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Porphyra 334

Alias: Porphyra-334; Porphyra 334; Porphyra334; mytilin B; Porphyra 334; 70579-26-9; Porphyra 334 [INCI]; UNII-9KIR0IH75D; 9KIR0IH75D; porphyra-334; Porphyra 334; 70579-26-9; Porphyra 334 [INCI]; UNII-9KIR0IH75D; 9KIR0IH75D; L-Threonine, N-((5S)-3-((carboxymethyl)amino)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-2-cyclohexen-1-ylidene)-, (N(E))-; (2S,3R)-2-[[(5R)-3-(Carboxymethylimino)-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohexen-1-yl]amino]-3-hydroxybutanoic acid;
Cat No.:V18372 Purity: ≥98%
Porphyra 334 is an antioxidant and anti-photoaging agent.
Porphyra 334
Porphyra 334 Chemical Structure CAS No.: 70579-26-9
Product category: Plants
This product is for research use only, not for human use. We do not sell to patients.
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2mg
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25mg
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description
Porphyra 334 is an antioxidant and anti-photoaging agent. Porphyra 334 inhibits the production of ROS and the expression of MMPs after UVA irradiation. Porphyra-334 has various applications in cosmetics and toiletries because of its anti‑photoaging activities and may serve as a novel anti-aging agent.
Biological Activity I Assay Protocols (From Reference)
Targets
antioxidative and anti-photoaging compound
ln Vitro
The significant increase in life expectancy is closely related to the growing interest in the impact of aging on the function and appearance of the skin. Skin aging is influenced by several factors, and solar ultraviolet (UV) irradiation is considered one of the most important causes of skin photoaging. The aim of this study was to examine the anti-photoaging role of porphyra-334 from Porphyra (P.) yezoensis, a mycosporine-like amino acid (MAA), using high-performance liquid chromatography (HPLC), and electrospray ionization‑mass spectrometry (ESI-MS). In the present study, extracted UV‑absorbing compounds from P. yezoensis included palythine, asterina-330 and porphyra-334. Porphyra-334 was the most abundant MAA in P. yezoensis, and it was therefore used for conducting antiphotoaging experiments. The effect of porphyra-334 on the prevention of photoaging was investigated by measuring reactive oxygen species (ROS) production and matrix metalloproteinase (MMP) levels, as well as extracellular matrix (ECM) components and protein expression in UVA‑irradiated human skin fibroblasts. Porphyra-334 suppressed ROS production and the expression of MMPs following UVA irradiation, while increasing levels of ECM components, such as procollagen, type I collagen, elastin. These results suggest that porphyra-334 has various applications in cosmetics and toiletries because of its anti‑photoaging activities and may serve as a novel anti-aging agent.[1]
Enzyme Assay
Elastase activity using the synthetic substrate N-Succinyl-Ala-Ala-Ala-p-nitroanilide was measured as previously described. Briefly, 100 μl of enzyme solution was dispensed into 96-well plates, which were pre-incubated for 15 min at 37°C. Following the addition of 2 μl 55.3 mM STANA, the plates were further incubated for 1 h at 37°C. The release of p-nitroaniline was measured by absorbance at 410 nm and enzymatic activity was expressed as a percentage of total p-nitroaniline.[1]
Cell Assay
Cell viability was determined using a 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxy-phenyl)-2- (4-sulfophenyl)-2H-tetrazolium (MTS) assay according to the manufacturer’s instructions. Briefly, 2x104 cells/well were plated and allowed to attach to 96-well plates. The cells were then exposed to serial concentrations of porphyra-334 for 24 h. After 24 h, a soluble MTS reagent was added and absorbance of the formazan was measured directly in 96-well plates at 490 nm using a multi-plate reader. Relative cell viability was calculated as the percent viability relative to the untreated control cells. Each experiment was performed in triplicate.[1]
References

[1]. Protective effect of porphyra-334 on UVA-induced photoaging in human skin fibroblasts. Int J Mol Med. 2014 Sep;34(3):796-803.

[2]. Antioxidative activities of a mycosporine-like amino acid, porphyra-334. Fisheries Science, 2008, 74: 1166-1172.

Additional Infomation
Porphyra 334 has been reported in Scytonema, Synechococcus, and other organisms with data available.
Antioxidative activities of porphyra-334, a mycosporine-like amino acid extracted from laver were evaluated. Oxidation of linoleic acid induced by an alkyl-radical 2,2′-azobis (2-amidinopropane) dihydrochloride (AAPH) was successfully suppressed by porphyra-334 (0–200 μM). The simultaneous application of 0.02 μM α-tocopherol and 50 μM porphyra-334 effectively suppressed the AAPH induced oxidation level to approximately 40% of a single application of porphyra-334 after 10 min reaction. Porphyra-334 (0–200 μM) efficiently suppressed the lipid peroxidation induced by singlet oxygen although the antioxidative effect observed was relatively moderate at the initial stage of oxidation. These results suggested that porphyra-334 may function as an antioxidant which influences the storage stability of laver.[2]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H22N2O8
Molecular Weight
346.333084583282
Exact Mass
346.137
Elemental Analysis
C, 48.55; H, 6.40; N, 8.09; O, 36.96
CAS #
70579-26-9
PubChem CID
91864535
Appearance
Solid powder
Source
Palythoa tuberculosa
LogP
-1.8
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
8
Heavy Atom Count
24
Complexity
559
Defined Atom Stereocenter Count
3
SMILES
C[C@H]([C@@H](C(=O)O)NC1=C(C(=NCC(=O)O)C[C@](C1)(CO)O)OC)O
InChi Key
VIZAVBQHHMQOQF-FCDTZTNESA-N
InChi Code
InChI=1S/C14H22N2O8/c1-7(18)11(13(21)22)16-9-4-14(23,6-17)3-8(12(9)24-2)15-5-10(19)20/h7,11,15,17-18,23H,3-6H2,1-2H3,(H,19,20)(H,21,22)/b16-9+/t7-,11+,14+/m1/s1
Chemical Name
(2S,3R)-2-(((S,E)-3-((carboxymethyl)amino)-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene)amino)-3-hydroxybutanoic acid
Synonyms
Porphyra-334; Porphyra 334; Porphyra334; mytilin B; Porphyra 334; 70579-26-9; Porphyra 334 [INCI]; UNII-9KIR0IH75D; 9KIR0IH75D; porphyra-334; Porphyra 334; 70579-26-9; Porphyra 334 [INCI]; UNII-9KIR0IH75D; 9KIR0IH75D; L-Threonine, N-((5S)-3-((carboxymethyl)amino)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-2-cyclohexen-1-ylidene)-, (N(E))-; (2S,3R)-2-[[(5R)-3-(Carboxymethylimino)-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohexen-1-yl]amino]-3-hydroxybutanoic acid;
HS Tariff Code
2934.99.03.00
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8874 mL 14.4371 mL 28.8742 mL
5 mM 0.5775 mL 2.8874 mL 5.7748 mL
10 mM 0.2887 mL 1.4437 mL 2.8874 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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