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MedKoo Cat#: 471004 | Name: Succinylacetone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Succinylacetone is an inhibitor of δ-aminolevulinic acid dehydratase

Chemical Structure

Succinylacetone
Succinylacetone
CAS#51568-18-4

Theoretical Analysis

MedKoo Cat#: 471004

Name: Succinylacetone

CAS#: 51568-18-4

Chemical Formula: C7H10O4

Exact Mass: 158.0579

Molecular Weight: 158.15

Elemental Analysis: C, 53.16; H, 6.37; O, 40.46

Price and Availability

Size Price Availability Quantity
50mg USD 350.00
100mg USD 550.00
250mg USD 1,000.00
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Related CAS #
No Data
Synonym
NSC 174804; NSC174804; NSC-174804
IUPAC/Chemical Name
4,6-dioxoheptanoic acid
InChi Key
WYEPBHZLDUPIOD-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H10O4/c1-5(8)4-6(9)2-3-7(10)11/h2-4H2,1H3,(H,10,11)
SMILES Code
CC(CC(CCC(O)=O)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Succinylacetone is an inhibitor of δ-aminolevulinic acid dehydratase (Ki = 300 nM for human erythrocyte enzyme).
In vitro activity:
Differential mechanism occurs in response to succinylacetone in colon cancer cells. Succinylacetone induced apoptosis in HCT116 and HT29 cells but not in SW480 cells. Mitochondria of HT29 cells were swollen, indicating damage, whereas in HCT116 cells, several mitochondria had a diminished size. Succinylacetone inhibited ATP production through different mechanisms in each cell line: reducing complex III activity in HT29 cells and pyruvate dehydrogenase (PDH) activity in HCT116 cells. Reference: Molecules. 2019 Oct 3;24(19):3575. https://pubmed.ncbi.nlm.nih.gov/31623369/
In vivo activity:
The findings of this study suggest that succinylacetone disrupts hemoenzyme function without impacting blood pressure regulation or sodium excretion, leading to potential in hypertyrosinemia treatment. Rats treated with succinylacetone showed decreased heme levels and enzyme activity but no change in blood pressure. Succinylacetone also affected blood vessel function but did not alter sodium excretion. Reference: J Pharmacol Exp Ther. 2010 Apr;333(1):290-6. https://pubmed.ncbi.nlm.nih.gov/20071481/

