Ammonium 1-pyrrolidinedithiocarbamate

Pyrrolidinedithiocarbamic acid (PDTC) is a metal chelating compound that potently and reversibly inhibits NF-κB activation in vitro (100 μM). At 300 μM, it prevents TNF-α gene expression and protein production in human monocytes after LPS application. In vascular smooth muscle cells, PDTC (10 μM) arrests the cell cycle at the G₁ phase with upregulation of p21^Cip1 through the p38 MAPK pathway. PDTC (100 μM) also has antioxidant properties.

pale yellow crystalline solid

Ammonium pyrrolidinedithiocarbamate has been used:

• to inhibit nuclear factor κB (NF-κB) mobilization and TNF (tumor necrosis factor) production in human monocytes
• to reduce neutrophil activity in rats
• to prevent Ca²⁺ influx in adriamycin (ADR)-treated podocytes

to abrogate the microRNA-146a promoter luciferase reporter activity in human brain cells

1-Pyrrolidinecarbodithioic Acid induces apoptosis in rat smooth muscle cells and inhibits apoptosis in leukemia HL-60 cells. It also prevents induction of nitric oxide synthetase by inhibiting translation of NOS mRNA;

Ammonium pyrrolidinedithiocarbamate is a nuclear factor κB (NF-κB) inhibitor. It functions as a chelating agent, which allows the preconcentration of trace metals from solution. Pyrrolidinedithiocarbamate (PDTC) has antioxidant properties. It inhibits apoptosis in lymphocytes, neurons and vascular endothelial cells.

Prevents induction of nitric oxide synthetase by inhibiting translation of NOS mRNA; induces apoptosis in rat smooth muscle cells and inhibits apoptosis in leukemia HL-60 cells.

Purify the salt by recrystallising twice by dissolving in MeOH and adding Et2O. It has also been purified by recrystallisation from EtOH. It is used for the precipitation of As, Bi, Cd, Co, Cu, Fe, Mn, Ni, Pb, Sb, Su, V and Zn from acidic solutions [Kinrade & van Loon Anal Chem 46 1894 1974]. The ethyl ester has b 87-89o/0.01mm. [Synthesis and Polarography: Kitagawa & Taku Bull Chem Soc Jpn 64 2151 1973, Malissa & Sch.ffmann Mikrochim Acta 187 1955, Beilstein 20 III/IV 195, 20/1 V 331.]

[1] R SCHRECK. Dithiocarbamates as potent inhibitors of nuclear factor kappa B activation in intact cells.[J]. Journal of Experimental Medicine, 1992, 175 5: 1181-1194. DOI: 10.1084/jem.175.5.1181
[2] H. ZIEGLER-HEITBROCK. Pyrrolidine dithiocarbamate inhibits NF-kappa B mobilization and TNF production in human monocytes.[J]. Journal of immunology, 1993, 151 12 1: 6986-6993. DOI: 10.4049/jimmunol.151.12.6986
[3] SUNG-KWON MOON. PDTC, metal chelating compound, induces G1 phase cell cycle arrest in vascular smooth muscle cells through inducing p21Cip1 expression: Involvement of p38 mitogen activated protein kinase[J]. Journal of Cellular Physiology, 2003, 198 2: 310-323. DOI: 10.1002/jcp.10728
[4] SUOWEN XU . Tanshinone II-A inhibits oxidized LDL-induced LOX-1 expression in macrophages by reducing intracellular superoxide radical generation and NF-κB activation[J]. Translational Research, 2012, 160 2: Pages 114-124. DOI: 10.1016/j.trsl.2012.01.008