Table 1.
Cytotoxic activities of 7‐deazapurine nucleosides
| Compound | IC50 [μM] (cell line) | Ref. |
|---|---|---|
| Natural compounds | ||
| Tubercidin (3) | 0.001 (A549) | 12 |
| Toyocamycin (4) | 0.012 (HTB‐81) | 13 |
| Sangivamycin (5) | 0.006 (A549) | 14 |
| 7‐Substituted 7‐deazapurine ribonucleosides | ||
| 7‐Iodotubercidin (6a) | 2.6a (HeLa) | 35 |
| 7‐Bromotubercidin (6b) | 2.9a (HeLa) | 35 |
| 7‐Chlorotubercidin (6c) | 13.3a (HeLa) | 35 |
| 7‐Fluorotubercidin (6d) | 1 (L‐1210) | 36 |
| AB61 (7a) | 0.01 (A549); 0.00036 (CCRF‐CEM) | 42 |
| 7b | 0.35 (A549); 0.10 (CCRF‐CEM); 0.003 (HCT15) | 12 |
| 7c | >20 (A549); > 10 (CCRF‐CEM) | 12 |
| 7d | 0.701 (A549); >10 (CCRF‐CEM); 0.152 (Du145) | 12 |
| 8 | 43.76 (A549); 64.44 (CCRF‐CEM) | 41 |
| 9a | 0.03 (A549); 0.02 (CCRF‐CEM); | 44 |
| 9b | 0.05 (A549); 0.05 (CCRF‐CEM); 0.01 (HCT116p53‐/‐) | 44 |
| 9c | 2.57 (A549); 0.18 (CCRF‐CEM); | 44 |
| 9d | 4.60 (A549); 2.91 (CCRF‐CEM); 0.15 (K562) | 44 |
| 9e | 0.11 (A549); 0.04 (CCRF‐CEM) | 44 |
| 10a‐c | >20 (A549); >20 (CCRF‐CEM) | 44 |
| 11a | 0.01 (CCRF‐CEM); 0.001 (Hs578) | 12 |
| 11b | 0.14 (A549); >20 (CCRF‐CEM); 0.03 (HCT116) | 44 |
| 11c | 0.39 (A549); 0.09 (CCRF‐CEM) | 44 |
| 11d | 19.2 (A549); 5.60 (CCRF‐CEM); 0.11 (K562‐TAX) | 44 |
| 12a | 0.4 (HeLa) | 45 |
| 12b | 0.2 (HeLa) | 45 |
| Sugar‐modified 7‐substituted 7‐deazapurine nucleosides | ||
| 13a | 4.25 (CCRF‐CEM) | 46 |
| 13b | NAb (CCRF‐CEM) | 46 |
| 13c | NA (CCRF‐CEM) | 46 |
| 13d | 7.50 (CCRF‐CEM) | 46 |
| 13e | >10 (CCRF‐CEM) | 47 |
| 13f | 3.44 (CCRF‐CEM) | 47 |
| 14a | 6.64 (CCRF‐CEM) | 46 |
| 14b | 6.08 (NCI‐H23) | 46 |
| 14c | NA (CCRF‐CEM) | 46 |
| 14d | 8.49 (Hs578) | 46 |
| 14e | >10 (CCRF‐CEM) | 47 |
| 14f | 6.63 (CCRF‐CEM) | 47 |
| 15 | 0.18 (CCRF‐CEM); 0.002 (Du145) | 46 |
| 16a | 0.64 (CCRF‐CEM); 0.15 (HepG2) | 47 |
| 16b | 0.42 (CCRF‐CEM); 0.35 (HepG2) | 47 |
| 17 | 3.5 (CCRF‐CEM) | 48 |
| 18 | 7.13 (A549); 16.63 (CCRF‐CEM) | 49 |
| 8‐Substituted deazapurine nucleosides | ||
| ARC (21a) | 0.97 (SW620); 0.49 (DM366); 0.20 (SK‐N‐AS) | 54, 55, 56 |
| Xylocydine (22a) | >50 (A549) | 64 |
| JRS‐15 (23b) | 12.42 (HepG2) | 64 |
| 24 | 2.6 (PA‐1) | 70 |
| 6‐Substituted 7‐deazapurine ribonucleosides and pronucleotides | ||
| 25a | 0.088 (A549); 0.31 (CCRF‐CEM); 0.007 (Du145) | 71 |
| 25b | 0.045 (A549); 0.29 (CCRF‐CEM); 0.009 (Du145) | 71 |
| 25c | >10 (A549); 4.0 (CCRF‐CEM); 1.1 (Du145) | 71 |
| 26a | 0.11 (A549); 1.4 (CCRF‐CEM); 0.005 (Du145) | 71 |
| 26b | 0.061 (A549); 0.27 (CCRF‐CEM); 0.009 (Du145) | 71 |
| 27a | >10 (A549); 3.8 (CCRF‐CEM) | 71 |
