Streptolydigin | CAS#7229-50-7 | antibiotic

MedKoo Cat#: 563727 | Name: Streptolydigin

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Description:

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

Streptolydigin is an antibiotic, inhibiting RNA polymerase by sequestering the active center in a catalytically inactive conformation.

Chemical Structure

Streptolydigin

CAS#7229-50-7

Theoretical Analysis

MedKoo Cat#: 563727

Name: Streptolydigin

CAS#: 7229-50-7

Chemical Formula: C32H44N2O9

Exact Mass: 600.3047

Molecular Weight: 600.71

Elemental Analysis: C, 63.98; H, 7.38; N, 4.66; O, 23.97

Price and Availability

Size	Price	Availability
5mg	USD 750.00	2 Weeks
10mg	USD 1,200.00	2 Weeks
25mg	USD 2,450.00	2 Weeks

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Related CAS #

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Synonym

Streptolydigin; Antibiotic D-45; Portamycin; NSC 3360;

IUPAC/Chemical Name

(2S)-2-[(2S,4E)-4-[(2E,4E,6R)-6-[(1R,2S,3R,5R,6R)-2,5-dimethylspiro[4,9-dioxabicyclo[3.3.1]non-7-ene-6,2'-oxirane]-3-yl]-1-hydroxy-4-methylhepta-2,4-dienylidene]-1-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]-3,5-dioxopyrrolidin-2-yl]-N-methylpropanamide

InChi Key

KVTPRMVXYZKLIG-NCAOFHFGSA-N

InChi Code

InChI=1S/C32H44N2O9/c1-16(14-17(2)28-18(3)23-12-13-32(15-40-32)31(6,42-23)43-28)8-9-22(36)25-27(37)26(19(4)29(38)33-7)34(30(25)39)24-11-10-21(35)20(5)41-24/h8-9,12-14,17-21,23-24,26,28,35-36H,10-11,15H2,1-7H3,(H,33,38)/b9-8+,16-14+,25-22+/t17-,18+,19+,20+,21+,23-,24+,26+,28-,31-,32-/m1/s1

SMILES Code

C[C@@H]([C@@H](C(/C1=C(O)/C=C/C(C)=C/[C@H]([C@@H]2[C@@H](C)[C@@](O3)([H])C=C[C@]4(OC4)[C@@]3(C)O2)C)=O)N([C@H]5O[C@@H](C)[C@@H](O)CC5)C1=O)C(NC)=O

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

To be determined

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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Streptolydigin inhibits nucleic acid chain elongation by binding to RNA polymerase, thus inhibiting RNA synthesis inside a cell. Streptolydigin inhibits bacterial RNA polymerase, but not eukaryotic RNA polymerase.

In vitro activity:

This study shows that streptolydigin is not a suitable drug for tuberculosis treatment. Streptolydigin on S. salivarius and M. smegmatis showed susceptibility (MICs of 1.6 mg/L and 6.25 mg/L respectively), while M. tuberculosis exhibited resistance (MICs ≥ 100 mg/L). A porin mutant of M. smegmatis was also resistant, suggesting porins aid streptolydigin uptake. This resistance likely stems from M. tuberculosis’s lack of MspA-like porins. Reference: Tuberculosis (Edinb). 2013 Jul;93(4):401-4. https://pubmed.ncbi.nlm.nih.gov/23591156/

In vivo activity:

To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 600.71 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. Speer A, Rowland JL, Niederweis M. Mycobacterium tuberculosis is resistant to streptolydigin. Tuberculosis (Edinb). 2013 Jul;93(4):401-4. doi: 10.1016/j.tube.2013.03.002. Epub 2013 Apr 13. PMID: 23591156; PMCID: PMC3681836. 2. Pronin SV, Martinez A, Kuznedelov K, Severinov K, Shuman HA, Kozmin SA. Chemical synthesis enables biochemical and antibacterial evaluation of streptolydigin antibiotics. J Am Chem Soc. 2011 Aug 10;133(31):12172-84. doi: 10.1021/ja2041964. Epub 2011 Jul 20. PMID: 21714556; PMCID: PMC3174773.

In vitro protocol:

In vivo protocol:

