5-Amino-4-oxopentanoic acid
(Synonyms: 5-氨基乙酰丙酸; 5-ALA; δ-Aminolevulinic acid; 5-Amino-4-oxopentanoic acid) 目录号 : GC32608
5-Amino-4-oxopentanoic acid是一种天然存在的非蛋白原性氨基酸，是光敏剂原卟啉IX（PpIX）的前药。5-Amino-4-oxopentanoic acid可以被波长约为635nm（580至740nm）的激光激活，发出红色荧光（620至710nm），作为多种癌症的光诊断剂。
Cas No.:106-60-5
Sample solution is provided at 25 µL, 10mM.
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5-Amino-4-oxopentanoic acid is a naturally occurring non-proteinogenic amino acid and a prodrug of the photosensitizer protoporphyrin IX (PpIX). 5-Amino-4-oxopentanoic acid can be activated by laser light at a wavelength of about 635nm (580 to 740nm) to emit red fluorescence (620 to 710nm), and can be used as a photodiagnostic agent for a variety of cancers[1-4].
5-Amino-4-oxopentanoic acid can inhibit the viability of U87MG cells with an IC50 of 500μg/mL. 5-Amino-4-oxopentanoic acid (250μg/mL) can induce apoptosis of U87MG cells, promote the expression of Bax and p53, and inhibit the expression of Bcl-2. 5-Amino-4-oxopentanoic acid increased the accumulation of U87MG cells in the SUB-G1 population, reduced the expression of cyclin D1, and reduced the migration ability of U87MG cells[2]. When using photodynamic therapy, HCC cells were treated with different concentrations (0-0.6mM) of 5-Amino-4-oxopentanoic acid at different illumination doses (0-3.6J/cm2). 5-Amino-4-oxopentanoic acid inhibited the viability of HCC cells in a dose-dependent manner[3].
5-Amino-4-oxopentanoic acid (200mg/kg)-mediated photodynamic therapy can inhibit the growth rate of mouse tumors in the SCID mouse hepatocellular carcinoma model[3]. 5-Amino-4-oxopentanoic acid (30 or 300mg/kg/day) can promote caspase 3-dependent apoptosis in the carcinogenesis of transgenic prostate adenocarcinoma (FVB-TRAMP) mice by supporting the functional expression of mitochondrial cytochrome c and cytochrome c oxidase subunit 4 (COX4), thereby reducing the tumor burden in mice[4].
References:
[1] Pignatelli P, Umme S, D’Antonio D L, et al. Reactive oxygen species produced by 5-aminolevulinic acid photodynamic therapy in the treatment of cancer[J]. International Journal of Molecular Sciences, 2023, 24(10): 8964.
[2] Jalili-Nik M, Abbasinezhad-Moud F, Sahab-Negah S, et al. Antitumor effects of 5-Aminolevulinic acid on human malignant glioblastoma cells[J]. International Journal of Molecular Sciences, 2021, 22(11): 5596.
[3] Kumar A, Pecquenard F, Baydoun M, et al. An Efficient 5-Aminolevulinic Acid Photodynamic Therapy Treatment for Human Hepatocellular Carcinoma[J]. International Journal of Molecular Sciences, 2023, 24(13): 10426.
[4] Onishi K, Miyake M, Tatsumi Y, et al. Inhibitory Effect of Orally Administered 5-Aminolevulinic Acid on Prostate Carcinogenesis in the FVB-Transgenic Adenocarcinoma of a Mouse Prostate (FVB-TRAMP) Model[J]. Asian Pacific Journal of Cancer Prevention: APJCP, 2020, 21(12): 3743.
