AICAR | CAS# 3031-94-5 | Antineoplastic

MedKoo Cat#: 573592 | Name: AICAR

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Description:

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

AICAR, also known as AICA riboside, is a purine precursor with antineoplastic activity. It is important in treatment of metabolic diseases such as type 2 diabetes as well as possible treatment of various cancer types.

Chemical Structure

AICAR

CAS#3031-94-5 (free base)

Theoretical Analysis

MedKoo Cat#: 573592

Name: AICAR

CAS#: 3031-94-5 (free base)

Chemical Formula: C9H15N4O8P

Exact Mass: 338.0627

Molecular Weight: 338.21

Elemental Analysis: C, 31.96; H, 4.47; N, 16.57; O, 37.84; P, 9.16

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks

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Related CAS #

3031-94-5 (free base) 681006-28-0 (phosphate)

Synonym

AICA-Ribotide; AICA-Riboside-5'-phosphate; 5-Aminoimidazole-4-Carboxamide Ribonucelotide; NSC 283955; NSC283955; NSC-283955; NSC 29222; NSC29222; NSC-29222

IUPAC/Chemical Name

1H-Imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)- (9CI)

InChi Key

NOTGFIUVDGNKRI-UUOKFMHZSA-N

InChi Code

1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1

SMILES Code

c1nc(c(n1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)N)C(=O)N

Appearance

Solid powder

Purity

>93% (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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

An AMPK activator.

In vitro activity:

Western blot analysis showed an increased level of Nanog in R1/E treated with 1 mM AICAR or 2 mM metformin in the absence of LIF with fold changes of 8 and 5, respectively (Figure 3A). Subsequent experiments using confocal microscopy immunofluorescence analyses were performed in R1/E stem cells treated with 1 mM AICAR for 120 h in the presence and absence of LIF (Figure 3B). Results show Nanog marker expression in treated cells with AICAR and LIF compared to AICAR untreated cells in the presence of LIF. In the absence of LIF, a stronger increment of Nanog marker expression was observed in treated cells with AICAR. Similar results were detected in Oct3/4 protein expression by western blot analysis (Figure 3C), reinforcing the role of AICAR in pluripotency. Reference: ACS Omega. 2020 Aug 18; 5(32): 20270–20282. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7439381/

In vivo activity:

AICAR treatment in hypoxic mice prevented more than half of the fetal growth reduction (p < 0.05), with hypoxic + AICAR mice being only 16% smaller than normoxic + VEH mice. Neither AICAR nor ComC treatment had any effect on fetal weight in normoxic mice, and ComC had no effect on fetal weight in hypoxic mice. In VEH mice, placental weight was increased with hypoxia compared to normoxia (Fig. 1, p < 0.05), an effect that was prevented with AICAR treatment (p < 0.05). In normoxic mice, ComC increased placental weight (p < 0.05) but AICAR had no effect. ComC had no effect on placental weight in hypoxic mice. Together, these changes resulted in reduced placental efficiency, as calculated by the ratio of fetal to placental weights, in hypoxic compared to normoxic VEH mice (Fig. 1, p < 0.001). AICAR treatment in hypoxic mice improved placental efficiency compared to VEH (p < 0.05), thus restoring values to those seen in VEH animals under conditions of normoxia. Neither litter size nor resorption number were altered by hypoxia or drug treatment (data not shown). Reference: J Physiol. 2020 Sep;598(18):4093-4105. https://pubmed.ncbi.nlm.nih.gov/32592403/

	Solvent	mg/mL	mM	comments
Solubility
	PBS (pH 7.2)	1.0	2.96

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 338.21 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.

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. Alba G, Martínez R, Postigo-Corrales F, López S, Santa-María C, Jiménez J, Cahuana GM, Soria B, Bedoya FJ, Tejedo JR. AICAR Stimulates the Pluripotency Transcriptional Complex in Embryonic Stem Cells Mediated by PI3K, GSK3β, and β-Catenin. ACS Omega. 2020 Aug 4;5(32):20270-20282. doi: 10.1021/acsomega.0c02137. PMID: 32832780; PMCID: PMC7439381. 2. Guo XH, Lai XJ, Cai XL, Peng Y, Wu FH, Yin MZ, Li Y, Zhang JL, Zhao G. AICAR-induced activation of AMPK inhibits the migration of TSCC cells by targeting ZO-1. Oral Dis. 2020 Jan;26(1):228-233. doi: 10.1111/odi.13212. Epub 2019 Nov 19. PMID: 31604003. 3. Ahmad I, Molyvdas A, Jian MY, Zhou T, Traylor AM, Cui H, Liu G, Song W, Agarwal A, Jilling T, Aggarwal S, Matalon S. AICAR decreases acute lung injury by phosphorylating AMPK and upregulating heme oxygenase-1. Eur Respir J. 2021 May 28:2003694. doi: 10.1183/13993003.03694-2020. Epub ahead of print. PMID: 34049949. 4. Lane SL, Houck JA, Doyle AS, Bales ES, Lorca RA, Julian CG, Moore LG. AMP-activated protein kinase activator AICAR attenuates hypoxia-induced murine fetal growth restriction in part by improving uterine artery blood flow. J Physiol. 2020 Sep;598(18):4093-4105. doi: 10.1113/JP279341. Epub 2020 Jul 6. PMID: 32592403; PMCID: PMC7749723.

