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MedKoo Cat#: 540049 | Name: Blasticidin S hydrochloride
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Description:

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

Blasticidin S hydrochloride is a protein translation inhibitor that induces deformations in P-site tRNA. It inhibits aflatoxin production in species of Aspergillus.

Chemical Structure

Blasticidin S hydrochloride
Blasticidin S hydrochloride
CAS#3513-03-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 540049

Name: Blasticidin S hydrochloride

CAS#: 3513-03-9 (HCl)

Chemical Formula: C17H27ClN8O5

Exact Mass: 458.1793

Molecular Weight: 458.90

Elemental Analysis: C, 44.49; H, 5.93; Cl, 7.72; N, 24.42; O, 17.43

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
25mg USD 450.00 2 Weeks
50mg USD 750.00 2 Weeks
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Related CAS #
2079-00-7 (free base) 3513-03-9 (HCl)
Synonym
Blasticidin S hydrochloride
IUPAC/Chemical Name
(2S,3S,6R)-6-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-((R)-3-amino-5-(1-methylguanidino)pentanamido)-3,6-dihydro-2H-pyran-2-carboxylic acid hydrochloride
InChi Key
YQXYQOXRCNEATG-ZAYJLJTISA-N
InChi Code
InChI=1S/C17H26N8O5.ClH/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29;/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29);1H/t9-,10+,13-,14+;/m1./s1
SMILES Code
O=C([C@@H]1[C@@H](NC(C[C@H](N)CCN(C(N)=N)C)=O)C=C[C@H](N2C=CC(N)=NC2=O)O1)O.[H]Cl
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Blasticidin S HCl is a nucleoside antibiotic isolated from Stretomyces girseochromogenes, and acts as a DNA and protein synthesis inhibitor, used to select transfected cells carrying bsr or BSD resistance genes.
In vitro activity:
Upon titration of BlaS (blasticidin S) into the translation reaction, the synthesis of luciferase decreased in a dose-dependent manner (Figure 1A). Inhibition of translation was observed at BlaS concentrations as low as 5 nM, and translation was completely inhibited by concentrations above 175 nM. The half-maximal inhibitory concentration (IC50) was determined to be 21 nM. Reference: Nucleic Acids Res. 2021 Jul 21; 49(13): 7665–7679. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8287960/
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
Water 48.3 105.25
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 458.90 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
Formulation protocol:
1. Powers KT, Stevenson-Jones F, Yadav SKN, Amthor B, Bufton JC, Borucu U, Shen D, Becker JP, Lavysh D, Hentze MW, Kulozik AE, Neu-Yilik G, Schaffitzel C. Blasticidin S inhibits mammalian translation and enhances production of protein encoded by nonsense mRNA. Nucleic Acids Res. 2021 Jul 21;49(13):7665-7679. doi: 10.1093/nar/gkab532. PMID: 34157102; PMCID: PMC8287960. 2. Stokowa-Sołtys K, Jeżowska-Bojczuk M. A rice fungicide blasticidin S efficiently binds Cu(II) ions and prevents DNA from metal-induced damage. J Inorg Biochem. 2013 Oct;127:73-8. doi: 10.1016/j.jinorgbio.2013.06.014. Epub 2013 Jun 29. PMID: 23880034.
In vitro protocol:
1. Powers KT, Stevenson-Jones F, Yadav SKN, Amthor B, Bufton JC, Borucu U, Shen D, Becker JP, Lavysh D, Hentze MW, Kulozik AE, Neu-Yilik G, Schaffitzel C. Blasticidin S inhibits mammalian translation and enhances production of protein encoded by nonsense mRNA. Nucleic Acids Res. 2021 Jul 21;49(13):7665-7679. doi: 10.1093/nar/gkab532. PMID: 34157102; PMCID: PMC8287960. 2. Stokowa-Sołtys K, Jeżowska-Bojczuk M. A rice fungicide blasticidin S efficiently binds Cu(II) ions and prevents DNA from metal-induced damage. J Inorg Biochem. 2013 Oct;127:73-8. doi: 10.1016/j.jinorgbio.2013.06.014. Epub 2013 Jun 29. PMID: 23880034.
In vivo protocol:
TBD