| 27b | 0.38 (A549); 2.7 (CCRF‐CEM); 0.013 (Du145) | 71 |
| 28a | 2.00 (CCRF‐CEM); 0.017 (HCT116) | 72 |
| 28b | 18.60 (CCRF‐CEM); 0.011 (Du145) | 72 |
| 28c | >10 (CCRF‐CEM) | 72 |
| 29a | 17.67 (CCRF‐CEM); 0.007 (Du145) | 72 |
| 29b | >10 (CCRF‐CEM); 0.022 (Du145) | 72 |
| 30a | 3.44 (CCRF‐CEM); 1.03 (HCT116) | 73 |
| 30b | 3.34 (CCRF‐CEM); 1.02 (HeLa S3) | 73 |
| 30c | 1.13 (CCRF‐CEM); 0.58 (HeLa S3) | 73 |
| 31a | 8.47 (CCRF‐CEM); 1.41 (HepG2) | 73 |
| 31b | >10 (CCRF‐CEM); 1.53 (HepG2) | 73 |
| 31c | 2.09 (CCRF‐CEM); 0.68 (HCT116) | 73 |
| 32a | 29.4 (A549); 2.22 (CCRF‐CEM) | 74 |
| 32b–d | >150 (A549); > 150 (CCRF‐CEM) | 74 |
| Sugar‐modified 6‐substituted 7‐deazapurine nucleosides | ||
| 33a‐e | NA (CCRF‐CEM) | 75, 76 |
| 34 | NA (A549); NA (CCRF‐CEM) | 49 |
| Other 7‐deazapurine nucleosides | ||
| 35a | 0.03 (A549); 0.01 (CCRF‐CEM) | 44 |
| 35b–e | >150 (A549); >150 (CCRF‐CEM) | 74 |
| 36a | 0.028 (HepG2); 0.090 (HeLa S3) | 77 |
| 36b–h | >50 (HepG2); >50 (HeLa S3) | 77 |
| 37 | 115 (CCRF‐CEM); 1.8 (HeLa) | 78 |
| 38 | 36.20 (A549) | 79 |
| Fused 7‐deazapurine nucleosides | ||
| 41a | 7.9 (CCRF‐CEM) | 91 |
| 41b | 20.2 (CCRF‐CEM); 2.0 (L‐1210) | 91, 92 |
| 42 | 0.175 (HepG2) | 93 |
| 43a | 18 (CCRF‐CEM); 11 (HeLa S3) | 94 |
| 43b | 12 (CCRF‐CEM) | 94 |
| 44a | >50 (A549); 47.62 (CCRF‐CEM) | 95 |
| 44b | 11.9 (A549); 6.22 (CCRF‐CEM); 2.5 (U2OS) | 95 |
| 44c | 0.21 (A549); 0.02 (CCRF‐CEM) | 95 |
| 44d | 0.22 (A549); 0.13 (CCRF‐CEM); 0.11 (HL60) | 95 |
| 44e | 0.66 (A549); 0.027 (CCRF‐CEM) | 95 |
| 45a | >50 (A549); >50 (CCRF‐CEM) | 95 |
| 45b | 30.11 (A549); 0.3 (CCRF‐CEM) | 95 |
| 45c | 0.72 (A549); 0.03 (CCRF‐CEM) | 95 |
| 45d | 1.23 (A549); 0.22 (CCRF‐CEM) | 95 |
| 45e | 0.80 (A549); 0.20 (CCRF‐CEM) | 95 |
minimal cytotoxic concentration; bNA = inactive.
Cell lines mentioned in the table: A549, human lung carcinoma; CCRF‐CEM, human lymphoblastic leukemia; DM366, human melanoma; Du145, human prostate carcinoma; HCT116, human colorectal carcinoma; HCT116p53−/−, human colorectal carcinoma, p53 mutated; HCT15, human colorectal adenocarcinoma; HeLa, human cervical adenocarcinoma; HeLa S3, human cervical adenocarcinoma, HepG2, human hepatocellular carcinoma; HL60, human acute promyelocytic leukemia; Hs578, human breast carcinoma; HTB‐81, human prostate carcinoma; K562, human chronic myelogenous leukemia; K562‐TAX, human colorectal carcinoma, taxol‐resistant; L‐1210, mouse lymphocytic leukemia; NCI‐H23, human lung adenocarcinoma; PA‐1, human teratocarcinoma; SK‐N‐AS, human neuroblastoma; SW620, human colon adenocarcinoma; U2OS, human osteosarcoma.