To be determined

1: DEBOER C, DIETZ A, SAVAGE GM, SILVER WS. Streptolydigin, a new antimicrobial antibiotic. I. Biologic studies of streptolydigin. Antibiot Annu. 1955-1956;3:886-92. PMID: 13355381. 2: CRUM GF, DEVRIES WH, EBLE TE, LARGE CM, SHELL JW. Streptolydigin, a new antimicrobial antibiotic. II. Isolation and characterization. Antibiot Annu. 1955-1956;3:893-6. PMID: 13355382. 3: LEWIS C, NIKITAS CT, SCHWARTZ DF, WILKINS JR. Streptolydigin, a new antimicrobial antibiotic. III. In vitro and in vivo laboratory studies. Antibiot Annu. 1955-1956;3:897-902. PMID: 13355383. 4: RINEHART KL Jr, BECK JR, BORDERS DB, EPSTEIN WW, KINSTLE TH, SPICER LD, KRAUSS D, BUTTON AC. STRUCTURE OF STREPTOLYDIGIN. Antimicrob Agents Chemother (Bethesda). 1963;161:346-8. PMID: 14274922. 5: Siddhikol C, Erbstoeszer JW, Weisblum B. Mode of action of streptolydigin. J Bacteriol. 1969 Jul;99(1):151-5. doi: 10.1128/jb.99.1.151-155.1969. PMID: 4308412; PMCID: PMC249980. 6: Schleif R. Isolation and characterization of streptolydigin resistant RNA polymerase. Nature. 1969 Sep 6;223(5210):1068-9. doi: 10.1038/2231068a0. PMID: 4897821. 7: Reusser F. Streptolydigin, an inhibitor of oxidative phosphorylation in rat liver mitochondria. J Bacteriol. 1969 Dec;100(3):1335-41. doi: 10.1128/jb.100.3.1335-1341.1969. PMID: 4311869; PMCID: PMC250331. 8: Tipper DJ, Pratt I. Cell wall polymers of Bacillus sphaericus 9602. II. Synthesis of the first enzyme unique to cortex synthesis during sporulation. J Bacteriol. 1970 Aug;103(2):305-17. doi: 10.1128/jb.103.2.305-317.1970. PMID: 4988239; PMCID: PMC248080. 9: Sokolova EV, Ovadis MI, Gorlenko ZM, Khesin RB. Localization of streptolydigin resistant mutation in E. coli chromosome and effect of streptolydigin on T2 phage development in stl-r and stl-s strains of E. coli. Biochem Biophys Res Commun. 1970 Nov 25;41(4):870-6. doi: 10.1016/0006-291x(70)90164-6. PMID: 4920473. 10: Cassani G, Burgess RR, Goodman HM, Gold L. Inhibition of RNA polymerase by streptolydigin. Nat New Biol. 1971 Apr 14;230(15):197-200. doi: 10.1038/newbio230197a0. PMID: 5280166. 11: von der Helm K, Krakow JS. Inhibition of RNA polymerase by streptolydigin. Nat New Biol. 1972 Jan 19;235(55):82-3. doi: 10.1038/newbio235082a0. PMID: 4501346. 12: Doolittle WF. Ribosomal ribonucleic acid synthesis and maturation in the blue-green alga Anacystis nidulans. J Bacteriol. 1972 Aug;111(2):316-24. doi: 10.1128/jb.111.2.316-324.1972. PMID: 4626497; PMCID: PMC251284. 13: Milanesi G, Cassani G. Transcription after bacteriophage SPP1 infection in Bacillus subtilis. J Virol. 1972 Aug;10(2):187-92. doi: 10.1128/JVI.10.2.187-192.1972. PMID: 4627475; PMCID: PMC356449. 14: Schekman R, Wickner W, Westergaard O, Brutlag D, Geider K, Bertsch LL, Kornberg A. Initiation of DNA synthesis: synthesis of phiX174 replicative form requires RNA synthesis resistant to rifampicin. Proc Natl Acad Sci U S A. 1972 Sep;69(9):2691-5. doi: 10.1073/pnas.69.9.2691. PMID: 4560696; PMCID: PMC427018. 15: Iwakura Y, Ishihama A, Yura T. RNA polymerase mutants of Escherichia coli. Streptolydigin resistance and its relation to rifampicin resistance. Mol Gen Genet. 1973 Mar 1;121(2):181-96. doi: 10.1007/BF00277531. PMID: 4571524. 16: Haworth SR, Brown LR. Genetic analysis of ribonucleic acid polymerase mutants of Bacillus subtilis. J Bacteriol. 1973 Apr;114(1):103-13. doi: 10.1128/jb.114.1.103-113.1973. PMID: 4144588; PMCID: PMC251745. 17: Clewell DB, Evenchik BG. Effects of rifampicin, streptolydigin and actinomycin D on the replication of Col E1 plasmid DNA in Escherichia coli. J Mol Biol. 1973 Apr 15;75(3):503-13. doi: 10.1016/0022-2836(73)90457-9. PMID: 4579715. 18: Duchamp DJ, Branfman AR, Button AC, Rinehart KL Jr. X-ray structure of tirandamycic acid p-bromophenacyl ester. Complete stereochemical assignments of tirandamycin and streptolydigin. J Am Chem Soc. 1973 Jun 13;95(12):4077-8. doi: 10.1021/ja00793a058. PMID: 4710070. 19: Laurent SJ. Initiation of deoxyribonucleic acid replication in a temperature-sensitive mutant of B. subtilis: evidence for a transcriptional step. J Bacteriol. 1973 Oct;116(1):141-5. doi: 10.1128/jb.116.1.141-145.1973. PMID: 4200838; PMCID: PMC246401. 20: Mindlin SZ, Danilevskaia ON, Vel'kov VV, Sokolova EV. Geneticheskiĭ izuchenie mutatsiĭ, izmeniaiushchikh dominirovanie alleleĭ chuvstvitel'nosti RNK-polimerazy Escherichia coli K-12 k rifampitsinu i streptolidiginu [Genetic study of mutations changing the dominance of alleles of sensitivity of Escherichia coli K-12 RNA polymerase to rifampicin and streptolydigin]. Genetika. 1973 Dec;9(12):84-94. Russian. PMID: 4619996.