Makaluvamine A

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

MedKoo CAT#: 584671

CAS#: 146555-78-4

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

Chemical Structure

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Makaluvamine A
CAS# 146555-78-4
Instruction

Theoretical Analysis

MedKoo Cat#: 584671
Name: Makaluvamine A
CAS#: 146555-78-4
Chemical Formula: C11H11N3O
Exact Mass: 201.09
Molecular Weight: 201.229
Elemental Analysis: C, 65.66; H, 5.51; N, 20.88; O, 7.95

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: 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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.