Introduction：Basic information about CAS 213261-59-7|RITA (NSC 652287), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | RITA (NSC 652287) |
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| CAS Number | 213261-59-7 | Molecular Weight | 292.373 |
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| Density | 1.4±0.1 g/cm3 | Boiling Point | 464.9±40.0 °C at 760 mmHg |
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| Molecular Formula | C14H12O3S2 | Melting Point | 160 °C |
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| MSDS | / | Flash Point | 235.0±27.3 °C |
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Names
| Name | [5-[5-[5-(hydroxymethyl)thiophen-2-yl]furan-2-yl]thiophen-2-yl]methanol |
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| Synonym | More Synonyms |
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RITA (NSC 652287) BiologicalActivity
| Description | RITA is an inhibitor of p53-HDM-2 interaction, binds to p53dN, with a Kd of 1.5 nM, and also induces DNA-DNA cross-links. |
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| Related Catalog | Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Cell Cycle/DNA Damage >>DNA Alkylator/CrosslinkerSignaling Pathways >>Apoptosis >>MDM-2/p53Research Areas >>Cancer |
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| Target | Kd: 1.5 nM (p53dN)[1] DNA Crosslinker[2] |
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| In Vitro | RITA inhibits p53-HDM-2 interaction, binding to p53dN, with a Kd of 1.5 nM. RITA (10 μM) blocks complex formation between p53 and HDM-2 in HCT116 cells and HDFs and in NHF-ERMyc cells irrespective of c-Myc expression. RITA (0.5 μM) reduces the viability of tumor cells in a wild-type p53-dependent manner. Moreover, RITA (0.1 μM) induces p53-dependent apoptosis. RITA induces p53 but does not via DNA damage-signaling pathway[1]. RITA (NSC 652287) induces DNA-DNA cross-links. RITA induces G2-M cell cycle arrest at 10 nM and causes apoptosis at 100 nM. RITA (100 nM) also elevates p53 and causes dose-dependent effects on p21WAF1 protein levels[2]. RITA inhibits the growth of HeLa and CaSki cells, with IC50s of 1 and 10 μM. In addition, RITA (1 μM) stabilizes p53 by inhibiting p53/E6AP interaction[3]. |
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| In Vivo | RITA (0.1, 1 or 10 mg/kg, i.p.) shows potent antitumor activity in SCID mice bearing HCT116 and HCT116 TP53−/− xenografts[1]. RITA (10 mg/kg, i.p.) also suppresses the growth of HeLa cells in SCID mice[3]. |
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| Cell Assay | For the cell viability assay, 3,000 cells per well are plated in a 96-well plate and treated with RITA for 48 h, after which cell viability is assessed with the proliferation reagent WST-1. For colony formation assay, cells are seeded in 12-well plates and treated with RITA for 24 h, after which the medium is replaced and the cells are allowed to grow for 10-14 d. The colonies are stained with crystal violet. For growth curves, 3000 cells/mL are plated in 12-well plates, treated with RITA, and counted over 5 d[3]. |
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| Animal Admin | Mice[1] Female SCID mice, 4-6 weeks old, are implanted with subcutaneous xenografts using 1 × 106 cells in 90% Matrigel. Palpable tumors are established 3-6 d after the cells are injected, at which point RITA treatment is initiated. RITA is administered either 0.1, 1 or 10 mg/kg every day by intravenous or intraperitoneal injection in a total volume of 100 μL phosphate buffered saline. Xenografts are measured every 2 d. Tumor volumes are plotted for control and treated groups by dividing the average tumor volume for each data point by average starting tumor volume[1]. |
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| References | [1]. Issaeva N, et al. Small molecule RITA binds to p53, blocks p53-HDM-2 interaction and activates p53 function in tumors. Nat Med. 2004 Dec;10(12):1321-8. Epub 2004 Nov 21. [2]. Nieves-Neira W, et al. DNA protein cross-links produced by NSC 652287, a novel thiophene derivative active against human renal cancer cells. Mol Pharmacol. 1999 Sep;56(3):478-84. [3]. Zhao CY, et al. Rescue of p53 function by small-molecule RITA in cervical carcinoma by blocking E6-mediated degradation. Cancer Res. 2010 Apr 15;70(8):3372-81. |
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Chemical & Physical Properties
| Density | 1.4±0.1 g/cm3 |
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| Boiling Point | 464.9±40.0 °C at 760 mmHg |
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| Melting Point | 160 °C |
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| Molecular Formula | C14H12O3S2 |
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| Molecular Weight | 292.373 |
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| Flash Point | 235.0±27.3 °C |
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| Exact Mass | 292.022797 |
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| PSA | 110.08000 |
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| LogP | 2.48 |
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| Vapour Pressure | 0.0±1.2 mmHg at 25°C |
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| Index of Refraction | 1.661 |
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| InChIKey | KZENBFUSKMWCJF-UHFFFAOYSA-N |
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| SMILES | OCc1ccc(-c2ccc(-c3ccc(CO)s3)o2)s1 |
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| Storage condition | Store at -20°C |
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Safety Information
Synonyms
| p53 Activator III,RITA |
| (Furan-2,5-diyldithiene-5,2-diyl)dimethanol |
| RITA |
| (2,5-Furandiyldi-5,2-thienediyl)dimethanol |
| 2-Thiophenemethanol, 5,5'-(2,5-furandiyl)bis- |
| SOS BISMETHANOL |
| Reactivation of p53 and Induction of Tumor cell Apoptosis |
| NSC 652287 |
| 5,5'-(2,5-Furandiyl)bis-2-thiophenemethanol |
| NSC652287 |