In vitro protocol:

In vivo protocol:

1. Ahmad I, Molyvdas A, Jian MY, Zhou T, Traylor AM, Cui H, Liu G, Song W, Agarwal A, Jilling T, Aggarwal S, Matalon S. AICAR decreases acute lung injury by phosphorylating AMPK and upregulating heme oxygenase-1. Eur Respir J. 2021 May 28:2003694. doi: 10.1183/13993003.03694-2020. Epub ahead of print. PMID: 34049949. 2. Lane SL, Houck JA, Doyle AS, Bales ES, Lorca RA, Julian CG, Moore LG. AMP-activated protein kinase activator AICAR attenuates hypoxia-induced murine fetal growth restriction in part by improving uterine artery blood flow. J Physiol. 2020 Sep;598(18):4093-4105. doi: 10.1113/JP279341. Epub 2020 Jul 6. PMID: 32592403; PMCID: PMC7749723.

1: Višnjić D, Lalić H, Dembitz V, Tomić B, Smoljo T. AICAr, a Widely Used AMPK Activator with Important AMPK-Independent Effects: A Systematic Review. Cells. 2021 May 4;10(5):1095. doi: 10.3390/cells10051095. PMID: 34064363; PMCID: PMC8147799. 2: Hinkle JS, Rivera CN, Vaughan RA. AICAR stimulates mitochondrial biogenesis and BCAA catabolic enzyme expression in C2C12 myotubes. Biochimie. 2022 Apr;195:77-85. doi: 10.1016/j.biochi.2021.11.004. Epub 2021 Nov 16. PMID: 34798200. 3: Wu Y, Duan X, Gao Z, Yang N, Xue F. AICAR attenuates postoperative abdominal adhesion formation by inhibiting oxidative stress and promoting mesothelial cell repair. PLoS One. 2022 Sep 1;17(9):e0272928. doi: 10.1371/journal.pone.0272928. PMID: 36048820; PMCID: PMC9436141. 4: Tukhovskaya EA, Shaykhutdinova ER, Pakhomova IA, Slashcheva GA, Goryacheva NA, Sadovnikova ES, Rasskazova EA, Kazakov VA, Dyachenko IA, Frolova AA, Brovkin AN, Kaluzhsky VE, Beburov MY, Murashev AN. AICAR Improves Outcomes of Metabolic Syndrome and Type 2 Diabetes Induced by High-Fat Diet in C57Bl/6 Male Mice. Int J Mol Sci. 2022 Dec 11;23(24):15719. doi: 10.3390/ijms232415719. PMID: 36555360; PMCID: PMC9778872. 5: Pyla R, Hartney TJ, Segar L. AICAR promotes endothelium-independent vasorelaxation by activating AMP-activated protein kinase via increased ZMP and decreased ATP/ADP ratio in aortic smooth muscle. J Basic Clin Physiol Pharmacol. 2022 May 4;33(6):759-768. doi: 10.1515/jbcpp-2021-0308. PMID: 35503763; PMCID: PMC9664587. 6: Sobolevsky T, Piper T, Ahrens B, Thevis M. AICAr to SAICAr ratio can serve as additional marker of AICAr use. Drug Test Anal. 2022 Nov;14(11-12):2017-2025. doi: 10.1002/dta.3399. Epub 2022 Nov 16. PMID: 36342242. 7: Torres RJ, Puig JG. Aicar effect in early neuronal development. Nucleosides Nucleotides Nucleic Acids. 2018;37(5):261-272. doi: 10.1080/15257770.2018.1453073. Epub 2018 Apr 10. PMID: 29634397. 8: Liu J, Liang L, Li X, Peng YL, Zhang J, Wang XL, Liu J, Nie L. AICAR suppresses cell proliferation and synergizes with decitabine in myelodysplastic syndrome via DNA damage induction. Biotechnol Lett. 2021 Jun;43(6):1131-1142. doi: 10.1007/s10529-021-03112-2. Epub 2021 Mar 31. PMID: 33788127. 9: Khorraminejad-Shirazi M, Sani M, Talaei-Khozani T, Dorvash M, Mirzaei M, Faghihi MA, Monabati A, Attar A. AICAR and nicotinamide treatment synergistically augment the proliferation and attenuate senescence-associated changes in mesenchymal stromal cells. Stem Cell Res Ther. 2020 Feb 3;11(1):45. doi: 10.1186/s13287-020-1565-6. PMID: 32014016; PMCID: PMC6998366. 