Preparing Stock Solutions

The following data is based on the product molecular weight 158.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Lee PJ, Woo SJ, Yoo HM, Cho N, Kim HP. Differential Mechanism of ATP Production Occurs in Response to Succinylacetone in Colon Cancer Cells. Molecules. 2019 Oct 3;24(19):3575. doi: 10.3390/molecules24193575. PMID: 31623369; PMCID: PMC6803967. 2. Zheng KC, Yalowich JC, Kagan VE, Keohavong P. Increased mutant frequencies in the HPRT gene locus of leukemia HL-60 cells treated with succinylacetone. Cell Biol Toxicol. 2006 Sep;22(5):361-70. doi: 10.1007/s10565-006-0171-4. Epub 2006 Jul 11. PMID: 16838078. 3. Yang F, Li J, Deng H, Wang Y, Lei C, Wang Q, Xiang J, Liang L, Xia J, Pan X, Li X, Long Q, Chang L, Xu P, Huang A, Wang K, Tang N. GSTZ1-1 Deficiency Activates NRF2/IGF1R Axis in HCC via Accumulation of Oncometabolite Succinylacetone. EMBO J. 2019 Aug 1;38(15):e101964. doi: 10.15252/embj.2019101964. Epub 2019 Jun 28. PMID: 31267557; PMCID: PMC6669923. 4. Bourque SL, Benjamin CD, Adams MA, Nakatsu K. Lack of hemodynamic effects after extended heme synthesis inhibition by succinylacetone in rats. J Pharmacol Exp Ther. 2010 Apr;333(1):290-6. doi: 10.1124/jpet.109.162966. Epub 2010 Jan 13. PMID: 20071481.
In vitro protocol:
1. Lee PJ, Woo SJ, Yoo HM, Cho N, Kim HP. Differential Mechanism of ATP Production Occurs in Response to Succinylacetone in Colon Cancer Cells. Molecules. 2019 Oct 3;24(19):3575. doi: 10.3390/molecules24193575. PMID: 31623369; PMCID: PMC6803967. 2. Zheng KC, Yalowich JC, Kagan VE, Keohavong P. Increased mutant frequencies in the HPRT gene locus of leukemia HL-60 cells treated with succinylacetone. Cell Biol Toxicol. 2006 Sep;22(5):361-70. doi: 10.1007/s10565-006-0171-4. Epub 2006 Jul 11. PMID: 16838078.
In vivo protocol:
1. Yang F, Li J, Deng H, Wang Y, Lei C, Wang Q, Xiang J, Liang L, Xia J, Pan X, Li X, Long Q, Chang L, Xu P, Huang A, Wang K, Tang N. GSTZ1-1 Deficiency Activates NRF2/IGF1R Axis in HCC via Accumulation of Oncometabolite Succinylacetone. EMBO J. 2019 Aug 1;38(15):e101964. doi: 10.15252/embj.2019101964. Epub 2019 Jun 28. PMID: 31267557; PMCID: PMC6669923. 2. Bourque SL, Benjamin CD, Adams MA, Nakatsu K. Lack of hemodynamic effects after extended heme synthesis inhibition by succinylacetone in rats. J Pharmacol Exp Ther. 2010 Apr;333(1):290-6. doi: 10.1124/jpet.109.162966. Epub 2010 Jan 13. PMID: 20071481.
1: Chen WS, Liu MH, Tsou YL, Wu HP, Lin HC, Liang CY, Wang CH. Extensive Dysregulation of Phenylalanine Metabolism Is Associated With Stress Hyperphenylalaninemia and 30-Day Death in Critically Ill Patients With Acute Decompensated Heart Failure. J Am Heart Assoc. 2024 Sep 17;13(18):e035821. doi: 10.1161/JAHA.124.035821. Epub 2024 Sep 11. PMID: 39258552. 2: Wang S, Lin X, Zhou Y, Yang X, Ou M, Zhang L, Wang Y, Gao J. Investigation of newborn blood metabolomics in varying intrauterine growth conditions. J Pediatr (Rio J). 2024 Aug 21:S0021-7557(24)00102-5. doi: 10.1016/j.jped.2024.07.009. Epub ahead of print. PMID: 39178913. 3: Rehsi P, Witek K, Emmett E, Carling R, Turner C, Dalton N, Hutchin T, Hadzic N, Dhawan A, Vara R. Hereditary tyrosinaemia type 1 in the absence of succinylacetone: 4-oxo 6-hydroxyhepanoate (4OHHA), a putative diagnostic biomarker. JIMD Rep. 2024 Jun 18;65(4):255-261. doi: 10.1002/jmd2.12436. PMID: 38974614; PMCID: PMC11224492. 4: Kumar BV, Kadiyala P, Ponmalar P, Pauline L, Srinivasan S. Establishment of Age Specific Reference Interval for Aminoacids and Acylcarnitine in Dried Blood Spot by Tandem Mass Spectrometry. Indian J Clin Biochem. 2024 Apr;39(2):233-240. doi: 10.1007/s12291-023-01128-1. Epub 2023 Mar 9. PMID: 38577134; PMCID: PMC10987407. 5: Gramer G, Wortmann SB, Fang-Hoffmann J, Kohlmüller D, Okun JG, Prokisch H, Meitinger T, Hoffmann GF. New Cases of Maleylacetoacetate Isomerase Deficiency with Detection by Newborn Screening and Natural History over 32 Years: Experience from a German Newborn Screening Center. Int J Neonatal Screen. 2024 Feb 27;10(1):17. doi: 10.3390/ijns10010017. PMID: 38535121; PMCID: PMC10970868. 6: Khan SA, Fakih M, Taufiq N, Ahmerin A, Bangash A, Iqbal Malik M. Clinical Spectrum of Hereditary Tyrosinemia Type 1 in a Cohort of Pakistani Children. Clin Med Insights Pediatr. 2024 Mar 6;18:11795565241236176. doi: 10.1177/11795565241236176. PMID: 38456192; PMCID: PMC10919130. 7: López-Mejía L, Guillén-Lopez S, Vela-Amieva M, Santillán-Martínez R, Abreu M, González-Herrra MD, Díaz-Martínez R, Reyes-Magaña JG. Importance of genetic sequencing studies in managing chronic neonatal diarrhea: a case report of a novel variant in the glucose-galactose transporter SLC5A1. Front Pediatr. 