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AB142215

3-Deazaneplanocin A

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(1 Publication)

MW 262.26 Da, Purity >98%. Potent S-adenosylhomocysteine hydrolase (SAHH) and histone methyltransferase (HMT) inhibitor. Induces cancer cell selective apoptosis. Shows antitumor effects in vivo.

View Alternative Names

Adenosylhomocysteinase, AdoHcyase, S adenosylhomocysteine hydrolase, S-adenosyl-L-homocysteine hydrolase, SAHH_HUMAN, ahcY

1 Images
Chemical Structure - 3-Deazaneplanocin A (AB142215)
  • Chemical Structure

Lab

Chemical Structure - 3-Deazaneplanocin A (AB142215)

2D chemical structure image of ab142215, 3-Deazaneplanocin A

Key facts

CAS number

102052-95-9

Purity

>98%

Form

Solid

form

Molecular weight

262.26 Da

Molecular formula

C<sub>1</sub><sub>2</sub>H<sub>1</sub><sub>4</sub>N<sub>4</sub>O<sub>3</sub>

PubChem

73087

Nature

Synthetic

Biochemical name

3-Deazaneplanocin

Biological description

Potent S-adenosylhomocysteine hydrolase (SAHH) and histone methyltransferase (HMT) inhibitor. Induces cancer cell selective apoptosis. Shows antitumor effects in vivo.

Canonical smiles

C1=CN=C(C2=C1N(C=N2)C3C=C(C(C3O)O)CO)N

Isomeric smiles

C1=CN=C(C2=C1N(C=N2)[C@@H]3C=C([C@H]([C@H]3O)O)CO)N

InChi

InChI=1S/C12H14N4O3/c13-12-9-7(1-2-14-12)16(5-15-9)8-3-6(4-17)10(18)11(8)19/h1-3,5,8,10-11,17-19H,4H2,(H2,13,14)/t8-,10-,11+/m1/s1

InChiKey

OMKHWTRUYNAGFG-IEBDPFPHSA-N

IUPAC Name

(1S,2R,5R)-5-(4-aminoimidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol

Product details

This product is manufactured by BioVision, an Abcam company and was previously called 2060 3-Deazaneplanocin A. 2060-250 is the same size as the 250 μg size of ab142215.

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months

Supplementary information

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

S-Adenosylhomocysteine hydrolase also known as SAHH plays a critical mechanical role in cellular metabolism. It catalyzes the reversible hydrolysis of S-adenosylhomocysteine (SAH) to homocysteine and adenosine. This enzyme approximately 48 kDa in mass is ubiquitously expressed in most tissues highlighting its universal importance in biological systems. SAHH maintains the cellular methylation balance by regulating the concentrations of SAH a byproduct of methylation reactions.
Biological function summary

S-Adenosylhomocysteine hydrolase acts as an important player in the methylation processes within the cell. By breaking down SAH it ensures proper methylation of DNA proteins and lipids through the recycling of homocysteine and adenosine. SAHH operates as a homotetramer forming a complex essential for its enzymatic function. The balance maintained by SAHH in cellular methylation allows for proper gene expression and signal transduction within various cellular processes.

Pathways

S-Adenosylhomocysteine hydrolase plays an essential role in the methionine cycle and one-carbon metabolism pathways. These pathways are interconnected with the folate cycle important for nucleotide synthesis and cellular methylation. SAHH works with enzymes like methionine synthase and adenosylmethionine linking it to regulation of homocysteine levels. These interconnections are fundamental for maintaining cellular function and homeostasis.

S-Adenosylhomocysteine hydrolase dysregulation can have significant implications. Hyperhomocysteinemia a condition characterized by high levels of homocysteine in the blood often results from SAHH dysfunction leading to cardiovascular diseases. Additionally aberrant SAHH activity connects to certain types of cancer as altered methylation patterns can disrupt normal cell proliferation. The interplay of SAHH with other proteins such as methylenetetrahydrofolate reductase (MTHFR) illustrates the complex network within which this enzyme operates affecting disease outcomes.

Product protocols

Publications (1)

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

European journal of nutrition 52:127-34 PubMed22209966

2012

Plasma homocysteine level and hepatic sulfur amino acid metabolism in mice fed a high-fat diet.

Applications

Unspecified application

Species

Unspecified reactive species

Kang Uk Yun,Chang Seon Ryu,Jung Min Oh,Chung Hyun Kim,Kye Sook Lee,Chul-Ho Lee,Hyun-Sun Lee,Bong-Hee Kim,Sang Kyum Kim
View all publications

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