Indolmycin

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

MedKoo CAT#: 584976

CAS#: 21200-24-8

Description: Indolmycin is a topical agent for control of staphylococcal infections.

Chemical Structure

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Indolmycin
CAS# 21200-24-8
Instruction

Theoretical Analysis

MedKoo Cat#: 584976
Name: Indolmycin
CAS#: 21200-24-8
Chemical Formula: C14H15N3O2
Exact Mass: 257.12
Molecular Weight: 257.293
Elemental Analysis: C, 65.36; H, 5.88; N, 16.33; O, 12.44

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Indolmycin; Indolemycin; PA 155 A; PA-155-A

IUPAC/Chemical Name: 2-Oxazolin-4-one, 5-(1-indol-3-ylethyl)-2-(methylamino)-, (1R,5S)-(-)-

InChi Key: GNTVWGDQPXCYBV-PELKAZGASA-N

InChi Code: InChI=1S/C14H15N3O2/c1-8(12-13(18)17-14(15-2)19-12)10-7-16-11-6-4-3-5-9(10)11/h3-8,12,16H,1-2H3,(H,15,17,18)/t8-,12+/m1/s1

SMILES Code: O=C1N=C(NC)O[C@H]1[C@@H](C2=CNC3=C2C=CC=C3)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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 257.29 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:
In vitro protocol:
In vivo protocol:

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Reconstitution Calculator

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1: Williams TL, Yin YW, Carter CW Jr. Selective Inhibition of Bacterial Tryptophanyl-tRNA Synthetases by Indolmycin Is Mechanism-based. J Biol Chem. 2016 Jan 1;291(1):255-65. doi: 10.1074/jbc.M115.690321. Epub 2015 Nov 9. PubMed PMID: 26555258; PubMed Central PMCID: PMC4697160.

2: Du YL, Alkhalaf LM, Ryan KS. In vitro reconstitution of indolmycin biosynthesis reveals the molecular basis of oxazolinone assembly. Proc Natl Acad Sci U S A. 2015 Mar 3;112(9):2717-22. doi: 10.1073/pnas.1419964112. Epub 2015 Feb 17. PubMed PMID: 25730866; PubMed Central PMCID: PMC4352800.

3: Hurdle JG, O'Neill AJ, Chopra I. Anti-staphylococcal activity of indolmycin, a potential topical agent for control of staphylococcal infections. J Antimicrob Chemother. 2004 Aug;54(2):549-52. Epub 2004 Jul 8. PubMed PMID: 15243028.

4: Kitabatake M, Ali K, Demain A, Sakamoto K, Yokoyama S, Söll D. Indolmycin resistance of Streptomyces coelicolor A3(2) by induced expression of one of its two tryptophanyl-tRNA synthetases. J Biol Chem. 2002 Jun 28;277(26):23882-7. Epub 2002 Apr 22. PubMed PMID: 11970956.

5: Vecchione JJ, Sello JK. A novel tryptophanyl-tRNA synthetase gene confers high-level resistance to indolmycin. Antimicrob Agents Chemother. 2009 Sep;53(9):3972-80. doi: 10.1128/AAC.00723-09. Epub 2009 Jun 22. PubMed PMID: 19546369; PubMed Central PMCID: PMC2737876.

6: Thøgersen MS, Delpin MW, Melchiorsen J, Kilstrup M, Månsson M, Bunk B, Spröer C, Overmann J, Nielsen KF, Gram L. Production of the Bioactive Compounds Violacein and Indolmycin Is Conditional in a maeA Mutant of Pseudoalteromonas luteoviolacea S4054 Lacking the Malic Enzyme. Front Microbiol. 2016 Sep 16;7:1461. eCollection 2016. PubMed PMID: 27695447; PubMed Central PMCID: PMC5025454.

7: Werner RG. Uptake of indolmycin in gram-positive bacteria. Antimicrob Agents Chemother. 1980 Dec;18(6):858-62. PubMed PMID: 7235673; PubMed Central PMCID: PMC352978.

8: Hornemann U, Speedie MK, Hurley LH, Floss HG. Demonstration of a C-methylating enzyme in cell free extracts of indolmycin-producing Streptomyces griseus. Biochem Biophys Res Commun. 1970 May 22;39(4):594-9. PubMed PMID: 5490210.

9: Bogosian G, Haydock PV, Somerville RL. Indolmycin-mediated inhibition and stimulation of transcription at the trp promoter of Escherichia coli. J Bacteriol. 1983 Feb;153(2):1120-3. PubMed PMID: 6337120; PubMed Central PMCID: PMC221749.

10: Hasuoka A, Nakayama Y, Adachi M, Kamiguchi H, Kamiyama K. Development of a stereoselective practical synthetic route to indolmycin, a candidate anti-H. pylori agent. Chem Pharm Bull (Tokyo). 2001 Dec;49(12):1604-8. PubMed PMID: 11767081.

11: Werner RG, Thorpe LF, Reuter W, Nierhaus KH. Indolmycin inhibits prokaryotic tryptophanyl-tRNA ligase. Eur J Biochem. 1976 Sep;68(1):1-3. PubMed PMID: 786633.

12: Chan TH, Hill RK. The absolute configuration of indolmycin. J Org Chem. 1970 Oct;35(10):3519-21. PubMed PMID: 5507097.

13: Harnden MR, Bailey S, Boyd MR, Taylor DR, Wright ND. Thiazolinone analogues of indolmycin with antiviral and antibacterial activity. J Med Chem. 1978 Jan;21(1):82-7. PubMed PMID: 619151.

14: Pasaje CF, Cheung V, Kennedy K, Lim EE, Baell JB, Griffin MD, Ralph SA. Selective inhibition of apicoplast tryptophanyl-tRNA synthetase causes delayed death in Plasmodium falciparum. Sci Rep. 2016 Jun 9;6:27531. doi: 10.1038/srep27531. PubMed PMID: 27277538; PubMed Central PMCID: PMC4899734.

15: Hurley LH, Bialek D. Regulation of antibiotic production: catabolite inhibition and the dualistic effect of glucose on indolmycin production. J Antibiot (Tokyo). 1974 Jan;27(1):49-56. PubMed PMID: 4210488.

16: Werner RG, Reuter W. Interaction of indolmycin in the metabolism of tryptophan in rat liver. Arzneimittelforschung. 1979;29(1):59-63. PubMed PMID: 582120.

17: Hornemann U, Hurley LH, Speedie MK, Floss HG. The biosynthesis of indolmycin. J Am Chem Soc. 1971 Jun 16;93(12):3028-35. PubMed PMID: 5095271.

18: Harnden MR, Wright ND. Total synthesis of thiazolinone analogues of indolmycin. J Chem Soc Perkin 1. 1977;(9):1012-8. PubMed PMID: 559006.

19: Speedie MK, Hornemann U, Floss HG. Isolation and characterization of tryptophan transaminase and indolepyruvate C-methyltransferase. Enzymes involved in indolmycin biosynthesis in Streptomyces griseus. J Biol Chem. 1975 Oct 10;250(19):7819-25. PubMed PMID: 809439.

20: Preobrazhenskaya MN, Balashova EG, Turchin KF, Padeiskaya EN, Uvarova NV, Pershin GN, Suvorov NN. Total synthesis of antibiotic indolmycin and its stereoisomers. Tetrahedron. 1968 Oct;24(19):6131-43. PubMed PMID: 5729561.