Cyclolinopeptide A

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 598944

CAS#: 33302-55-5

Description: Cyclolinopeptide A is a cyclic nonapeptide isolated from linseed oil.

Chemical Structure

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Cyclolinopeptide A
CAS# 33302-55-5
Instruction

Theoretical Analysis

MedKoo Cat#: 598944
Name: Cyclolinopeptide A
CAS#: 33302-55-5
Chemical Formula: C57H85N9O9
Exact Mass: 1,039.65
Molecular Weight: 1,040.360
Elemental Analysis: C, 65.81; H, 8.24; N, 12.12; O, 13.84

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Cyclolinopeptide A; Linus cyclopeptide 9;

IUPAC/Chemical Name: (6S,9S,12S,15S,18S,21S,24S,26aS,31aR)-21,24-dibenzyl-12-((S)-sec-butyl)-6,9,18-triisobutyl-15-isopropylicosahydro-1H-dipyrrolo[1,2-a:1',2'-d][1,4,7,10,13,16,19,22,25]nonaazacycloheptacosine-5,8,11,14,17,20,23,26,31(31aH)-nonaone

InChi Key: DTEHCBOGAUCOJT-ZPEAOGKNSA-N

InChi Code: InChI=1S/C57H85N9O9/c1-11-37(10)48-55(73)61-40(28-33(2)3)49(67)62-44(30-35(6)7)56(74)66-27-19-25-46(66)57(75)65-26-18-24-45(65)53(71)60-43(32-39-22-16-13-17-23-39)51(69)59-42(31-38-20-14-12-15-21-38)50(68)58-41(29-34(4)5)52(70)63-47(36(8)9)54(72)64-48/h12-17,20-23,33-37,40-48H,11,18-19,24-32H2,1-10H3,(H,58,68)(H,59,69)(H,60,71)(H,61,73)(H,62,67)(H,63,70)(H,64,72)/t37-,40-,41-,42-,43-,44-,45-,46+,47-,48-/m0/s1

SMILES Code: O=C([C@@H](NC([C@@H](NC([C@H](CC(C)C)NC([C@H](Cc1ccccc1)NC([C@@H](NC([C@H]2N(C([C@@H]3N(CCC3)C4=O)=O)CCC2)=O)Cc5ccccc5)=O)=O)=O)C(C)C)=O)[C@@H](C)CC)N[C@@H](CC(C)C)C(N[C@H]4CC(C)C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,040.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Huben K, Jewgiński M, Pabis A, Paluch P, Luy B, Jankowski S. The structure of cyclolinopeptide A in chloroform refined by RDC measurements. J Pept Sci. 2014 Nov;20(11):901-7. doi: 10.1002/psc.2683. Epub 2014 Aug 11. PubMed PMID: 25111589.

2: Jędrzejczak K, Hrynczyszyn P, Artym J, Kocięba M, Zimecki M, Zabrocki J, Jankowski S. Synthesis and biological activity of cyclolinopeptide A analogues modified with γ(3)-bis(homophenylalanine). Eur J Med Chem. 2014 Oct 30;86:515-27. doi: 10.1016/j.ejmech.2014.09.014. Epub 2014 Sep 6. PubMed PMID: 25203781.

3: Gaymes TJ, Cebrat M, Siemion IZ, Kay JE. Cyclolinopeptide A (CLA) mediates its immunosuppressive activity through cyclophilin-dependent calcineurin inactivation. FEBS Lett. 1997 Nov 24;418(1-2):224-7. PubMed PMID: 9414131.

4: Wieczorek Z, Pedyczak A, Bodalski T, Lisowski M, Trojnar J, Zimecki M, Siemion IZ. Immunosuppressive activity of tyrosine analogues of cyclolinopeptide A. Arch Immunol Ther Exp (Warsz). 1992;40(3-4):213-6. PubMed PMID: 1300986.

5: Gallo P, Rossi F, Saviano M, Pedone C, Colonna G, Ragone R. Specific interaction between bovine cyclophilin A and synthetic analogues of cyclolinopeptide A. J Biochem. 1998 Nov;124(5):880-5. PubMed PMID: 9792908.

6: Raghothama S, Ramakrishnan C, Balasubramanian D, Balaram P. Conformational analysis of cyclolinopeptide A, a cyclic nonapeptide: nuclear Overhauser effect and energy minimization studies. Biopolymers. 1989 Feb;28(2):573-88. PubMed PMID: 2713453.

