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Coproporphyrin III (Zincphyrin) Sale

(Synonyms: 粪卟啉二盐酸盐,Zincphyrin) 目录号 : GC30166

粪卟啉 III (Zincphyrin) (Zincphyrin) 是一种天然存在的卟啉衍生物,主要存在于尿液中。

Coproporphyrin III (Zincphyrin) Chemical Structure

Cas No.:14643-66-4

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10mM (in 1mL DMSO)
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1mg
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5mg
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产品描述

Coproporphyrin III is a porphyrin derivative.

Coproporphyrin III methyl ester is repeatedly isolated in considerable amount from both feces and urine. A great increase of coproporphyrin III excretion is unaccompanied by symptoms or signs of porphyria, metal or chemical poisoning or liver disease[1]. Primary cultures of chick embryo hepatocytes have been used to study the mechanism by which chemicals cause accumulation of intermediates of the heme synthetic pathway. In the presence of the porphyrin precursor, 5-aminolevulinate (ALA), addition of insulin causes a striking increase in accumulation of uroporphyrin I and coproporphyrin III. Antioxidants abolishes the uroporphyrin I accumulation and increases coproporphyrin III[2].

Urinary DMA and porphyrin profile can be used as an early warning biomarker for chronic MMA exposure before the onset of cancer. After 4 weeks the level of coproporphyrin III concentration significantly increases in all the treatment groups compared to the control[3].

[1]. Watson CJ, et al. Studies of coproporphyrin. iii. idiopathic coproporphyrinuria; a hitherto unrecognized form characterized by lack of symptoms in spite of the excretion of large amounts of coproporphyrin. J Clin Invest. 1949 May;28(3):465-8. [2]. Trask HW, et al. Effect of insulin and glucagon on accumulation of uroporphyrin and coproporphyrin from 5-aminolevulinate in hepatocyte cultures. Arch Biochem Biophys. 2005 Jul 1;439(1):1-11. [3]. Krishnamohan M, et al. Urinary arsenic and porphyrin profile in C57BL/6J mice chronically exposed to monomethylarsonous acid (MMAIII) for two years. Toxicol Appl Pharmacol. 2007 Oct 1;224(1):89-97.

Chemical Properties

Cas No. 14643-66-4 SDF
别名 粪卟啉二盐酸盐,Zincphyrin
Canonical SMILES O=C(O)CCC1=C2/C=C3C(CCC(O)=O)=C(C)C(/C=C(N/4)/C(C)=C(CCC(O)=O)C4=C\C5=N/C(C(CCC(O)=O)=C5C)=C\C(N2)=C1C)=N/3
分子式 C36H38N4O8 分子量 654.71
溶解度 DMSO : ≥ 83.3 mg/mL (127.23 mM) 储存条件 Store at -20°C
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。
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。

溶解性数据

制备储备液
1 mg 5 mg 10 mg
1 mM 1.5274 mL 7.637 mL 15.2739 mL
5 mM 0.3055 mL 1.5274 mL 3.0548 mL
10 mM 0.1527 mL 0.7637 mL 1.5274 mL
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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)
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Research Update

Antitumor effect of photodynamic therapy with Zincphyrin, zinc-coproporphyrin III, in mice

Biosci Biotechnol Biochem 2001 Feb;65(2):363-70.11302170 10.1271/bbb.65.363

We studied the antitumor effects of photodynamic therapy (PDT) with Zincphyrin, Coproporphyrin III with zinc, derived from Streptomyces sp. AC8007, in vitro and in vivo. The photokilling effect of Zincphyrin in the presence of 0.78-100 microg/ml with visible light of 27.2 mW x min/cm2 for 10 min was lower than the hematoporphyrin (Hp) used as a control with L5178Y or sarcoma-180 cells. On the other hand, Zincphyrin apparently reduced tumor growth after intraperitoneal injection at doses of 12.5-50 mg/kg with light irradiation of 75.48 mW x min/cm2 for 10 min in sarcoma-180-bearing mice. Although no mice treated with Zincphyrin died, Hp did cause the death of mice. In B-16 melanoma-bearing mice, both Zincphyrin and Hp had a similar phototherapic effect. Further improvement of the phototherapic effect was observed with the continuous administration of Zincphyrin at 12.5 mg/kg per day for 3 days. The concentration of Zincphyrin in the serum reached a maximum level of 16 microg/ml within 20 min, and the concentration remained at 4.2 microg/ml at 1 hour after the onset of treatment, indicating its rapid action in the body. No animals died after the intraperitoneal administration of Zincphyrin at 100 mg/kg plus exposure to light of 10 mW x min/cm2 for 2 hours, and the body weight of the mice did not decrease. In contrast, all animals receiving 100 mg/kg of Hp under the same conditions died. These results indicate that Zincphyrin would be a useful photosensitizer with low phototoxicity.

