10-Hydroxycamptothecin - 10mM in DMSO , CAS No.64439-81-2

CAS: 64439-81-2 Cat. No.: H425263 Peso molecular: 364.35 Número EC: 613-598-9

GRADE & PURITY 10mM in DMSO

Synonyms

(+/-)-10-HCPT | Hydroxy camptothecine | STL565783 | 10-Hydroxyl-20(S)-Camptothecin | Neuro_000051 | 10-Hydroxycamptothecin | BCP10548 | (+/-)-10-Hydroxycamptothecin | 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione,4-ethyl-4,9-dihydroxy-

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

application：

A Camptothecin derivative; a topoisomerase inhibitor for cancer therapy.

Specifications

Sinónimos

(+/-)-10-HCPT | Hydroxy camptothecine | STL565783 | 10-Hydroxyl-20(S)-Camptothecin | Neuro_000051 | 10-Hydroxycamptothecin | BCP10548 | (+/-)-10-Hydroxycamptothecin | 1H-Pyrano[3', 4':6, 7]indolizino[1, 2-b]quinoline-3, 14(4H, 12H)-dione, 4-ethyl-4, 9-dihydroxy-

Especificaciones y pureza

10mM in DMSO

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

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

Tipo de acción

INHIBITOR

Nombres e identificadores

• Sonrisas canónicas: CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)O)O
• IUPAC Name: 19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• InChIKey: HAWSQZCWOQZXHI-UHFFFAOYSA-N
• INCHI: 1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-6-12(23)3-4-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3
• Isómeros SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)O)O
• Peso molecular: 364.35
• Reaxy-Rn: 5889587
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5889587&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Clase Camptothecins

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Clase: Camptothecins
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Camptothecins
• Alternative Parents: Hydroxyquinolines Pyranopyridines Pyridinones 1-hydroxy-2-unsubstituted benzenoids Tertiary alcohols Heteroaromatic compounds Carboxylic acid esters Lactams Lactones Azacyclic compounds Oxacyclic compounds Monocarboxylic acids and derivatives Organonitrogen compounds Hydrocarbon derivatives Organopnictogen compounds Carbonyl compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Camptothecin - Hydroxyquinoline - Pyranopyridine - Quinoline - 1-hydroxy-2-unsubstituted benzenoid - Pyridinone - Pyridine - Benzenoid - Heteroaromatic compound - Tertiary alcohol - Carboxylic acid ester - Lactam - Lactone - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Oxacycle - Monocarboxylic acid or derivatives - Organic nitrogen compound - Alcohol - Organic oxygen compound - Carbonyl group - Organonitrogen compound - Organooxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
• 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)

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

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

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

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

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

KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

Discover Target: KDM4E

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

SMN1 Tchem Survival motor neuron protein (34246 Activities)

Discover Target: SMN1

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

Objetivos asociados (no humanos)

Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

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

Impa1 Inositol monophosphatase 1 (16203 Activities)

Discover Target: Impa1

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

Mecanismos de acción

Propiedades químicas y físicas

• Punto de inflamación (°C): 450.1ºC
• Punto de ebullición (°C): 820.7ºC
• Punto de fusión (°C): 230-237°C
• Peso molecular: 364.400 g/mol
• XLogP3: 0.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 364.106 Da
• Monoisotopic Mass: 364.106 Da
• Topological Polar Surface Area: 100.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 774.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

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12. Ting Wang, Pengfei Li, Yao Sun, Xiaomei Song, Hao Li, Liting Qin, Juying Zhou, Qin Huang, Fuhou Lei.  (2019)  Camptothecin-imprinted polymer microspheres with rosin-based cross-linker for separation of camptothecin from Camptotheca acuminata fruit.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2019.116085]

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14. Yang Zhou, Tao Hong, Li Tong, Wei Liu, Xueting Yang, Jianghan Luo, Fuling Wang, Jian Li, Lijun Yan.  (2018)  Astragalus polysaccharide combined with 10-hydroxycamptothecin inhibits metastasis in non-small cell lung carcinoma cell lines via the MAP4K3/mTOR signaling pathway.  INTERNATIONAL JOURNAL OF MOLECULAR MEDICINE,  42  (6): (3093-3104).  [PMID:30221690] [10.3892/ijmm.2018.3868]

15. Xiaoxia Ye, Xiaofeng Yang, Piaopiao Wei, Kangbing Wu.  (2018)  N-methylpyrrolidone exfoliated graphene as sensitive electrochemical sensing platform for 10-Hydroxycamptothecine.  JOURNAL OF ELECTROANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.jelechem.2018.04.048]

16. Lei Yu, Xin Wang, Zhi‑Feng Chen, Bo Jiang, Dong‑Yu Shang, Yong‑Xue Sun, Jing‑Hui Yang, Lian‑Fang Zhang, Yu‑Bin Ji.  (2017)  Cytisine induces apoptosis of HepG2 cells.  Molecular Medicine Reports,  16  (3): (3363-3370).  [PMID:28713951] [10.3892/mmr.2017.6991]

17. Jihang Dai, Yu Sun, Lianqi Yan, Jingcheng Wang, Xiaolei Li, Jun He.  (2017)  Upregulation of NOXA by 10-Hydroxycamptothecin plays a key role in inducing fibroblasts apoptosis and reducing epidural fibrosis.  PeerJ,      [PMID:28097065] [10.7717/peerj.2858]

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19. Kunjing Li, Yinfeng Li, Lu Wang, Lingxi Yang, Baoxian Ye.  (2015)  Study the voltammetric behavior of 10-Hydroxycamptothecin and its sensitive determination at electrochemically reduced graphene oxide modified glassy carbon electrode.  Arabian Journal of Chemistry,      [PMID:] [10.1016/j.arabjc.2015.05.014]

20. Liu Zhen-feng, Wang Guo-lin, Dong Meng-jie, Jin Jian-wen, Li Jia-jun, Zhang Qian, Zhao Kui, Yang Shu-ye, Lin Xiang-tong.  (2013)  Radiosynthesis of 10-(2-[18F]fluoroethoxy)-20(S)-camptothecin as a potential positron emission tomography tracer for the imaging of topoisomerase I in cancers.  JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY,  299  (3): (1509-1515).  [PMID:] [10.1007/s10967-013-2862-7]

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25. Xiaoju Zhou, Chenyuan Wang, Haojie Ke, Rui Zhang, Xiaoya Yu, Wei Li, Shi Chen, Lianrong Wang.  (2025)  Microneedle Patches Loaded with cRGD-Modified pH-Sensitive Hydroxycamptothecin Liposomes for Melanoma Therapy.  MOLECULAR PHARMACEUTICS,      [PMID:41115013] [10.1021/acs.molpharmaceut.5c00721]

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