protein tyrosine kinase

Protein tyrosine kinase inhibitor PTK is a group of enzymes, which catalyze the phosphate group in the ATP to be transferred to the many important tyrosine residues in the protein, resulting in residues phosphorylation, thereby activating various substrates enzymes, affecting the growth, proliferation and differentiation of cells through a series of reactions. So far, it has been proved that many PTK inhibitors have anti-cancer activity, and some can induce differentiation of leukemia cells; the combination of PTK inhibitors with other anti-cancer drugs in the treatment of cancer has also achieved some encouraging results.

(1) Receptor tyrosine kinase (RTK) is a large and important class of cell surface receptor family. All RTK is composed of three parts:
(1) containing the extracellular domain of the ligand binding site,
(2) single-transmembrane hydrophobic α helix region,
(3) intracellular domain containing the tyrosine kinase activity. It has been found of more than 50 different RTK and can be divided into six subfamilies according to the structure (Figure 32-15). Its extracellular ligand is a soluble or membrane bound polypeptide or protein hormones, including insulin and various growth factors, mainly including epidermal growth factor (EGF), platelet-derived growth factor (PDGF), macrophage colony stimulating factor ( M-CSF), insulin, insulin-like growth factor -1 (IGF-1), hepatocyte growth factor (HGF), nerve growth factor (NGF) and vascular endothelial growth factor (VEGF) and so on.

(2) The activation of the receptor tyrosine kinase is a very complex process. First it need to have the ligand-mediated dimerization, leading to the formation of homologous or heterogonous dimer through dimerization, thus achieving the phosphorylation of the tyrosine of the intracellular region of the receptor of each other inside the dimer, namely, the achievement of auto-phosphorylation of the receptor. It has been now found, the ligand-mediated receptor dimerization (oligomerization) is the universal mechanism of activating single-transmembrane enzymes coupled receptor. For different types of ligands, the specific mechanism may be slightly different: some ligands are dimer themselves (e.g., PDGF, etc.), which contain the surface of the two binding receptors, allowing the cross-link of the two receptors together; some ligand is monomer type (e.g. hGH), but their surfaces have two different sites that can be contacted with two receptor molecules to form a 1: 2 ratio of ligand - receptor complex. Furthermore, fibroblast growth factor itself is a monomer, and can’t induce the dimerization of the receptor, requiring forming multivalent complex with heparin sulfate proteoglycan, thereby combining the two or more receptors.

(3) Imatinib mesylate belongs to a new type of tyrosine kinase inhibitor, belonging to the derivatives of 2-phenylaminopyrimidine. About 95% of chronic myelogenous leukemia (CML) patients had Ph1 chromosome-positive, namely the proto-oncogene ABL in the chromosome 9 undergoes ectopia into the part of the chromosome 22 called the breakpoint cluster region (BCR) that is a oncogene; the two kinds of genes get recombination together, producing a fusion protein p-210, compared with the normal C-ABL protein p-150, p-210 has high tyrosine kinase activity, being able to stimulate the proliferation of white blood cells, leading to leukemia. The drug can strongly inhibit the activity of ABL tyrosine kinase activity both in vivo and in vitro, specifically inhibiting the expression of ABL as well as the proliferation of the BCR-ABL cells, thereby can be used for the treatment of CML. In addition, the drug is capable of inhibiting the tyrosine kinase of the platelet-derived growth factor (PDGF) and stem cell factor (SCF) receptor, and can inhibit the PDGF and SCF-mediated biochemical reactions, but does not affect the signaling transduction of other stimulating factors such as epidermal growth factor.

(4) Tyrosine kinase receptor pathways: tyrosine kinase receptor pathway is one of the most important networks in the intracellular signaling pathways. The signals of most growth factors exert the regulatory function through this signaling pathway. Growth factor receptors have tyrosine kinase activity themselves, or alternatively play a role through binding to intra-membrane tyrosine protein kinases. Protein tyrosine kinases consists of four main components: the part located outside the cell is the ligand recognition and binding site, followed by a part of transmembrane structure and the intracellular part is the catalytic region of the tyrosine protein kinase; the adjustment portion is located at the carboxyl terminus of the peptide tail. When the agonist binds to the extracellular membrane recognition site, the intra-membrane tyrosine protein kinase will be activated, subject to auto-phosphorylation, and then change the action of the effector. Various kinds of structural changes with some of them being the mutations in a very small number of amino acid residues of the key region can lead to emergence of the oncogene of tyrosine kinase class which has been loss of control.

