Puromycin dihydrochloride from Streptomyces alboniger - BioReagent, for cell culture , CAS No.58-58-2

CAS: 58-58-2 Cat. No.: P432999 Peso molecular: 544.44 Beilstein Registry Number: 3853613 Número EC: 200-387-8

GRADE & PURITY BioReagent, for Cell culture

Synonyms

EX-A6693 | FS-5016 | SCHEMBL4317 | Adenosine, 3'-(((2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyl-, dihydrochloride | Puromycin HCl | Tox21_111352 | P-540 | Q7320232 | (S)-3'-((2-Amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-d

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

General Description

Puromycin is a broad spectrum antibiotic produced by Streptomyces alboniger . It is an analog of the 3′ end of aminoacyl-tRNA. It is an inhibitor of peptidyl transferase and is active in both prokaryotes and eukaryotes. Chemical structure: peptidyl nucleoside

Application

Puromycin dihydrochloride is a part of the amino-nucleoside family of antibiotics and is derived from Streptomyces alboniger . It is a broad spectrum antibiotic with antitumor activity, as an inhibitor of protein synthesis and has been used to study transcription regulatory mechanisms that control the sequential and coordinate expression of genes during cell differentiation. The recommended working concentration in eukaryotic cell culture is 1-10 μg/mL. Puromycin dihydrochloride from Streptomyces alboniger has been used: in the preparation of puromycin stock solution for puromycin sensitivity assay. to select lentivirus-infected cells containing puromycin resistant selection marker. Used as a selective agent for cells that contain the resistance gene puromycin N-acetyl-transferase (PAC). Recommended for use at a range of 1-10 μg/ml. Sterilize stock solution by filtration using 0.22 μm filter then store in aliquots at −20 °C.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place

Specifications

Sinónimos

EX-A6693 | FS-5016 | SCHEMBL4317 | Adenosine, 3'-(((2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N, N-dimethyl-, dihydrochloride | Puromycin HCl | Tox21_111352 | P-540 | Q7320232 | (S)-3'-((2-Amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-d

Especificaciones y pureza

BioReagent, for cell culture

Mecanismos bioquímicos y fisiológicos

Puromycin associates in a non-specific manner with growing polypeptide chains, and thus, leads to premature termination of translation. It inhibits protein synthesis in two ways. It associates with the donor substrate, peptidyl-tRNA, in the P site and thu

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

BioReagent, for Cell culture

Nota

Note: As supplied, this product remains active for four years when stored at -20°C.

Nombres e identificadores

• Pubchem Sid: 488189807
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488189807
• Sonrisas canónicas: COC1=CC=C(C[C@H](N)C(=O)NC2[C@@H](CO)O[C@H]([C@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1
• IUPAC 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
• InChIKey: MKSVFGKWZLUTTO-FZFAUISWSA-N
• 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
• Isómeros 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)OC)N)O.Cl.Cl
• WGK Alemania: 3
• RTECS: AU7355000
• CAS alternativo: 53-79-2
• Peso molecular: 544.44
• Beilstein: 3853613
• Reaxy-Rn: 39769009
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=39769009&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Clase Purine nucleosides
      • Subclass Purine 3'-deoxyribonucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Clase: Purine nucleosides
• Subclass: Purine 3'-deoxyribonucleosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Purine 3'-deoxyribonucleosides
• Alternative Parents: Phenylalanine and derivatives Alpha amino acid amides Glycosylamines 6-alkylaminopurines Amphetamines and derivatives Pentoses Dialkylarylamines Anisoles Methoxybenzenes Phenoxy compounds Aralkylamines Aminopyrimidines and derivatives Alkyl aryl ethers N-substituted imidazoles Imidolactams Fatty amides Tetrahydrofurans Heteroaromatic compounds Secondary carboxylic acid amides Secondary alcohols Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Hydrochlorides Monoalkylamines Organic oxides Organopnictogen compounds Primary alcohols Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Purine 3'-deoxyribonucleoside - Phenylalanine or derivatives - Alpha-amino acid amide - Glycosyl compound - N-glycosyl compound - 6-alkylaminopurine - 6-aminopurine - Alpha-amino acid or derivatives - Amphetamine or derivatives - Pentose monosaccharide - Imidazopyrimidine - Purine - Phenoxy compound - Anisole - Phenol ether - Methoxybenzene - Dialkylarylamine - Aralkylamine - Aminopyrimidine - Alkyl aryl ether - Benzenoid - Fatty acyl - Fatty amide - Monocyclic benzene moiety - Monosaccharide - Pyrimidine - N-substituted imidazole - Imidolactam - Tetrahydrofuran - Imidazole - Heteroaromatic compound - Azole - Secondary alcohol - Carboxamide group - Secondary carboxylic acid amide - Amino acid or derivatives - Carboxylic acid derivative - Ether - Azacycle - Organoheterocyclic compound - Oxacycle - Hydrochloride - Organic oxide - Carbonyl group - Hydrocarbon derivative - Primary aliphatic amine - Alcohol - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Amine - Primary alcohol - Primary amine - Organic nitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. These are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TRPM7 Tchem Transient receptor potential cation channel subfamily M member 7 (19 Activities)

