Lavendustin C
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MedKoo CAT#: 407435

CAS#: 125697-93-0

Description: Lavendustin C, also known as HDBA and NSC 666251, is a potent inhibitor of epidermal growth factor (EGF) receptor-associated tyrosine kinase with an IC50 value of 0.012 µM. HDBA inhibits tyrosine kinase-associated neutrophil degranulation and superoxide generation


Chemical Structure

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Lavendustin C
CAS# 125697-93-0

Theoretical Analysis

MedKoo Cat#: 407435
Name: Lavendustin C
CAS#: 125697-93-0
Chemical Formula: C14H13NO5
Exact Mass: 275.08
Molecular Weight: 275.260
Elemental Analysis: C, 61.09; H, 4.76; N, 5.09; O, 29.06

Price and Availability

Size Price Availability Quantity
5mg USD 310 2 Weeks
10mg USD 585 2 Weeks
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Synonym: Lavendustin C; HDBA, NSC 666251.

IUPAC/Chemical Name: 5-[[(2,5-dihydroxyphenyl)methyl]amino]-2-hydroxy-benzoic acid

InChi Key: LULATDWLDJOKCX-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H13NO5/c16-10-2-4-12(17)8(5-10)7-15-9-1-3-13(18)11(6-9)14(19)20/h1-6,15-18H,7H2,(H,19,20)

SMILES Code: O=C(O)C1=CC(NCC2=CC(O)=CC=C2O)=CC=C1O

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: >2 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:

Product Data:
Biological target: Lavendustin C is a potent Ca2+ calmodulin-dependent kinase II (CaMK II) inhibitor with an IC50 of 0.2 µM.
In vitro activity: Inhibition studies using calmodulin inhibitor W-7, and calcium/calmodulin kinase inhibitors, KN-62 and lavendustin C, were found to inhibit budding by cells induced to re-enter the yeast cell cycle and to favor the yeast to mycelium transition. Reference: BMC Microbiol. 2007 Nov 29;7:107. https://pubmed.ncbi.nlm.nih.gov/18047672/
In vivo activity: The present sutdy has examined the relationship between the CaMKII (Ca(2+)/calmodulin-dependent protein kinase II) pathway and endothelial dysfunction in aortas from GK (Goto-Kakizaki) Type 2 diabetic rats. The ACh (acetylcholine)-induced relaxation and NO production were each attenuated in diabetic aortas (compared with those from age-matched control rats). The ACh-induced relaxations, NO production, eNOS phosphorylation, and CaMKII phosphorylation were inhibited by KN93 and/or by lavendustin C (inhibitors of CaMKII) in control aortas, but not in diabetic ones. Reference: Clin Sci (Lond). 2012 Sep;123(6):375-86. https://pubmed.ncbi.nlm.nih.gov/22494112/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 108.99
DMSO 30.0 108.99

Preparing Stock Solutions

The following data is based on the product molecular weight 275.26 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: 1. Valle-Aviles L, Valentin-Berrios S, Gonzalez-Mendez RR, Rodriguez-Del Valle N. Functional, genetic and bioinformatic characterization of a calcium/calmodulin kinase gene in Sporothrix schenckii. BMC Microbiol. 2007 Nov 29;7:107. doi: 10.1186/1471-2180-7-107. PMID: 18047672; PMCID: PMC2242797. 2. Burt HM, Jackson JK, Salari H. Inhibition of crystal-induced neutrophil activation by a protein tyrosine kinase inhibitor. J Leukoc Biol. 1994 Jan;55(1):112-9. doi: 10.1002/jlb.55.1.112. PMID: 8283135. 3. Kobayashi T, Nemoto S, Ishida K, Taguchi K, Matsumoto T, Kamata K. Involvement of CaM kinase II in the impairment of endothelial function and eNOS activity in aortas of Type 2 diabetic rats. Clin Sci (Lond). 2012 Sep;123(6):375-86. doi: 10.1042/CS20110621. PMID: 22494112. 4. Bai GY, Piao FL, Kim SY, Yuan K, Kim SZ, Kim SH. Augmentation of insulin-stimulated ANP release through tyrosine kinase and PI 3-kinase in diabetic rats. Peptides. 2006 Nov;27(11):2756-63. doi: 10.1016/j.peptides.2006.05.014. Epub 2006 Jul 10. PMID: 16828931.
In vitro protocol: 1. Valle-Aviles L, Valentin-Berrios S, Gonzalez-Mendez RR, Rodriguez-Del Valle N. Functional, genetic and bioinformatic characterization of a calcium/calmodulin kinase gene in Sporothrix schenckii. BMC Microbiol. 2007 Nov 29;7:107. doi: 10.1186/1471-2180-7-107. PMID: 18047672; PMCID: PMC2242797. 2. Burt HM, Jackson JK, Salari H. Inhibition of crystal-induced neutrophil activation by a protein tyrosine kinase inhibitor. J Leukoc Biol. 1994 Jan;55(1):112-9. doi: 10.1002/jlb.55.1.112. PMID: 8283135.
In vivo protocol: 1. Kobayashi T, Nemoto S, Ishida K, Taguchi K, Matsumoto T, Kamata K. Involvement of CaM kinase II in the impairment of endothelial function and eNOS activity in aortas of Type 2 diabetic rats. Clin Sci (Lond). 2012 Sep;123(6):375-86. doi: 10.1042/CS20110621. PMID: 22494112. 2. Bai GY, Piao FL, Kim SY, Yuan K, Kim SZ, Kim SH. Augmentation of insulin-stimulated ANP release through tyrosine kinase and PI 3-kinase in diabetic rats. Peptides. 2006 Nov;27(11):2756-63. doi: 10.1016/j.peptides.2006.05.014. Epub 2006 Jul 10. PMID: 16828931.