2024 Feb 19;12:1284671. doi: 10.3389/fped.2024.1284671. PMID: 38440183; PMCID: PMC10909829. 8: Zharmakhanova G, Kononets V, Balmagambetova S, Syrlybayeva L, Nurbaulina E, Zhussupova Z, Sakhanova S, Ayaganov D, Kim S, Zhumalina A. Selective screening for inborn errors of metabolism using tandem mass spectrometry in West Kazakhstan children: study protocol. Front Genet. 2024 Jan 12;14:1278750. doi: 10.3389/fgene.2023.1278750. PMID: 38283151; PMCID: PMC10811460. 9: Rokaitė R, Čibirkaitė A, Zeleckytė V, Lazdinytė G, Dženkaitis M. A Lithuanian Case of Tyrosinemia Type 1 with a Literature Review: A Rare Cause of Acute Liver Failure in Childhood. Medicina (Kaunas). 2024 Jan 11;60(1):135. doi: 10.3390/medicina60010135. PMID: 38256395; PMCID: PMC10820469. 10: Dijkstra AM, Evers-van Vliet K, Heiner-Fokkema MR, Bodewes FAJA, Bos DK, Zsiros J, van Aerde KJ, Koop K, van Spronsen FJ, Lubout CMA. A False-Negative Newborn Screen for Tyrosinemia Type 1-Need for Re-Evaluation of Newborn Screening with Succinylacetone. Int J Neonatal Screen. 2023 Dec 4;9(4):66. doi: 10.3390/ijns9040066. PMID: 38132825; PMCID: PMC10744279. 11: Bo T, Van Wijk K, Nakajima O. Heme Biosynthesis is Crucial for Cell Survival and Mitochondrial OXPHOS after X Irradiation. Radiat Res. 2024 Jan 1;201(1):48-54. doi: 10.1667/RADE-23-00035.1. PMID: 37988802. 12: Nauli R, Wanandi SI, Sadikin M, Antarianto RD, Jusman SWA. Inhibition of ALA dehydratase activity in heme biosynthesis reduces cytoglobin expression which is related to the proliferation and viability of keloid fibroblasts. J Clin Biochem Nutr. 2023 Nov;73(3):185-190. doi: 10.3164/jcbn.23-25. Epub 2023 Aug 9. PMID: 37970551; PMCID: PMC10636574. 13: Luo H, Wang Q, Yang F, Liu R, Gao Q, Cheng B, Lin X, Huang L, Chen C, Xiang J, Wang K, Qin B, Tang N. Signaling metabolite succinylacetone activates HIF-1α and promotes angiogenesis in GSTZ1-deficient hepatocellular carcinoma. JCI Insight. 2023 Oct 31;8(23):e164968. doi: 10.1172/jci.insight.164968. PMID: 37906252; PMCID: PMC10896004. 14: Jansen HI, van Haeringen M, Bouva MJ, den Elzen WPJ, Bruinstroop E, van der Ploeg CPB, van Trotsenburg ASP, Zwaveling-Soonawala N, Heijboer AC, Bosch AM, de Jonge R, Hoogendoorn M, Boelen A. Optimizing the Dutch newborn screening for congenital hypothyroidism by incorporating amino acids and acylcarnitines in a machine learning-based model. Eur Thyroid J. 2023 Nov 3;12(6):e230141. doi: 10.1530/ETJ-23-0141. PMID: 37855424; PMCID: PMC10692681. 15: Mori J, Furukawa T, Kodo K, Nakajima H, Yuasa M, Kubota M, Shigematsu Y. A patient with urinary succinylacetone-negative hereditary tyrosinemia type 1. Pediatr Int. 2023 Jan-Dec;65(1):e15644. doi: 10.1111/ped.15644. PMID: 37795850. 16: van Vliet K, Dijkstra AM, Bouva MJ, van der Krogt J, Bijsterveld K, van der Sluijs F, de Sain-van der Velden MG, Koop K, Rossi A, Thomas JA, Patera CA, Kiewiet MBG, Waters PJ, Cyr D; Québec NTBC Study Group; Boelen A, van Spronsen FJ, Heiner-Fokkema MR. Maleic acid is a biomarker for maleylacetoacetate isomerase deficiency; implications for newborn screening of tyrosinemia type 1. J Inherit Metab Dis. 2023 Nov;46(6):1104-1113. doi: 10.1002/jimd.12669. Epub 2023 Aug 10. PMID: 37545091. 17: Yu L, Peng Y, Jiang L, Qiu L. Sequential Diagnosis and Treatment for Colon Cancer via Derived Iridium and Indocyanine Green Hybrid Nanomicelles. ACS Appl Mater Interfaces. 2023 Jul 26;15(29):34617-34630. doi: 10.1021/acsami.3c07742. Epub 2023 Jul 12. PMID: 37437265. 18: França TCL, Muniz-Santos R, Caetano LC, Souza GHMF, Goulart HF, Assis M, Bottino A, Bassini A, Santana AEG, Prado ES, Cameron LC. A sportomics soccer investigation unveils an exercise-induced shift in tyrosine metabolism leading to hawkinsinuria. Front Nutr. 2023 Jun 13;10:1169188. doi: 10.3389/fnut.2023.1169188. PMID: 37384105; PMCID: PMC10296188. 19: Doty RT, Lausted CG, Munday AD, Yang Z, Yan X, Meng C, Tian Q, Abkowitz JL. The transcriptomic landscape of normal and ineffective erythropoiesis at single- cell resolution. Blood Adv. 2023 Sep 12;7(17):4848-4868. doi: 10.1182/bloodadvances.2023010382. PMID: 37352261; PMCID: PMC10469080. 20: Zhang Q, Zhang C, Wang Y, Wang W, Xu R, Hui L, Feng X, Wang X, Zheng L, Zhou B, Jiang Y, Hao S. [Clinical features and genetic analysis of a child with acute form of Tyrosinemia type I due to a novel variant of FAH gene]. Zhonghua Yi Xue Yi Chuan Xue Za Zhi. 2023 Feb 10;40(2):171-176. Chinese. doi: 10.3760/cma.j.cn511379-20211119-00921. PMID: 36709935.

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