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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H25N3O6
Molecular Weight 367.3969
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TYROSERVALTIDE

SMILES

CC(C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC1=CC=C(O)C=C1)C(O)=O

InChI

InChIKey=TYFLVOUZHQUBGM-IHRRRGAJSA-N
InChI=1S/C17H25N3O6/c1-9(2)14(17(25)26)20-16(24)13(8-21)19-15(23)12(18)7-10-3-5-11(22)6-4-10/h3-6,9,12-14,21-22H,7-8,18H2,1-2H3,(H,19,23)(H,20,24)(H,25,26)/t12-,13-,14-/m0/s1

HIDE SMILES / InChI

Molecular Formula C17H25N3O6
Molecular Weight 367.3969
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Substance Class Chemical
Created
by admin
on Sat Dec 16 11:38:19 GMT 2023
Edited
by admin
on Sat Dec 16 11:38:19 GMT 2023
Record UNII
X5HXZ8M01A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TYROSERVALTIDE
Common Name English
TYR-SER-VAL
Common Name English
CMS-024-02
Code English
L-VALINE, N-(N-L-TYROSYL-L-SERYL)-
Systematic Name English
L-TYROSYL-L-SERYL-L-VALINE
Systematic Name English
(2S)-2-(((2S)-2-(((2S)-2-AMINO-3-(4-HYDROXYPHENYL)PROPANOYL)AMINO)-3-HYDROXY-PROPANOYL)AMINO)-3-METHYL-BUTANOIC ACID
Systematic Name English
TYROSERVATIDE
Common Name English
Code System Code Type Description
CAS
154039-16-4
Created by admin on Sat Dec 16 11:38:19 GMT 2023 , Edited by admin on Sat Dec 16 11:38:19 GMT 2023
PRIMARY
FDA UNII
X5HXZ8M01A
Created by admin on Sat Dec 16 11:38:19 GMT 2023 , Edited by admin on Sat Dec 16 11:38:19 GMT 2023
PRIMARY
PUBCHEM
11303106
Created by admin on Sat Dec 16 11:38:19 GMT 2023 , Edited by admin on Sat Dec 16 11:38:19 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY
Tripeptide compound tyroservaltide (YSV) has obvious inhibitory effect on experimental liver cancer. This study was to evaluate the inhibitory effect of YSV on the invasion and metastasis of mouse melanoma cell line B16-F10. YSV (100 microg/ml, 48 h) inhibited the proliferation of B16-F10 cells, with an inhibitory rate of 24.36%; YSV (100 microg/ml, 24 h) inhibited the adhesiveness of B16-F10 cells to Matrigel, with an inhibitory rate of 36.51%; YSV (10 microg/ml, 48 h) inhibited the invasiveness of B16-F10 cells, with an inhibitory rate of 36.53%; YSV (640 microg.(kg.d)-1) inhibited lung metastasis by B16-F10 cells, with an inhibitory rate of 62.21%. The expression of ICAM-1 in lung tissue was lower in YSV group than in normal saline group. YSV can inhibit the growth, invasion, and metastasis of B16-F10 cells.
ACTIVE MOIETY
Nude mice bearing xenografts of the human BEL-7402 hepatoma were given daily i.p. injections of YSV or saline (as a control) after the tumor were transplanted. Calculating tumor volume and measuring tumor weight determined the extent of inhibition of xenografts. The ultrastructure of tumor cells was observed by electron microscopy. Proliferating cell nuclear antigen (PCNA) expression in tissues of the YSV-treated group was observed by immunohistochemistry. Apoptosis of tumor tissue cells was assayed by the terminal transferase uridyl nick end labeling (TUNEL) method. At doses of 80 microg/kg/d and 160 microg/kg/d, YSV could significantly inhibit growth of tumors transplanted into nude mice, with inhibition rates of 60% and 64%, respectively, compared with that of the controls (P < 0.05). Moreover, YSV changed the ultrastructure of tumor cells, resulting in necrosis and apoptosis of the tumor cells. Compared with the saline group, the expression of PCNA in tumor tissue decreased and the count of apoptotic cell increased. Therefore, YSV can significantly inhibit the growth of human hepatocarcinoma BEL-7402 in nude mice, decrease the expression of PCNA in tumor tissue, and induce tumor cell apoptosis.