6-Aminonicotinamide
(Synonyms: 6-氨基烟酰胺) 目录号 : GC10462
6-Aminonicotinamide是一种有效的烟酰胺抗代谢物，是竞争性 NADP+ 依赖性酶葡萄糖-6-磷酸脱氢酶 (G6PD) 的抑制剂(Ki=0.46μM)。
Cas No.:329-89-5
Sample solution is provided at 25 µL, 10mM.
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6-Aminonicotinamide is a potent nicotinamide antimetabolite and a competitive inhibitor of the NADP⁺-dependent enzyme glucose-6-phosphate dehydrogenase (G6PD) (Ki=0.46μM)[1-2]. 6-Aminonicotinamide interferes with glycolysis, leading to ATP depletion, and is widely used in cancer research, such as in prostate cancer and breast cancer studies[3-4].
In vitro, treatment of HepAD38, HepG2-NTCP, and primary human hepatocytes (PHHs) with 6-Aminonicotinamide (12.5–25μM) for 24 hours, 6-Aminonicotinamide significantly inhibits the replication and transcription of hepatitis B virus (HBV), reduces HBsAg secretion, HBV RNA levels, and core DNA levels, and slightly decreases cccDNA[5]. Pretreatment of MYCN-amplified neuroblastoma cells (SJ-N-JF) with 6-Aminonicotinamide (0.8–100μM) for 18 hours, followed by 5-aminolevulinic acid (5-ALA; 250–500μM)-mediated photodynamic therapy (PDT; 633nm, 17.5mW/cm²) for 10–15 minutes, 6-Aminonicotinamide synergistically enhances the cytotoxicity of PDT, induces necrotic cell death, inhibits glucose-6-phosphate dehydrogenase (G6PD) activity, reduces the NADPH/NADP⁺ and GSH/GSSG ratios, and disrupts glutathione redox balance[6].
In vivo, a single intraperitoneal injection of 6-Aminonicotinamide (5–20mg/kg) in pregnant mice (gestational days 7–14), 6-Aminonicotinamide induces developmental abnormalities in the fetuses, including skeletal malformations, cleft palate, micrognathia, and spina bifida[7]. Intraperitoneal injection of 6-Aminonicotinamide (50mg/kg) in newborn mice (postnatal day 1), 6-Aminonicotinamide leads to rapidly progressive hydrocephalus by day 9 after injection, accompanied by aqueductal occlusion due to vacuolization of ependymal cells and periaqueductal gliosis, resulting in ventricular dilation and neurological dysfunction[8].
References:
[1] Ntsala LP, Lemmerer A. 6-Amino-nicotinamide. Acta Crystallogr Sect E Struct Rep Online. 2012 Aug 1;68(Pt 8):o2449.
[2] Johnson WJ, McColl JD. 6-Aminonicotinamide--a Potent Nicotinamide Antagonist. Science. 1955 Oct 28;122(3174):834.
[3] Cheikh IA, Hayar B, Ghanem N, et al. Therapeutic Targeting of the Pentose Phosphate Pathway in Colorectal Cancer Using 6-Aminonicotinamide and 5-Fluorouracil. Mol Carcinog. 2025 Jul;64(7):1222-1235.
[4] Varshney R, Dwarakanath B, Jain V. Radiosensitization by 6-aminonicotinamide and 2-deoxy-D-glucose in human cancer cells. Int J Radiat Biol. 2005 May;81(5):397-408.
[5] Ren F, Yang X, Hu ZW, et al. Niacin analogue, 6-Aminonicotinamide, a novel inhibitor of hepatitis B virus replication and HBsAg production. EBioMedicine. 2019 Nov;49:232-246.
[6] Okamura SM, Chelakkot VS, Linn Z, et al. 6-Aminonicotinamide enhances the efficacy of 5-aminolevulinic acid-mediated photodynamic therapy for neuroblastoma. BMC Cancer. 2025 Nov 25;25(1):1815.
[7] Curley FJ, Ingalls TH, Zappasodi P. 6-aminonicotinamide-induced skeletal malformations in mice. Arch Environ Health. 1968 Mar;16(3):309-15.
[8] Aikawa H, Suzuki K, Ito N, et al. 6-Aminonicotinamide-induced hydrocephalus in suckling mice. J Neuropathol Exp Neurol. 1984 Sep;43(5):511-21.
