| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Thrombin
|
|---|---|
| ln Vitro |
C-terminal fragment analogues of the leech anticoagulant peptide hirudin represent a unique class of thrombin inhibitors that blocks thrombin's cleavage of fibrinogen but does not block the catalytic site of thrombin. In this paper, a series of synthetic peptides were prepared by solid-phase methodology to determine the optimal N-terminal and position 56 functionalities for these C-terminal fragment analogues of hirudin. Inhibition of fibrin clot formation by thrombin in vitro was used as a measure of anticoagulant activity. In the minimal C-terminal sequence necessary for anticoagulant activity, hirudin56-64, an L aromatic amino acid is required at position 56. Phe56----Tyr substitution retained potency, whereas p-Cl-Phe56 and phenylglycine56 substitutions resulted in decreased potencies. Removal of the cationic amino functionality from the vicinity of Asp55 results in increased potency (e.g., hirudin54-65, Ac-hirudin55-65) and [desNH2-Asp55]hirudin55-65 has a marked increase in potency over hirudin55-65. [DesNH2-Phe56]hirudin56-65 and related analogues show no detectable anticoagulant activity. The sensitivity of position 56 to modification demonstrates the significance of this residue in the interaction between the C-terminal region of hirudin and thrombin [1].
|
| References |
[1]. N-terminal requirements of small peptide anticoagulants based on hirudin54-65. J Med Chem. 1988 May;31(5):1009-11.
[2]. Peptide screening. Current Opinion in Biotechnology, 1992, 3(1): 49-54. |
| Additional Infomation |
Since the late 1990s, there has been a number of advances in the preparation and screening of a wide variety of peptides. Peptide screening methods based on peptide exposure to coat proteins (generated via fusion phage constructs) have been developed. Further progress has also been made in chemical synthesis strategies, increasing the variety of peptides produced, including light-guided, spatially addressable chemical synthesis, monopeptide synthesis, and iterative peptide selection and synthesis. [2]
|
| Molecular Formula |
C68H95N13O29S
|
|---|---|
| Molecular Weight |
1590.62000
|
| Exact Mass |
1589.607
|
| CAS # |
125441-00-1
|
| Related CAS # |
113274-56-9; 109528-49-6
|
| PubChem CID |
44264556
|
| Sequence |
Ac-Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-Tyr(SO3H)-Leu-Gln-OH; Ac-Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-{Try(SO3H)}-Leu-Gln; N-acetyl-glycyl-L-alpha-aspartyl-L-phenylalanyl-L-alpha-glutamyl-L-alpha-glutamyl-L-isoleucyl-L-prolyl-L-alpha-glutamyl-L-alpha-glutamyl-O4-sulfo-L-tyrosyl-L-leucyl-L-glutamine
|
| SequenceShortening |
GDFEEIPEEXLQ; Ac-GDFEEIPEE-{Try(SO3H)}-LQ
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.4±0.1 g/cm3
|
| Index of Refraction |
1.591
|
| LogP |
-0.55
|
| Hydrogen Bond Donor Count |
19
|
| Hydrogen Bond Acceptor Count |
29
|
| Rotatable Bond Count |
50
|
| Heavy Atom Count |
111
|
| Complexity |
3450
|
| Defined Atom Stereocenter Count |
12
|
| SMILES |
CCC(C(NC(C(NC(C(NC(C(NC(C(NC(CNC(C)=O)=O)CC(O)=O)=O)CC1=CC=CC=C1)=O)CCC(O)=O)=O)CCC(O)=O)=O)C(N2CCCC2C(NC(C(NC(C(NC(C(NC(C(NC(C(O)=O)CCC(N)=O)=O)CC(C)C)=O)CC3=CC=C(OS(=O)(O)=O)C=C3)=O)CCC(O)=O)=O)CCC(O)=O)=O)=O)C
|
| InChi Key |
XYECDVVWKGPHGI-ZOYPVGNLSA-N
|
| InChi Code |
InChI=1S/C68H95N13O29S/c1-6-35(4)57(80-61(98)43(22-27-55(91)92)73-58(95)40(19-24-52(85)86)74-63(100)46(30-37-11-8-7-9-12-37)79-65(102)48(32-56(93)94)71-51(84)33-70-36(5)82)67(104)81-28-10-13-49(81)66(103)75-42(21-26-54(89)90)59(96)72-41(20-25-53(87)88)60(97)78-47(31-38-14-16-39(17-15-38)110-111(107,108)109)64(101)77-45(29-34(2)3)62(99)76-44(68(105)106)18-23-50(69)83/h7-9,11-12,14-17,34-35,40-49,57H,6,10,13,18-33H2,1-5H3,(H2,69,83)(H,70,82)(H,71,84)(H,72,96)(H,73,95)(H,74,100)(H,75,103)(H,76,99)(H,77,101)(H,78,97)(H,79,102)(H,80,98)(H,85,86)(H,87,88)(H,89,90)(H,91,92)(H,93,94)(H,105,106)(H,107,108,109)/t35-,40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,57-/m0/s1
|
| Chemical Name |
(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-acetamidoacetyl)amino]-3-carboxypropanoyl]amino]-3-phenylpropanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-(4-sulfooxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-5-amino-5-oxopentanoic acid
|
| Synonyms |
Acetyl-Hirudin (54-65) (sulfated); 125441-00-1; MFCD00076566; CHEMBL1159670; Acetyl-Hirudin (54-65) (sulfated) (Ac-Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-Tyr(SO3H)-Leu-Gln-OH)
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.6287 mL | 3.1434 mL | 6.2869 mL | |
| 5 mM | 0.1257 mL | 0.6287 mL | 1.2574 mL | |
| 10 mM | 0.0629 mL | 0.3143 mL | 0.6287 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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