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Key Documents

SML1575

Sigma-Aldrich

Cyclosporin H

≥97% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C62H111N11O12
CAS Number:
83602-39-5
Molecular Weight:
1202.61
UNSPSC Code:
51111800
NACRES:
NA.77

biological source

Tolypocladium inflatum

Quality Level

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

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

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 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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H350,H360

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Repr. 1B

Storage Class Code

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rana Gbyli et al.
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Treatment options for patients with relapsed/refractory acute myeloid leukemia (AML) and myelodysplastic syndromes (MDS) are scarce. Recurring mutations, such as mutations in isocitrate dehydrogenase-1 and -2 (IDH1/2) are found in subsets of AML and MDS, are therapeutically targeted by mutant
Ya-Wen Fu et al.
Nucleic acids research, 49(2), 969-985 (2021-01-06)
Investigations of CRISPR gene knockout editing profiles have contributed to enhanced precision of editing outcomes. However, for homology-directed repair (HDR) in particular, the editing dynamics and patterns in clinically relevant cells, such as human iPSCs and primary T cells, are
Woon Yong Kwon et al.
Proceedings of the National Academy of Sciences of the United States of America, 118(17) (2021-04-24)
Secondary infections typically worsen outcomes of patients recovering from septic shock. Neutrophil [polymorphonuclear leukocytes (PMNs)] migration to secondarily inoculated sites may play a key role in inhibiting progression from local bacterial inoculation to secondary infection. Mitochondrial N-formyl peptide (mtFP) occupancy
Irene Sambri et al.
EBioMedicine, 61, 103050-103050 (2020-10-13)
Mutations of the mitochondrial protein paraplegin cause hereditary spastic paraplegia type 7 (SPG7), a so-far untreatable degenerative disease of the upper motoneuron with still undefined pathomechanism. The intermittent mitochondrial permeability transition pore (mPTP) opening, called flickering, is an essential process

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