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AB142744

5-Azacytidine, DNMT1 inhibitor

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(11 Publications)

MW 244.2 Da, Purity >98%. Potent DNA methyltransferase 1 (DNMT1) inhibitor (IC50 = 0.2 μM). Incorporated into DNA, inhibits DNMT1 activity to induce DNA hypomethylation. Interferes with protein synthesis. Shows anti-metabolic and anti-cancer activities in vitro. Active in vivo. At high doses the compound can have effects on other DNA methyltransferases.

View Alternative Names

ADCADN, AIM, AIS, ANDR_HUMAN, AR, AR8, ATAD5_HUMAN, ATPase family AAA domain containing 5, ATPase family AAA domain-containing protein 5, Aging-associated gene 9 protein, Androgen nuclear receptor variant 2, Androgen receptor, Androgen receptor (dihydrotestosterone receptor; testicular feminization; spinal and bulbar muscular atrophy; Kennedy disease), Apoptosis associated protein, Beta globin chain, Beta-globin, C17orf41, CD113t C, CXXC finger protein 9, CXXC-type zinc finger protein 9, CXXC9, Chromosome fragility-associated gene 1 protein, Cytosolic NADP-isocitrate dehydrogenase, DHTR, DNA (cytosine-5)-methyltransferase 1, DNA MTase, DNA MTase HsaI, DNA methyltransferase 1, DNA methyltransferase HsaI, DNA methyltransferase M.HsaI., DNMT, DNMT1_HUMAN, Dihydro testosterone receptor, Dihydrotestosterone receptor (DHTR), Dnmt1o, ELG1, ERR a, ERR-alpha, ERR1 protein, ERR1_HUMAN, ESRL 1, ESRR A, Enhanced level of genomic instability 1 homolog, Epididymis luminal protein 216, Epididymis secretory protein Li 26, Epididymis secretory sperm binding protein Li 162eP, Estrogen receptor related 1, Estrogen receptor-like 1, Estrogen-related receptor alpha, Estrra, FLJ16293, FRAG1, G3PD, G3PDH, G3P_HUMAN, GAPD, GAPDH, GCCR, GCRST, GCR_HUMAN, GR, Glucocorticoid receptor, Glyceraldehyde-3-phosphate dehydrogenase, Grl1, Growth arrest and DNA damage inducible 34, Growth arrest and DNA damage-inducible protein GADD34, HBB_HUMAN, HEL-216, HEL-S-162eP, HEL-S-26, HSN1E, HUMARA, HYSP1, Hemoglobin beta, Hemoglobin beta chain, Hemoglobin subunit beta, ICDH, IDCD, IDH, IDH1, IDHC_HUMAN, IDP, IDPC, IMD42, Isocitrate dehydrogenase (NADP(+)) 1 cytosolic, Isocitrate dehydrogenase 1 (NADP+) soluble, Isocitrate dehydrogenase [NADP] cytoplasmic, KD, Kennedy disease (KD), LVV-hemorphin-7, M.HsaI, MCMT, MGC104992, MGC129539, Met1, MommeD2, Myeloid differentiation primary response protein MyD116 homolog, NADP dependent isocitrate dehydrogenase cytosolic, NADP dependent isocitrate dehydrogenase peroxisomal, NADP(+)-specific ICDH, NF-E2-related factor 2, NF2L2_HUMAN, NR1F3, NR3B1, NR3C4, NRF2, Nfe2l2, Nuclear factor, Nuclear factor (erythroid derived 2) like 2, Nuclear factor erythroid 2-related factor 2, Nuclear factor erythroid derived 2 like 2, Nuclear receptor ROR-gamma, Nuclear receptor RZR-gamma, Nuclear receptor subfamily 1 group F member 3, Nuclear receptor subfamily 3 group B member 1, Nuclear receptor subfamily 3 group C member 1, Nuclear receptor subfamily 3 group C member 4, Nuclear receptor subfamily 3 group C member 4 (NR3C4), Oxalosuccinate decarboxylase, PICD, PR15A_HUMAN, Peptidyl-cysteine S-nitrosylase GAPDH, Ppp1r15a, Protein phosphatase 1 regulatory (inhibitor) subunit 15A, Protein phosphatase 1 regulatory subunit 15A, RAR related orphan nuclear receptor variant 2, RAR related orphan receptor C, isoform a, RAR related orphan receptor gamma, RAR-related orphan receptor C, RORG_HUMAN, RZR GAMMA, RZRG, Retinoic acid binding receptor gamma, Retinoid-related orphan receptor-gamma, Rorc, SBMA, SMAX1, Spinal and bulbar muscular atrophy, Spinal and bulbar muscular atrophy (SBMA), Steroid hormone receptor ERR1, TFM, TOR, Testicular Feminization (TFM), androgen receptor splice variant 4b, chromosome fragility associated gene 1, erythroid derived 2, estrogen receptor related receptor alpha, glucocorticoid nuclear receptor variant 1, hERR1, like 2, mMmul, nr3c1, nuclear factor erythroid 2 like 2, nuclear receptor subfamily 3, group C, member 1 (glucocorticoid receptor)