6-Aminonicotinamide是一种有效的烟酰胺抗代谢物，是竞争性 NADP+ 依赖性酶葡萄糖-6-磷酸脱氢酶 (G6PD) 的抑制剂(Ki=0.46μM)[1-2]。6-Aminonicotinamide干扰糖酵解，导致ATP耗竭，多被用于癌症（如前列腺癌、乳腺癌）的相关研究[3-4]。
在体外，6-Aminonicotinamide（12.5–25μM）处理HepAD38、HepG2-NTCP和原代人肝细胞（PHHs）24小时后，6-Aminonicotinamide能显著抑制乙型肝炎病毒（HBV）的复制和转录，降低HBsAg分泌、HBV RNA水平和核心DNA水平，并轻微减少cccDNA[5]。6-Aminonicotinamide（0.8–100μM）预处理MYCN扩增的神经母细胞瘤细胞（SJ-N-JF）18小时，随后进行5-氨基乙酰丙酸（5-ALA；250–500μM）介导的光动力疗法（PDT；633nm，17.5mW/cm²）10-15分钟，6-Aminonicotinamide可协同增强PDT的细胞毒性，诱导坏死性细胞死亡，抑制葡萄糖-6-磷酸脱氢酶（G6PD）活性，降低NADPH/NADP+和GSH/GSSG比值，破坏谷胱甘肽氧化还原平衡[6]。
在体内，在孕鼠（妊娠第7–14天）单次腹腔注射6-Aminonicotinamide（5-20mg/kg）处理后，6-Aminonicotinamide可诱导胎鼠出现骨骼畸形、腭裂、小颌畸形及脊柱裂等发育异常 [7]。新生小鼠（出生第1天）腹腔注射6-Aminonicotinamide（50mg/kg），6-Aminonicotinamide在注射后第9天引发快速进展的脑积水，伴随中脑导水管因室管膜细胞空泡化及周围胶质水肿而闭塞，导致脑室扩张、神经功能障碍[8]。
| Cell experiment [1]: | |
Cell lines | SJ-N-JF, NB-19, and NH-12 human neuroblastoma cells (MYCN-amplified and non-amplified) |
Preparation Method | Cells were maintained in RPMI-1640 medium supplemented with 10% fetal bovine serum at 37°C, 5% CO₂. Cells were pretreated with 6-Aminonicotinamide at concentrations of 0.8–100μM for 18 hours, followed by 5-aminolevulinic acid (5-ALA; 250–500μM) for 6 hours and red light irradiation (633nm, 17.5mW/cm²) for 10–15 minutes. |
Reaction Conditions | 0.8-100μM; 48h |
Applications | 6-Aminonicotinamide synergistically enhanced 5-ALA-mediated photodynamic therapy (PDT) cytotoxicity in MYCN-amplified neuroblastoma cells. The combination significantly suppressed the glutathione redox system, reducing NADPH/NADP⁺ and GSH/GSSG ratios, and increased intracellular protoporphyrin IX (PpIX) accumulation. This led to lipid peroxidation and necrotic cell death, as evidenced by membrane rupture and ballooning, without inducing apoptosis or ferroptosis. The combination index (CI) for 6-Aminonicotinamide and 5-ALA-PDT was <1, confirming synergism. |
| Animal experiment [2]: | |
Animal models | Pregnant white mice |
Preparation Method | Pregnant mice were intraperitoneally administered a single dose of 6-Aminonicotinamide at 5–20mg/kg body weight on gestational days 7–14. |
Dosage form | 5–20mg/kg; i.p.; Single injection on specific gestational days. |
Applications | 6-Aminonicotinamide induced dose- and time-dependent teratogenic effects in fetal mice. Skeletal malformations included vertebral defects, rib anomalies, cleft palate, micrognathia, and spina bifida. |
References: | |
| Cas No. | 329-89-5 | SDF | |
| 别名 | 6-氨基烟酰胺 | ||
| 化学名 | 6-amino-3-pyridinecarboxamide | ||
| Canonical SMILES | Nc1ccc(cn1)C(=O)N | ||
| 分子式 | C6H7N3O | 分子量 | 137.1 |
| 溶解度 | ≥ 13.7mg/mL in DMSO | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 7.2939 mL | 36.4697 mL | 72.9395 mL |
| 5 mM | 1.4588 mL | 7.2939 mL | 14.5879 mL |
| 10 mM | 729.4 μL | 3.647 mL | 7.2939 mL |
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动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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- Purity: >98.50%
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