(5) Receptor tyrosine protein kinase: tyrosine protein kinase (TPK) exerts its function through making the tyrosine residues of the substrate protein subject to phosphorylation. It includes the receptor type and non-receptor type.
This class of receptor has the protein tyrosine kinase activity itself with their ligands being mostly multi-cell growth factor such as platelet-derived growth factor (PDGF), vascular endothelial growth factor (EGF) and fibroblast growth factor (FGF) and so on. After the binding of ligand to the receptor, through itself and the phosphorylation of the tyrosine residues of the substrate protein and thus triggered enzymatic cascades, the ligand-receptor can regulate cell growth, differentiation and metabolism.
Such receptor molecules can be divided into three structural regions, namely, the extracellular ligand binding domain, intracellular tyrosine kinase active region as well as the transmembrane regions connecting the above two structure domains. Such receptor not only has tyrosine protein kinase activity but also contains the phosphorylation site of tyrosine residue itself, meaning that it can be subject to tyrosine phosphorylation itself. When the ligand binds to the receptor, the receptor can undergo dimerization, activating the tyrosine kinase activity of the receptor as well as making their tyrosine residues subject to phosphorylation. Moreover, the tyrosine auto-phosphorylation can cause its conformational change and make it become the recognition sites of the tyrosine kinase substrates to be recognized by downstream signaling molecules, thus promoting the signal transmission and amplification through cascade phosphorylation reactions.

(6) Receptor of the protein tyrosine kinases: This class of receptor doesn’t have tyrosine kinase activity itself, but its cytoplasmic region contains the tyrosine kinase activity site, when the receptor binds with the ligand, being able to bind to and activate the JAK protein-tyrosine kinases, thus initiating the intracellular signal transduction.

