Puromycin Dihydrochloride | CAS#58-58-2 | antibiotic

MedKoo Cat#: 561474 | Name: Puromycin Dihydrochloride

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Description:

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

Puromycin Dihydrochloride is an antibiotic. It inhibits protein synthesis by binding to RNA. Puromycin Dihydrochloride has antimicrobial, antitrypanosomal, and antineoplastic properties.

Chemical Structure

Puromycin Dihydrochloride

CAS#58-58-2 (2HCl)

Theoretical Analysis

MedKoo Cat#: 561474

Name: Puromycin Dihydrochloride

CAS#: 58-58-2 (2HCl)

Chemical Formula: C22H31Cl2N7O5

Exact Mass: 0.0000

Molecular Weight: 544.43

Elemental Analysis: C, 48.54; H, 5.74; Cl, 13.02; N, 18.01; O, 14.69

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 375.00
100mg	USD 550.00
500mg	USD 950.00

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Related CAS #

53-79-2 (free base) 58-58-2 (2HCl) 3506-23-8 (HCl)

Synonym

Puromycin Dihydrochloride; Puromycin 2HCl;

IUPAC/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-methoxyphenyl)propanamide dihydrochloride

InChi Key

MKSVFGKWZLUTTO-FZFAUISWSA-N

InChi Code

InChI=1S/C22H29N7O5.2ClH/c1-28(2)19-17-20(25-10-24-19)29(11-26-17)22-18(31)16(15(9-30)34-22)27-21(32)14(23)8-12-4-6-13(33-3)7-5-12;;/h4-7,10-11,14-16,18,22,30-31H,8-9,23H2,1-3H3,(H,27,32);2*1H/t14-,15+,16+,18+,22+;;/m0../s1

SMILES Code

O=C(N[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N(C)C)N=CN=C23)[C@@H]1O)[C@@H](N)CC4=CC=C(OC)C=C4.[H]Cl.[H]Cl

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, ethanol, methanol, and water

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Puromycin inhibits protein synthesis by binding to RNA. It is an antineoplastic and antitrypanosomal agent and is used in research as an inhibitor of protein synthesis. It also serves an an anticancer drug by suppressing the growth and metastasis in esophagus cancer cells by Akt phosphorylation.

In vitro activity:

The effects of Puromycin aminonucleoside (PAN) were investigated on podocytes in the context of diabetic nephropathy. PAN treatment had a dose- and time-dependent inhibitory effect on podocyte proliferation, suggesting its role in suppressing cell growth. KLF5 overexpression induced cell cycle arrest in podocytes when regulated by PAN. KLF5 overexpression was shown to inhibit PAN-induced apoptosis of podocyte. Reference: Mol Med Rep. 2018 Oct;18(4):3843-3849. https://pubmed.ncbi.nlm.nih.gov/30106142/

In vivo activity:

In adult zebrafish, puromycin administration led to kidney injury, causing rapid clearance of substances from the kidney and resulting in morphological changes in the kidney structure, which recovered over time. During the process of nephron injury and regeneration, various molecular markers associated with kidney injury and repair showed significant changes, including increased expression of renal progenitor marker lhx1a and upregulation of NFκB, TNFα, Nampt, and p-ERK. Reference: Anim Cells Syst (Seoul). 2023 Apr 20;27(1):112-119. https://pubmed.ncbi.nlm.nih.gov/37089626/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	91.84
	Ethanol	5.0	9.18
	Methanol	250.0	459.20
	Water	50.0	91.84

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 544.43 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.

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

Formulation protocol:

1. Li Y, Sui X, Hu X, Hu Z. Overexpression of KLF5 inhibits puromycin‑induced apoptosis of podocytes. Mol Med Rep. 2018 Oct;18(4):3843-3849. doi: 10.3892/mmr.2018.9366. Epub 2018 Aug 9. PMID: 30106142; PMCID: PMC6131625. 2. Hernández-Damián J, Tecalco-Cruz AC, Ríos-López DG, Vázquez-Victorio G, Vázquez-Macías A, Caligaris C, Sosa-Garrocho M, Flores-Pérez B, Romero-Avila M, Macías-Silva M. Downregulation of SnoN oncoprotein induced by antibiotics anisomycin and puromycin positively regulates transforming growth factor-β signals. Biochim Biophys Acta. 2013 Nov;1830(11):5049-58. doi: 10.1016/j.bbagen.2013.07.006. Epub 2013 Jul 18. PMID: 23872350. 3. Koun S, Park HJ, Jung SM, Cha JJ, Cha DR, Kang YS. Puromycin-induced kidney injury and subsequent regeneration in adult zebrafish. Anim Cells Syst (Seoul). 2023 Apr 20;27(1):112-119. doi: 10.1080/19768354.2023.2203211. PMID: 37089626; PMCID: PMC10120544. 4. Sakamoto H, Hirakawa Y, Ishida KI, Keeling PJ, Kita K, Matsuzaki M. Puromycin selection for stable transfectants of the oyster-infecting parasite Perkinsus marinus. Parasitol Int. 2019 Apr;69:13-16. doi: 10.1016/j.parint.2018.10.011. Epub 2018 Oct 30. PMID: 30389616.

