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MedKoo Cat#: 581654 | Name: Debromohymenialdisine
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Description:

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

Debromohymenialdisine is an antineoplastic agent, a protein kinase inhibitor isolated from Marine Organisms, Terrestrial Plants, and Microorganisms.

Chemical Structure

Debromohymenialdisine
Debromohymenialdisine
CAS#75593-17-8

Theoretical Analysis

MedKoo Cat#: 581654

Name: Debromohymenialdisine

CAS#: 75593-17-8

Chemical Formula: C11H11N5O2

Exact Mass: 245.0913

Molecular Weight: 245.24

Elemental Analysis: C, 53.87; H, 4.52; N, 28.56; O, 13.05

Price and Availability

Size Price Availability Quantity
100µg USD 350.00 2 Weeks
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Related CAS #
75593-17-8 125118-55-0
Synonym
Debromohymenialdisine; Dbha-SKF; SK&F 108753; SK&F-108753; SK&F108753; DBH; SKF 108753; SKF108753; SKF-108753; Debromo Hymenialdisine; (Z)-Debromohymenialdisine; (Z)-2-Debromohymenialdisine
IUPAC/Chemical Name
(4Z)-4-(2-amino-1,5-dihydro-5-oxo-4H-imidazol-4-ylidene)-4,5,6,7-tetrahydro-pyrrolo[2,3-c]azepin-8(1H)-one
InChi Key
JYRJOQGKGMHTOO-VURMDHGXSA-N
InChi Code
InChI=1S/C11H11N5O2/c12-11-15-8(10(18)16-11)6-2-4-14-9(17)7-5(6)1-3-13-7/h1,3,13H,2,4H2,(H,14,17)(H3,12,15,16,18)/b8-6-
SMILES Code
O=C(C1=C/2C=CN1)NCCC2=C3N=C(N)NC\3=O
Appearance
Solid powder
Purity
>90% (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 245.24 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: Hamed ANE, Schmitz R, Bergermann A, Totzke F, Kubbutat M, Müller WEG, Youssef DTA, Bishr MM, Kamel MS, Edrada-Ebel R, Wätjen W, Proksch P. Bioactive pyrrole alkaloids isolated from the Red Sea: marine sponge Stylissa carteri. Z Naturforsch C. 2018 Apr 25;73(5-6):199-210. doi: 10.1515/znc-2017-0161. PubMed PMID: 29353267. 2: O'Rourke A, Kremb S, Bader TM, Helfer M, Schmitt-Kopplin P, Gerwick WH, Brack-Werner R, Voolstra CR. Alkaloids from the Sponge Stylissa carteri Present Prospective Scaffolds for the Inhibition of Human Immunodeficiency Virus 1 (HIV-1). Mar Drugs. 2016 Feb 4;14(2). pii: E28. doi: 10.3390/md14020028. PubMed PMID: 26861355; PubMed Central PMCID: PMC4771981. 3: Yang ZX, Sun YH, He JG, Cao H, Jiang GQ. Increased activity of CHK enhances the radioresistance of MCF-7 breast cancer stem cells. Oncol Lett. 2015 Dec;10(6):3443-3449. Epub 2015 Oct 2. PubMed PMID: 26788148; PubMed Central PMCID: PMC4665200. 4: Anisimov MM, Chaikina EL, Utkina NK. Alkaloids from marine sponges as stimulators of initial stages of development of agricultural plants. Nat Prod Commun. 2014 Apr;9(4):459-60. PubMed PMID: 24868854. 5: Saleem RS, Lansdell TA, Tepe JJ. Synthesis and evaluation of debromohymenialdisine-derived Chk2 inhibitors. Bioorg Med Chem. 2012 Feb 15;20(4):1475-81. doi: 10.1016/j.bmc.2011.12.054. Epub 2012 Jan 11. PubMed PMID: 22285028. 6: Song YF, Qu Y, Cao XP, Zhang W. Cellular localization of debromohymenialdisine and hymenialdisine in the marine sponge Axinella sp. using a newly developed cell purification protocol. Mar Biotechnol (NY). 2011 Oct;13(5):868-82. doi: 10.1007/s10126-010-9347-2. Epub 2011 Jan 19. PubMed PMID: 21246234. 7: Harper LJ, Costea DE, Gammon L, Fazil B, Biddle A, Mackenzie IC. Normal and malignant epithelial cells with stem-like properties have an extended G2 cell cycle phase that is associated with apoptotic resistance. BMC Cancer. 2010 Apr 28;10:166. doi: 10.1186/1471-2407-10-166. PubMed PMID: 20426848; PubMed Central PMCID: PMC2868812. 8: Pires IM, Ward TH, Dive C. Oxaliplatin responses in colorectal cancer cells are modulated by CHK2 kinase inhibitors. Br J Pharmacol. 