Aminoimidazole carboxamide
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| Category | Others |
| Catalog number | BBF-04668 |
| CAS | 360-97-4 |
| Molecular Weight | 126.1 |
| Molecular Formula | C4H6N4O |
| Purity | > 95 % by HPLC |
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Description
Aminoimidazole carboxamide is an imidazole derivative and a metabolite of antitumor drugs BIC and DIC.
Specification
| Synonyms | Aminoimidazole-4-carboxamide, 5-; 5-Aminoimidazole-4-carboxamide |
| Storage | Store at -20 ℃ |
| IUPAC Name | 4-amino-1H-imidazole-5-carboxamide |
| Canonical SMILES | C1=NC(=C(N1)C(=O)N)N |
| InChI | InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8) |
| InChI Key | DVNYTAVYBRSTGK-UHFFFAOYSA-N |
Properties
| Appearance | White to off-white crystalline powder |
| Melting Point | 164-170 ℃ (lit.) |
| Density | 1.538 g/cm3 |
| Solubility | Soluble in DMSO |
| LogP | 0.37230 |
Reference Reading
1. Aminoimidazole Carboxamide Ribotide Exerts Opposing Effects on Thiamine Synthesis in Salmonella enterica
Jannell V Bazurto, Nicholas J Heitman, Diana M Downs J Bacteriol. 2015 Sep;197(17):2821-30. doi: 10.1128/JB.00282-15. Epub 2015 Jun 22.
In Salmonella enterica, the thiamine biosynthetic intermediate 5-aminoimidazole ribotide (AIR) can be synthesized de novo independently of the early purine biosynthetic reactions. This secondary route to AIR synthesis is dependent on (i) 5-amino-4-imidazolecarboxamide ribotide (AICAR) accumulation, (ii) a functional phosphoribosylaminoimidazole-succinocarboxamide (SAICAR) synthetase (PurC; EC 6.3.2.6), and (iii) methionine and lysine in the growth medium. Studies presented here show that AICAR is a direct precursor to AIR in vivo. PurC-dependent conversion of AICAR to AIR was recreated in vitro. Physiological studies showed that exogenous nutrients (e.g., methionine and lysine) antagonize the inhibitory effects of AICAR on the ThiC reaction and decreased the cellular thiamine requirement. Finally, genetic results identified multiple loci that impacted the effect of AICAR on thiamine synthesis and implicated cellular aspartate levels in AICAR-dependent AIR synthesis. Together, the data here clarify the mechanism that allows conditional growth of a strain lacking the first five biosynthetic enzymes, and they provide additional insights into the complexity of the metabolic network and its plasticity. Importance: In bacteria, the pyrimidine moiety of thiamine is derived from aminoimidazole ribotide (AIR), an intermediate in purine biosynthesis. A previous study described conditions under which AIR synthesis is independent of purine biosynthesis. This work is an extension of that previous study and describes a new synthetic pathway to thiamine that depends on a novel thiamine precursor and a secondary activity of the biosynthetic enzyme PurC. These findings provide mechanistic details of redundancy in the synthesis of a metabolite that is essential for nucleotide and coenzyme biosynthesis. Metabolic modifications that allow the new pathway to function or enhance it are also described.
2. AICAr, a Widely Used AMPK Activator with Important AMPK-Independent Effects: A Systematic Review
Dora Višnjić, Hrvoje Lalić, Vilma Dembitz, Barbara Tomić, Tomislav Smoljo Cells. 2021 May 4;10(5):1095. doi: 10.3390/cells10051095.
5-Aminoimidazole-4-carboxamide ribonucleoside (AICAr) has been one of the most commonly used pharmacological modulators of AMPK activity. The majority of early studies on the role of AMPK, both in the physiological regulation of metabolism and in cancer pathogenesis, were based solely on the use of AICAr as an AMPK-activator. Even with more complex models of AMPK downregulation and knockout being introduced, AICAr remained a regular starting point for many studies focusing on AMPK biology. However, there is an increasing number of studies showing that numerous AICAr effects, previously attributed to AMPK activation, are in fact AMPK-independent. This review aims to give an overview of the present knowledge on AMPK-dependent and AMPK-independent effects of AICAr on metabolism, hypoxia, exercise, nucleotide synthesis, and cancer, calling for caution in the interpretation of AICAr-based studies in the context of understanding AMPK signaling pathway.
3. Case report of a rare purine synthesis disorder due to 5-aminoimidazole-4-carboxamide ribonucleotide formyltransferase (AICAR) deficiency
Praisy Joy, Vrisha Madhuri, Thomas Palocaren, Sweta Das, Suneetha Susan Cleave Abraham, Sophy Korula, Beena Koshy, John Jose, Mahalakshmi Chandran, Sumita Danda Brain Dev. 2022 Oct;44(9):645-649. doi: 10.1016/j.braindev.2022.05.004. Epub 2022 May 28.
Background: AICA (5-aminoimidazole-4-carboxamide) ribosiduria is an inborn error in purine biosynthesis caused due to biallelic pathogenic variants in the 5-aminoimidazole-4-carboxamide ribonucleotide-formyltransferase/imp cyclohydrolase (ATIC) gene located on chromosome 2q35. ATIC codes for a bifunctional enzyme, AICAR transformylase and inosine monophosphate (IMP) cyclohydrolase, which catalyse the last two steps of de novo purine synthesis. This disorder has been previously reported in only 4 cases worldwide, and herein, we report the first from India. Case report: The proband presented with global developmental delay, developmental hip dysplasia (DDH), acyanotic heart disease and nystagmoid eye movements. Whole exome sequencing (WES) identified compound heterozygous pathogenic variants in the ATIC. A novel splice site variant; c.1321-2A > G and a previously reported missense variant; c.1277A > G (p.Lys426Arg) were identified. Segregation analysis of parents showed the father to be a heterozygous carrier for the splice site variant and the mother, a heterozygous carrier for the missense variant. Conclusion: This case of a rare genetic disorder of purine biosynthesis of ATIC deficiency is the first case reported from India. Early diagnosis lead to early interventional therapy and genetic counselling.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
