Prodigiosin
(Synonyms: 灵菌红素; Prodigiosine) 目录号 : GC44690A natural red pigment and antibiotic
Cas No.:82-89-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Prodigiosin is a natural red bacterial pigment that has antibiotic, antitumor, and immunosuppressant properties. It blocks T cell proliferation at a concentration of 30 ng/ml, by interfering with IL-2 receptor expression. Prodigiosin induces apoptosis in cancer cells by diverse mechanisms and rescues deficient p53 signaling. Prodigiosin derivatives can uncouple vacuolar H+-ATPase and inhibit osteoclast function. Prodigiosin is cytolytic against the red tide dinoflagellate Cochlodinium at very low concentrations (1 ppb), suggesting an application in controlling algal blooms.
| Cas No. | 82-89-3 | SDF | |
| 别名 | 灵菌红素; Prodigiosine | ||
| Canonical SMILES | CC1=N/C(C=C1CCCCC)=C/C(N2)=C(OC)C=C2C3=CC=CN3 | ||
| 分子式 | C20H25N3O | 分子量 | 323.4 |
| 溶解度 | DMSO : 25 mg/mL (77.30 mM; Need ultrasonic) | 储存条件 | Store at -20°C,protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0921 mL | 15.4607 mL | 30.9215 mL |
| 5 mM | 0.6184 mL | 3.0921 mL | 6.1843 mL |
| 10 mM | 0.3092 mL | 1.5461 mL | 3.0921 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Prodigiosin: a promising biomolecule with many potential biomedical applications
Bioengineered 2022 Jun;13(6):14227-14258.PMID:35734783DOI:10.1080/21655979.2022.2084498.
Pigments are among the most fascinating molecules found in nature and used by human civilizations since the prehistoric ages. Although most of the bio-dyes reported in the literature were discovered around the eighties, the necessity to explore novel compounds for new biological applications has made them resurface as potential alternatives. Prodigiosin (PG) is an alkaloid red bio-dye produced by diverse microorganisms and composed of a linear tripyrrole chemical structure. PG emerges as a really interesting tool since it shows a wide spectrum of biological activities, such as antibacterial, antifungal, algicidal, anti-Chagas, anti-amoebic, antimalarial, anticancer, antiparasitic, antiviral, and/or immunosuppressive. However, PG vehiculation into different delivery systems has been proposed since possesses low bioavailability because of its high hydrophobic character (XLogP3-AA = 4.5). In the present review, the general aspects of the PG correlated with synthesis, production process, and biological activities are reported. Besides, some of the most relevant PG delivery systems described in the literature, as well as novel unexplored applications to potentiate its biological activity in biomedical applications, are proposed.
Prodigiosin-like pigments
CRC Crit Rev Microbiol 1975 May;3(4):469-85.PMID:1095305DOI:10.3109/10408417509108758.
Prodigiosin, the bright red tripyrrole pigment from Serratia marcescens, has also been identified in Pseudomonas magnesiorubra, Vibrio psychroerythrus, and two Gram-negative rod-shaped mesophilic marine bacteria not members of the genus Serratia. Prodigiosin is sometimes bound to proteins; thus, extracts may require acid treatment before isolation of the pigment. Higher homologs of Prodigiosin have been detected by mass spectroscopy. A mutant strain of S. marcescens produced nor-prodigiosin, in which the methoxy group of Prodigiosin is replaced by a hydroxy group. Another mutant strain produced a blue tetrapyrrole pigment whose structure is a dimer of Prodigiosin's rings A and B. Three novel biosynthetic analogs of Prodigiosin have been obtained using a colorless mutant which does make rings A and B but not ring C and which can couple rings A and B with some added monopyrroles similar to ring C. The structures of three prodiginine (prodigiosin-like) pigments from streptomyces have been elucidated. All have the methoxytripyrrole aromatic nucleus of Prodigiosin and all have an 11 carbon aliphatic side chain attached at carbon 2 of ring C. In two of the pigments the side chain is also linked to another carbon of ring C. The earlier literature about prodiginine pigments from actinomycetes has been interpreted and evaluated in light of the most recent findings. The structure elucidation of six prodiginine pigments from Actinomadurae (Nocardiae) has been completed. Only one, undecylprodiginine, is the same as from a streptomycete. For three of the six pigments, nine carbon side chains are observed and in four of them the side chain is attached to carbon 5 of ring A as well as carbon 2 of ring C so that a large ring is formed which includes the three pyrrole moieties. A section on identification summarized useful methods and presents information with which any known prodiginine pigment can be identified. The final step in the biosynthesis of Prodigiosin was known to be the coupling of methoxybipyrrolecarboxaldehyde (rings A and B) with methylpentylpyrrole (ring C). Recent work using 13C-labeled precursors and Fourier transform 13C nuclear magnetic resonance has shown the pattern of incorporation for acetate, proline, glycine, serine alanine, and methionine into Prodigiosin. Each pyrrole ring is constructed in a different way. Two of the streptomyces pigments have also been investigated; the pattern of incorporation is similar to that for Prodigiosin. The biological activities of some prodiginine pigments are summarized. All show activity against several Gram-positive bacteria; some have anti-malarial activity. Prodigiosin has been tested clinically against coccidioidomycosis.
High-level production of microbial Prodigiosin: A review
J Basic Microbiol 2021 Jun;61(6):506-523.PMID:33955034DOI:10.1002/jobm.202100101.
Prodigiosin is a natural red pigment derived primarily from secondary metabolites of microorganisms, especially Serratia marcescens. It can also be chemically synthesized. Prodigiosin has been proven to have antitumor, antibacterial, antimalaria, anti-insect, antialgae, and immunosuppressive activities, and is gaining increasing important in the global market because of its great potential application value in clinical medicine development, environmental treatment, preparation of food additives, and so on. Due to the low efficiency of Prodigiosin chemical synthesis, high-level Prodigiosin of production by microorganisms are necessary for Prodigiosin applications. In this paper, the production of Prodigiosin by microorganism in recent decades is reviewed. The methods and strategies for increasing the yield of Prodigiosin are discussed from the aspects of medium composition, additives, factors affecting production conditions, strain modification, and fermentation methods.
Recent Advances in Prodigiosin as a Bioactive Compound in Nanocomposite Applications
Molecules 2022 Aug 5;27(15):4982.PMID:35956931DOI: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 towards Serratia 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 by Serratia 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.
Prodigiosin-Loaded Poly(lactic acid) to Combat the Biofilm-Associated Infections
ACS Appl Bio Mater 2022 May 16;5(5):2143-2151.PMID:35467829DOI:10.1021/acsabm.1c01187.
Poly(lactic acid) (PLA) is an emerging biobased implant material. Despite its biocompatibility and the aseptic procedures followed during orthopedic surgery, bacterial infection remains an obstacle to implementing PLA-based implants. To tackle this issue, prodigiosin-incorporated PLA has been developed, which possesses improved hydrophobicity with a contact angle of 111 ± 1.5°. The degradation temperature of the Prodigiosin is 215 °C, which is more than the melting temperature of PLA, which supports the processability and sterilization of the PLA-based implants without any toxic gases. Further, Prodigiosin improves the transparency of PLA and acts as a nucleation site. The spherulite density increases three times compared to that of neat PLA. The inherent methoxy group of Prodigiosin is an active site responsible for the inhibition of bacterial attack and biofilm formation. The in vitro study on biofilm formation shows excellent inhibition activity against implant-associated pathogens such as Klebsiella aerogenes and Staphylococcus aureus.