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MedKoo Cat#: 562167 | Name: Prodigiosin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Prodigiosin is a secondary metabolite of Serratia marcescens and a red tripyrrole pigment from the prodiginine family. It displays a wide range of biological activities, including acting as an antimalarial, antifungal, immunosuppressant, and antibiotic agent.

Chemical Structure

Prodigiosin
CAS#82-89-3 (free base)

Theoretical Analysis

MedKoo Cat#: 562167

Name: Prodigiosin

CAS#: 82-89-3 (free base)

Chemical Formula: C20H25N3O

Exact Mass: 323.1998

Molecular Weight: 323.44

Elemental Analysis: C, 74.27; H, 7.79; N, 12.99; O, 4.95

Price and Availability

Size Price Availability Quantity
10mg USD 2,150.00 2 Weeks
25mg USD 4,250.00 2 Weeks
50mg USD 7,650.00 2 Weeks
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Related CAS #
82-89-3 (free base) 112373-40-7 (HCl)
Synonym
Prodigiosin; BRN 4526727; NSC 47147;
IUPAC/Chemical Name
(2Z,5Z)-4-methoxy-5-((5-methyl-4-pentyl-1H-pyrrol-2-yl)methylene)-1,5-dihydro-2,2'-bipyrrolylidene
InChi Key
WKGQSEFBQTWRPT-UUPRNIFOSA-N
InChi Code
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/h7,9-13,22-23H,4-6,8H2,1-3H3/b18-17-,19-12-
SMILES Code
CCCCCC1=C(C)NC(/C=C(C(OC)=C/2)\NC2=C3N=CC=C/3)=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 323.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Eluu SC, Obayemi JD, Yiporo D, Salifu AA, Oko AO, Onwudiwe K, Aina T, Oparah JC, Ezeala CC, Etinosa PO, Osafo SA, Ugwu MC, Esimone CO, Soboyejo WO. Luteinizing Hormone-Releasing Hormone (LHRH)-Conjugated Cancer Drug Delivery from Magnetite Nanoparticle-Modified Microporous Poly-Di-Methyl-Siloxane (PDMS) Systems for the Targeted Treatment of Triple Negative Breast Cancer Cells. J Funct Biomater. 2024 Jul 28;15(8):209. doi: 10.3390/jfb15080209. PMID: 39194647. 2: García-Martín J, García-Abad L, Santamaría RI, Díaz M. Functional connexion of bacterioferritin in antibiotic production and morphological differentiation in Streptomyces coelicolor. Microb Cell Fact. 2024 Aug 24;23(1):234. doi: 10.1186/s12934-024-02510-1. PMID: 39182107; PMCID: PMC11344345. 3: Zheng Q, Zhang W, Wang L, Wen X, Wu J, Ren Y, Fu R. Functional dyeing of cellulose macromolecule/synthetic fibers two-component fabrics with sustainable microbial prodigiosins. Int J Biol Macromol. 2024 Aug 22;278(Pt 3):134964. doi: 10.1016/j.ijbiomac.2024.134964. Epub ahead of print. PMID: 39179072. 4: Pantelic L, Skaro Bogojevic S, Andrejević TP, Pantović BV, Marković VR, Ašanin DP, Milanović Ž, Ilic-Tomic T, Nikodinovic-Runic J, Glišić BĐ, Lazic J. Copper(II) and Zinc(II) Complexes with Bacterial Prodigiosin Are Targeting Site III of Bovine Serum Albumin and Acting as DNA Minor Groove Binders. Int J Mol Sci. 2024 Aug 1;25(15):8395. doi: 10.3390/ijms25158395. PMID: 39125963; PMCID: PMC11313072. 5: Esteves NC, Scharf BE. Serratia marcescens ATCC 274 increases production of the red pigment prodigiosin in response to Chi phage infection. Sci Rep. 2024 Jul 31;14(1):17750. doi: 10.1038/s41598-024-68747-3. PMID: 39085460; PMCID: PMC11291754. 6: Liu W, Shi R, Zhang Y, Li C, Zhou X, Jensen MS, Yang J, Zhao S, Liu J, Zhu J, Liu C, Sun D. ROK family regulator NagC promotes prodigiosin biosynthesis independent of N-acetylglucosamine in Serratia sp. ATCC 39006. Appl Environ Microbiol. 2024 Jul 24;90(7):e0089124. doi: 10.1128/aem.00891-24. Epub 2024 Jul 2. PMID: 38953369; PMCID: PMC11267903. 7: Yang HA, Han TH, Haam K, Lee KS, Kim J, Han TS, Lee MS, Ban HS. Prodigiosin regulates cancer metabolism through interaction with GLUT1. Nat Prod Res. 2024 Jun 24:1-8. doi: 10.1080/14786419.2024.2367241. Epub ahead of print. PMID: 38913075. 8: Lu Y, Liu D, Jiang R, Li Z, Gao X. Prodigiosin: unveiling the crimson wonder - a comprehensive journey from diverse bioactivity to synthesis and yield enhancement. Front Microbiol. 2024 Jun 5;15:1412776. doi: 10.3389/fmicb.2024.1412776. PMID: 38903802; PMCID: PMC11188435. 9: Zhao H, Jiang M, Wang X, Gao H, Zhang Y, Wang J, Zhang X, Zhao D, Zhang F. Pathogenic fungi synergistically cooperate with Serratia marcescens to increase cockroach mortality. Pestic Biochem Physiol. 2024 Jun;202:105951. doi: 10.1016/j.pestbp.2024.105951. Epub 2024 May 10. PMID: 38879336. 10: Wei N, Zha F, Zhou L, Xu H, Liu Z, Meng Q, Zhu T, Yin J, Yu Z. ppGpp is a dual-role regulator involved in balancing iron absorption and prodiginine biosynthesis in Pseudoalteromonas. Mol Microbiol. 2024 Jul;122(1):68-80. doi: 10.1111/mmi.15285. Epub 2024 Jun 6. PMID: 38845079. 11: Pandey P, Rao L, Shekhar BR, Das DK, Vavilala SL. Molecular insights into flavone-mediated quorum sensing interference: A novel strategy against Serratiamarcescens biofilm-induced antibiotic resistance". Chem Biol Interact. 2024 Jun 1;396:111027. doi: 10.1016/j.cbi.2024.111027. Epub 2024 May 10. PMID: 38735452. 12: Xue W, Zhu B, Zhao K, Huang Q, Luo H, Shou Y, Huang Z, Guo H. Targeting LRP6: A new strategy for cancer therapy. Pharmacol Res. 2024 Jun;204:107200. doi: 10.1016/j.phrs.2024.107200. Epub 2024 May 6. PMID: 38710241. 13: Darya GH, Zare O, Karbalaei-Heidari HR, Zeinali S, Sheardown H, Rastegari B. Enzyme-responsive mannose-grafted magnetic nanoparticles for breast and liver cancer therapy and tumor-associated macrophage immunomodulation. Expert Opin Drug Deliv. 2024 Apr;21(4):663-677. doi: 10.1080/17425247.2024.2347300. Epub 2024 May 6. PMID: 38680108. 14: Pereira RFS, de Carvalho CCCR. Improving Bioprocess Conditions for the Production of Prodigiosin Using a Marine Serratia rubidaea Strain. Mar Drugs. 2024 Mar 23;22(4):142. doi: 10.3390/md22040142. PMID: 38667759; PMCID: PMC11051444. 15: Lin X, Dong L, Miao Q, Huang Z, Wang F. Cycloheptylprodigiosin from marine bacterium Spartinivicinus ruber MCCC 1K03745T induces a novel form of cell death characterized by Golgi disruption and enhanced secretion of cathepsin D in non-small cell lung cancer cell lines. Eur J Pharmacol. 2024 Jul 5;974:176608. doi: 10.1016/j.ejphar.2024.176608. Epub 2024 Apr 23. PMID: 38663542. 16: Cruz-Bautista R, Zelarayan-Agüero A, Ruiz-Villafán B, Escalante-Lozada A, Rodríguez-Sanoja R, Sánchez S. An overview of the two-component system GarR/GarS role on antibiotic production in Streptomyces coelicolor. Appl Microbiol Biotechnol. 2024 Apr 24;108(1):306. doi: 10.1007/s00253-024-13136-z. PMID: 38656376; PMCID: PMC11043171. 17: Gugu TH, Eze CO, Kenechukwu FC, Khumaini Mudhar Bintang MA, Patil SB, Basarkar GD, Attama AA, Ibezim EC, Upasani CD, Srichana T. Retraction notice to "Mechanistic insight into the bioactivity of prodigiosin-entrapped lipid nanoparticles against triple-negative breast, lung and colon cancer cell lines" [Heliyon 9 (2023) e16963]. Heliyon. 2024 Mar 6;10(6):e27689. doi: 10.1016/j.heliyon.2024.e27689. PMID: 38618648; PMCID: PMC11009883. 18: Handayani DP, Isnansetyo A, Istiqomah I. New investigation of encoding secondary metabolites gene by genome mining of a marine bacterium, Pseudoalteromonas viridis BBR56. BMC Genomics. 2024 Apr 13;25(1):364. doi: 10.1186/s12864-024-10266-6. PMID: 38615000; PMCID: PMC11015633. 19: Liu H, Chu F, Wu Y, Gu X, Ran T, Wang W, Xu D. Reduced OxyR positively regulates the prodigiosin biosynthesis in Serratia marcescens FS14. Biochem Biophys Res Commun. 2024 May 28;710:149877. doi: 10.1016/j.bbrc.2024.149877. Epub 2024 Apr 2. PMID: 38581956. 20: Girão M, Freitas S, Martins TP, Urbatzka R, Carvalho MF, Leão PN. Decylprodigiosin: a new member of the prodigiosin family isolated from a seaweed-associated Streptomyces. Front Pharmacol. 2024 Mar 21;15:1347485. doi: 10.3389/fphar.2024.1347485. PMID: 38576493; PMCID: PMC10991731.