RSL3 - Moligand™, ≥98% , CAS No.1219810-16-8

CAS: 1219810-16-8 Cat. No.: R302648 Peso molecular: 440.88 PubChem CID: 1750826

GRADE & PURITY Moligand™, ≥98%

Synonyms

(1S,3R)-RSL3 | 1S,3R-RSL3 | (1S,3R)-Methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

Storage

Conservar a -20°C

Shipped In

Hielera + almohadillas de hielo

Descripción general

RSL3 ((1S,3R)-RSL3) es un inhibidor de la glutatión peroxidasa 4 (GPX4) (activador de la ferroptosis), reduce la expresión de la proteína GPX4 e induce la muerte ferroptósica de las células cancerosas de cabeza y cuello. RSL3 aumenta la expresión de p62 y Nrf2 e inactiva Keap1 en células HN3-rslR

Specifications

Sinónimos

(1S, 3R)-RSL3 | 1S, 3R-RSL3 | (1S, 3R)-Methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2, 3, 4, 9-tetrahydro-1H-pyrido[3, 4-b]indole-3-carboxylate

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Inhibidor de la glutatión peroxidasa 4 (GPX4). Induce la ferroptosis. Aumenta los niveles de peroxidasa lipídica in vitro. Inhibe la formación y progresión de tumores in vivo.

Condiciones de almacenamiento de almacenamiento

Conservar a -20°C

Enviado en

Hielera + almohadillas de hielo

Grado

Moligand™

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 504760629
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504760629
• Sonrisas canónicas: COC(=O)C1CC2=C(C(N1C(=O)CCl)C3=CC=C(C=C3)C(=O)OC)NC4=CC=CC=C24
• IUPAC Name: methyl (1S,3R)-2-(2-chloroacetyl)-1-(4-methoxycarbonylphenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
• InChIKey: TXJZRSRTYPUYRW-NQIIRXRSSA-N
• INCHI: 1S/C23H21ClN2O5/c1-30-22(28)14-9-7-13(8-10-14)21-20-16(15-5-3-4-6-17(15)25-20)11-18(23(29)31-2)26(21)19(27)12-24/h3-10,18,21,25H,11-12H2,1-2H3/t18-,21+/m1/s1
• Isómeros SMILES: COC(=O)[C@H]1CC2=C([C@@H](N1C(=O)CCl)C3=CC=C(C=C3)C(=O)OC)NC4=CC=CC=C24
• PubChem CID: 1750826
• Peso molecular: 440.88

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Clase Harmala alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Clase: Harmala alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Harmala alkaloids
• Alternative Parents: Alpha amino acid esters Beta carbolines 3-alkylindoles Benzoic acid esters Benzoyl derivatives Dicarboxylic acids and derivatives Methyl esters Heteroaromatic compounds Tertiary carboxylic acid amides Chloroacetamides Pyrroles Azacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organochlorides Organonitrogen compounds Organopnictogen compounds Alkyl chlorides Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Harman - Alpha-amino acid ester - Beta-carboline - Pyridoindole - Alpha-amino acid or derivatives - Benzoate ester - 3-alkylindole - Benzoic acid or derivatives - Indole - Indole or derivatives - Benzoyl - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Benzenoid - Methyl ester - Tertiary carboxylic acid amide - Pyrrole - Chloroacetamide - Heteroaromatic compound - Carboxamide group - Carboxylic acid ester - Carboxylic acid derivative - Organoheterocyclic compound - Azacycle - Organic nitrogen compound - Organohalogen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organochloride - Organopnictogen compound - Alkyl chloride - Organic oxygen compound - Organooxygen compound - Alkyl halide - Organonitrogen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as harmala alkaloids. These are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
• 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)

GPX4 Tchem Phospholipid hydroperoxide glutathione peroxidase (1 Activities)

Discover Target: GPX4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Calu-1 (518 Activities)

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

HT-1080 (3966 Activities)

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

MCF7 (126967 Activities)

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

MIA PaCa-2 (5949 Activities)

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

Objetivos asociados (no humanos)

