SML1575

Cyclosporin H

From Tolypocladium inflatum, ≥97% (HPLC), lentiviral transduction enhancer, powder

• Synonym(s): 1,4,7,10,13,16,19,22,25,28,31-Undecaazacyclotritriacontane, cyclic peptide deriv, 5-(N-Methyl-D-valine)-Cyclosporin A
• Empirical Formula (Hill Notation): C₆₂H₁₁₁N₁₁O₁₂
• CAS Number: 83602-39-5
• Molecular Weight: 1202.61
• UNSPSC Code: 51111800
• NACRES: NA.77
• Assay: ≥97% (HPLC)
• Form: powder
• Storage condition: desiccated, protect from light

Properties

• Product Name: Cyclosporin H, ≥97% (HPLC)
• biological source: Tolypocladium inflatum
• Quality Segment: 100
• assay: ≥97% (HPLC)
• form: powder
• optical activity: [α]/D -100 to -115°, c = 0.5 in methanol
• storage condition: desiccated, protect from light
• color: white to beige
• storage temp.: −20°C
• 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](C\C=C\C)C)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)C
• 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

Description

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.

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.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302,H350,H360
• pcodes: P202 - P264 - P270 - P280 - P301 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 1B - Repr. 1B
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable