Lavendamycin

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

MedKoo CAT#: 598480

CAS#: 81645-09-2

Description: Lavendamycin is a naturally occurring chemical discovered in fermentation broth of the soil bacterium Streptomyces lavendulae. Lavendamycin has antibiotic properties and significant anti-proliferative effects against several cancer cell lines.

Chemical Structure

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Lavendamycin
CAS# 81645-09-2
Instruction

Theoretical Analysis

MedKoo Cat#: 598480
Name: Lavendamycin
CAS#: 81645-09-2
Chemical Formula: C22H14N4O4
Exact Mass: 398.10
Molecular Weight: 398.370
Elemental Analysis: C, 66.33; H, 3.54; N, 14.06; O, 16.06

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.

Request quote for custom synthesis

Synonym: Lavendamycin; NSC 322370; NSC-322370; NSC322370;

IUPAC/Chemical Name: 1-(7-amino-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-methyl-9H-pyrido[3,4-b]indole-3-carboxylic acid

InChi Key: IGQJRDIREIWBQP-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H14N4O4/c1-9-16-10-4-2-3-5-13(10)24-20(16)19(26-17(9)22(29)30)14-7-6-11-15(27)8-12(23)21(28)18(11)25-14/h2-8,24H,23H2,1H3,(H,29,30)

SMILES Code: O=C(C1=C(C)C2=C(C(C3=NC4=C(C(C=C(N)C4=O)=O)C=C3)=N1)NC5=C2C=CC=C5)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: 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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 398.37 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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1: Xia X, Lin S, Xia XX, Cong FS, Zhong JJ. Significance of agitation-induced shear stress on mycelium morphology and lavendamycin production by engineered Streptomyces flocculus. Appl Microbiol Biotechnol. 2014 May;98(10):4399-407. doi: 10.1007/s00253-014-5555-4. Epub 2014 Feb 13. PubMed PMID: 24522728.

2: Boger DL, Yasuda M, Mitscher LA, Drake SD, Kitos PA, Thompson SC. Streptonigrin and lavendamycin partial structures. Probes for the minimum, potent pharmacophore of streptonigrin, lavendamycin, and synthetic quinoline-5,8-diones. J Med Chem. 1987 Oct;30(10):1918-28. PubMed PMID: 3656364.

3: Ramesh S, Nagarajan R. A formal synthesis of lavendamycin methyl ester, nitramarine, and their analogues: a Povarov approach. J Org Chem. 2013 Jan 18;78(2):545-58. doi: 10.1021/jo302389s. Epub 2012 Dec 20. PubMed PMID: 23215629.

4: McElroy WT, DeShong P. Siloxane-based cross-coupling of bromopyridine derivatives: studies for the synthesis of streptonigrin and lavendamycin. Org Lett. 2003 Dec 11;5(25):4779-82. PubMed PMID: 14653672.

5: Cai W, Hassani M, Karki R, Walter ED, Koelsch KH, Seradj H, Lineswala JP, Mirzaei H, York JS, Olang F, Sedighi M, Lucas JS, Eads TJ, Rose AS, Charkhzarrin S, Hermann NG, Beall HD, Behforouz M. Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents. Bioorg Med Chem. 2010 Mar 1;18(5):1899-909. doi: 10.1016/j.bmc.2010.01.037. Epub 2010 Jan 25. PubMed PMID: 20149966; PubMed Central PMCID: PMC2841014.

6: Verniest G, Wang X, De Kimpe N, Padwa A. Heteroaryl cross-coupling as an entry toward the synthesis of lavendamycin analogues: a model study. J Org Chem. 2010 Jan 15;75(2):424-33. doi: 10.1021/jo902287t. PubMed PMID: 20017470.

7: Hassani M, Cai W, Koelsch KH, Holley DC, Rose AS, Olang F, Lineswala JP, Holloway WG, Gerdes JM, Behforouz M, Beall HD. Lavendamycin antitumor agents: structure-based design, synthesis, and NAD(P)H:quinone oxidoreductase 1 (NQO1) model validation with molecular docking and biological studies. J Med Chem. 2008 Jun 12;51(11):3104-15. doi: 10.1021/jm701066a. Epub 2008 May 6. PubMed PMID: 18457384.

8: England DB, Padwa A. Gold-catalyzed cycloisomerization of N-Propargylindole-2-carboxamides: application toward the synthesis of lavendamycin analogues. Org Lett. 2008 Aug 21;10(16):3631-4. doi: 10.1021/ol801385h. Epub 2008 Jul 16. PubMed PMID: 18627172.