5-Amino-4-oxopentanoic acid是一种天然存在的非蛋白原性氨基酸，是光敏剂原卟啉IX（PpIX）的前药。5-Amino-4-oxopentanoic acid可以被波长约为635nm（580至740nm）的激光激活，发出红色荧光（620至710nm），作为多种癌症的光诊断剂[1-4]。
5-Amino-4-oxopentanoic acid可抑制U87MG细胞的活力，IC50为500μg/mL。5-Amino-4-oxopentanoic acid（250μg/mL）可诱导U87MG细胞凋亡，促进Bax和p53表达，抑制Bcl-2表达。5-Amino-4-oxopentanoic acid增加了U87MG 细胞在SUB-G1群体中的积累，降低了细胞周期蛋白D1的表达，降低了U87MG细胞的迁移能力[2]。使用光动力疗法时，在不同照明剂量（0-3.6J/cm2）下使用不同浓度（0-0.6mM）的5-Amino-4-oxopentanoic acid处理HCC细胞，5-Amino-4-oxopentanoic acid以剂量依赖性的方式抑制HCC细胞活力[3]。
5-Amino-4-oxopentanoic acid（200mg/kg）介导的光动力疗法可抑制SCID小鼠肝细胞癌模型中小鼠肿瘤的生长速率[3]。5-Amino-4-oxopentanoic acid（30或300mg/kg/day）可通过支持线粒体细胞色素c和细胞色素c氧化酶亚基4（COX4）的功能表达，促进转基因小鼠前列腺腺癌（FVB-TRAMP）小鼠癌变中caspase 3依赖性细胞凋亡，从而减轻小鼠肿瘤负荷[4]。
| Cell experiment [1]: | |
Cell lines | U87MG cells |
Preparation Method | U87MG cells were treated with different concentrations of 5-Amino-4-oxopentanoic acid at different time intervals (1, 2 and 7 days). Cell viability was detected by MTT assay. |
Reaction Conditions | 0–3750μg/mL, 1, 2 and 7 days |
Applications | 5-Amino-4-oxopentanoic acid exerted a significant inhibitory effect on the viability of U87MG cells in a time- as well as dose-dependent manner. The half-maximal inhibitory concentration (IC50) of 5-Amino-4-oxopentanoic acid was 2500μg/mL after 2 days, which was reduced to 500μg/mL after 7 days. |
| Animal experiment [2]: | |
Animal models | SCID Mice Model of HCC |
Preparation Method | Mice were divided into four groups: Non-Treated, 5-Amino-4-oxopentanoic acid Only, Light Only, and 5-Amino-4-oxopentanoic acid photodynamic therapy (PDT) Treated. For the 5-Amino-4-oxopentanoic acid Only and 5-Amino-4-oxopentanoic acid PDT condition, 100μL of 5-Amino-4-oxopentanoic acid solution dissolved in distilled water was injected intraperitoneally at a dose of 200mg/kg per mice 18h before illumination. For the Light Only and 5-Amino-4-oxopentanoic acid PDT group, the mice were anesthetized and subjected to illumination using laser-set at 635nm with 32.4J/cm2. |
Dosage form | 200mg/kg, 20 days, i.p. |
Applications | Mice treated with 5-Amino-4-oxopentanoic acid PDT had reduced tumor growth rates compared to Non-Treated. |
References: [1] Jalili-Nik M, Abbasinezhad-Moud F, Sahab-Negah S, et al. Antitumor effects of 5-Aminolevulinic acid on human malignant glioblastoma cells[J]. International Journal of Molecular Sciences, 2021, 22(11): 5596. [2] Kumar A, Pecquenard F, Baydoun M, et al. An Efficient 5-Aminolevulinic Acid Photodynamic Therapy Treatment for Human Hepatocellular Carcinoma[J]. International Journal of Molecular Sciences, 2023, 24(13): 10426. | |
| Cas No. | 106-60-5 | SDF | |
| 别名 | 5-氨基乙酰丙酸; 5-ALA; δ-Aminolevulinic acid; 5-Amino-4-oxopentanoic acid | ||
| Canonical SMILES | NCC(=O)CCC(O)=O | ||
| 分子式 | C5H9NO3 | 分子量 | 131.13 |
| 溶解度 | DMSO : 100 mg/mL (762.60 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| 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 | 7.626 mL | 38.1301 mL | 76.2602 mL |
| 5 mM | 1.5252 mL | 7.626 mL | 15.252 mL |
| 10 mM | 0.7626 mL | 3.813 mL | 7.626 mL |
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| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
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2.
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Quality Control & SDS
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- Purity: >98.00%
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