10: Yan S, Yuan D, Li Q, Li S, Zhang F. AICAR enhances the cytotoxicity of PFKFB3 inhibitor in an AMPK signaling-independent manner in colorectal cancer cells. Med Oncol. 2021 Nov 10;39(1):10. doi: 10.1007/s12032-021-01601-y. PMID: 34761330. 11: Tsai WL, Hsu CN, Tain YL. Whether AICAR in Pregnancy or Lactation Prevents Hypertension Programmed by High Saturated Fat Diet: A Pilot Study. Nutrients. 2020 Feb 11;12(2):448. doi: 10.3390/nu12020448. PMID: 32053935; PMCID: PMC7071394. 12: Guo F, Liu SQ, Gao XH, Zhang LY. AICAR induces AMPK-independent programmed necrosis in prostate cancer cells. Biochem Biophys Res Commun. 2016 May 27;474(2):277-283. doi: 10.1016/j.bbrc.2016.04.077. Epub 2016 Apr 18. PMID: 27103440. 13: Nie J, Liu A, Tan Q, Zhao K, Hu K, Li Y, Yan B, Zhou L. AICAR activates ER stress-dependent apoptosis in gallbladder cancer cells. Biochem Biophys Res Commun. 2017 Jan 8;482(2):246-252. doi: 10.1016/j.bbrc.2016.11.050. Epub 2016 Nov 12. PMID: 27847321. 14: Kim YK, Hong HK, Yoo HS, Park SP, Park KH. AICAR upregulates ABCA1/ABCG1 expression in the retinal pigment epithelium and reduces Bruch's membrane lipid deposit in ApoE deficient mice. Exp Eye Res. 2021 Dec;213:108854. doi: 10.1016/j.exer.2021.108854. Epub 2021 Nov 19. PMID: 34808137. 15: Morishita M, Kawamoto T, Hara H, Onishi Y, Ueha T, Minoda M, Katayama E, Takemori T, Fukase N, Kurosaka M, Kuroda R, Akisue T. AICAR induces mitochondrial apoptosis in human osteosarcoma cells through an AMPK-dependent pathway. Int J Oncol. 2017 Jan;50(1):23-30. doi: 10.3892/ijo.2016.3775. Epub 2016 Nov 21. PMID: 27878239; PMCID: PMC5182012. 16: Tsogbadrakh B, Ryu H, Ju KD, Lee J, Yun S, Yu KS, Kim HJ, Ahn C, Oh KH. AICAR, an AMPK activator, protects against cisplatin-induced acute kidney injury through the JAK/STAT/SOCS pathway. Biochem Biophys Res Commun. 2019 Feb 12;509(3):680-686. doi: 10.1016/j.bbrc.2018.12.159. Epub 2019 Jan 4. PMID: 30616891. 17: Pokrywka A, Cholbinski P, Kaliszewski P, Kowalczyk K, Konczak D, Zembron- Lacny A. Metabolic modulators of the exercise response: doping control analysis of an agonist of the peroxisome proliferator-activated receptor δ (GW501516) and 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR). J Physiol Pharmacol. 2014 Aug;65(4):469-76. PMID: 25179079. 18: Jiang L, Liu T, Xie L, Ouyang C, Ji J, Huang T. AICAR prolongs corneal allograft survival via the AMPK-mTOR signaling pathway in mice. Biomed Pharmacother. 2019 May;113:108558. doi: 10.1016/j.biopha.2019.01.019. Epub 2019 Mar 8. PMID: 30856534. 19: Hashempour S, Shahabadi N, Adewoye A, Murphy B, Rouse C, Salvatore BA, Stratton C, Mahdavian E. Binding Studies of AICAR and Human Serum Albumin by Spectroscopic, Theoretical, and Computational Methodologies. Molecules. 2020 Nov 19;25(22):5410. doi: 10.3390/molecules25225410. PMID: 33228044; PMCID: PMC7699360. 20: Zhu XY, Liu W, Liang HT, Tang L, Zou P, You Y, Zhu XJ. AICAR and Decitabine Enhance the Sensitivity of K562 Cells to Imatinib by Promoting Mitochondrial Activity. Curr Med Sci. 2020 Oct;40(5):871-878. doi: 10.1007/s11596-020-2266-1. Epub 2020 Oct 29. PMID: 33123902.