TPEN

TPEN
Names
Preferred IUPAC name
N1,N1,N2,N2-Tetrakis[(pyridin-2-yl)methyl]ethane-1,2-diamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.110.079 Edit this at Wikidata
EC Number
  • 605-520-7
UNII
  • InChI=1S/C26H28N6/c1-5-13-27-23(9-1)19-31(20-24-10-2-6-14-28-24)17-18-32(21-25-11-3-7-15-29-25)22-26-12-4-8-16-30-26/h1-16H,17-22H2
    Key: CVRXLMUYFMERMJ-UHFFFAOYSA-N
  • c1ccc(nc1)CN(CCN(Cc1ccccn1)Cc1ccccn1)Cc1ccccn1
Properties
C26H28N6
Molar mass 424.552 g·mol−1
Appearance Crystalline solid[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

TPEN (N,N,N′,N′-tetrakis(2-pyridinylmethyl)-1,2-ethanediamine[1]) is an intracellular membrane-permeable ion chelator.[2] TPEN has a high affinity for many transition metals and should not be considered specific or selective for a particular ion. Chelators can be used in chelation therapy to remove toxic metals in the body. TPEN is a chelator that has a high affinity for zinc. For example, one study showed that TPEN is a stronger chelator compared to other chelators like pentetic acid (DTPA) when high levels of zinc are present (15 μM). When low levels of zinc were present however (0, 3, 6, 9 and 12 μM zinc), there was no significant difference.[2] TPEN is a hexadentate ligand which also forms complexes with other soft metal ions such as Cd2+.[3]

  1. ^ a b "TPEN (CAS 16858-02-9)". www.caymanchem.com.
  2. ^ a b Cho, Young-Eun; Lomeda, Ria-Ann R.; Ryu, Sang-Hoon; Lee, Jong-Hwa; Beattie, John H.; Kwun, In-Sook (25 May 2007). "Cellular Zn depletion by metal ion chelators (TPEN, DTPA and chelex resin) and its application to osteoblastic MC3T3-E1 cells". Nutrition Research and Practice. 1 (1): 29–35. doi:10.4162/nrp.2007.1.1.29. PMC 2882573. PMID 20535382.
  3. ^ Takeshita, Kenji; Ishida, Masaru; Kondo, Misako; Nakano, Yoshio; Seida, Yoshimi (2004). "Recovery of Noble Metals by Hexadentate Ligand TPEN and Acidic Extractant D2EHPA". Asian Pacific Confederation of Chemical Engineering Congress Program and Abstracts. 2004: 238. doi:10.11491/apcche.2004.0.238.0.