MedKoo Cat#: 584671 | Name: Makaluvamine A

Description:

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

Makaluvamine A comes from the fruiting bodies of Didymium bahiense that act as active anti-cancer agents and DNA topo II inhibitors.

Chemical Structure

Makaluvamine A
Makaluvamine A
CAS#146555-78-4

Theoretical Analysis

MedKoo Cat#: 584671

Name: Makaluvamine A

CAS#: 146555-78-4

Chemical Formula: C11H11N3O

Exact Mass: 201.0902

Molecular Weight: 201.23

Elemental Analysis: C, 65.66; H, 5.51; N, 20.88; O, 7.95

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 #
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Synonym
Makaluvamine A
IUPAC/Chemical Name
Pyrrolo(4,3,2-de)quinolin-8(1H)-one, 7-amino-3,4-dihydro-1-methyl-
InChi Key
RUIRYCQUTHWLMZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H11N3O/c1-14-5-6-2-3-13-8-4-7(12)11(15)10(14)9(6)8/h4-5H,2-3,12H2,1H3
SMILES Code
O=C1C2=C3C(CCN=C3C=C1N)=CN2C
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 201.23 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: Ishibashi M, Iwasaki T, Imai S, Sakamoto S, Yamaguchi K, Ito A. Laboratory culture of the myxomycetes: formation of fruiting bodies of Didymium bahiense and its plasmodial production of Makaluvamine A. J Nat Prod. 2001 Jan;64(1):108-10. PubMed PMID: 11170681. 2: Nijampatnam B, Nadkarni DH, Wu H, Velu SE. Antibacterial and Antibiofilm Activities of Makaluvamine Analogs. Microorganisms. 2014;2(3):128-39. doi: 10.3390/microorganisms2030128. PubMed PMID: 25767719; PubMed Central PMCID: PMC4354892. 3: Wang W, Rayburn ER, Velu SE, Nadkarni DH, Murugesan S, Zhang R. In vitro and in vivo anticancer activity of novel synthetic makaluvamine analogues. Clin Cancer Res. 2009 May 15;15(10):3511-8. doi: 10.1158/1078-0432.CCR-08-2689. PubMed PMID: 19451594; PubMed Central PMCID: PMC3769181. 4: Boucle S, Melin C, Clastre M, Guillard J. Design, synthesis and evaluation of new marine alkaloid-derived pentacyclic structures with anti-tumoral potency. Mar Drugs. 2015 Jan 19;13(1):655-65. doi: 10.3390/md13010655. PubMed PMID: 25607930; PubMed Central PMCID: PMC4306956. 5: Walmsley TA, Matcher GF, Zhang F, Hill RT, Davies-Coleman MT, Dorrington RA. Diversity of bacterial communities associated with the Indian Ocean sponge Tsitsikamma favus that contains the bioactive pyrroloiminoquinones, tsitsikammamine A and B. Mar Biotechnol (NY). 2012 Dec;14(6):681-91. doi: 10.1007/s10126-012-9430-y. Epub 2012 Feb 5. PubMed PMID: 22310802. 6: Ding Q, Chichak K, Lown JW. Pyrroloquinoline and pyridoacridine alkaloids from marine sources. Curr Med Chem. 1999 Jan;6(1):1-27. Review. PubMed PMID: 9873113. 7: Barrows LR, Radisky DC, Copp BR, Swaffar DS, Kramer RA, Warters RL, Ireland CM. Makaluvamines, marine natural products, are active anti-cancer agents and DNA topo II inhibitors. Anticancer Drug Des. 1993 Oct;8(5):333-47. PubMed PMID: 8251041. 8: Shinkre BA, Raisch KP, Fan L, Velu SE. Analogs of the marine alkaloid makaluvamines: synthesis, topoisomerase II inhibition, and anticancer activity. Bioorg Med Chem Lett. 2007 May 15;17(10):2890-3. Epub 2007 Feb 25. PubMed PMID: 17368022; PubMed Central PMCID: PMC2706148. 9: Yamada F. [Development of synthetic methods for 4-substituted indoles and their applications for the syntheses of natural products]. Yakugaku Zasshi. 2000 Apr;120(4):363-73. Review. Japanese. PubMed PMID: 10774258.