2010 Mar;159(6):1326-38. doi: 10.1111/j.1476-5381.2009.00607.x. Epub 2010 Jan 28. PubMed PMID: 20128802; PubMed Central PMCID: PMC2848936. 9: Lountos GT, Tropea JE, Zhang D, Jobson AG, Pommier Y, Shoemaker RH, Waugh DS. Crystal structure of checkpoint kinase 2 in complex with NSC 109555, a potent and selective inhibitor. Protein Sci. 2009 Jan;18(1):92-100. doi: 10.1002/pro.16. PubMed PMID: 19177354; PubMed Central PMCID: PMC2708046. 10: Chiou SH, Kao CL, Chen YW, Chien CS, Hung SC, Lo JF, Chen YJ, Ku HH, Hsu MT, Wong TT. Identification of CD133-positive radioresistant cells in atypical teratoid/rhabdoid tumor. PLoS One. 2008 May 7;3(5):e2090. doi: 10.1371/journal.pone.0002090. PubMed PMID: 18509505; PubMed Central PMCID: PMC2396792. 11: Jobson AG, Cardellina JH 2nd, Scudiero D, Kondapaka S, Zhang H, Kim H, Shoemaker R, Pommier Y. Identification of a Bis-guanylhydrazone [4,4'-Diacetyldiphenylurea-bis(guanylhydrazone); NSC 109555] as a novel chemotype for inhibition of Chk2 kinase. Mol Pharmacol. 2007 Oct;72(4):876-84. Epub 2007 Jul 6. Erratum in: Mol Pharmacol. 2008 Oct;74(4):1170. PubMed PMID: 17616632. 12: Oliver AW, Paul A, Boxall KJ, Barrie SE, Aherne GW, Garrett MD, Mittnacht S, Pearl LH. Trans-activation of the DNA-damage signalling protein kinase Chk2 by T-loop exchange. EMBO J. 2006 Jul 12;25(13):3179-90. Epub 2006 Jun 22. PubMed PMID: 16794575; PubMed Central PMCID: PMC1500991. 13: Papeo G, Posteri H, Borghi D, Varasi M. A new glycociamidine ring precursor: syntheses of (Z)-hymenialdisine, (Z)-2-debromohymenialdisine, and (+/-)-endo-2-debromohymenialdisine. Org Lett. 2005 Dec 8;7(25):5641-4. PubMed PMID: 16321011. 14: Foloppe N, Fisher LM, Francis G, Howes R, Kierstan P, Potter A. Identification of a buried pocket for potent and selective inhibition of Chk1: prediction and verification. Bioorg Med Chem. 2006 Mar 15;14(6):1792-804. Epub 2005 Nov 9. PubMed PMID: 16289938. 15: Lougheed JC, Chen RH, Mak P, Stout TJ. Crystal structures of the phosphorylated and unphosphorylated kinase domains of the Cdc42-associated tyrosine kinase ACK1. J Biol Chem. 2004 Oct 15;279(42):44039-45. Epub 2004 Aug 11. PubMed PMID: 15308621. 16: Sharma V, Tepe JJ. Potent inhibition of checkpoint kinase activity by a hymenialdisine-derived indoloazepine. Bioorg Med Chem Lett. 2004 Aug 16;14(16):4319-21. PubMed PMID: 15261294. 17: Kawabe T. G2 checkpoint abrogators as anticancer drugs. Mol Cancer Ther. 2004 Apr;3(4):513-9. Review. PubMed PMID: 15078995. 18: Castedo M, Perfettini JL, Roumier T, Valent A, Raslova H, Yakushijin K, Horne D, Feunteun J, Lenoir G, Medema R, Vainchenker W, Kroemer G. Mitotic catastrophe constitutes a special case of apoptosis whose suppression entails aneuploidy. Oncogene. 2004 May 27;23(25):4362-70. PubMed PMID: 15048075. 19: Hutchins JR, Dikovskaya D, Clarke PR. Regulation of Cdc2/cyclin B activation in Xenopus egg extracts via inhibitory phosphorylation of Cdc25C phosphatase by Ca(2+)/calmodulin-dependent protein [corrected] kinase II. Mol Biol Cell. 2003 Oct;14(10):4003-14. Epub 2003 Jul 11. Erratum in: Mol Biol Cell. 2005 Mar;16(3):1568. PubMed PMID: 14517314; PubMed Central PMCID: PMC206995. 20: Tasdemir D, Mallon R, Greenstein M, Feldberg LR, Kim SC, Collins K, Wojciechowicz D, Mangalindan GC, Concepción GP, Harper MK, Ireland CM. Aldisine alkaloids from the Philippine sponge Stylissa massa are potent inhibitors of mitogen-activated protein kinase kinase-1 (MEK-1). J Med Chem. 2002 Jan 17;45(2):529-32. PubMed PMID: 11784156.

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