Cyclosporin O | CAS#unknown | Macrocyclic immunosuppressive peptide

MedKoo Cat#: 465374 | Name: Cyclosporin O

Description:

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

Cyclosporin O is a macrocyclic immunosuppressive peptide, exhibiting a higher plasma concentration than Cyclophilin A.

Chemical Structure

Cyclosporin O

CAS#unknown

Theoretical Analysis

MedKoo Cat#: 465374

Name: Cyclosporin O

CAS#: unknown

Chemical Formula: C60H109N11O11

Exact Mass: 1159.8308

Molecular Weight: 1160.60

Elemental Analysis: C, 62.09; H, 9.47; N, 13.28; O, 15.16

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Cyclosporin O; Cyclosporin-O; CsO; Cs O; Cs-O;

IUPAC/Chemical Name

(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-6,9,18,24,33-pentaisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-30-propyl-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

NLGBWFHSHJPDQX-DTKOGYIOSA-N

InChi Code

InChI=1S/C60H109N11O11/c1-25-26-42-56(78)65(18)32-48(72)66(19)43(27-33(2)3)54(76)64-49(38(12)13)59(81)67(20)44(28-34(4)5)52(74)61-40(16)51(73)62-41(17)55(77)69(22)46(30-36(8)9)57(79)70(23)47(31-37(10)11)58(80)71(24)50(39(14)15)60(82)68(21)45(29-35(6)7)53(75)63-42/h33-47,49-50H,25-32H2,1-24H3,(H,61,74)(H,62,73)(H,63,75)(H,64,76)/t40-,41+,42-,43-,44-,45-,46-,47-,49-,50-/m0/s1

SMILES Code

O=C(N(C)[C@@H](CC(C)C)C1=O)[C@@H](NC([C@@H](N(C(CN(C([C@H](CCC)NC([C@@H](N(C)C([C@H](C(C)C)N(C([C@@H](N(C([C@H](CC(C)C)N(C)C([C@@H](C)NC([C@@H](N1)C)=O)=O)=O)C)CC(C)C)=O)C)=O)CC(C)C)=O)=O)C)=O)C)CC(C)C)=O)C(C)C

Appearance

Solid powder

Purity

>98% (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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 1,160.60 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: Lee D, Lee S, Choi J, Song YK, Kim MJ, Shin DS, Bae MA, Kim YC, Park CJ, Lee KR, Choi JH, Seo J. Interplay among Conformation, Intramolecular Hydrogen Bonds, and Chameleonicity in the Membrane Permeability and Cyclophilin A Binding of Macrocyclic Peptide Cyclosporin O Derivatives. J Med Chem. 2021 Jun 24;64(12):8272-8286. doi: 10.1021/acs.jmedchem.1c00211. Epub 2021 Jun 7. PMID: 34096287. 2: Sureshbabu VV, Tantry SJ, Chennakrishnareddy G, Nagendra G. Total synthesis of cyclosporin O: exploring the utility of Bsmoc-NMe-amino acid fluorides and KOAt. Protein Pept Lett. 2009;16(3):312-9. doi: 10.2174/092986609787601813. PMID: 19275747. 3: Tantry SJ, Venkataramanarao R, Chennakrishnareddy G, Sureshbabu VV. Total synthesis of cyclosporin O by convergent approach employing Fmoc-amino acid chlorides mediated by zinc dust. J Org Chem. 2007 Nov 23;72(24):9360-3. doi: 10.1021/jo701329w. Epub 2007 Oct 27. PMID: 17963403. 4: Sewald N. Efficient, racemization-free peptide coupling of N-alkyl amino acids by using amino acid chlorides generated in situ--total syntheses of the cyclopeptides cyclosporin O and omphalotin A. Angew Chem Int Ed Engl. 2002 Dec 16;41(24):4661-3. doi: 10.1002/anie.200290008. PMID: 12481318. 5: Li P, Xu JC. The development of highly efficient onium-type peptide coupling reagents based upon rational molecular design. J Pept Res. 2001 Aug;58(2):129-39. doi: 10.1034/j.1399-3011.2001.00867.x. PMID: 11532072. 6: Li P, Xu JC. Total synthesis of cyclosporin O both in solution and in the solid phase using novel thiazolium-, immonium-, and pyridinium-type coupling reagents: BEMT, BDMP, and BEP. J Org Chem. 2000 May 19;65(10):2951-8. doi: 10.1021/jo991687c. PMID: 10814183.