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MedKoo Cat#: 598480 | Name: Lavendamycin

Description:

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

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

Lavendamycin
Lavendamycin
CAS#81645-09-2

Theoretical Analysis

MedKoo Cat#: 598480

Name: Lavendamycin

CAS#: 81645-09-2

Chemical Formula: C22H14N4O4

Exact Mass: 398.1015

Molecular Weight: 398.37

Elemental Analysis: C, 66.33; H, 3.54; N, 14.06; O, 16.06

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
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

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
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.

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