Discover Target: TRPM7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: H2O: soluble 50mg/mL, clear, colorless to faintly yellow
• Sensibilidad: Heat, moisture and light sensitive
• Punto de fusión (°C): 174°C(lit.)
• Peso molecular: 544.400 g/mol
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 543.176 Da
• Monoisotopic Mass: 543.176 Da
• Topological Polar Surface Area: 161.000 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 680.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

XLogP3

Referencias

1. Jing Zhou, Tongyu Wu, Chun Li, Zhuozhou Hu, Liang Han, Xiangxiang Li, Jingjing Liu, Wenyang Zhao, Jia Kang, Xinping Chen.  (2023)  Alfuzosin ameliorates diabetes by boosting PGK1 activity in diabetic mice.  LIFE SCIENCES,      [PMID:36758669] [10.1016/j.lfs.2023.121491]

2. Song Runjie, Ma Shuoqian, Xu Jiajia, Ren Xin, Guo Peilan, Liu Huijiao, Li Peng, Yin Fan, Liu Mei, Wang Qiang, Yu Lei, Liu Jiali, Duan Binwei, Rahman Nafis A., Wołczyński Sławomir, Li Guangming, Li Xiangdong.  (2023)  A novel polypeptide encoded by the circular RNA ZKSCAN1 suppresses HCC via degradation of mTOR.  Molecular Cancer,  22  (1): (1-20).  [PMID:36691031] [10.1186/s12943-023-01719-9]

3. Zhuozhou Hu, Jing Zhou, Liang Han, Xiangxiang Li, Chun Li, Tongyu Wu, Jingjing Liu, Wenyang Zhao, Jia Kang, Xinping Chen.  (2022)  Acyclovir alleviates insulin resistance via activating PKM1 in diabetic mice.  LIFE SCIENCES,      [PMID:35751919] [10.1016/j.lfs.2022.120725]

4. Qiong Yang, Maochen Xing, Ke Wang, Qiang Wei, Jiarui Zhao, Yuan Wang, Kai Ji, Shuliang Song.  (2022)  Application of Fucoidan in Caco-2 Model Establishment.  Pharmaceuticals,  15  (4): (418).  [PMID:35455415] [10.3390/ph15040418]

5. Bo Zhang, Ting Jiang, Li Ling, Zhonglian Cao, Jingjing Zhao, Yanyan Tuo, Xiaojian She, Shun Shen, Xinguo Jiang, Yu Hu, Zhiqing Pang.  (2016)  Enhanced Antitumor Activity of EGFP-EGF1-Conjugated Nanoparticles by a Multitargeting Strategy.  ACS Applied Materials & Interfaces,      [PMID:26890991] [10.1021/acsami.6b00036]

6. Jia Liu, Liuting Zheng, Xinyue Li, Wei Tang, Manyu Guo, Yuxing Wang, Xiaoqi Tan, Jiajia Chang, Huiyue Zhao, Dongsheng Zhu, Yu-qiang Ma, Da Huo.  (2025)  Emerging of Ultrafine Membraneless Organelles as the Missing Piece of Nanostress: Mechanism of Biogenesis and Implications at Multilevels.  ACS Nano,      [PMID:39882824] [10.1021/acsnano.4c15876]

