MedKoo Cat#: 464014 | Name: Trypacidin
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Description:

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

Trypacidin is a fungal metabolite originally isolated from A. fumigatus. It is active against B. subtilis and M. bovis, as well as T. cruzi and T. gondii. It reduces viability and induces lysis of A549 human lung cancer cells. Trypacidin increases survival in a mouse model of T. gondii infection when administered in six doses of 12.5 mg/kg each.

Chemical Structure

Trypacidin
Trypacidin
CAS#1900-29-4

Theoretical Analysis

MedKoo Cat#: 464014

Name: Trypacidin

CAS#: 1900-29-4

Chemical Formula: C18H16O7

Exact Mass: 344.0896

Molecular Weight: 344.32

Elemental Analysis: C, 62.79; H, 4.68; O, 32.53

Price and Availability

Size Price Availability Quantity
1mg USD 500.00 2 Weeks
5mg USD 1,000.00 2 Weeks
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Related CAS #
No Data
Synonym
Trypacidin;
IUPAC/Chemical Name
methyl 4,6'-dimethoxy-6-methyl-3,4'-dioxo-3H-spiro[benzofuran-2,1'-cyclohexane]-2',5'-diene-2'-carboxylate
InChi Key
KMZYINVXZDQCKC-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H16O7/c1-9-5-12(22-2)15-13(6-9)25-18(16(15)20)11(17(21)24-4)7-10(19)8-14(18)23-3/h5-8H,1-4H3
SMILES Code
O=C1C2(OC3=CC(C)=CC(OC)=C13)C(C(OC)=O)=CC(C=C2OC)=O
Appearance
Solid powder
Purity
>95% (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).
HS Tariff Code
2934.99.9001
More Info
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 344.32 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.