1 Images
Chemical Structure - 5-Azacytidine, DNMT1 inhibitor (AB142744)
  • Chemical Structure

Lab

Chemical Structure - 5-Azacytidine, DNMT1 inhibitor (AB142744)

2D chemical structure image of ab142744, 5-Azacytidine, DNMT1 inhibitor

Key facts

CAS number

320-67-2

Purity

>98%

Form

Solid

form

Molecular weight

244.2 Da

Molecular formula

C<sub>8</sub>H<sub>1</sub><sub>2</sub>N<sub>4</sub>O<sub>5</sub>

PubChem

9444

Nature

Synthetic

Solubility

Soluble in water to 50 mM

Soluble in DMSO to 100 mM

Biochemical name

Azacitidine

Biological description

Potent DNA methyltransferase 1 (DNMT1) inhibitor (IC50 = 0.2 μM). Incorporated into DNA, inhibits DNMT1 activity to induce DNA hypomethylation. Interferes with protein synthesis. Shows anti-metabolic and anti-cancer activities in vitro. Active in vivo. At high doses the compound can have effects on other DNA methyltransferases.

Canonical smiles

C1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N

Isomeric smiles

C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N

InChi

InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1

InChiKey

NMUSYJAQQFHJEW-KVTDHHQDSA-N

IUPAC Name

4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
Ambient
Appropriate long-term storage conditions
Ambient
Storage information
The product can be stored for up to 12 months

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

GAPDH also known as Glyceraldehyde-3-phosphate dehydrogenase is a multifunctional enzyme with a mass of approximately 36 kDa. It is widely expressed across various tissues where it primarily participates in glycolysis by catalyzing the sixth step converting glyceraldehyde-3-phosphate to 13-bisphosphoglycerate. The Glucocorticoid Receptor also called NR3C1 is a nuclear receptor involved in gene expression regulation and is predominantly found in the cytoplasm before ligand binding. GADD34 a growth arrest and DNA damage-inducible protein plays a role in stress responses. DNA methyltransferase 1 (Dnmt1) is important for maintenance methylation; it has a structural mass around 183 kDa and is expressed mainly in proliferating cells. Atad5 is involved in DNA replication while LVV hemorphin 7 a peptide appears in extracellular spaces. The Androgen Receptor and Estrogen Related Receptor alpha are nuclear receptors that bind to androgens and estrogen respectively. ROR gamma and Nrf2 are transcription factors where Nrf2 acts as a cellular defense regulator while IDH1 is an enzyme involved in the citric acid cycle.
Biological function summary

Several of these proteins participate in various essential processes. GAPDH is known for its central role in metabolism but also engages in cellular processes like apoptosis and gene expression. The Glucocorticoid and Androgen Receptors as part of the nuclear receptor family regulate genes that control development metabolism and immune response. Dnmt1 maintains DNA methylation patterns across cell divisions influenced by inhibitors such as 5-azacytidine widely studied for cancer treatments. Estrogen Related Receptor alpha although not directly binding estrogen influences metabolic pathways. ROR gamma impacts immune system function whereas Nrf2 orchestrates the antioxidative response by regulating genes involved in redox homeostasis.

Pathways

GAPDH integrates into the glycolytic pathway influencing energy yield and apoptosis through interactions with Bcl-2 dependent networks. The Glucocorticoid Receptor integrates into the inflammatory signaling pathways modulating responses to external stimuli and stress. Dnmt1 is critical in the epigenetic pathway particularly in DNA methylation wherein it recruits other proteins to maintain genomic DNA methylation status. Nrf2 participates in the oxidative stress response pathway working alongside proteins like Keap1 in cellular defense. IDH1 is an important component of the tricarboxylic acid (TCA) cycle linking to metabolic enzymes influencing bioenergetics and macromolecule synthesis.

Dnmt1 plays a significant role in cancer impacting tumorigenic processes through DNA methylation changes sometimes targeted by demethylating agents like 5-azacytidine. Aberrant Dnmt1 activity can connect to oncogenes and tumor suppressors like p53. The Glucocorticoid Receptor has implications in inflammatory diseases and disorders including rheumatoid arthritis and asthma due to its regulatory function on inflammation and immune response. Nrf2's dysfunction is associated with neurodegenerative diseases due to oxidative stress connecting it to antioxidant response elements. IDH1 mutations significantly feature in gliomas and acute myeloid leukemia contributing to oncogenic metabolism alteration.

Product protocols

Publications (11)

Recent publications for all applications. Explore the full list and refine your search

Heliyon 10:e32553 PubMed39183840

2024

Effects of EZH2 inhibitor, trichostatin A, and 5-azacytidine combinatorial treatment on osteogenic differentiation of dental pulp stem cells.

