Tigapotide

DCTPepD ID  DCTPepD0041

Active Ingredients   Tigapotide

Description  A synthetic 15-mer peptide corresponding to amino acids 31-45 of the 94-amino acid isoform of human prostate secretory protein (PSP-94) with potential anti-metastasis and anti-angiogenesis activities. PSP-94-derived peptide PCK3145 may inhibit the secretion of the metastasis-related protein matrix metalloproteinase-9 (MMP-9) and its potential binding to its cell surface receptor CD44; may interfere with the vascular endothelial growth factor (VEGF) signaling pathway, resulting in an anti-angiogenesis effect; and may reduce the levels of parathyroid hormone-related protein (PTHrP), decreasing plasma calcium levels. PSP-94, one of three predominant proteins found in seminal fluid, may be down-regulated in prostate cancer, representing a potential survival mechanism for prostate cancer cells. MMP-9 is implicated in the invasion and metastasis of cancer. PTHrP may be expressed by various tumor cell types, resulting in the hypercalcemia of malignancy.

Synonyms  PCK3145; Prostate-Secretory Protein-94-Derived Peptide PCK3145; Tigapotide

Disease  Hormone Refractory Prostate Cancer (HRPC)

Classification

  

Peptide and derivative Antiangiogenesis agent

Structure Information


Molecular Formula  C82H119N21O34S3

Molecular Weight  2039.1

Active Sequence  EWQTDNXETXTXYET

Sequence Length  15

Modification  X=Cys(ACM)

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  (4S)-5-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2R)-3-(acetamidomethylsulfanyl)-1-[[(2S)-1-[[(2S,3R)-1-[[(2R)-3-(acetamidomethylsulfanyl)-1-[[(2S,3R)-1-[[(2R)-3-(acetamidomethylsulfanyl)-1-[[(2S)-1-[[(2S)-4-carboxy-1-[[(1S,2R)-1-carboxy-2-hydroxypropyl]amino]-1-oxobutan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-amino-1,4-dioxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-5-amino-1,5-dioxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-amino-5-oxopentanoic acid

InChI  InChI=1S/C82H119N21O34S3/c1-35(104)64(100-69(123)48(17-20-58(84)112)90-73(127)52(93-68(122)46(83)16-21-60(114)115)25-43-28-86-47-11-9-8-10-45(43)47)79(133)96-54(27-63(120)121)75(129)95-53(26-59(85)113)74(128)97-55(29-138-32-87-39(5)108)76(130)92-49(18-22-61(116)117)70(124)101-65(36(2)105)80(134)99-57(31-140-34-89-41(7)110)78(132)102-66(37(3)106)81(135)98-56(30-139-33-88-40(6)109)77(131)94-51(24-42-12-14-44(111)15-13-42)72(126)91-50(19-23-62(118)119)71(125)103-67(38(4)107)82(136)137/h8-15,28,35-38,46,48-57,64-67,86,104-107,111H,16-27,29-34,83H2,1-7H3,(H2,84,112)(H2,85,113)(H,87,108)(H,88,109)(H,89,110)(H,90,127)(H,91,126)(H,92,130)(H,93,122)(H,94,131)(H,95,129)(H,96,133)(H,97,128)(H,98,135)(H,99,134)(H,100,123)(H,101,124)(H,102,132)(H,103,125)(H,114,115)(H,116,117)(H,118,119)(H,120,121)(H,136,137)/t35-,36-,37-,38-,46+,48+,49+,50+,51+,52+,53+,54+,55+,56+,57+,64+,65+,66+,67+/m1/s1

InChI_Key ZRXXHPDJLAQCPC-SFJRRRFZSA-N

SMILES  O=C(O)CC[C@H](N)C(N[C@@H](CC1=CNC2=C1C=CC=C2)C(N[C@@H](CCC(N)=O)C(N[C@@H]([C@H](O)C)C(N[C@@H](CC(O)=O)C(N[C@@H](CC(N)=O)C(N[C@@H](CSCNC(C)=O)C(N[C@@H](CCC(O)=O)C(N[C@@H]([C@H](O)C)C(N[C@@H](CSCNC(C)=O)C(N[C@@H]([C@H](O)C)C(N[C@@H](CSCNC(C)=O)C(N[C@@H](CC3=CC=C(O)C=C3)C(N[C@@H](CCC(O)=O)C(N[C@H](C(O)=O)[C@H](O)C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O

External Codes


PubChem CID  16155604

DrugBank Accession Number  DB04985

NCI Thesaurus Code  C78474  

UNII  1WZ6S45S94   GSRS

CAS  848084-83-3



Drug approval


Drug indication
    For the treatment of late stage Hormone Refractory Prostate Cancer (HRPC) for which no effective therapy currently exists.

    The drug is not approved.

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT00695851 A Phase I Randomized Dose-Seeking Trial of PCK3145 in Asymptomatic, Castrate Metastatic Prostate Cancer Patients. Prostate Cancer Phase 1 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





DCTPep is developed by Dr.Zheng's team.