In vitro protocol:

In vivo protocol:

1. Koun S, Park HJ, Jung SM, Cha JJ, Cha DR, Kang YS. Puromycin-induced kidney injury and subsequent regeneration in adult zebrafish. Anim Cells Syst (Seoul). 2023 Apr 20;27(1):112-119. doi: 10.1080/19768354.2023.2203211. PMID: 37089626; PMCID: PMC10120544. 2. Sakamoto H, Hirakawa Y, Ishida KI, Keeling PJ, Kita K, Matsuzaki M. Puromycin selection for stable transfectants of the oyster-infecting parasite Perkinsus marinus. Parasitol Int. 2019 Apr;69:13-16. doi: 10.1016/j.parint.2018.10.011. Epub 2018 Oct 30. PMID: 30389616.

1: Larsson P, De Rosa MC, Righino B, Olsson M, Florea BI, Forssell-Aronsson E, Kovács A, Karlsson P, Helou K, Parris TZ. Integrated transcriptomics- and structure-based drug repositioning identifies drugs with proteasome inhibitor properties. Sci Rep. 2024 Aug 13;14(1):18772. doi: 10.1038/s41598-024-69465-6. PMID: 39138277; PMCID: PMC11322189. 2: Kim J, Park S, Kim SJ, Yoo I, Kim H, Hwang S, Sim KM, Kim I, Jun E. High- throughput drug screening using a library of antibiotics targeting cancer cell lines that are resistant and sensitive to gemcitabine. Biochem Biophys Res Commun. 2024 Oct 20;730:150369. doi: 10.1016/j.bbrc.2024.150369. Epub 2024 Jul 7. PMID: 39013264. 3: Wang G, Chen R, Huang P, Hong J, Cao J, Wu Q, Zheng W, Lin L, Han Q, Chen Y, Xia N. Adefovir dipivoxil efficiently inhibits the proliferation of pseudorabies virus in vitro and in vivo. Antiviral Res. 2021 Feb;186:105014. doi: 10.1016/j.antiviral.2021.105014. Epub 2021 Jan 7. PMID: 33422610. 4: Iwamoto M, Mori C, Hiraoka Y, Haraguchi T. Puromycin resistance gene as an effective selection marker for ciliate Tetrahymena. Gene. 2014 Jan 25;534(2):249-55. doi: 10.1016/j.gene.2013.10.049. Epub 2013 Nov 1. PMID: 24185080. 5: Sawada T, Yanagisawa T, Tanaka N, Takuma S. Ultrastructural changes in rat- molar cementoblasts after administration of puromycin. J Biol Buccale. 1989 Sep;17(3):167-77. PMID: 2808332. 6: Worthington VC, Hipkiss AR. Effect of ATP depletion on the disappearance of high-molecular-weight aggregates formed in rabbit reticulocytes after exposure to puromycin dihydrochloride. Biochem Soc Trans. 1981 Feb;9(1):148-9. doi: 10.1042/bst0090148. PMID: 7215650. 7: McKay MJ, Daniels RS, Hipkiss AR. Breakdown of aberrant protein in rabbit reticulocytes decreases with cell age. Biochem J. 1980 Apr 15;188(1):279-83. doi: 10.1042/bj1880279. PMID: 7406886; PMCID: PMC1162566. 8: Réz G, Kiss A, Bucsek MJ, Kovács J. Attachment of ribosomes to endoplasmic membranes in mouse pancreas. Degranulation in vivo caused by the inducers of autophagocytosis neutral red, vinblastine, puromycin, and cadmium ions, and prevention by cycloheximide. Chem Biol Interact. 1976 Apr;13(1):77-87. doi: 10.1016/0009-2797(76)90015-6. PMID: 1260947. 9: Fleetwood MK, Gander GW, Goodale F. Effect of metabolic inhibitors on pyrogen production by rabbit leukocytes. Proc Soc Exp Biol Med. 1975 Jun;149(2):336-9. doi: 10.3181/00379727-149-38802. PMID: 1153406. 10: Sundaralingam M, Arora SK. Crystal structure of the aminoglycosyl antibiotic puromycin dihydrochloride pentahydrate. Models for the terminal 3'-aminoacyladenosine moieties of transfer RNA's and protein-nucleic acid interactions. J Mol Biol. 1972 Oct 28;71(1):49-70. doi: 10.1016/0022-2836(72)90400-7. PMID: 4634987. 11: Sundaralingam M, Arora SK. Stereochemistry of nucleic acids and their constituents. IX. The conformation of the antibiotic puromycin dihydrochloride pentahydrate. Proc Natl Acad Sci U S A. 1969 Nov;64(3):1021-6. doi: 10.1073/pnas.64.3.1021. PMID: 5264134; PMCID: PMC223338. 12: Flexner JB, Flexner LB. Puromycin: effect on memory of mice when injected with various cations. Science. 1969 Sep 12;165(3898):1143-4. doi: 10.1126/science.165.3898.1143. PMID: 5801598. 13: LEVINE S. EFFECT OF ACTINOMYCIN D AND PUROMYCIN DIHYDROCHLORIDE ON ACTION OF INTERFERON. Virology. 1964 Dec;24:586-8. doi: 10.1016/0042-6822(64)90211-9. PMID: 14240406.

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Description:

Chemical Structure

Theoretical Analysis

Price and Availability

Preparing Stock Solutions

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