1: de Carpentier F, Le Peillet J, Boisset ND, Crozet P, Lemaire SD, Danon A. Blasticidin S Deaminase: A New Efficient Selectable Marker for Chlamydomonas reinhardtii. Front Plant Sci. 2020 Mar 5;11:242. doi: 10.3389/fpls.2020.00242. PMID: 32211000; PMCID: PMC7066984. 2: Gannett C, Banks P, Chuong C, Weger-Lucarelli J, Mevers E, Lowell AN. Semisynthetic blasticidin S ester derivatives show enhanced antibiotic activity. RSC Med Chem. 2023 Mar 8;14(4):782-789. doi: 10.1039/d2md00412g. PMID: 37122539; PMCID: PMC10131614. 3: Powers KT, Stevenson-Jones F, Yadav SKN, Amthor B, Bufton JC, Borucu U, Shen D, Becker JP, Lavysh D, Hentze MW, Kulozik AE, Neu-Yilik G, Schaffitzel C. Blasticidin S inhibits mammalian translation and enhances production of protein encoded by nonsense mRNA. Nucleic Acids Res. 2021 Jul 21;49(13):7665-7679. doi: 10.1093/nar/gkab532. PMID: 34157102; PMCID: PMC8287960. 4: Buck JM, Río Bártulos C, Gruber A, Kroth PG. Blasticidin-S deaminase, a new selection marker for genetic transformation of the diatom Phaeodactylum tricornutum. PeerJ. 2018 Nov 14;6:e5884. doi: 10.7717/peerj.5884. PMID: 30488015; PMCID: PMC6250098. 5: Fujii H. pSIR-bsr, a self-inactivating retrovirus vector expressing the blasticidin S-resistance gene. Biol Methods Protoc. 2021 Dec 6;6(1):bpab022. doi: 10.1093/biomethods/bpab022. PMID: 34926829; PMCID: PMC8678448. 6: Li L, Wu J, Deng Z, Zabriskie TM, He X. Streptomyces lividans blasticidin S deaminase and its application in engineering a blasticidin S-producing strain for ease of genetic manipulation. Appl Environ Microbiol. 2013 Apr;79(7):2349-57. doi: 10.1128/AEM.03254-12. Epub 2013 Feb 1. PMID: 23377931; PMCID: PMC3623232. 7: TAKEUCHI S, HIRAYAMA K, UEDA K, SAKAI H, YONEHARA H. Blasticidin S, a new antibiotic. J Antibiot (Tokyo). 1958 Jan;11(1):1-5. PMID: 13525246. 8: Izumi M, Miyazawa H, Kamakura T, Yamaguchi I, Endo T, Hanaoka F. Blasticidin S-resistance gene (bsr): a novel selectable marker for mammalian cells. Exp Cell Res. 1991 Dec;197(2):229-33. doi: 10.1016/0014-4827(91)90427-v. Erratum in: Exp Cell Res 1993 Feb;204(2):388. PMID: 1720391. 9: Yoshinari T, Sakuda S, Watanabe M, Kamata Y, Ohnishi T, Sugita-Konishi Y. New metabolic pathway for converting blasticidin S in Aspergillus flavus and inhibitory activity of aflatoxin production by blasticidin S metabolites. J Agric Food Chem. 2013 Aug 21;61(33):7925-31. doi: 10.1021/jf402745c. Epub 2013 Aug 12. PMID: 23879927. 10: Svidritskiy E, Korostelev AA. Mechanism of Inhibition of Translation Termination by Blasticidin S. J Mol Biol. 2018 Mar 2;430(5):591-593. doi: 10.1016/j.jmb.2018.01.007. PMID: 29366636; PMCID: PMC5831496. 11: Lee YH, Hou X, Chen R, Feng J, Liu X, Ruszczycky MW, Gao JM, Wang B, Zhou J, Liu HW. Radical S-Adenosyl Methionine Enzyme BlsE Catalyzes a Radical- Mediated 1,2-Diol Dehydration during the Biosynthesis of Blasticidin S. J Am Chem Soc. 2022 Mar 16;144(10):4478-4486. doi: 10.1021/jacs.1c12010. Epub 2022 Mar 3. PMID: 35238201; PMCID: PMC8934444. 12: Yoshinari T, Sugita-Konishi Y, Ohnishi T, Terajima J. Inhibitory Activities of Blasticidin S Derivatives on Aflatoxin Production by Aspergillus Flavus. Toxins (Basel). 2017 May 26;9(6):176. doi: 10.3390/toxins9060176. PMID: 28587144; PMCID: PMC5488026. 13: Svidritskiy E, Ling C, Ermolenko DN, Korostelev AA. Blasticidin S inhibits translation by trapping deformed tRNA on the ribosome. Proc Natl Acad Sci U S A. 2013 Jul 23;110(30):12283-8. doi: 10.1073/pnas.1304922110. Epub 2013 Jul 3. PMID: 23824292; PMCID: PMC3725078. 14: Wang X, Zhao Y, Gao Y, Luo X, Du A, Deng Z, Zabriskie TM, He X, Jiang M. A [3Fe-4S] cluster and tRNA-dependent aminoacyltransferase BlsK in the biosynthesis of Blasticidin S. Proc Natl Acad Sci U S A. 2021 Jul 27;118(30):e2102318118. doi: 10.1073/pnas.2102318118. PMID: 34282016; PMCID: PMC8325364. 15: Li H, Zhao J, Ding W, Zhang Q. Glucuronyl C4 dehydrogenation by the radical SAM enzyme BlsE involved in blasticidin S biosynthesis. Chem Commun (Camb). 2022 Mar 10;58(21):3561-3564. doi: 10.1039/d1cc07132g. PMID: 35199117. 16: Cone MC, Petrich AK, Gould SJ, Zabriskie TM. Cloning and heterologous expression of blasticidin S biosynthetic genes from Streptomyces griseochromogenes. J Antibiot (Tokyo). 1998 Jun;51(6):570-8. doi: 10.7164/antibiotics.51.570. PMID: 9711220. 17: Ichikawa Y, Hirata K, Ohbayashi M, Isobe M. Total synthesis of (+)-blasticidin s. Chemistry. 2004 Jul 5;10(13):3241-51. doi: 10.1002/chem.200305358. PMID: 15224333. 18: Otake N, Takeuchi S, Endo T, Yonehara H. The structure of blasticidin S. Tetrahedron Lett. 1965 May;(19):1411-9. doi: 10.1016/s0040-4039(00)90080-7. PMID: 5842139. 19: Kinoshita T, Tanaka N, Umezawa H. Binding of blasticidin S to ribosomes. J Antibiot (Tokyo). 1970 Jun;23(6):288-90. doi: 10.7164/antibiotics.23.288. PMID: 4917792. 20: Ishiguro J, Miyazaki M. Characterization of blasticidin S-resistant mutants of Saccharomyces cerevisiae. Curr Genet. 1985;9(2):179-81. doi: 10.1007/BF00436968. PMID: 3916720.