Cyclosporin Analogue Set

Cyclosporin Analogue Set

Catalog Product Name / CAS / Description Structure
BBF-05745

Cyclosporin A (59865-13-3)

Inquiry

It is produced by the strain of Polypocladiurn inflatum. It has a strong immunosuppressive action, but also has anti-inflammatory and weak antifungal effects. The mechanism of immunosuppression is the combination of cyclosporin A and cyclosporin-binding protein in T cells, which inhibits the activity of Calcineurin, and then impedes the transposition of intracellular transcription factors into the nucleus, and inhibits the interleukin-2 transcription, resulting in immunosuppression. It is mainly used for kidney transplantation, bone marrow and heart transplantation, and is one of the most important immunosuppressive agents in clinical application.

BBF-05766

A rearranged degradation product formed by acid treatment of cyclosporin A under aqueous and non-aqueous conditions.

BBF-05757

Dihydrocyclosporin A is a closely related co-metabolite of cyclosporin A. It has no immunosuppressive activity and has been used as a control to determine the role of immunosuppression in cyclosporin A pharmacology, especially in the treatment of parasitic infections.

BBF-05747

Cyclosporin Impurity 4 is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

BBF-05767

Geclosporin (74436-00-3)

Inquiry

Geclosporin is an impurity of cycloporine, which is an immunosuppressant used in the treatment of rheumatoid arthritis, psoriasis, Crohn's disease, nephrotic syndrome, etc.

BBF-05764

Cyclosporin H (83602-39-5)

Inquiry

The minor analogues of the cyclosporin family have immunological activity because they do not bind to immunophilins. It is an inhibitor of phorbol ester that effectively promotes tumors on mouse skin, and effectively inhibits calcium/calmodulin-dependent phosphorylation of EF-2 in vitro. It is an effective and selective formyl peptide receptor antagonist and formyl peptide-induced superoxide formation inhibitor.

BBF-05753

Cyclosporin D (63775-96-2)

Inquiry

Cyclosporin D is a group of nonpolar cyclic oligopeptides with immunosupppressant activity. Cyclosporin D is a minor analogue of the cyclosporin complex produced by Trichoderma.

BBF-05762

Cyclosporin B (63775-95-1)

Inquiry

Cyclosporin B is a minor analogue of the cyclosporin complex produced by Trichoderma. An immunosuppressant that has revolutionized organ transplantation through its use in the prevention of graft rejection.

BBF-05763

Cyclosporin C (59787-61-0)

Inquiry

A minor analogue of the cyclosporin complex produced by a number of fungal species, including trichoderma, tolypocladium, fusarium, nectria and acremonium. It has the immunosuppressant activity but has been much less extensively investigated than the major analogue, cyclosporin A. Cyclosporin C is a broad-spectrum antifungal agent against filamentous phytopathogenic fungi but no activity against bacteria or yeasts.

BBF-05752

Cyclosporin L Related Compound 1 is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

BBF-05748

Cyclosporine metabolite M17 is a metabolite of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

BBF-05750

Cyclosporin AM 9 is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

BBF-05749

Cyclosporin AM 4N is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

BBF-05756

(E)-2-Butenyl-4-methyl-threonine is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

BBF-05760

Cyclosporin E (63798-73-2)

Inquiry

Cyclosporin E is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

BBF-05738

α-D-galactopyranosyl 1-phosphate-[1-13C] (dipotassium salt) is the labelled analogue of α-D-galactopyranosyl 1-phosphate (dipotassium salt), which is the phosphate conjugate of α-D-Galactose. α-D-Galactose is a natural aldohexose which is ubiquitous in bacteria, plants, and animals, including human brains.

BBF-05755

Cyclosporin L Related Compound 3 is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

BBF-05741

Cyclosporin Impurity 6 is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

BBF-05765

Cyclosporin U (108027-45-8)

Inquiry

Cyclosporin U is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

BBF-05758

Cyclosporin T (108027-44-7)

Inquiry

Cyclosporin T is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

BOC Sciences provides a diversity of metabolites fermented and separated from plants, microorganisms, fungi and other organisms. We have been committed to providing customers with high-quality cyclosporin and its analogues at the best price.

Our Cyclosporin Analogue Set includes:

  • Cyclosporin A
  • Cyclosporin impurities
  • Cyclosporin co-metabolite
  • Cyclosporin metabolite

In addition, BOC Sciences provide fermentation CDMO services containing strain development, metabolic pathway engineering, fermentation process optimization, microbial GMP production. We have the ability to provide customized cyclosporin analogues for customers in the pharmaceutical and other industries.

Structure and Synthesis of Cyclosporin

Cyclosporin is a non-ribosomal cyclic polypeptide composed of 11 normal and abnormal amino acids. It was first isolated and identified in 1971, and more than 30 structural analogues have been found successively.

Cyclosporin A (CsA) is the first Cyclosporin analogue approved by FDA as an anti-immune rejection drug, hydrophilic immunosuppressive active sites can be formed on the residues of amino acids 1, 2, 3 and 11. CsA is produced by the strain of Polypocladiurn inflatum. The molecule contains several unusual amino acids such as L-2-aminobutyric acid and D-alanine. In addition, the CsA molecule contains seven N-methylated peptide bonds. Biosynthesis of CsA is catalyzed by a specific polypeptide polyenzyme, Cyclosporin synthase. This enzyme catalyzes CsA synthesis from unmethylated precursor amino acids through a sulfur template mechanism. When these substrate amino acids bind to the enzyme in the form of thioesters, they are catalyzed by methyltransferases in Cyclosporin synthase for N-methylation reactions.

The mechanism of Cyclosporin synthesis have been reported. It was proved that the SimG pathway in gene cluster was responsible for the synthesis of abnormal amino acid 2-butyl-4-methyl-threonine Bmt, and the racemase SimB was responsible for the conversion of L-alanine to D-alanine, and then the sequence addition and cycination of 11 substrates were mediated by SimA to produce CsA.

Synthesis mechanism and biological function of Cyclosporin Fig 1. Synthesis mechanism and biological function of Cyclosporin (Yang, 2018)

Application of Cyclosporin

Cyclosporin is a potent immunomodulatory agent with an increasing number of clinical applications. Cyclosporin is different from cytotoxic drugs in that it only inhibits T cell-mediated cellular immunity without significantly affecting the body's general defense ability. Cyclosporin can selectively act on the initial stage of T lymphocyte activation and inhibit the interleukin 2 produced after the activation of helper T cells, while it had no effect on inhibitory T cells. Cyclosporin also inhibits the production of interferon by lymphocytes.

Reference

  1. Yang, X. et al. Cyclosporine Biosynthesis in Tolypocladium inflatum Benefits Fungal Adaptation to the Environment., MBio, 2018, 9.
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