MedKoo Cat#: 597593 | Name: Dihydrodaunomycin HCl

Description:

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

Dihydrodaunomycin HCl is a metabolite of Daunorubicin.

Chemical Structure

Dihydrodaunomycin HCl
CAS#28008-53-9

Theoretical Analysis

MedKoo Cat#: 597593

Name: Dihydrodaunomycin HCl

CAS#: 28008-53-9

Chemical Formula: C27H32ClNO10

Exact Mass: 0.0000

Molecular Weight: 566.00

Elemental Analysis: C, 57.30; H, 5.70; Cl, 6.26; N, 2.47; O, 28.27

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Related CAS #
28008-55-1 (free base)
Synonym
Dihydrodaunomycin hydrochloride; Antibiotic RP 20798; RP 20798; RP-20798; RP20798; Daunorubicinol HCl; Dihydrodaunomycin HCl
IUPAC/Chemical Name
10-((4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(1-hydroxyethyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride
InChi Key
LQLMJJJLWJUAMM-UHFFFAOYSA-N
InChi Code
InChI=1S/C27H31NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10-11,14,16-17,22,29-30,32,34-35H,7-9,28H2,1-3H3;1H
SMILES Code
O=C1C2=C(O)C(CC(C(O)C)(O)CC3OC4CC(N)C(O)C(C)O4)=C3C(O)=C2C(C5=C1C=CC=C5OC)=O.[H]Cl
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
Product Data
Biological target:
Dihydrodaunomycin HCl is a metabolite of Daunorubicin.
In vitro activity:
This study investigated if the internalization of PMPs protected the monocytic AML cell line, THP-1, from apoptosis by decreasing the initial cellular damage inflicted by treatment with daunorubicin, or via direct modulation of the apoptotic response. Levels of daunorubicin-induced DNA damage, assessed by measuring gH2AX, were reduced in both 2N and 4N cells after PMP co-incubation. Measuring different BCL2-family proteins before and after treatment with daunorubicin revealed that PMPs downregulated the pro-apoptotic PUMA protein. Reference: Int J Mol Sci. 2021 Jul 6;22(14):7264. https://pubmed.ncbi.nlm.nih.gov/34298882/
In vivo activity:
Compared with the control group, the rats in the DNR (danorubicin) group exhibited disorderly-arranged focal myocardial tissues with marked intramyocardial cellular infiltration, partial myocardial fibrinolysis and vacuolization (Fig. 2A). Reference: Biomed Pharmacother. 2020 Jan;121:109157. https://pubmed.ncbi.nlm.nih.gov/31731195/

Preparing Stock Solutions

The following data is based on the product molecular weight 566.00 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. Cacic D, Nordgård O, Meyer P, Hervig T. Platelet Microparticles Decrease Daunorubicin-Induced DNA Damage and Modulate Intrinsic Apoptosis in THP-1 Cells. Int J Mol Sci. 2021 Jul 6;22(14):7264. doi: 10.3390/ijms22147264. PMID: 34298882; PMCID: PMC8304976. 2. Silveira VS, Borges KS, Santos VS, Ruckert MT, Vieira GM, Vasconcelos EJR, Nagano LFP, Tone LG, Scrideli CA. SHOC2 scaffold protein modulates daunorubicin-induced cell death through p53 modulation in lymphoid leukemia cells. Sci Rep. 2020 Sep 16;10(1):15193. doi: 10.1038/s41598-020-72124-1. PMID: 32938995; PMCID: PMC7495473. 3. Chen Q, Zhang Y, Zhu H, Yuan X, Luo X, Wu X, Chen S, Chen Y, Xu J, Issa HA, Zheng Z, Hu J, Yang T. Bone marrow mesenchymal stem cells alleviate the daunorubicin-induced subacute myocardial injury in rats through inhibiting infiltration of T lymphocytes and antigen-presenting cells. Biomed Pharmacother. 2020 Jan;121:109157. doi: 10.1016/j.biopha.2019.109157. Epub 2019 Nov 12. PMID: 31731195. 4. Al-Kuraishy HM, Al-Gareeb AI. Potential Effects of Pomegranate on Lipid Peroxidation and Pro-inflammatory Changes in Daunorubicin-induced Cardiotoxicity in Rats. Int J Prev Med. 2016 Jun 20;7:85. doi: 10.4103/2008-7802.184314. PMID: 27413516; PMCID: PMC4926549.
In vitro protocol:
1. Cacic D, Nordgård O, Meyer P, Hervig T. Platelet Microparticles Decrease Daunorubicin-Induced DNA Damage and Modulate Intrinsic Apoptosis in THP-1 Cells. Int J Mol Sci. 2021 Jul 6;22(14):7264. doi: 10.3390/ijms22147264. PMID: 34298882; PMCID: PMC8304976. 2. Silveira VS, Borges KS, Santos VS, Ruckert MT, Vieira GM, Vasconcelos EJR, Nagano LFP, Tone LG, Scrideli CA. SHOC2 scaffold protein modulates daunorubicin-induced cell death through p53 modulation in lymphoid leukemia cells. Sci Rep. 2020 Sep 16;10(1):15193. doi: 10.1038/s41598-020-72124-1. PMID: 32938995; PMCID: PMC7495473.
In vivo protocol:
1. Chen Q, Zhang Y, Zhu H, Yuan X, Luo X, Wu X, Chen S, Chen Y, Xu J, Issa HA, Zheng Z, Hu J, Yang T. Bone marrow mesenchymal stem cells alleviate the daunorubicin-induced subacute myocardial injury in rats through inhibiting infiltration of T lymphocytes and antigen-presenting cells. Biomed Pharmacother. 2020 Jan;121:109157. doi: 10.1016/j.biopha.2019.109157. Epub 2019 Nov 12. PMID: 31731195. 2. Al-Kuraishy HM, Al-Gareeb AI. Potential Effects of Pomegranate on Lipid Peroxidation and Pro-inflammatory Changes in Daunorubicin-induced Cardiotoxicity in Rats. Int J Prev Med. 2016 Jun 20;7:85. doi: 10.4103/2008-7802.184314. PMID: 27413516; PMCID: PMC4926549.
1: Bachur NR, Huffman DH. Daunorubicin metabolism: estimation of daunorubicin reductase. Br J Pharmacol. 1971 Dec;43(4):828-33. PubMed PMID: 5152029; PubMed Central PMCID: PMC1665705. 2: Aszalos AA, Bachur NR, Hamilton BK, Langlykke AF, Roller PP, Sheikh MY, Sutphin MS, Thomas MC, Wareheim DA, Wright LH. Microbial reduction of the side-chain carbonyl of daunorubicin and N-acetyldaunorubicin. J Antibiot (Tokyo). 1977 Jan;30(1):50-8. PubMed PMID: 838632.