HT-22 (3261 Activities)

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

4T1 (1737 Activities)

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

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Solvent:DMSO, Max Conc. mg/mL: 44.09, Max Conc. mM: 100
• Sensibilidad: Moisture sensitive
• Peso molecular: 440.900 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 440.114 Da
• Monoisotopic Mass: 440.114 Da
• Topological Polar Surface Area: 88.700 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 695.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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

Referencias

1. Wuyang Shi, Shibo Sun, Haowen Liu, Yao Meng, Kangshuai Ren, Guoying Wang, Minghui Liu, Jiaqi Wu, Yue Zhang, Huang Huang, Meiyun Shi, Weiping Xu, Qiang Ma, Bingbing Sun, Jianqiang Xu.  (2024)  Guiding bar motif of thioredoxin reductase 1 modulates enzymatic activity and inhibitor binding by communicating with the co-factor FAD and regulating the flexible C-terminal redox motif.  Redox Biology,      [PMID:38277963] [10.1016/j.redox.2024.103050]

2. Xiaosi Lin, Le Dong, Qing Miao, Zhaobin Huang, Fang Wang.  (2024)  Cycloheptylprodigiosin from marine bacterium Spartinivicinus ruber MCCC 1K03745T induces a novel form of cell death characterized by Golgi disruption and enhanced secretion of cathepsin D in Non-small cell lung cancer cell lines.  EUROPEAN JOURNAL OF PHARMACOLOGY,      [PMID:38663542] [10.1016/j.ejphar.2024.176608]

3. Haoze Song, Jing Liang, Yuanyuan Guo, Yang Liu, Kuiru Sa, Guohong Yan, Wen Xu, Wei Xu, Lixia Chen, Hua Li.  (2023)  A potent GPX4 degrader to induce ferroptosis in HT1080 cells.  EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,      [PMID:38194774] [10.1016/j.ejmech.2023.116110]

4. Weili Wu, Yingying Zhao, Baifu Qin, Xin Jiang, Chuyue Wang, Rong Hu, Rui Ma, Mong-Hong Lee, Huanliang Liu, Kai Li, Ping Yuan.  (2023)  Non-canonical role of UCKL1 on ferroptosis defence in colorectal cancer.  EBioMedicine,      [PMID:37343364] [10.1016/j.ebiom.2023.104650]

5. Zhao Hongting, Zhang Meng, Zhang Jinghua, Sun Zichen, Zhang Wenxin, Dong Weichen, Cheng Chen, Yao Yongzhong, Li Kuanyu.  (2023)  Hinokitiol-iron complex is a ferroptosis inducer to inhibit triple-negative breast tumor growth.  Cell and Bioscience,  13  (1): (1-15).  [PMID:37179385] [10.1186/s13578-023-01044-0]

6. Yu-Chen Chen, Qiong Zheng, Hui Lu, Yi-Xin Zhuang, Ting-Ting Gong, Lie-Feng Ma, Zha-Jun Zhan.  (2023)  Neuroprotective flavonoids from Epimedium brevicornu by inhibition of ferroptosis.  Phytochemistry Letters,      [PMID:] [10.1016/j.phytol.2023.04.003]

7. Fan Zhang, Hualong Zhen, Hengshun Cheng, Fengying Hu, Yunfei Jia, Binbin Huang, Minmin Jiang.  (2022)  Di-(2-ethylhexyl) phthalate exposure induces liver injury by promoting ferroptosis via downregulation of GPX4 in pregnant mice.  Frontiers in Cell and Developmental Biology,      [PMID:36438553] [10.3389/fcell.2022.1014243]

8. Yi-Xuan Zeng, Ni-Ren Li, Bing-Ying Deng, Yu-Feng Gu, Si-Fan Lu, Yi Liu.  (2025)  Coix Seed Oil Alleviates DSS-Induced Ulcerative Colitis via Intestinal Barrier Repair and Ferroptosis Regulation.  Journal of Inflammation Research,      [PMID:39995826] [10.2147/JIR.S501745]

