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Cyclosporin H

SIGMA/SML1575 - ≥97% (HPLC)

Synonym: 1,4,7,10,13,16,19,22,25,28,31-Undecaazacyclotritriacontane, cyclic peptide deriv; 5-(N-Methyl-D-valine)-Cyclosporin A

CAS Number: 83602-39-5
Empirical Formula (Hill Notation): C62H111N11O12
Molecular Weight: 1202.61
Linear Formula: C62H111N11O12
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SML1575-1MG 1 mg
 $119.00
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45-SML1575-5MG 5 mg
 $480.00
1/EA		 Add To Favorites
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assay ≥97% (HPLC)
biological source Tolypocladium inflatum
color white to beige
form powder
InChI 1S/C63H113N11O12/c1-26-28-29-41(15)53(76)52-56(79)66-44(27-2)58(81)67(18)34-49(75)68(19)46(31-36(5)6)60(83)72(23)50(39(11)12)62(85)69(20)45(30-35(3)4)55(78)64-42(16)54(77)65-43(17)57(80)70(21)47(32-37(7)8)59(82)71(22)48(33-38(9)10)61(84)73(24)51(40(13)14)63(86)74(52)25/h26,28,35-48,50-53,76H,27,29-34H2,1-25H3,(H,64,78)(H,65,77)(H,66,79)/b28-26+/t41-,42+,43-,44+,45+,46+,47+,48+,50-,51+,52?,53-/m1/s1
InChI key BQQHPBPTWWXRMU-SXHXJWHLSA-N
optical activity [α]/D -100 to -115°, c = 0.5 in methanol
Quality Level 100 
SMILES string N1([C@@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N(C(C(=O)N[C@H](C(=O)N(CC(=O)N([C@H](C1=O)CC(C)C)C)C)CC)[C@H](O)[C@@H](CC=CC)C)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)C
storage condition desiccated
  protect from light
storage temp. −20°C
Application: Cyclosporin H has been used:
• to pre-culture the lineage depleted murine Flt3ITDIDH2R140Q BM cells for transduction
• as a formyl peptide receptor (FPR) antagonist to study the role of FPR1 in calcium mobilization in polymorphonuclear leukocytes (PMNs)
• as one of the small molecules to study its effect on the homology-directed repair (HDR) editing efficiency in human-induced pluripotent stem cells (iPSCs) and T cells
Biochem/physiol Actions: Cyclosporin H is a selective inhibitor of formyl peptide receptor-1 (FPR-1) and formyl peptide-induced superoxide formation in neutrophils.
Biochem/physiol Actions: Cyclosporin H is a selective inhibitor of formyl peptide receptor-1 (FPR-1) and formyl peptide-induced superoxide formation in neutrophils. Cyclosporin H does not bind cyclophilin or evoke an immunosuppressant response. Cyclosporin H has been reported to inhibit tumor promoting phorbol ester TPA/PMA in mouse skin cells and to inhibit calcium/calmodulin-dependent EF-2 phosphorylation.
Packaging: 1, 5 mg in glass bottle
Purity ≥97% (HPLC)
Storage Temp. −20°C
UNSPSC 51111800

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