Pirarubicin - 10mM in DMSO , CAS No.72496-41-4

CAS: 72496-41-4 Cat. No.: P425675 Molecular Weight: 627.64 EC Number: 999-185-7

GRADE & PURITY 10mM in DMSO

Synonyms

DTXSID2046755 | s1393 | SCHEMBL8323 | Pirarubicinum | Pirarubicinum [Latin] | DTXCID0026755 | THP-doxorubicin | Pirarubicina | Theprubicin | D58G680W0G | Pirarubicine | HY-13725 | 4'-O-Tetrahydropyranyladriamycin | NCGC00167982-01 | (7S,9S)-7-[(2R,4S,5S,6

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Pirarubicin is an anthracycline antibiotic, and also a DNA/RNA synthesis inhibitor by intercalating into DNA and interacts with topoisomerase II, used as an antineoplastic agent.

Specifications

Synonyms

DTXSID2046755 | s1393 | SCHEMBL8323 | Pirarubicinum | Pirarubicinum [Latin] | DTXCID0026755 | THP-doxorubicin | Pirarubicina | Theprubicin | D58G680W0G | Pirarubicine | HY-13725 | 4'-O-Tetrahydropyranyladriamycin | NCGC00167982-01 | (7S, 9S)-7-[(2R, 4S, 5S, 6

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Topoisomerase II inhibitor. Intercalates into DNA and inhibits DNA replication. Analogue of doxorubicin. Expresses anti-tumor activity in vivo.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)OC6CCCCO6
• IUPAC Name: (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• InChIKey: KMSKQZKKOZQFFG-YXRRJAAWSA-N
• INCHI: 1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1
• Isomeric SMILES: C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O[C@@H]6CCCCO6
• Molecular Weight: 627.64
• Reaxy-Rn: 25807399
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25807399&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Anthracyclines

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Anthracyclines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Anthracyclines
• Alternative Parents: Tetracenequinones Aminoglycosides Anthraquinones O-glycosyl compounds Tetralins Anisoles Aryl ketones Alkyl aryl ethers Oxanes Monosaccharides Tertiary alcohols Alpha-hydroxy ketones Vinylogous acids Polyols Oxacyclic compounds Acetals Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Anthracycline - Anthracyclinone-skeleton - Aminoglycoside core - Tetracenequinone - 9,10-anthraquinone - 1,4-anthraquinone - Anthracene - Glycosyl compound - O-glycosyl compound - Tetralin - Anisole - Aryl ketone - Alkyl aryl ether - Amino saccharide - Benzenoid - Monosaccharide - Oxane - Alpha-hydroxy ketone - Vinylogous acid - Tertiary alcohol - Ketone - Polyol - Oxacycle - Organoheterocyclic compound - Acetal - Ether - Organonitrogen compound - Carbonyl group - Organooxygen compound - Primary amine - Primary aliphatic amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Amine - Organic nitrogen compound - Alcohol - Primary alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
• 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

Associated Targets(Human)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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HT-29 (80576 Activities)

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HEK293 (82097 Activities)

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FEN1 Tchem Flap endonuclease 1 (12055 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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HTT Tchem Huntingtin (19182 Activities)

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SNCA Tchem Alpha-synuclein (10960 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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BLM Tchem Bloom syndrome protein (4248 Activities)

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

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EYA2 Tbio Eyes absent homolog 2 (5884 Activities)

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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

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KMT2A Tchem Histone-lysine N-methyltransferase MLL (17327 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Plasmodium falciparum (966862 Activities)

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L1210 (27553 Activities)

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L5178Y (1809 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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pfk 6-phospho-1-fructokinase (7870 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 627.600 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 7
• Exact Mass: 627.232 Da
• Monoisotopic Mass: 627.232 Da
• Topological Polar Surface Area: 204.000 Ų
• Heavy Atom Count: 45
• Formal Charge: 0
• Complexity: 1120.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• 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: 1

References

1. Fan Qi, Lulu Wang, Luopeng Bi, Xiaoqing Han, Jiao Yan, Pangpan Song, Xingbo Wan, Yanjing Wang, Yaqing Kang, Xiaobo Ding, Yanbo Wang, Haiyuan Zhang.  (2023)  Homologous Targeting And Adhesion Abilities of Cellular Microvesicles for Enhanced Intravesical Therapy of Bladder Cancer.  Advanced Therapeutics,      [PMID:] [10.1002/adtp.202300280]

2. Yuhong Lin, Zhangcheng Fu, Yongfei Liu, Jingyi Chen, Kai Zhao, Chunhua Lu, Xiankun Tu.  (2023)  A dual-functional nanomedicine combining fluorinated antisense oligonucleotide with chemotherapeutic drug for synergistic gene-chemo tumor treatment.  MATERIALS & DESIGN,      [PMID:] [10.1016/j.matdes.2023.112457]

3. Shi Hongwei, Tang Heng, Ai Wen, Zeng Qingfu, Yang Hong, Zhu Fengqing, Wei Yunjie, Feng Rui, Wen Li, Pu Peng, He Quan.  (2021)  Schisandrin B Antagonizes Cardiotoxicity Induced by Pirarubicin by Inhibiting Mitochondrial Permeability Transition Pore (mPTP) Opening and Decreasing Cardiomyocyte Apoptosis.  Frontiers in Pharmacology,      [PMID:34721023] [10.3389/fphar.2021.733805]

4. Hongwei Shi, Qingfu Zeng, Yunjie Wei, Hong Yang, Heng Tang, Dan Wang, Peng Pu, Rui Feng.  (2021)  Canagliflozin is a potential cardioprotective drug but exerts no significant effects on pirarubicin‑induced cardiotoxicity in rats.  Molecular Medicine Reports,  24  (4): (1-8).  [PMID:34368866] [10.3892/mmr.2021.12342]

5. Xie Ruirui, Liu Yanyan, Yang Peipei, Huang Lan, Zou Xun, Liu Jiamin, Ren Qingfan, Tao Jia, Zhao Peng.  (2020)  “French fries”-like luminescent metal organic frameworks for the fluorescence determination of cytochrome c released by apoptotic cells and screening of anticancer drug activity.  MICROCHIMICA ACTA,  187  (4): (1-9).  [PMID:32166378] [10.1007/s00604-020-4207-x]

6. Xinglu Jiang, Xiaobo Fan, Wei Xu, Chenggui Zhao, Hailu Wu, Rui Zhang, Guoqiu Wu.  (2019)  Self-assembled peptide nanoparticles responsive to multiple tumor microenvironment triggers provide highly efficient targeted delivery and release of antitumor drug.  JOURNAL OF CONTROLLED RELEASE,      [PMID:31682910] [10.1016/j.jconrel.2019.10.031]

7. Chuanmin Zhang, Jingli Wang, Mengyue Fan, Lei Han, Bolian Xiao, Xiaoli Xie, Yao Fu, Yongqing Zhai, Chao Wang, Ning Zhang, Zhilong Xu, Lijuan Wang.  (2024)  Folate functionalized pH-sensitive nanoparticulate system to decrease the toxicity and enhance the anti-cancer activity of pirarubicin for lymphoma therapy via downregulation of H3K18la and H3K9la.  JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.jddst.2024.105829]