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Structure Chemical Name CAS MF
AZD-9291 AZD-9291 1421373-65-0 C28H33N7O2
Lenvatinib Lenvatinib 417716-92-8 C21H19ClN4O4
Dacomitinib (PF299804) Dacomitinib (PF299804) 1110813-31-4 C24H25ClFN5O2
Masitinib Masitinib 790299-79-5 C28H30N6OS
Unii-33Y9anm545 Unii-33Y9anm545 635702-64-6 C21H24ClN7O2S
Linifanib (ABT-869) Linifanib (ABT-869) 796967-16-3 C21H18FN5O
Palbociclib Palbociclib 571190-30-2 C24H29N7O2
Cabozantinib Cabozantinib 849217-68-1 C28H24FN3O5
PELITINIB PELITINIB 257933-82-7 C24H23ClFN5O2
Tivozanib Tivozanib 475108-18-0 C22H19ClN4O5
Ceritinib (LDK378) Ceritinib (LDK378) 1032900-25-6 C28H36ClN5O3S
SU 11274 SU 11274 658084-23-2 C28H30ClN5O4S
Orantinib (SU6668) Orantinib (SU6668) 252916-29-3 C18H18N2O3
WZ4002 WZ4002 1213269-23-8 C25H27ClN6O3
Linsitinib Linsitinib 867160-71-2 C26H23N5O
Alectinib Alectinib 1256580-46-7 C30H34N4O2
BIBW2992 DiMaleate BIBW2992 DiMaleate 850140-73-7 C28H29ClFN5O7
CO-1686 CO-1686 1374640-70-6 C27H28F3N7O3
J&J Ex-61 J&J Ex-61 943540-75-8 C19H13F2N7
NVP-TAE684 NVP-TAE684 761439-42-3 C30H40ClN7O3S
N-(1,3-Benzodioxol-5-ylmethyl)-4-benzofuro[3,2-d]pyrimidin-4-yl-1-piperazinecarbothioamide N-(1,3-Benzodioxol-5-ylmethyl)-4-benzofuro[3,2-d]pyrimidin-4-yl-1-piperazinecarbothioamide 850879-09-3 C23H21N5O3S
Foretinib (GSK1363089) Foretinib (GSK1363089) 849217-64-7 C34H34F2N4O6
BMS-754807 BMS-754807 1001350-96-4 C23H24FN9O
AEE788 AEE788 497839-62-0 C27H32N6
Crenolanib Crenolanib 670220-88-9 C26H29N5O2
AVL-292 AVL-292 1202757-89-8 C22H22FN5O3
AC480 (BMS-599626) AC480 (BMS-599626) 714971-09-2 C27H27FN8O3
AMG-706 AMG-706 857876-30-3 C22H29N5O9P2
Golvatinib (E7050) Golvatinib (E7050) 928037-13-2 C33H37F2N7O4
LY 2874455 LY 2874455 1254473-64-7 C21H19Cl2N5O2
AP26113 AP26113 1197958-12-5 C26H34ClN6O2P
GW441756 GW441756 504433-23-2 C17H13N3O
2-(2-ETHYL-2,3-DIHYDRO-2-BENZOFURANYL)-1H-IMIDAZOLE 2-(2-ETHYL-2,3-DIHYDRO-2-BENZOFURANYL)-1H-IMIDAZOLE 189224-48-4 C13H14N2O
Vatalanib Dihydrochloride Vatalanib Dihydrochloride 212141-51-0 C20H17Cl3N4
WZ8040 WZ8040 1214265-57-2 C24H25ClN6OS
Insulin-like Growth Factor-1 Receptor Inhibitor Insulin-like Growth Factor-1 Receptor Inhibitor 468740-43-4 C25H26ClN5O3
Momelotinib Momelotinib 1056634-68-4 C23H22N6O2
AZD8931 AZD8931 848942-61-0 C23H25ClFN5O3
5-(3-Benzyloxyphenyl)-7-[trans-3-[(pyrrolidin-1-yl)methyl]cyclobutyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 5-(3-Benzyloxyphenyl)-7-[trans-3-[(pyrrolidin-1-yl)methyl]cyclobutyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 475488-23-4 C28H31N5O
Cabozantinib Malate Cabozantinib Malate 1140909-48-3 C32H30FN3O10
OSI-420 OSI-420 183320-51-6 C21H22ClN3O4
4-Benzyl-2-(naphthalen-1-yl)-[1,2,4]thiadiazolidine-3,5-dione 4-Benzyl-2-(naphthalen-1-yl)-[1,2,4]thiadiazolidine-3,5-dione 865854-05-3 C19H14N2O2S
XL518 XL518 934660-93-2 C21H21F3IN3O2
ALK/IGF1R inhibitor ALK/IGF1R inhibitor 1356962-20-3 C24H25ClN6O
SGX-523 SGX-523 1022150-57-7 C18H13N7S
1-Cyclopentyl-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 1-Cyclopentyl-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 1092788-83-4 C17H17N7
AG 1478 HYDROCHLORIDE AG 1478 HYDROCHLORIDE 153436-53-4 C16H14ClN3O2
PD04217903 PD04217903 956905-27-4 C19H16N8O
Ki8751 Ki8751 228559-41-9 C24H18F3N3O4
(2R)-1-[[5-[(Z)-[5-[[(2,6-DICHLOROPHENYL)METHYL]SULFONYL]-1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE]METHYL]-2,4-DIMETHYL-1H-PYRROL-3-YL]CARBONYL]-2-(1-PYRROLIDINYLMETHYL)PYRROLIDINE (2R)-1-[[5-[(Z)-[5-[[(2,6-DICHLOROPHENYL)METHYL]SULFONYL]-1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE]METHYL]-2,4-DIMETHYL-1H-PYRROL-3-YL]CARBONYL]-2-(1-PYRROLIDINYLMETHYL)PYRROLIDINE 477575-56-7 C32H34Cl2N4O4S
