Basifungin | CAS#127785-64-2 | inositol phosphorylceramide synthase inhibitor

MedKoo Cat#: 584809 | Name: Basifungin

Description:

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

Basifungin, also known as Aureobasidin A, is an inositol phosphorylceramide synthase inhibitor that is isolated from the culture medium of Aureobasidium pullulans R 106.

Chemical Structure

Basifungin

CAS#127785-64-2

Theoretical Analysis

MedKoo Cat#: 584809

Name: Basifungin

CAS#: 127785-64-2

Chemical Formula: C60H92N8O12

Exact Mass: 1116.6835

Molecular Weight: 1117.44

Elemental Analysis: C, 64.49; H, 8.30; N, 10.03; O, 17.18

Price and Availability

Size	Price	Availability
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
200mg	USD 1,950.00	2 Weeks
500mg	USD 3,450.00	2 Weeks
1g	USD 4,950.00	2 Weeks
2g	USD 7,650.00	2 Weeks

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Related CAS #

127785-64-2

Synonym

Basifungin; Aureobasidin A; LY 295337; LY295337; NK 204 R106-1

IUPAC/Chemical Name

Valine, 3-hydroxy-N-(N-(N-(N-(1-(N-(N-(N-(2-hydroxy-3-methyl-1-oxopentyl)-N-methylvalyl)phenylalanyl)-N-methylphenylalanyl)prolyl)alloisoleucyl)-N-methylvalyl)leucyl)-N-methyl-, alpha-1-lactone

InChi Key

BGBIMGBOAIOSPU-PHHQQPDVSA-N

InChi Code

InChI=1S/C60H92N8O12/c1-17-38(9)46(56(76)65(14)47(36(5)6)51(71)61-42(32-35(3)4)54(74)67(16)60(58(78)80-60)59(11,12)79)63-50(70)44-30-25-31-68(44)55(75)45(34-41-28-23-20-24-29-41)64(13)53(73)43(33-40-26-21-19-22-27-40)62-52(72)48(37(7)8)66(15)57(77)49(69)39(10)18-2/h19-24,26-29,35-39,42-49,69,79H,17-18,25,30-34H2,1-16H3,(H,61,71)(H,62,72)(H,63,70)/t38-,39?,42+,43+,44+,45+,46+,47+,48+,49?,60+/m1/s1

SMILES Code

CC(C)(O)[C@@]1(C(O1)=O)N(C([C@H](CC(C)C)NC([C@H](C(C)C)N(C([C@H]([C@H](C)CC)NC([C@H]2N(C([C@H](CC3=CC=CC=C3)N(C([C@H](CC4=CC=CC=C4)NC([C@H](C(C)C)N(C(C(O)C(C)CC)=O)C)=O)=O)C)=O)CCC2)=O)=O)C)=O)=O)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

Soluble in DMSO

Shelf Life

>3 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).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Basifungin is an inositol phosphorylceramide synthase inhibitor.

In vitro activity:

The antifungal activity of Aureobasidin A (AbA) was studied in vitro in comparison with clinically effective antifungal agents, amphotericin B and fluconazole. AbA was highly active in vitro against many pathogenic fungi, including Candida albicans, Cryptococcus neoformans, Blastomyces dermatitidis and Histoplasma capsulatum. The activity was superior to amphotericin B in most cases. AbA exhibited fungicidal action toward growing cultures of C. albicans. Reference: J Antibiot (Tokyo). 1993 Sep;46(9):1414-20. https://www.jstage.jst.go.jp/article/antibiotics1968/46/9/46_9_1414/_article

In vivo activity:

AbA was highly tolerated by mice and showed good efficacy in the treatment of murine systemic candidiasis when given orally or subcutaneously. AbA's fungicidal action in mice with candidiasis was more effective than fluconazole and amphotericin B. Reference: J Antibiot (Tokyo). 1993 Sep;46(9):1414-20. https://www.jstage.jst.go.jp/article/antibiotics1968/46/9/46_9_1414/_article

Preparing Stock Solutions

The following data is based on the product molecular weight 1,117.44 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

Formulation protocol:

1. Takesako K, Kuroda H, Inoue T, Haruna F, Yoshikawa Y, Kato I, Uchida K, Hiratani T, Yamaguchi H. Biological properties of aureobasidin A, a cyclic depsipeptide antifungal antibiotic. J Antibiot (Tokyo). 1993 Sep;46(9):1414-20. doi: 10.7164/antibiotics.46.1414. PMID: 8226319.