Recalculate based on batch purity %
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: Steenwyk JL, Mead ME, Knowles SL, Raja HA, Roberts CD, Bader O, Houbraken J, Goldman GH, Oberlies NH, Rokas A. Variation Among Biosynthetic Gene Clusters, Secondary Metabolite Profiles, and Cards of Virulence Across Aspergillus Species. Genetics. 2020 Oct;216(2):481-497. doi: 10.1534/genetics.120.303549. Epub 2020 Aug 17. PMID: 32817009; PMCID: PMC7536862. 2: Blachowicz A, Chiang AJ, Romsdahl J, Kalkum M, Wang CCC, Venkateswaran K. Proteomic characterization of Aspergillus fumigatus isolated from air and surfaces of the International Space Station. Fungal Genet Biol. 2019 Mar;124:39-46. doi: 10.1016/j.fgb.2019.01.001. Epub 2019 Jan 3. PMID: 30611835. 3: Zhang H, Zhu HT, Wang D, Yang CR, Zhang YJ. Sphingofungins G and H: new five- membered lactones from Aspergillus penicilliodes Speg. Nat Prod Res. 2019 May;33(9):1284-1291. doi: 10.1080/14786419.2018.1470627. Epub 2018 May 10. PMID: 29745730. 4: Hagiwara D, Sakai K, Suzuki S, Umemura M, Nogawa T, Kato N, Osada H, Watanabe A, Kawamoto S, Gonoi T, Kamei K. Temperature during conidiation affects stress tolerance, pigmentation, and trypacidin accumulation in the conidia of the airborne pathogen Aspergillus fumigatus. PLoS One. 2017 May 9;12(5):e0177050. doi: 10.1371/journal.pone.0177050. PMID: 28486558; PMCID: PMC5423626. 5: Weber J, Valiante V, Nødvig CS, Mattern DJ, Slotkowski RA, Mortensen UH, Brakhage AA. Functional Reconstitution of a Fungal Natural Product Gene Cluster by Advanced Genome Editing. ACS Synth Biol. 2017 Jan 20;6(1):62-68. doi: 10.1021/acssynbio.6b00203. Epub 2016 Sep 13. PMID: 27611015. 6: Mattern DJ, Schoeler H, Weber J, Novohradská S, Kraibooj K, Dahse HM, Hillmann F, Valiante V, Figge MT, Brakhage AA. Identification of the antiphagocytic trypacidin gene cluster in the human-pathogenic fungus Aspergillus fumigatus. Appl Microbiol Biotechnol. 2015 Dec;99(23):10151-61. doi: 10.1007/s00253-015-6898-1. Epub 2015 Aug 18. PMID: 26278536. 7: Throckmorton K, Lim FY, Kontoyiannis DP, Zheng W, Keller NP. Redundant synthesis of a conidial polyketide by two distinct secondary metabolite clusters in Aspergillus fumigatus. Environ Microbiol. 2016 Jan;18(1):246-59. doi: 10.1111/1462-2920.13007. Epub 2015 Sep 3. PMID: 26242966; PMCID: PMC4750049. 8: Pinheiro EA, Carvalho JM, Santos DC, Feitosa AO, Marinho PS, Guilhon GM, Santos LS, Souza AL, Marinho AM. Chemical constituents of Aspergillus sp EJC08 isolated as endophyte from Bauhinia guianensis and their antimicrobial activity. An Acad Bras Cienc. 2013;85(4):1247-53. doi: 10.1590/0001-3765201395512. Epub 2013 Oct 21. PMID: 24141408. 9: Gauthier T, Wang X, Sifuentes Dos Santos J, Fysikopoulos A, Tadrist S, Canlet C, Artigot MP, Loiseau N, Oswald IP, Puel O. Trypacidin, a spore-borne toxin from Aspergillus fumigatus, is cytotoxic to lung cells. PLoS One. 2012;7(2):e29906. doi: 10.1371/journal.pone.0029906. Epub 2012 Feb 3. PMID: 22319557; PMCID: PMC3272003. 10: Frisvad JC, Rank C, Nielsen KF, Larsen TO. Metabolomics of Aspergillus fumigatus. Med Mycol. 2009;47 Suppl 1:S53-71. doi: 10.1080/13693780802307720. Epub 2008 Sep 1. PMID: 18763205. 11: Larsen TO, Smedsgaard J, Nielsen KF, Hansen MA, Samson RA, Frisvad JC. Production of mycotoxins by Aspergillus lentulus and other medically important and closely related species in section Fumigati. Med Mycol. 2007 May;45(3):225-32. doi: 10.1080/13693780601185939. PMID: 17464844. 12: Fischer G, Müller T, Schwalbe R, Ostrowski R, Dott W. Species-specific profiles of mycotoxins produced in cultures and associated with conidia of airborne fungi derived from biowaste. Int J Hyg Environ Health. 2000 Oct;203(2):105-16. doi: 10.1078/S1438-4639(04)70015-2. PMID: 11109562. 13: Fischer G, Müller T, Ostrowski R, Schwalbe R, Dott W. Mykotoxine als Expositionsparameter in Bioaerosolen von Kompostierungsanlagen [Mycotoxins as exposure parameters in bioaerosols of composting sites]. Schriftenr Ver Wasser Boden Lufthyg. 1999;104:149-62. German. PMID: 10803222. 14: Fischer G, Müller T, Ostrowski R, Dott W. Mycotoxins of Aspergillus fumigatus in pure culture and in native bioaerosols from compost facilities. Chemosphere. 1999 Apr;38(8):1745-55. doi: 10.1016/s0045-6535(98)00391-9. PMID: 10101846. 15: Gutteridge WE, Knowler J, Coombes JD. Growth of Trypanosoma cruzi in human heart tissue cells and effects of aminonucleoside of puromycin, trypacidin and aminopterin. J Protozool. 1969 Aug;16(3):521-5. doi: 10.1111/j.1550-7408.1969.tb02311.x. PMID: 5343467. 16: Parker GF, Jenner PC. Distribution of trypacidin in cultures of Aspergillus fumigatus. Appl Microbiol. 1968 Aug;16(8):1251-2. PMID: 5675513; PMCID: PMC547628. 17: Turner WB. The production of trypacidin and monomethylsulochrin by Aspergillus fumigatus. J Chem Soc Perkin 1. 1965 Sep:6658-9. doi: 10.1039/jr9650006658. PMID: 5891972. 18: EBRINGER L, BALAN J, CATAR G, HORAKOVA K, EBRINGEROVA J. EFFECT OF TRYPACIDIN ON TOXOPLASMA GONDII IN TISSUE CULTURE AND IN MICE. Exp Parasitol. 1965 Apr;16:182-9. doi: 10.1016/0014-4894(65)90042-1. PMID: 14281215. 19: BALAN J, KJAER A, KOVAC S, SHAPIRO RH. THE STRUCTURE OF TRYPACIDIN. Acta Chem Scand. 1965;19:528-30. doi: 10.3891/acta.chem.scand.19-0528. PMID: 14298281. 20: EBRINGER L, CATAR G, BALAN J, NEMEC P, KOV'AC S. ANTIPROTOZOAL ANTIBIOTICS. III. PRELIMINARY REPORT ON THE EFFECT OF TRYPACIDIN ON EXPERIMENTAL TOXOPLASMOSIS. J Antibiot (Tokyo). 1963 Jul;16:161-2. PMID: 14044930.