Racemetyrosine

A dysfunctional and modified form of the non-essential amino acid tyrosine and an inhibitor of tyrosine hydroxylase (TH; tyrosine 3-monooxygenase), with potential antineoplastic activity. Upon administration, racemetyrosine is specifically taken up by cancer cells through the transporter L-amino acid transferase-1 (LAT1; CD98). As a tyrosine derivative and faulty amino acid protein building block, racemetyrosine prevents protein synthesis in cancer cells. Specifically, this prevents mucin-1 (MUC1) protein synthesis. MUC1 is highly overexpressed by most cancer cells and regulates the increased reactive oxygen species (ROS) in cancer cells created from the altered metabolism that cancer cells utilize, by upregulating key antioxidant defenses and preventing ROS-mediated apoptosis. In the absence of MUC1, ROS levels are increased, leading to an increase in oxidative stress, and induction of apoptosis. Also, being a protective transmembrane protein, MUC1 is part of the protective layer on the outside of cancer cells and plays a key role in shielding the cancer cell from the immune system. The loss of MUC1 compromises the cell membrane, thereby making the cancer cell more vulnerable to be recognized and attacked by the immune system. Normal cells do not regularly take up certain non-essential amino acids, such as tyrosine, but readily convert phenylalanine to tyrosine, so normal healthy cells are not expected to consume racemetyrosine. In addition, racemetyrosine competes with tyrosine at the tyrosine-binding site of TH, thereby inhibiting TH, an enzyme that activates molecular oxygen to catalyze the hydroxylation of tyrosine to dihydroxyphenylalanine (Dopa), which is an intermediate to catecholamine (dopamine, norepinephrine, and epinephrine) production. This inhibits the synthesis of catecholamines.

http://purl.obolibrary.org/obo/NCIT_C74152

620-30-4

658-48-0

C10H13NO3

C74152

CTRP

FDA

A dysfunctional and modified form of the non-essential amino acid tyrosine and an inhibitor of tyrosine hydroxylase (TH; tyrosine 3-monooxygenase), with potential antineoplastic activity. Upon administration, racemetyrosine is specifically taken up by cancer cells through the transporter L-amino acid transferase-1 (LAT1; CD98). As a tyrosine derivative and faulty amino acid protein building block, racemetyrosine prevents protein synthesis in cancer cells. Specifically, this prevents mucin-1 (MUC1) protein synthesis. MUC1 is highly overexpressed by most cancer cells and regulates the increased reactive oxygen species (ROS) in cancer cells created from the altered metabolism that cancer cells utilize, by upregulating key antioxidant defenses and preventing ROS-mediated apoptosis. In the absence of MUC1, ROS levels are increased, leading to an increase in oxidative stress, and induction of apoptosis. Also, being a protective transmembrane protein, MUC1 is part of the protective layer on the outside of cancer cells and plays a key role in shielding the cancer cell from the immune system. The loss of MUC1 compromises the cell membrane, thereby making the cancer cell more vulnerable to be recognized and attacked by the immune system. Normal cells do not regularly take up certain non-essential amino acids, such as tyrosine, but readily convert phenylalanine to tyrosine, so normal healthy cells are not expected to consume racemetyrosine. In addition, racemetyrosine competes with tyrosine at the tyrosine-binding site of TH, thereby inhibiting TH, an enzyme that activates molecular oxygen to catalyze the hydroxylation of tyrosine to dihydroxyphenylalanine (Dopa), which is an intermediate to catecholamine (dopamine, norepinephrine, and epinephrine) production. This inhibits the synthesis of catecholamines.

Racemetyrosine

X88TTO174Z

http://purl.obolibrary.org/obo/NCIT_C127896

http://purl.obolibrary.org/obo/NCIT_C63923

http://purl.obolibrary.org/obo/NCIT_C176424

http://purl.obolibrary.org/obo/NCIT_C116977

http://purl.obolibrary.org/obo/NCIT_C116978

Racemetyrosine

Racemetirosine

802001

802001

802001

Racemetyrosine

NCIT:C74152

Racemetyrosine

Pharmacologic Substance

C0949561

http://purl.obolibrary.org/obo/NCIT_C270

http://purl.obolibrary.org/obo/NCIT_C471