In vitro protocol:

In vivo protocol:

1: Tan HW, Tay ST. The inhibitory effects of aureobasidin A on Candida planktonic and biofilm cells. Mycoses. 2013 Mar;56(2):150-6. doi: 10.1111/j.1439-0507.2012.02225.x. Epub 2012 Aug 12. PubMed PMID: 22882276. 2: Alqaisi AQI, Mbekeani AJ, Llorens MB, Elhammer AP, Denny PW. The antifungal Aureobasidin A and an analogue are active against the protozoan parasite Toxoplasma gondii but do not inhibit sphingolipid biosynthesis. Parasitology. 2018 Feb;145(2):148-155. doi: 10.1017/S0031182017000506. Epub 2017 May 10. PubMed PMID: 28486997; PubMed Central PMCID: PMC5964465. 3: Takesako K, Kuroda H, Inoue T, Haruna F, Yoshikawa Y, Kato I, Uchida K, Hiratani T, Yamaguchi H. Biological properties of aureobasidin A, a cyclic depsipeptide antifungal antibiotic. J Antibiot (Tokyo). 1993 Sep;46(9):1414-20. PubMed PMID: 8226319. 4: Wuts PG, Simons LJ, Metzger BP, Sterling RC, Slightom JL, Elhammer AP. Generation of Broad-Spectrum Antifungal Drug Candidates from the Natural Product Compound Aureobasidin A. ACS Med Chem Lett. 2015 Apr 23;6(6):645-9. doi: 10.1021/acsmedchemlett.5b00029. eCollection 2015 Jun 11. PubMed PMID: 26101567; PubMed Central PMCID: PMC4468416. 5: Katsuki Y, Yamaguchi Y, Tani M. Overexpression of PDR16 confers resistance to complex sphingolipid biosynthesis inhibitor aureobasidin A in yeast Saccharomyces cerevisiae. FEMS Microbiol Lett. 2018 Feb 1;365(3). doi: 10.1093/femsle/fnx255. PubMed PMID: 29240942. 6: Alqaisi AQI, Mbekeani AJ, Llorens MB, Elhammer AP, Denny PW. The antifungal Aureobasidin A and an analogue are active against the protozoan parasite Toxoplasma gondii but do not inhibit sphingolipid biosynthesis - Corrigendum. Parasitology. 2018 Feb;145(2):156. doi: 10.1017/S0031182017000877. Epub 2017 Jun 9. PubMed PMID: 28595661; PubMed Central PMCID: PMC5964473. 7: Munusamy K, Vadivelu J, Tay ST. A study on Candida biofilm growth characteristics and its susceptibility to aureobasidin A. Rev Iberoam Micol. 2018 Apr - Jun;35(2):68-72. doi: 10.1016/j.riam.2017.07.001. Epub 2018 Mar 12. PubMed PMID: 29544734. 8: Wang XH, Guo XJ, Li HY, Gou P. Characteristics of inositol phosphorylceramide synthase and effects of aureobasidin A on growth and pathogenicity of Botrytis cinerea. J Gen Appl Microbiol. 2015;61(4):108-16. doi: 10.2323/jgam.61.108. PubMed PMID: 26377130. 9: Endo M, Takesako K, Kato I, Yamaguchi H. Fungicidal action of aureobasidin A, a cyclic depsipeptide antifungal antibiotic, against Saccharomyces cerevisiae. Antimicrob Agents Chemother. 1997 Mar;41(3):672-6. PubMed PMID: 9056012; PubMed Central PMCID: PMC163770. 10: Ikai K, Shiomi K, Takesako K, Kato I, Naganawa H. NMR studies of aureobasidins A and E. J Antibiot (Tokyo). 1991 Nov;44(11):1199-207. PubMed PMID: 1761416. 11: Takahashi T, Ohara Y, Sawatari M, Sueno K. Isolation and characterization of sake yeast mutants with enhanced isoamyl acetate productivity. J Biosci Bioeng. 