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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
Pricing and availability is not currently available.

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

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

Application

Cyclosporin H has been used:
  • to pre-culture the lineage depleted murine Flt3ITDIDH2R140Q BM cells for transduction[1]
  • as a formyl peptide receptor (FPR) antagonist to study the role of FPR1 in calcium mobilization in polymorphonuclear leukocytes (PMNs)[2]
  • 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[3]

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.

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000423905
0000423904
0000423904
0000423905
0000382835

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Rana Gbyli et al.
Leukemia, 36(5), 1313-1323 (2022-03-12)
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
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
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
Giulia Rigotto et al.
Cells, 10(8) (2021-08-28)
In Alzheimer's disease (AD), the molecular mechanisms involved in the neurodegeneration are still incompletely defined, though this aspect is crucial for a better understanding of the malady and for devising effective therapies. Mitochondrial dysfunctions and altered Ca2+ signaling have long

Questions

1–2 of 2 Questions  

  1. シクロスポリンHのGMPグレードはありますか？

    1 answer

    1. Unfortunately, a GMP version of this item is not currently offered. This is the only Cyclosporin H product available at this time.

      Helpful?

  2. È possibile avere il datasheet del prodotto? 

    1 answer

    1. This product is not tested for use in any specific application and does not include a protocol. It may be helpful to review the Peer Reviewed Papers section of the product page.

      Helpful?

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