Cyclosporin H | CAS# 83602-39-5 | Undecapeptide

MedKoo Cat#: 574059 | Name: Cyclosporin H

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Description:

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

Cyclosporin H is a natural cyclic undecapeptide that selectively antagonizes the formyl peptide receptor. Unlike Cyclosporin A, Cyclosporin H does not bind cyclophilin to evoke an immunosuppressant response. Cyclosporin H has been reported to inhibit phorbol ester-mediated effects in mouse skin and block calcium/calmodulin-dependent EF-2 phosphorylation in vitro.

Chemical Structure

Cyclosporin H

CAS#83602-39-5

Theoretical Analysis

MedKoo Cat#: 574059

Name: Cyclosporin H

CAS#: 83602-39-5

Chemical Formula: C62H111N11O12

Exact Mass: 1201.8414

Molecular Weight: 1202.64

Elemental Analysis: C, 61.92; H, 9.30; N, 12.81; O, 15.96

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 450.00	2 Weeks

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Related CAS #

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Synonym

5-(N-methyl-D-valine)-Cyclosporin A; Cyclosporin H; Sandoz 37-839; Sandoz37-839; Sandoz-37-839;

IUPAC/Chemical Name

(3R,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-((1R,2R,E)-1-hydroxy-2-methylhex-4-en-1-yl)-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone

InChi Key

PMATZTZNYRCHOR-JLPRAAIDSA-N

InChi Code

InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(3

SMILES Code

O[C@@H]([C@](C(N[C@H](C(N(CC(N(C)[C@H](C(N[C@@H](C(C)C)C(N(C)[C@H]1CC(C)C)=O)=O)CC(C)C)=O)C)=O)CC)=O)([H])N(C([C@@H](C(C)C)N(C([C@@H](N(C([C@H](CC(C)C)N(C([C@H](NC([C@@H](NC1=O)C)=O)C)=O)C)=O)C)CC(C)C)=O)C)=O)C)[C@H](C)C/C=C/C

Appearance

White Solid powder

Purity

>95% (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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,202.64 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.

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

1. Wenzel-Seifert, K., and Siefert, R. Cyclosporin H is a potent and selective formyl peptide receptor antagonist. Comparison with N-t-butoxycarbonyl-L-phenylalanyl-L-leucyl-L-phenylalanyl-L- leucyl-L-phenylalanine and cyclosporins A, B, C, D, and E. Journal of Immunology 150, 4591-4599 (1993). 2. Yan, P., Nanamori, M., Sun, M., et al. The immunosuppressant cyclosporin A antagonizes human formyl peptide receptor through inhibition of cognate ligand binding. Journal of Immunology 177(10), 7050-7058 (2006). 3. Zhou, C., Zhou, Y., Wang, J., et al. V101L of human formyl peptide receptor 1 (FPR1) increases receptor affinity and augments the antagonism mediated by cyclosporins. Biochemistry Journal 451(2), 245-255 (2013). 4. Sherry, B., Yarlett, N., Strupp, A., et al. Identification of cyclophilin as a proinflammatory secretory product of lipopolysaccharide-activated macrophages. Proceedings of the National Academy of Sciences of the United States of America 89(8), 3511-3515 (1992). 5. Gschwendt, M., Kittstein, W., and Marks, F. The weak immunosuppressant cyclosporine D as well as the immunologically inactive cyclosporine H are potent inhibitors in vivo of phorbol ester TPA-induced biological effects in mouse skin and of Ca2+/calmodulin dependent EF-2 phosphorylation in vitro. Biochemical and Biophysical Research Communications 150, 545-551 (1988).