2017 Jan;123(1):71-77. doi: 10.1016/j.jbiosc.2016.07.002. Epub 2016 Jul 27. PubMed PMID: 27475923. 12: Cerantola V, Guillas I, Roubaty C, Vionnet C, Uldry D, Knudsen J, Conzelmann A. Aureobasidin A arrests growth of yeast cells through both ceramide intoxication and deprivation of essential inositolphosphorylceramides. Mol Microbiol. 2009 Mar;71(6):1523-37. doi: 10.1111/j.1365-2958.2009.06628.x. Epub 2009 Feb 2. PubMed PMID: 19210614. 13: Aoki K, Uchiyama R, Yamauchi S, Katayama T, Itonori S, Sugita M, Hada N, Yamada-Hada J, Takeda T, Kumagai H, Yamamoto K. Newly discovered neutral glycosphingolipids in aureobasidin A-resistant zygomycetes: Identification of a novel family of Gala-series glycolipids with core Gal alpha 1-6Gal beta 1-6Gal beta sequences. J Biol Chem. 2004 Jul 30;279(31):32028-34. Epub 2004 May 20. PubMed PMID: 15155728. 14: Gostinčar C, Ohm RA, Kogej T, Sonjak S, Turk M, Zajc J, Zalar P, Grube M, Sun H, Han J, Sharma A, Chiniquy J, Ngan CY, Lipzen A, Barry K, Grigoriev IV, Gunde-Cimerman N. Genome sequencing of four Aureobasidium pullulans varieties: biotechnological potential, stress tolerance, and description of new species. BMC Genomics. 2014 Jul 1;15:549. doi: 10.1186/1471-2164-15-549. PubMed PMID: 24984952; PubMed Central PMCID: PMC4227064. 15: Tiberghien F, Kurome T, Takesako K, Didier A, Wenandy T, Loor F. Aureobasidins: structure-activity relationships for the inhibition of the human MDR1 P-glycoprotein ABC-transporter. J Med Chem. 2000 Jun 29;43(13):2547-56. PubMed PMID: 10891114. 16: Kuroda M, Hashida-Okado T, Yasumoto R, Gomi K, Kato I, Takesako K. An aureobasidin A resistance gene isolated from Aspergillus is a homolog of yeast AUR1, a gene responsible for inositol phosphorylceramide (IPC) synthase activity. Mol Gen Genet. 1999 Mar;261(2):290-6. PubMed PMID: 10102364. 17: Tani Y, Funatsu T, Ashida H, Ito M, Itonori S, Sugita M, Yamamoto K. Novel neogala-series glycosphingolipids with terminal mannose and glucose residues from Hirsutella rhossiliensis, an aureobasidin A-resistant ascomycete fungus. Glycobiology. 2010 Jan;20(4):433-41. doi: 10.1093/glycob/cwp190. Epub 2009 Dec 9. PubMed PMID: 20007186. 18: Ogawa A, Hashida-Okado T, Endo M, Yoshioka H, Tsuruo T, Takesako K, Kato I. Role of ABC transporters in aureobasidin A resistance. Antimicrob Agents Chemother. 1998 Apr;42(4):755-61. PubMed PMID: 9559778; PubMed Central PMCID: PMC105537. 19: Kurome T, Inoue T, Takesako K, Kato I. Syntheses of antifungal aureobasidin A analogs with alkyl chains for structure-activity relationship. J Antibiot (Tokyo). 1998 Mar;51(3):359-67. PubMed PMID: 9589073. 20: Shimizu T, Kinoshita H, Nihira T. Development of transformation system in Monascus purpureus using an autonomous replication vector with aureobasidin A resistance gene. Biotechnol Lett. 2006 Jan;28(2):115-20. PubMed PMID: 16369695.