Echinocandin B

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

MedKoo CAT#: 571102

CAS#: 54651-05-7

Description: Echinocandin B is a cyclic hexapeptide echinocandin antibiotic isolated from Aspergillus nidulans var. echinulatus with specific anti-yeast activity. It inhibits beta-1,3-glucan synthesis and thus attacks the cell wall of fungi.


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Echinocandin B is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571102
Name: Echinocandin B
CAS#: 54651-05-7
Chemical Formula: C52H81N7O16
Exact Mass: 1059.574
Molecular Weight: 1060.25
Elemental Analysis: C, 58.91; H, 7.70; N, 9.25; O, 24.14


Synonym: Echinocandin B; NSC 287461; A30912A; A 30912A; A-30912A; A22082; A 22082; A-22082

IUPAC/Chemical Name: (9Z,12Z)-N-((2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-23-((1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl)-2,11,12,15-tetrahydroxy-6,20-bis((R)-1-hydroxyethyl)-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl)octadeca-9,12-dienamide

InChi Key: FAUOJMHVEYMQQG-HVYQDZECSA-N

InChi Code: 1S/C52H81N7O16/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-38(65)53-35-26-37(64)48(71)57-50(73)42-43(66)29(2)27-59(42)52(75)40(31(4)61)55-49(72)41(45(68)44(67)32-21-23-33(62)24-22-32)56-47(70)36-25-34(63)28-58(36)51(74)39(30(3)60)54-46(35)69/h9-10,12-13,21-24,29-31,34-37,39-45,48,60-64,66-68,71H,5-8,11,14-20,25-28H2,1-4H3,(H,53,65)(H,54,69)(H,55,72)(H,56,70)(H,57,73)/b10-9-,13-12-/t29-,30+,31+,34+,35-,36-,37+,39-,40-,41-,42-,43-,44-,45-,48+/m0/s1

SMILES Code: CCCCC\C=C/C\C=C/CCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@@H](C)CN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]3C[C@@H](O)CN3C(=O)[C@@H](NC1=O)[C@@H](C)O)[C@H](O)[C@@H](O)c4ccc(O)cc4)[C@@H](C)O


Technical Data

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:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Shao L, Li J, Liu A, Chang Q, Lin H, Chen D. Efficient bioconversion of echinocandin B to its nucleus by overexpression of deacylase genes in different host strains. Appl Environ Microbiol. 2013 Feb;79(4):1126-33. doi: 10.1128/AEM.02792-12. Epub 2012 Dec 7. PubMed PMID: 23220968; PubMed Central PMCID: PMC3568618.

2: Hu ZC, Peng LY, Zheng YG. Enhancement of Echinocandin B Production by a UV- and Microwave-Induced Mutant of Aspergillus nidulans with Precursor- and Biotin-Supplying Strategy. Appl Biochem Biotechnol. 2016 Aug;179(7):1213-26. doi: 10.1007/s12010-016-2060-5. Epub 2016 Apr 2. PubMed PMID: 27039401.

3: Zou SP, Liu M, Wang QL, Xiong Y, Niu K, Zheng YG, Shen YC. Preparative separation of echinocandin B from Aspergillus nidulans broth using macroporous resin adsorption chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jan 26;978-979:111-7. doi: 10.1016/j.jchromb.2014.11.028. Epub 2014 Dec 4. PubMed PMID: 25541471.

4: Elefanti A, Mouton JW, Verweij PE, Tsakris A, Zerva L, Meletiadis J. Amphotericin B- and voriconazole-echinocandin combinations against Aspergillus spp.: Effect of serum on inhibitory and fungicidal interactions. Antimicrob Agents Chemother. 2013 Oct;57(10):4656-63. doi: 10.1128/AAC.00597-13. Epub 2013 Jul 15. PubMed PMID: 23856768; PubMed Central PMCID: PMC3811418.

5: Hüttel W, Youssar L, Grüning BA, Günther S, Hugentobler KG. Echinocandin B biosynthesis: a biosynthetic cluster from Aspergillus nidulans NRRL 8112 and reassembly of the subclusters Ecd and Hty from Aspergillus pachycristatus NRRL 11440 reveals a single coherent gene cluster. BMC Genomics. 2016 Aug 8;17:570. doi: 10.1186/s12864-016-2885-x. PubMed PMID: 27502607; PubMed Central PMCID: PMC4977696.

6: Niu K, Hu Y, Mao J, Zou S, Zheng Y. [Effect of microparticles on echinocandin B production by Aspergillus nidulans]. Sheng Wu Gong Cheng Xue Bao. 2015 Jul;31(7):1082-8. Chinese. PubMed PMID: 26647583.