7. Zikang Xing, Xuewen Li, Zhen Ning Tony He, Xin Fang, Heng Liang, Chunxiang Kuang, Aiying Li, Qing Yang.  (2024)  IDO1 Inhibitor RY103 Suppresses Trp-GCN2-Mediated Angiogenesis and Counters Immunosuppression in Glioblastoma.  Pharmaceutics,  16  (7): (870).  [PMID:39065567] [10.3390/pharmaceutics16070870]

8. Ping Yang, Zheng-Jian Wang, Hai-Tao Lu, Xu-Meng Feng, Jing-Long Ye, Guangchuan Wang, Cheng-Feng Qin, Qing Ye, Zhong-Yu Liu.  (2024)  Imaging of viral replication in live cells by using split fluorescent protein-tagged reporter flaviviruses.  VIROLOGY,      [PMID:39754862] [10.1016/j.virol.2024.110374]

9. Xinrui Meng, Jingjing Liu, Jia Kang, Menghan Wang, Zhanghui Guan, Dong Tian, Xinping Chen.  (2024)  Lamivudine protects mice from gastric ulcer by activating PGK1 to suppress ferroptosis.  BIOCHEMICAL PHARMACOLOGY,      [PMID:39029631] [10.1016/j.bcp.2024.116440]

10. Jingxin Sun, Zhehao Jin, Yong Jin, Haidan Yuan, Guangyu Jin, Jishan Quan.  (2025)  MRI-Based Multifunctional Nanoliposomes for Enhanced HCC Therapy and Diagnosis.  MOLECULAR PHARMACEUTICS,      [PMID:39809473] [10.1021/acs.molpharmaceut.4c00917]

11. Wei Li, Qingwen Zeng, Bing Wang, Chao Lv, Haoan He, Xi Yang, Bin Cheng, Xiaoan Tao.  (2024)  Oxidative stress promotes oral carcinogenesis via Thbs1-mediated M1-like tumor-associated macrophages polarization.  Redox Biology,      [PMID:39255693] [10.1016/j.redox.2024.103335]

12. Yao Yongchang, Chen Ke, Pan Qian, Gao Hui, Su Weixian, Zheng Shicong, Dong Weiqiang, Qian Dongyang.  (2024)  Redifferentiation of genetically modified dedifferentiated chondrocytes in a microcavitary hydrogel.  BIOTECHNOLOGY LETTERS,      [PMID:38523201] [10.1007/s10529-024-03475-2]

13. Xiuli Zhang, Mingjing Wei, Zhigang Zhang, Yarong Zeng, Feihong Zou, Sibo Zhang, Zhiping Wang, Fentian Chen, Hualong Xiong, Yufang Li, Lizhi Zhou, Tingting Li, Qingbing Zheng, Hai Yu, Jun Zhang, Ying Gu, Qinjian Zhao, Shaowei Li, Ningshao Xia.  (2024)  Risedronate-functionalized manganese-hydroxyapatite amorphous particles: A potent adjuvant for subunit vaccines and cancer immunotherapy.  JOURNAL OF CONTROLLED RELEASE,      [PMID:38244843] [10.1016/j.jconrel.2024.01.033]

14. Hui-Yue Zhao, Yuan-Qiang Chen, Xing-Yu Luo, Ming-Jie Cai, Jia-Yi Li, Xin-Yu Lin, Hao Zhang, Hong-Ming Ding, Guang-Liang Jiang, Yong Hu.  (2024)  Ligand Phase Separation-Promoted, “Squeezing-Out” Mode Explaining the Mechanism and Implications of Neutral Nanoparticles That Escaped from Lysosomes.  ACS Nano,      [PMID:38198577] [10.1021/acsnano.3c09452]

15. Zheng Liu-Ting, Yan Zeng-Shuai, Li Xin-Yue, Chang Jia-Jia, Tan Xiao-Qi, Wang Yu-Xing, Ding Hong-Ming, Liu Qin, Ma Yu-Qiang, Huo Da.  (2025)  Nanomaterial signatures program biomolecular condensates via triphasic separation for chemoplasticity remodeling.  Nature Communications,  16  (1): (1-24).  [PMID:41162367] [10.1038/s41467-025-64623-4]