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2: Kobayashi T, Nemoto S, Ishida K, Taguchi K, Matsumoto T, Kamata K. Involvement of CaM kinase II in the impairment of endothelial function and eNOS activity in aortas of Type 2 diabetic rats. Clin Sci (Lond). 2012 Sep;123(6):375-86. doi: 10.1042/CS20110621. PubMed PMID: 22494112.

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8: Yoon J, Ryu JS. A rapid synthesis of lavendustin-mimetic small molecules by click fragment assembly. Bioorg Med Chem Lett. 2010 Jul 1;20(13):3930-5. doi: 10.1016/j.bmcl.2010.05.014. Epub 2010 May 12. PubMed PMID: 20570145.

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11: Burt HM, Jackson JK, Salari H. Inhibition of crystal-induced neutrophil activation by a protein tyrosine kinase inhibitor. J Leukoc Biol. 1994 Jan;55(1):112-9. PubMed PMID: 8283135.

12: Valle-Aviles L, Valentin-Berrios S, Gonzalez-Mendez RR, Rodriguez-Del Valle N. Functional, genetic and bioinformatic characterization of a calcium/calmodulin kinase gene in Sporothrix schenckii. BMC Microbiol. 2007 Nov 29;7:107. PubMed PMID: 18047672; PubMed Central PMCID: PMC2242797.

13: Bai GY, Piao FL, Kim SY, Yuan K, Kim SZ, Kim SH. Augmentation of insulin-stimulated ANP release through tyrosine kinase and PI 3-kinase in diabetic rats. Peptides. 2006 Nov;27(11):2756-63. Epub 2006 Jul 10. PubMed PMID: 16828931.

14: Schneider JC, El Kebir D, Chéreau C, Lanone S, Huang XL, De Buys Roessingh AS, Mercier JC, Dall'Ava-Santucci J, Dinh-Xuan AT. Involvement of Ca2+/calmodulin-dependent protein kinase II in endothelial NO production and endothelium-dependent relaxation. Am J Physiol Heart Circ Physiol. 2003 Jun;284(6):H2311-9. Epub 2003 Jan 30. PubMed PMID: 12560211.

15: Zucchi R, Ghelardoni S, Carnicelli V, Frascarelli S, Ronca F, Ronca-Testoni S. Ca2+ channel remodeling in perfused heart: Effects of mechanical work and interventions affecting Ca2+ cycling on sarcolemmal and sarcoplasmic reticulum Ca2+ channels. FASEB J. 2002 Dec;16(14):1976-8. Epub 2002 Oct 18. PubMed PMID: 12397086.

16: Wang Z, Wilson GF, Griffith LC. Calcium/calmodulin-dependent protein kinase II phosphorylates and regulates the Drosophila eag potassium channel. J Biol Chem. 2002 Jul 5;277(27):24022-9. Epub 2002 Apr 29. PubMed PMID: 11980904.

17: Taybi T, Cushman JC. Signaling events leading to crassulacean acid metabolism induction in the common ice plant. Plant Physiol. 1999 Oct;121(2):545-56. PubMed PMID: 10517846; PubMed Central PMCID: PMC59417.

18: Imoto M, Sujikai I, Ui H, Umezawa K. Involvement of tyrosine kinase in growth factor-induced phospholipase C activation in NIH3T3 cells. Biochim Biophys Acta. 1993 Feb 24;1166(2-3):188-92. PubMed PMID: 8443236.