9. Zi-Han Xu, Ming-Min Xie, Chun-Lan Xie, Xian-Wen Yang, Jun-Song Wang.  (2025)  Deep-Sea-Derived Isobisvertinol Targets TLR4 to Exhibit Neuroprotective Activity via Anti-Inflammatory and Ferroptosis-Inhibitory Effects.  Marine Drugs,  23  (1): (49).  [PMID:39852551] [10.3390/md23010049]

10. Deshan Yao, Liuxiang Bao, Sichuan Wang, Meng Tan, Yuanyuan Xu, Tianxu Wu, Zhengang Zhang, Kaizheng Gong.  (2024)  Isoliquiritigenin alleviates myocardial ischemia-reperfusion injury by regulating the Nrf2/HO-1/SLC7A11/GPX4 axis in mice.  FREE RADICAL BIOLOGY AND MEDICINE,      [PMID:38734270] [10.1016/j.freeradbiomed.2024.05.012]

11. Chao Zhao, Xiaoyan Huang, Zhuoyang Wu, Wanlu Sun, Yi Pan, Yi Liu.  (2025)  pH-Responsive Self-Assembled Upconversion Photosensitizer and RSL3 Synergistically Induce Tumor Ferroptosis.  JOURNAL OF MEDICINAL CHEMISTRY,      [PMID:40665790] [10.1021/acs.jmedchem.5c01339]

12. Cong Zhang, Yangkun Xiong, Mingyang Gong, Haixia Zhao, Shan Li, Xin Chen, Xiaochuan Ye, Zhenpeng Qiu.  (2025)  Pachymic Acid Ameliorates Fructose-Driven Hyperuricemic Nephropathy in Mice by Suppressing Ferroptosis via Activating Nrf2/GPX-4 Pathway.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:40864644] [10.1021/acs.jafc.5c02398]

13. Xue Shi, Yun Zhao, Hong-Yu Gao, Wei Yang, Jun Liao, Hui-Han Wang, Xiao-Tian Wang, Wei Yan.  (2025)  NFS1, together with FXN, protects cells from ferroptosis and DNA damage in diffuse large B-cell lymphoma.  Redox Biology,      [PMID:41005206] [10.1016/j.redox.2025.103878]

14. Huiqin Zhou, Yunjia Peng, Xinhua Huo, Bingqing Li, Huasheng Liu, Jian Wang, Gaihua Zhang.  (2025)  Integrating Bulk and Single-Cell Transcriptomic Data to Identify Ferroptosis-Associated Inflammatory Gene in Alzheimer’s Disease.  Journal of Inflammation Research,      [PMID:39959647] [10.2147/JIR.S497418]

15. Weng Xiuhong, Wang Simin, Wang Qing, Wei Mingbo, Cheng Bo.  (2025)  Melatonin inhibits salivary gland epithelial cell ferroptosis via the NRF2/HO-1/GPX4 signaling pathway in primary Sjögren’s syndrome.  INFLAMMATION RESEARCH,  74  (1): (1-19).  [PMID:40413364] [10.1007/s00011-025-02047-y]

16. Jiajian Wang, Lanqing Zhang, Runfang Li, Rui Yang, Fan Yang, Fei Yu, Jihong Zhang.  (2025)  Gambogic acid restores wild-type-like p53 functions to induce ferroptosis in mutant p53 cancer cells.  BIOCHEMICAL PHARMACOLOGY,      [PMID:41213406] [10.1016/j.bcp.2025.117533]

17. Weichen Dong, Wenxin Zhang, Li Huang, Lulu Xiao, Yuanfei Luo, Linying Yuan, Yike Jiang, Anyu Liao, Hongting Zhao, Zhihui Liu, Jia Wang, Ying Zhao, Yulong Cai, Mengna Peng, Dong Yang, Yi Xie, Kuanyu Li, Wusheng Zhu.  (2026)  Restoring cardiolipin homeostasis mitigates cerebral ischemia–reperfusion injury by suppressing ATG5-mediated neuronal autophagy-dependent ferroptosis.  Journal of Advanced Research,      [PMID:] [10.1016/j.jare.2026.03.014]