7: Zou SP, Zhong W, Xia CJ, Gu YN, Niu K, Zheng YG, Shen YC. Mutagenesis breeding of high echinocandin B producing strain and further titer improvement with culture medium optimization. Bioprocess Biosyst Eng. 2015 Oct;38(10):1845-54. doi: 10.1007/s00449-015-1425-4. Epub 2015 Jun 20. PubMed PMID: 26091897.

8: Emri T, Majoros L, Tóth V, Pócsi I. Echinocandins: production and applications. Appl Microbiol Biotechnol. 2013 Apr;97(8):3267-84. doi: 10.1007/s00253-013-4761-9. Epub 2013 Mar 6. Review. PubMed PMID: 23463246.

9: Cacho RA, Jiang W, Chooi YH, Walsh CT, Tang Y. Identification and characterization of the echinocandin B biosynthetic gene cluster from Emericella rugulosa NRRL 11440. J Am Chem Soc. 2012 Oct 10;134(40):16781-90. doi: 10.1021/ja307220z. Epub 2012 Oct 1. PubMed PMID: 22998630; PubMed Central PMCID: PMC3482383.

10: Tóth V, Nagy CT, Pócsi I, Emri T. The echinocandin B producer fungus Aspergillus nidulans var. roseus ATCC 58397 does not possess innate resistance against its lipopeptide antimycotic. Appl Microbiol Biotechnol. 2012 Jul;95(1):113-22. doi: 10.1007/s00253-012-4027-y. Epub 2012 May 4. PubMed PMID: 22555909.

11: Kuhn DM, George T, Chandra J, Mukherjee PK, Ghannoum MA. Antifungal susceptibility of Candida biofilms: unique efficacy of amphotericin B lipid formulations and echinocandins. Antimicrob Agents Chemother. 2002 Jun;46(6):1773-80. PubMed PMID: 12019089; PubMed Central PMCID: PMC127206.

12: Julius JM, Gaikwad A, Lowry A, Lewis RE, Lozano RD, Dalrymple JL, Coleman RL, Smith JA. Defining the role of echinocandin catechol functional groups in the development of secondary hepatocellular carcinoma. J Antimicrob Chemother. 2012 Feb;67(2):422-9. doi: 10.1093/jac/dkr494. Epub 2011 Nov 30. PubMed PMID: 22129592.

13: Debono M, Abbott BJ, Fukuda DS, Barnhart M, Willard KE, Molloy RM, Michel KH, Turner JR, Butler TF, Hunt AH. Synthesis of new analogs of echinocandin B by enzymatic deacylation and chemical reacylation of the echinocandin B peptide: synthesis of the antifungal agent cilofungin (LY121019). J Antibiot (Tokyo). 1989 Mar;42(3):389-97. PubMed PMID: 2708132.

14: Cappelletty D, Eiselstein-McKitrick K. The echinocandins. Pharmacotherapy. 2007 Mar;27(3):369-88. Review. PubMed PMID: 17316149.

15: Denning DW. Echinocandin antifungal drugs. Lancet. 2003 Oct 4;362(9390):1142-51. Review. PubMed PMID: 14550704.

16: McCammon MT, Parks LW. Enrichment for auxotrophic mutants in Saccharomyces cerevisiae using the cell wall inhibitor, echinocandin B. Mol Gen Genet. 1982;186(2):295-7. PubMed PMID: 7050633.

17: Smith L, Lu SE. Medical claims and current applications of the potent echinocandin antifungals. Recent Pat Antiinfect Drug Discov. 2010 Jan;5(1):58-63. Review. PubMed PMID: 19929842.

18: Boeck LD, Fukuda DS, Abbott BJ, Debono M. Deacylation of echinocandin B by Actinoplanes utahensis. J Antibiot (Tokyo). 1989 Mar;42(3):382-8. PubMed PMID: 2708131.

19: Morrison VA. The role of caspofungin and the echinocandins in the antifungal armamentarium. Curr Opin Investig Drugs. 2002 Oct;3(10):1432-6. Review. PubMed PMID: 12431014.

20: Hodges RL, Hodges DW, Goggans K, Xuei X, Skatrud P, McGilvray D. Genetic modification of an echinocandin B-producing strain of Aspergillus nidulans to produce mutants blocked in sterigmatocystin biosynthesis. J Ind Microbiol. 1994 Nov;13(6):372-81. PubMed PMID: 7765669.