Synonym
Resorufin; OUL47; NSC12097; OUL-47; NSC-12097; OUL 47; NSC 12097
IUPAC/Chemical Name
7-Hydroxy-3H-phenoxazin-3-one
InChi Key
HSSLDCABUXLXKM-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H7NO3/c14-7-1-3-9-11(5-7)16-12-6-8(15)2-4-10(12)13-9/h1-6,14H
SMILES Code
O=C1C=CC2=NC3=C(C=C(O)C=C3)OC2=C1
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
Biological target:
Resorufin is a pink fluorescent dye.
In vitro activity:
An iodinated resorufin derivative (R1) induced photocytotoxicity after being triggered by endogenous monoamine oxidase (MAO) enzyme in cancer cells. R1 displayed differential cytotoxicity between cancer and normal cells, without any considerable dark toxicity. R1 marks the first example of a resorufin-based photosensitizer as well as the first anticancer drug that is activated by a MAO enzyme.
Reference: ACS Med Chem Lett. 2020 Nov 23;11(12):2491-2496. https://pubmed.ncbi.nlm.nih.gov/33335672/
In vivo activity:
This study used a resorufin-based fluorescence probe to sense various biogenic amines (Bas). Upon nucleophilic substitution reaction with BAs, the probe released resorufin, affording to strong fluorescence emission at 592 nm with rapid response (<8 min), good selectivity and a low detection limit (LOD = 0.47 μM). Resorufin has low cytotoxicity and good membrane permeability; it has been successfully used to visualize BAs in living cells and zebrafish with good performance.
Reference: RSC Adv. 2022 Nov 25;12(52):33870-33875. https://pubmed.ncbi.nlm.nih.gov/36505703/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
213.19
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.
| 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. Almammadov T, Atakan G, Leylek O, Ozcan G, Gunbas G, Kolemen S. Resorufin Enters the Photodynamic Therapy Arena: A Monoamine Oxidase Activatable Agent for Selective Cytotoxicity. ACS Med Chem Lett. 2020 Nov 23;11(12):2491-2496. doi: 10.1021/acsmedchemlett.0c00484. PMID: 33335672; PMCID: PMC7734820.
2. Sandholt IS, Olsen BB, Guerra B, Issinger OG. Resorufin: a lead for a new protein kinase CK2 inhibitor. Anticancer Drugs. 2009 Apr;20(4):238-48. doi: 10.1097/CAD.0b013e328326472e. PMID: 19177021.
3. Pei SL, Zhang J, Ge W, Liu C, Sheng R, Zeng L, Pan LH. A resorufin-based fluorescence probe for visualizing biogenic amines in cells and zebrafish. RSC Adv. 2022 Nov 25;12(52):33870-33875. doi: 10.1039/d2ra06482k. PMID: 36505703; PMCID: PMC9693732.
4. Su H, Wang N, Wang J, Wang H, Zhang J, Zhao W. A resorufin-based red-emitting fluorescent probe with high selectivity for tracking endogenous peroxynitrite in living cells and inflammatory mice. Spectrochim Acta A Mol Biomol Spectrosc. 2021 May 5;252:119502. doi: 10.1016/j.saa.2021.119502. Epub 2021 Jan 30. PMID: 33578120.
In vitro protocol:
1. Almammadov T, Atakan G, Leylek O, Ozcan G, Gunbas G, Kolemen S. Resorufin Enters the Photodynamic Therapy Arena: A Monoamine Oxidase Activatable Agent for Selective Cytotoxicity. ACS Med Chem Lett. 2020 Nov 23;11(12):2491-2496. doi: 10.1021/acsmedchemlett.0c00484. PMID: 33335672; PMCID: PMC7734820.
2. Sandholt IS, Olsen BB, Guerra B, Issinger OG. Resorufin: a lead for a new protein kinase CK2 inhibitor. Anticancer Drugs. 2009 Apr;20(4):238-48. doi: 10.1097/CAD.0b013e328326472e. PMID: 19177021.
In vivo protocol:
1. Pei SL, Zhang J, Ge W, Liu C, Sheng R, Zeng L, Pan LH. A resorufin-based fluorescence probe for visualizing biogenic amines in cells and zebrafish. RSC Adv. 2022 Nov 25;12(52):33870-33875. doi: 10.1039/d2ra06482k. PMID: 36505703; PMCID: PMC9693732.
2. Su H, Wang N, Wang J, Wang H, Zhang J, Zhao W. A resorufin-based red-emitting fluorescent probe with high selectivity for tracking endogenous peroxynitrite in living cells and inflammatory mice. Spectrochim Acta A Mol Biomol Spectrosc. 2021 May 5;252:119502. doi: 10.1016/j.saa.2021.119502. Epub 2021 Jan 30. PMID: 33578120.
1: Summers FA, Zhao B, Ganini D, Mason RP. Photooxidation of Amplex Red to resorufin: implications of exposing the Amplex Red assay to light. Methods Enzymol. 2013;526:1-17. doi: 10.1016/B978-0-12-405883-5.00001-6. Review. PubMed PMID: 23791091.
2: Jiao Y, Zhu B, Chen J, Duan X. Fluorescent sensing of fluoride in cellular system. Theranostics. 2015 Jan 1;5(2):173-87. doi: 10.7150/thno.9860. eCollection 2015. Review. PubMed PMID: 25553106; PubMed Central PMCID: PMC4279002.
3: Pomorski A, Krężel A. Exploration of biarsenical chemistry--challenges in protein research. Chembiochem. 2011 May 16;12(8):1152-67. doi: 10.1002/cbic.201100114. Epub 2011 Apr 28. Review. PubMed PMID: 21538762.
4: Löhr M, Hummel F, Faulmann G, Ringel J, Saller R, Hain J, Günzburg WH, Salmons B. Microencapsulated, CYP2B1-transfected cells activating ifosfamide at the site of the tumor: the magic bullets of the 21st century. Cancer Chemother Pharmacol. 2002 May;49 Suppl 1:S21-4. Epub 2002 Apr 12. Review. PubMed PMID: 12042985.
5: Deiss F, Sojic N, White DJ, Stoddart PR. Nanostructured optical fibre arrays for high-density biochemical sensing and remote imaging. Anal Bioanal Chem. 2010 Jan;396(1):53-71. doi: 10.1007/s00216-009-3211-0. Epub 2009 Nov 15. Review. PubMed PMID: 19916005.
6: Sarkar A, Ray D, Shrivastava AN, Sarker S. Molecular Biomarkers: their significance and application in marine pollution monitoring. Ecotoxicology. 2006 May;15(4):333-40. Epub 2006 May 5. Review. PubMed PMID: 16676218.
