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O-Propargyl-Puromycin (OP-puro) is an alkyne analog of puromycin which is a potent inhibitor of protein synthesis. OP-puro is incorporated into nascent polypeptide chains where it forms covalent adducts and terminates chain elongation on the ribosome. It has been used in combination with fluorescent azides to image nascent proteins in various cells.
| ln Vitro |
It is possible to visualize and selectively block developing proteins in both cells and animals using o-propargylpuromycin. O-propargyl-puromycin is two to three times less effective than unmodified puromycin at adsorbing reticulocyte lumen and protein synthesis in cultured cells. O-Propargyl-puromycin is linked to emerging elbow The copper(I)-catalyzed foldant-toggle cycloaddition reaction allows for the visualization or capture of these toggle bodies, which are rapidly transformed toggle chains that form covalent conjugates [1].
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| ln Vivo |
Whereas tissue from mice injected with O-Propargyl-Puromycin demonstrated that the drug may penetrate particular patterns of developing proteins, tissue from mice not injected with O-Propargyl-Puromycin displayed modest non-electrophoretic staining. According to their high activity, the cells in the crypts and base of intestinal villi in the small intestine have the greatest capacity for translation. The Paneth cells, which are packed with dead sexual vesicles and are situated at the base of the cavity, exhibit very strong staining. Prematurely terminated O-Propargyl-Puromycin conjugated peptides are known to easily localize to the endoplasmic reticulum (ER) lumen, as evidenced by strong O-Propargyl-Puromycin labeling of vesicles in Paneth cells [1].
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| References |
| Molecular Formula |
C24H29N7O5
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|---|---|
| Molecular Weight |
495.530964612961
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| Exact Mass |
495.223
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| CAS # |
1416561-90-4
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| PubChem CID |
71576433
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Index of Refraction |
1.679
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| LogP |
0.97
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
36
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| Complexity |
786
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| Defined Atom Stereocenter Count |
5
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| SMILES |
CN(C)C1=NC=NC2=C1N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)NC(=O)[C@H](CC4=CC=C(C=C4)OCC#C)N)O
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| InChi Key |
JXBIGWQNNSJLQK-IYRMOJGWSA-N
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| InChi Code |
InChI=1S/C24H29N7O5/c1-4-9-35-15-7-5-14(6-8-15)10-16(25)23(34)29-18-17(11-32)36-24(20(18)33)31-13-28-19-21(30(2)3)26-12-27-22(19)31/h1,5-8,12-13,16-18,20,24,32-33H,9-11,25H2,2-3H3,(H,29,34)/t16-,17+,18+,20+,24+/m0/s1
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| Chemical Name |
(2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-prop-2-ynoxyphenyl)propanamide
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ≥ 31 mg/mL (~62.56 mM)
H2O : < 0.1 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.05 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.05 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (5.05 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0180 mL | 10.0902 mL | 20.1804 mL | |
| 5 mM | 0.4036 mL | 2.0180 mL | 4.0361 mL | |
| 10 mM | 0.2018 mL | 1.0090 mL | 2.0180 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.
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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