N-(3-fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide N-(3-fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide 875337-44-3 C26H20FN5O2S2
Apatinib Apatinib 811803-05-1 C24H23N5O
TYRPHOSTIN AG 1296 TYRPHOSTIN AG 1296 146535-11-7 C16H14N2O2
TYRPHOSTIN AG 879 TYRPHOSTIN AG 879 148741-30-4 C18H24N2OS
Tie2 kinase inhibitor Tie2 kinase inhibitor 948557-43-5 C26H21N3O2S
BMS-794833 BMS-794833 1174046-72-0 C23H15ClF2N4O3
LRRK2-IN-1 LRRK2-IN-1 1234480-84-2 C31H38N8O3
ARRY-334543 ARRY-334543 845272-21-1 C22H19ClN6O2S
AVP-AEW541 AVP-AEW541 475489-16-8 C27H29N5O
ZM 306416 ZM 306416 690206-97-4 C16H13ClFN3O2
3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon 3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon 194413-58-6 C15H14N2O
AMG-208 AMG-208 1002304-34-8 C22H17N5O2
KRN 633 KRN 633 286370-15-8 C20H21ClN4O4
R428 R428 1037624-75-1 C30H34N8
lenvatinib Mesylate lenvatinib Mesylate 857890-39-2 C22H23ClN4O7S
CP-724714 CP-724714 537705-08-1 C27H27N5O3
OSI-930 OSI-930 728033-96-3 C22H16F3N3O2S
NVP-BVU 972 NVP-BVU 972 1185763-69-2 C20H16N6
UNC2881 UNC2881 1493764-08-1 C25H33N7O2
REVERSINE REVERSINE 656820-32-5 C21H27N7O
TYRPHOSTIN AG 1024 TYRPHOSTIN AG 1024 65678-07-1 C14H13BrN2O
PD153035 HCl PD153035 HCl 183322-45-4 C16H14BrN3O2.HCl
AMG 458 AMG 458 913376-83-7 C30H29N5O5
ARRY-380 ARRY-380 937265-83-3 C29H27N7O4S
NVP-BSK805 NVP-BSK805 1092499-93-8 C27H28F2N6O
3-(1-Methyl-1H-pyrazol-4-yl)-5-oxo-N-(2-pyridinylmethyl)-5H-benzo[4,5]cyclohepta[1,2-b]pyridine-7-methanesulfonamide 3-(1-Methyl-1H-pyrazol-4-yl)-5-oxo-N-(2-pyridinylmethyl)-5H-benzo[4,5]cyclohepta[1,2-b]pyridine-7-methanesulfonamide 1001917-37-8 C25H21N5O3S
N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine 1097917-15-1 C29H40N8O3S
E-3810 E-3810 1058137-23-7 C26H25N3O4
DCC-2618 DCC-2618 1225278-16-9 C26H21F2N5O3
GNF 5837 GNF 5837 1033769-28-6 C28H21F4N5O2
ANA12 ANA12 219766-25-3 C22H21N3O3S
IGF-1R  Inhibitor  II,  N-(5-Chloro-2-methoxyphenyl)-Nμ-(2-methylquinolin-4-yl)urea IGF-1R Inhibitor II, N-(5-Chloro-2-methoxyphenyl)-Nμ-(2-methylquinolin-4-yl)urea 196868-63-0 C18H16ClN3O2
5-[3-Methoxy-4-(4-methoxy-benzyloxy)-benzyl]-pyrimidine-2,4-diamine 5-[3-Methoxy-4-(4-methoxy-benzyloxy)-benzyl]-pyrimidine-2,4-diamine 870483-87-7 C20H22N4O3
1-{2-[5-(2-Methoxy-ethoxy)-benzoimidazol-1-yl]-quinolin-8-yl}-piperidin-4-ylamine 1-{2-[5-(2-Methoxy-ethoxy)-benzoimidazol-1-yl]-quinolin-8-yl}-piperidin-4-ylamine 343787-29-1 C24H27N5O2
NVP-BHG712 NVP-BHG712 940310-85-0 C26H20F3N7O
Tepotinib Tepotinib 1100598-32-0 C29H28N6O2
GSK1838705A GSK1838705A 1116235-97-2 C27H29FN8O3
TAK-285 TAK-285 871026-44-7 C26H25ClF3N5O3
3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione 3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione 905854-02-6 C23H19N3O2
WZ3146 WZ3146 1214265-56-1 C24H25ClN6O2
GDC-0941 Bimesylate GDC-0941 Bimesylate 957054-33-0 C24H30N7O6S3
Icotinib Icotinib 610798-31-7 C22H21N3O4
UNC2250 UNC2250 1493694-70-4 C24H36N6O2
PD168393 PD168393 194423-15-9 C17H13BrN4O
Capmatinib Capmatinib 1029712-80-8 C23H17FN6O
2-ButynaMide, N-[4-[(3-broMophenyl)aMino]-6-quinazolinyl]- 2-ButynaMide, N-[4-[(3-broMophenyl)aMino]-6-quinazolinyl]- 194423-06-8 C18H13BrN4O
SAR 131675 SAR 131675 1433953-83-3 C18H22N4O4
ZM 323881 hydrochloride ZM 323881 hydrochloride 193000-39-4 C22H19ClFN3O2
CNX-2006 CNX-2006 1375465-09-0 C26H27F4N7O2
SKLB1002 SKLB1002 1225451-84-2 C13H12N4O2S2
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