9: Seradj H, Cai W, Erasga NO, Chenault DV, Knuckles KA, Ragains JR, Behforouz M. Total synthesis of novel 6-substituted lavendamycin antitumor agents. Org Lett. 2004 Feb 19;6(4):473-6. PubMed PMID: 14961601.

10: Fang Y, Linardic CM, Richardson DA, Cai W, Behforouz M, Abraham RT. Characterization of the cytotoxic activities of novel analogues of the antitumor agent, lavendamycin. Mol Cancer Ther. 2003 Jun;2(6):517-26. PubMed PMID: 12813130.

11: Behforouz M, Cai W, Stocksdale MG, Lucas JS, Jung JY, Briere D, Wang A, Katen KS, Behforouz NC. Novel lavendamycin analogues as potent HIV-reverse transcriptase inhibitors: synthesis and evaluation of anti-reverse transcriptase activity of amide and ester analogues of lavendamycin. J Med Chem. 2003 Dec 18;46(26):5773-80. PubMed PMID: 14667230.

12: Hassani M, Cai W, Holley DC, Lineswala JP, Maharjan BR, Ebrahimian GR, Seradj H, Stocksdale MG, Mohammadi F, Marvin CC, Gerdes JM, Beall HD, Behforouz M. Novel lavendamycin analogues as antitumor agents: synthesis, in vitro cytotoxicity, structure-metabolism, and computational molecular modeling studies with NAD(P)H:quinone oxidoreductase 1. J Med Chem. 2005 Dec 1;48(24):7733-49. PubMed PMID: 16302813.

13: Balitz DM, Bush JA, Bradner WT, Doyle TW, O'Herron FA, Nettleton DE. Isolation of lavendamycin, a new antibiotic from Streptomyces lavendulae. J Antibiot (Tokyo). 1982 Mar;35(3):259-65. PubMed PMID: 7076573.

14: Abe N, Nakakita Y, Nakamura T, Enoki N, Uchida H, Takeo S, Munekata M. Novel cytocidal compounds, oxopropalines from Streptomyces sp. G324 producing lavendamycin. I. Taxonomy of the producing organism, fermentation, isolation and biological activities. J Antibiot (Tokyo). 1993 Nov;46(11):1672-7. PubMed PMID: 8270488.

15: Keyari CM, Kearns AK, Duncan NS, Eickholt EA, Abbott G, Beall HD, Diaz P. Synthesis of new quinolinequinone derivatives and preliminary exploration of their cytotoxic properties. J Med Chem. 2013 May 23;56(10):3806-19. doi: 10.1021/jm301689x. Epub 2013 May 1. PubMed PMID: 23574193; PubMed Central PMCID: PMC3752426.

16: Abe N, Enoki N, Nakakita Y, Uchida H, Nakamura T, Munekata M. Novel cytocidal compounds, oxopropalines from Streptomyces sp. G324 producing lavendamycin. II. Physico-chemical properties and structure elucidations. J Antibiot (Tokyo). 1993 Nov;46(11):1678-86. PubMed PMID: 8270489.

17: Behforouz M, Haddad J, Cai W, Arnold MB, Mohammadi F, Sousa AC, Horn MA. Highly Efficient and Practical Syntheses of Lavendamycin Methyl Ester and Related Novel Quinolindiones. J Org Chem. 1996 Sep 20;61(19):6552-6555. PubMed PMID: 11667519.

18: Hibino S, Okazaki M, Ichikawa M, Sato K, Motoshima A, Ueki H. In vitro oxidation of the 8-hydroxyquinoline moiety with metabolic activation system to a mutagenic quinoloquinone compound of lavendamycin analogs. Chem Pharm Bull (Tokyo). 1986 Mar;34(3):1376-9. PubMed PMID: 3089632.

19: Nissen F, Schollmeyer D, Detert H. Methyl 1-(7-acetamido-5,8-dimeth-oxy-quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl-ate. Acta Crystallogr Sect E Struct Rep Online. 2011 Jun 1;67(Pt 6):o1497-8. doi: 10.1107/S1600536811018794. Epub 2011 May 25. PubMed PMID: 21754865; PubMed Central PMCID: PMC3120419.

20: Behforouz M, Cai W, Mohammadi F, Stocksdale MG, Gu Z, Ahmadian M, Baty DE, Etling MR, Al-Anzi CH, Swiftney TM, Tanzer LR, Merriman RL, Behforouz NC. Synthesis and evaluation of antitumor activity of novel N-acyllavendamycin analogues and quinoline-5,8-diones. Bioorg Med Chem. 2007 Jan 1;15(1):495-510. Epub 2006 Oct 10. PubMed PMID: 17035024; PubMed Central PMCID: PMC1900071.