Tigapotide

Tigapotide is a type of antisense oligonucleotide, a short piece of DNA or RNA designed to bind to a specific target in the cell and modify gene expression. Tigapotide was developed as a potential treatment for various cancers, including pancreatic cancer.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: R1977

CAS No:848084-83-3

Chemical 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

Custom Peptide Synthesis
cGMP Peptide
  • Registration of APIs
  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C82H119N21O34S3
M.W/Mr.
2039.14

Tigapotide is a synthetic peptide compound characterized by its unique sequence and structural features, which confer notable biological activity relevant to vascular and cellular processes. As a member of the peptide class, it has attracted significant interest in biochemical and pharmacological research due to its capacity to modulate cellular interactions and influence signaling pathways. Its structural design enables targeted interactions with specific protein receptors, making it a valuable molecular tool for investigating mechanisms underlying vascular permeability, cell adhesion, and related cellular phenomena. The compound's versatility and specificity have established it as a resource for advanced studies in peptide biology, molecular signaling, and cellular microenvironment modulation.

Peptide-based vascular permeability research: One of the primary applications of Tigapotide is in the study of vascular permeability and endothelial barrier function. Researchers utilize this synthetic peptide to investigate how modulating intercellular junctions within endothelial layers affects fluid and solute exchange across blood vessel walls. By selectively interfering with adhesion molecules and tight junction proteins, it serves as a probe for delineating the molecular determinants of endothelial integrity and the regulatory mechanisms that control vascular leakage. Such studies are crucial for understanding the pathophysiology of tissue edema, inflammation, and tumor microenvironments, where abnormal permeability is a hallmark.

Cell adhesion and migration studies: Tigapotide is widely applied in the context of cell adhesion assays and migration models. Its ability to disrupt or modulate cell-cell and cell-matrix interactions allows researchers to dissect the roles of specific adhesion molecules and signaling cascades in cellular motility. This functional property is particularly relevant for exploring the mechanisms of tissue remodeling, angiogenesis, and metastasis in cancer biology. By serving as a tool to manipulate adhesion dynamics, the peptide supports detailed investigations into the molecular basis of cell migration and invasion.

Peptide signaling pathway analysis: The compound is an effective agent for probing intracellular signaling events initiated by peptide-receptor interactions. Its defined sequence enables selective activation or inhibition of signaling pathways involved in cytoskeletal rearrangement, cellular stress responses, and gene expression modulation. Researchers employ Tigapotide in in vitro and ex vivo models to map signal transduction cascades, facilitating the identification of downstream effectors and regulatory checkpoints. This application is instrumental in advancing the understanding of how extracellular cues are transduced into cellular responses.

Peptide synthesis and structure-activity relationship (SAR) studies: Tigapotide also serves as an important reference molecule in peptide synthesis and SAR research. Its well-characterized structure provides a template for designing analogs and derivatives to optimize biological activity or alter receptor specificity. Synthetic chemists and molecular biologists use it to explore the relationship between peptide sequence, conformation, and function, thereby informing the rational design of new peptide-based probes or modulators for research applications.

Analytical assay development: Another key use for Tigapotide lies in the development and validation of analytical assays targeting peptide detection, quantification, or functional assessment. Its defined sequence and stability make it suitable as a standard or positive control in mass spectrometry, high-performance liquid chromatography (HPLC), or bioactivity assays. These applications are essential for ensuring assay reliability, calibrating instrument performance, and supporting the rigorous analysis of peptide behavior in complex biological samples.

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
Canonical SMILES
CC(C(C(=O)NC(CC(=O)O)C(=O)NC(CC(=O)N)C(=O)NC(CSCNC(=O)C)C(=O)NC(CCC(=O)O)C(=O)NC(C(C)O)C(=O)NC(CSCNC(=O)C)C(=O)NC(C(C)O)C(=O)NC(CSCNC(=O)C)C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CCC(=O)O)C(=O)NC(C(C)O)C(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(CCC(=O)O)N)O
Isomeric SMILES
C[C@H]([C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CSCNC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSCNC(=O)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSCNC(=O)C)C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC2=CNC3=CC=CC=C32)NC(=O)[C@H](CCC(=O)O)N)O

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