Applications

Unspecified application

Species

Unspecified reactive species

Edit Hrubi,László Imre,Csaba Hegedüs

Genome biology 25:204 PubMed39090757

2024

Annelid methylomes reveal ancestral developmental and aging-associated epigenetic erosion across Bilateria.

Applications

Unspecified application

Species

Unspecified reactive species

Kero Guynes,Luke A Sarre,Allan M Carrillo-Baltodano,Billie E Davies,Lan Xu,Yan Liang,Francisco M Martín-Zamora,Paul J Hurd,Alex de Mendoza,José M Martín-Durán

Cell reports 42:112380 PubMed37061916

2023

Transient suppression of SUMOylation in embryonic stem cells generates embryo-like structures.

Applications

Unspecified application

Species

Unspecified reactive species

Jack-Christophe Cossec,Tatiana Traboulsi,Sébastien Sart,Yann Loe-Mie,Manuel Guthmann,Ivo A Hendriks,Ilan Theurillat,Michael L Nielsen,Maria-Elena Torres-Padilla,Charles N Baroud,Anne Dejean

Iranian journal of immunology : IJI 20:45-56 PubMed36932919

2023

Methyl-cpg-binding Domain Protein 2 Silencing Inhibits Th17 Differentiation of CD4+T cells Induced by Ovalbumin.

Applications

Unspecified application

Species

Unspecified reactive species

Yan Jiang,Linqiao Li,Qilu Pan,Xiaojing Du,Qian Han,Feixiang Ling,Rou Li,Lin Mai,Jianwei Huang,Shuyuan Chu,Libing Ma

Nature communications 14:1221 PubMed36869047

2023

ARF suppression by MYC but not MYCN confers increased malignancy of aggressive pediatric brain tumors.

Applications

Unspecified application

Species

Unspecified reactive species

Oliver J Mainwaring,Holger Weishaupt,Miao Zhao,Gabriela Rosén,Anna Borgenvik,Laura Breinschmid,Annemieke D Verbaan,Stacey Richardson,Dean Thompson,Steven C Clifford,Rebecca M Hill,Karl Annusver,Anders Sundström,Karl O Holmberg,Maria Kasper,Sonja Hutter,Fredrik J Swartling

Nature communications 13:1972 PubMed35418126

2022

Presenilin 2 N141I mutation induces hyperactive immune response through the epigenetic repression of REV-ERBα.

Applications

Unspecified application

Species

Unspecified reactive species

Hyeri Nam,Younghwan Lee,Boil Kim,Ji-Won Lee,Seohyeon Hwang,Hyun-Kyu An,Kyung Min Chung,Youngjin Park,Jihyun Hong,Kyungjin Kim,Eun-Kyoung Kim,Han Kyoung Choe,Seong-Woon Yu

International journal of molecular sciences 21: PubMed33322837

2020

The Reprimo-Like Gene Is an Epigenetic-Mediated Tumor Suppressor and a Candidate Biomarker for the Non-Invasive Detection of Gastric Cancer.

Applications

Unspecified application

Species

Unspecified reactive species

María Alejandra Alarcón,Wilda Olivares,Miguel Córdova-Delgado,Matías Muñoz-Medel,Tomas de Mayo,Gonzalo Carrasco-Aviño,Ignacio Wichmann,Natalia Landeros,Julio Amigo,Enrique Norero,Franz Villarroel-Espíndola,Arnoldo Riquelme,Marcelo Garrido,Gareth I Owen,Alejandro H Corvalán

RNA biology 18:237-247 PubMed32286153

2020

LARP1 isoform expression in human cancer cell lines.

Applications

Unspecified application

Species

Unspecified reactive species

Hagen Schwenzer,Mai Abdel Mouti,Pia Neubert,Josephine Morris,Joanne Stockton,Sarah Bonham,Martin Fellermeyer,James Chettle,Roman Fischer,Andrew D Beggs,Sarah P Blagden

Cancer management and research 11:9517-9528 PubMed31807076

2019

5-Aza-CdR Regulates RASSF1A By Inhibiting DNMT1 To Affect Colon Cancer Cell Proliferation, Migration And Apoptosis.

Applications

Unspecified application

Species

Unspecified reactive species

Jinyuan Chen,Lixiang Wu,Hong Xu,Shubang Cheng

BMC cancer 18:127 PubMed29394925

2018

Nc886 is epigenetically repressed in prostate cancer and acts as a tumor suppressor through the inhibition of cell growth.

Applications

Unspecified application

Species

Unspecified reactive species

Rafael Sebastián Fort,Cecilia Mathó,Murilo Vieira Geraldo,María Carolina Ottati,Alex Shimura Yamashita,Kelly Cristina Saito,Katia Ramos Moreira Leite,Manuel Méndez,Noemí Maedo,Laura Méndez,Beatriz Garat,Edna Teruko Kimura,José Roberto Sotelo-Silveira,María Ana Duhagon
View all publications

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