7: Mazzeo M, Isernia C, Rossi F, Saviano M, Pedone C, Paolillo L, Benedetti E, Pavone V. Conformational behaviour of a cyclolinopeptide A analogue: two-dimensional NMR study of cyclo(Pro1-Pro-Phe-Phe-Ac6c-Ile-ala-Val8). J Pept Sci. 1995 Sep-Oct;1(5):330-40. PubMed PMID: 9223012.

8: Katarzyńska J, Mazur A, Rudzińska E, Artym J, Zimecki M, Jankowski S, Zabrocki J. Cyclolinopeptide derivatives modify methotrexate-induced suppression of the humoral immune response in mice. Eur J Med Chem. 2011 Sep;46(9):4608-17. doi: 10.1016/j.ejmech.2011.07.040. Epub 2011 Jul 28. PubMed PMID: 21839548.

9: Zubrzak P, Banaś A, Kaczmarek K, Leplawy MT, Sochacki M, Kowalski ML, Szkudlińska B, Zabrocki J, Di Lello P, Isernia C, Saviano M, Pedone C, Benedetti E. Analogues of cyclolinopeptide A containing alpha-hydroxymethyl amino acid residues. Biopolymers. 2005;80(2-3):347-56. PubMed PMID: 15614802.

10: Bell A, McSteen PM, Cebrat M, Picur B, Siemion IZ. Antimalarial activity of cyclolinopeptide A and its analogues. Acta Pol Pharm. 2000 Nov;57 Suppl:134-6. PubMed PMID: 11293244.

11: Tancredi T, Zanotti G, Rossi F, Benedetti E, Pedone C, Temussi PA. Comparison of the conformations of cyclolinopeptide A in the solid state and in solution. Biopolymers. 1989 Jan;28(1):513-23. PubMed PMID: 2720121.

12: Castiglione Morelli MA, Pastore A, Pedone C, Temussi PA, Zanotti G, Tancredi T. Conformational study of cyclolinopeptide A. A distance geometry and molecular dynamics approach. Int J Pept Protein Res. 1991 Feb;37(2):81-9. PubMed PMID: 2019478.

13: Saviano M, Rossi F, Filizola M, Di Blasio B, Pedone C. [Aib5,6-D-Ala8]-cyclolinopeptide A, grown from a benzene/acetonitrile mixture. Acta Crystallogr C. 1995 Apr 15;51 ( Pt 4):663-6. PubMed PMID: 7619339.

14: Rempel B, Gui B, Maley J, Reaney M, Sammynaiken R. Biomolecular interaction study of Cyclolinopeptide A with human serum albumin. J Biomed Biotechnol. 2010;2010:737289. doi: 10.1155/2010/737289. Epub 2011 Mar 10. PubMed PMID: 21436992; PubMed Central PMCID: PMC3062964.

15: Benedetti E, Pedone C. Cyclolinopeptide A: inhibitor, immunosuppressor or other? J Pept Sci. 2005 May;11(5):268-72. PubMed PMID: 15838908.

16: Siemion IZ, Pedyczak A, Strug I, Wieczorek Z. Synthesis and biological studies on analogs of cyclolinopeptide A with a shortened peptide chain. Arch Immunol Ther Exp (Warsz). 1994;42(5-6):459-65. PubMed PMID: 8572907.

17: Saviano M, Aida M, Corongiu G. Molecular dynamics simulation in vacuo and in solution of cyclolinopeptide A: a conformational study. Biopolymers. 1991 Jul;31(8):1017-24. PubMed PMID: 1782353.

18: Wieczorek Z, Bengtsson B, Trojnar J, Siemion IZ. Immunosuppressive activity of cyclolinopeptide A. Pept Res. 1991 Sep-Oct;4(5):275-83. PubMed PMID: 1802239.

19: Drygała P, Olejnik J, Mazur A, Kierus K, Jankowski S, Zimecki M, Zabrocki J. Synthesis and immunosuppressive activity of cyclolinopeptide A analogues containing homophenylalanine. Eur J Med Chem. 2009 Sep;44(9):3731-8. doi: 10.1016/j.ejmech.2009.03.037. Epub 2009 Apr 5. PubMed PMID: 19487056.

20: Naider F, Benedetti E, Goodman M. Conformation of cyclolinopeptide a observed by circular dichroism. Proc Natl Acad Sci U S A. 1971 Jun;68(6):1195-8. PubMed PMID: 16591927; PubMed Central PMCID: PMC389152.