Zincphyrin, a novel Coproporphyrin III with zinc from Streptomyces sp

J Antibiot (Tokyo) 1993 Jan;46(1):196-200.8436554 10.7164/antibiotics.46.196

Production of singlet oxygen on irradiation of a photodynamic therapy agent, zinc-coproporphyrin III, with low host toxicity

Biometals 2003 Dec;16(4):591-7.12779244 10.1023/a:1023472508073

Zinc-coproporphyrin III (Zincphyrin) acts efficiently as a photodynamic therapy (PDT) agent in mice, while it shows no tumor cell-killing activity in vitro and has a high LD50 (low toxicity) in mice. It appears to have advantages over other porphyrins as a practical PDT reagent. In order to examine the action mechanism of Zincphyrin in PDT, we evaluated the photochemical characteristics of Zincphyrin by measurement of the near-infrared emission at 1268 nm, which provides direct evidence for formation of 1O2. Intense emission was observed in the presence of Zincphyrin, and was completely inhibited by NaN3, a 1O2 scavenger. Based on a quenching study, the rate constant of the reaction of 1O2 with NaN3 was determined to be 1.5-3.5 M(-1) s(-1), which is close to the reported value (3.8 x 10(8) M(-1) s(-1)). The intensity of the 1O2-specific emission was proportional to both the laser power and the concentration of Zincphyrin. The fluorescence quantum yield of Zincphyrin was 0.004 in phosphate buffer (100 mM, pH 7.4), which indicates that the excited state decays via other pathway(s) faster than through the fluorescence emission pathway. The lifetime of the triplet state of Zincphyrin (210 micros) was relatively long compared to that of other porphyrins, such as hematoporphyrin (Hp) (40 micros), coproporphyrin I (50 gs), or Coproporphyrin III (36 gs). These results demonstrate the photodynamic generation of 1O2 by Zincphyrin.

Is Coproporphyrin III a copper-acquisition compound in Paracoccus denitrificans?

Biochim Biophys Acta 2011 Mar;1807(3):311-8.21216223 10.1016/j.bbabio.2010.12.014

Paracoccus denitrificans is a soil bacterium which can respire aerobically and also denitrify if oxygen is absent. Both processes are highly dependent on copper enzymes and copper is therefore likely to be an essential trace element for the bacterium. If copper is not easily available, a copper-acquisition mechanism would be highly beneficial. In this paper, we have addressed the question of whether Paracoccus secretes a copper-acquisition compound functionally analogous to that found in some methanotrophs. Bacteria were grown both in copper-containing and copper-deficient denitrification media, cells were removed by centrifugation and the supernatant was analysed using chromatography and spectroscopy. Bacterial growth yield in the absence of copper was 70-80% of that in the copper-containing medium. A notable difference between the two culture conditions was that spent copper-deficient medium was pigmented, whereas the copper-containing medium was not. Spectrophotometry indicated that a red compound with an absorption maximum at 405 nm was produced under copper-limited conditions. In addition to the strong 405 nm maximum, the visible spectrum of the purified red molecule had weaker maxima at 535 nm and 570 nm, features typical of metallated tetrapyrroles. Mass spectrometry showed that the purified pigment had a molecular mass of 716.18. Moreover, the fine structure of the mass spectrum suggested the presence of zinc and was consistent with the chemical formula of C(36)H(36)N(4)O(8)Zn. The presence of zinc was also demonstrated using inductively coupled plasma atomic emission spectroscopy. Fragmentation analysis with mass spectrometry showed the release of consecutive 59 Da fragments, assignable to four -CH(2)-COOH moieties. Thin layer chromatography as well as NMR analysis of the C-13/N-15 labelled red pigment suggested that it is predominantly zinc Coproporphyrin III with a minor fraction of metal-free Coproporphyrin III. We propose that in a copper-poor environment P. denitrificans secretes Coproporphyrin III for copper chelation and subsequent uptake of the bound copper into the cell. Consistent with this idea, cell yields of copper-deficient cultures grown in the presence of 1 microM copper-coproporphyrin III were 90-95% of the yields of cultures grown in the normal copper-containing media. Coproporphyrin III may work as a copper-acquisition compound in P. denitrificans.

Coproporphyrin III Produced by the Bacterium Glutamicibacter arilaitensis Binds Zinc and Is Upregulated by Fungi in Cheese Rinds

mSystems 2018 Aug 21;3(4):e00036-18.30175236 PMC6104308

Microbial communities of fermented food microbiomes typically exhibit predictable patterns of microbial succession. However, the biochemical mechanisms that control the diversity and dynamics of these communities are not well described. Interactions between bacteria and fungi may be one mechanism controlling the development of cheese rind microbiomes. This study characterizes a specific bacterium-fungus interaction previously discovered on cheese rinds between the bacterium Glutamicibacter arilaitensis (formerly Arthrobacter arilaitensis) and fungi of the genus Penicillium and identifies the specialized metabolites produced during cocultures. G. arilaitensis was previously shown to produce an unknown pink pigment in response to the presence of Penicillium. Using a combination of mass spectrometry, nuclear magnetic resonance (NMR), and transcriptome sequencing (RNA-seq), we determined that this pigment production is associated with production of Coproporphyrin III. The discovery that Coproporphyrin III preferentially bound zinc over other trace metals found in cheese curds highlights the value of using analytical chemistry to confirm identity of predicted chemical species. IMPORTANCE Bacterium-fungus interactions play key roles in the assembly of cheese rind microbial communities, but the molecular mechanisms underlying these interactions are poorly characterized. Moreover, millions of people around the world enjoy eating cheeses and cheese rinds, but our understanding of the diversity of microbial metabolites ingested during cheese consumption is limited. The discovery of zinc Coproporphyrin III as the cause of pink pigment production by Glutamicibacter arilaitensis suggests that secretion of this molecule is important for microbial acquisition of trace metals.