosine phosphatase activityLow molecular weight protein-tyrosine phosphatase AMycobacterium tuberculosis H37Rv
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
cytosolLow molecular weight protein-tyrosine phosphatase AMycobacterium tuberculosis H37Rv
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID1171221Ratio of MIC for wild-type Staphylococcus aureus in presence of 2% HSA to MIC for wild-type Staphylococcus aureus2014Journal of medicinal chemistry, Dec-11, Volume: 57, Issue:23
Trends and exceptions of physical properties on antibacterial activity for Gram-positive and Gram-negative pathogens.
AID436177Cytotoxicity against human SKOV3 cells after 48 hrs by SRB assay2008Journal of natural products, Nov, Volume: 71, Issue:11
A 2-substituted prodiginine, 2-(p-hydroxybenzyl)prodigiosin, from Pseudoalteromonas rubra.
AID1171215Antibacterial activity against wild-type Escherichia coli2014Journal of medicinal chemistry, Dec-11, Volume: 57, Issue:23
Trends and exceptions of physical properties on antibacterial activity for Gram-positive and Gram-negative pathogens.
AID1171222Ratio of MIC for wild-type tolC-deficient Escherichia coli in presence of 2% HSA to MIC for tolC-deficient Escherichia coli in presence of 2% HSA2014Journal of medicinal chemistry, Dec-11, Volume: 57, Issue:23
Trends and exceptions of physical properties on antibacterial activity for Gram-positive and Gram-negative pathogens.
AID260712Antiproliferative activity against NCI-H460 cell line by MTS assay2006Bioorganic & medicinal chemistry letters, Feb, Volume: 16, Issue:3
Indoloprodigiosins from the C-10 bipyrrolic precursor: new antiproliferative prodigiosin analogs.
AID260708Antiproliferative activity against A549 cell line by MTS assay2006Bioorganic & medicinal chemistry letters, Feb, Volume: 16, Issue:3
Indoloprodigiosins from the C-10 bipyrrolic precursor: new antiproliferative prodigiosin analogs.
AID260709Antiproliferative activity against DLD1 cell line by MTS assay2006Bioorganic & medicinal chemistry letters, Feb, Volume: 16, Issue:3
Indoloprodigiosins from the C-10 bipyrrolic precursor: new antiproliferative prodigiosin analogs.
AID1171214Antibacterial activity against tolC-deficient Escherichia coli in presence of 2% HSA2014Journal of medicinal chemistry, Dec-11, Volume: 57, Issue:23
Trends and exceptions of physical properties on antibacterial activity for Gram-positive and Gram-negative pathogens.
AID1171213Antibacterial activity against tolC-deficient Escherichia coli2014Journal of medicinal chemistry, Dec-11, Volume: 57, Issue:23
Trends and exceptions of physical properties on antibacterial activity for Gram-positive and Gram-negative pathogens.
AID1171219Antibacterial activity against wild-type Staphylococcus aureus2014Journal of medicinal chemistry, Dec-11, Volume: 57, Issue:23
Trends and exceptions of physical properties on antibacterial activity for Gram-positive and Gram-negative pathogens.
AID260710Antiproliferative activity against HT29 cell line by MTS assay2006Bioorganic & medicinal chemistry letters, Feb, Volume: 16, Issue:3
Indoloprodigiosins from the C-10 bipyrrolic precursor: new antiproliferative prodigiosin analogs.
AID1171220Antibacterial activity against wild-type Staphylococcus aureus in presence of 2% HSA2014Journal of medicinal chemistry, Dec-11, Volume: 57, Issue:23
Trends and exceptions of physical properties on antibacterial activity for Gram-positive and Gram-negative pathogens.
AID643693Inhibition of Mycobacterium tuberculosis PTP-A2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Synthesis, biological evaluation, and molecular modeling of chalcone derivatives as potent inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatases (PtpA and PtpB).
AID260711Antiproliferative activity against MDA-MB-231 cell line by MTS assay2006Bioorganic & medicinal chemistry letters, Feb, Volume: 16, Issue:3
Indoloprodigiosins from the C-10 bipyrrolic precursor: new antiproliferative prodigiosin analogs.
AID436178Inhibition of human topoisomerase 12008Journal of natural products, Nov, Volume: 71, Issue:11
A 2-substituted prodiginine, 2-(p-hydroxybenzyl)prodigiosin, from Pseudoalteromonas rubra.
AID612143Antimalarial activity Plasmodium falciparum D6 after 72 hrs by SYBR Green I based fluorescence assay2011Journal of medicinal chemistry, Aug-11, Volume: 54, Issue:15
Antimalarial activity of natural and synthetic prodiginines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (705)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990162 (22.98)18.7374
1990's49 (6.95)18.2507
2000's163 (23.12)29.6817
2010's231 (32.77)24.3611
2020's100 (14.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (0.40%)5.53%
Reviews37 (4.95%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other707 (94.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]