[3-({10H-indolo[3,2-b]quinolin-11-yl}amino)propyl]dimethylamine

• ChemBase ID: 154574
• Molecular Formular: C20H22N4
• Molecular Mass: 318.41548
• Monoisotopic Mass: 318.18444672
• SMILES: CN(C)CCCNc1c2ccccc2nc2c1[nH]c1c2cccc1
• Canonical SMILES: CN(CCCNc1c2ccccc2nc2c1[nH]c1c2cccc1)C
• InChI: InChI=1S/C20H22N4/c1-24(2)13-7-12-21-18-14-8-3-5-10-16(14)22-19-15-9-4-6-11-17(15)23-20(18)19/h3-6,8-11,23H,7,12-13H2,1-2H3,(H,21,22)
• InChIKey: CTDCVGDSVHUYMA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-({10H-indolo[3,2-b]quinolin-11-yl}amino)propyl]dimethylamine
• IUPAC Traditional name: (3-{10H-indolo[3,2-b]quinolin-11-ylamino}propyl)dimethylamine
• Synonyms: SYUIQ-5; N′-(10H-Indolo [3,2-b]quinolin-11-yl)-N, N-dimethyl-propane-1,3-diamine

Database IDs

• CAS Number: 188630-47-9
• MDL Number: MFCD17215940
• PubChem SID: 162248712
• PubChem CID: 10567578

CALCULATED PROPERTIES

• Acid pKa: 13.779268
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.7753124
• LogD (pH = 7.4): 0.6631159
• Log P: 3.1857731
• Molar Refractivity: 100.0998 cm^3
• Polarizability: 41.804512 Å^3
• Polar Surface Area: 43.95 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: yellow powder

Safety Information

• European Hazard Symbols: Nature polluting (N)
• German water hazard class: 2
• Risk Statements: 50
• Safety Statements: 61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H22N4

DETAILS

Sigma Aldrich - S5826

Biochem/physiol Actions
SYUIQ-5 is a Cryptolepine derivative, which induces and stabilizes G-quadruplexes. In CNE2 and HeLa cancer cells SYUIQ-5 triggers rapid and potent telomere DNA damage through TRF2 delocalization from telomeres and induces cell death by autophagy. In low concentration the compound caused senescence and telomere shortening. It is a potent cytotoxic agent.