Naphthofluorescein

Modify Date: 2024-01-13 13:44:05

Naphthofluorescein Structure
Naphthofluorescein structure
Common Name Naphthofluorescein
CAS Number 61419-02-1 Molecular Weight 432.424
Density 1.6±0.1 g/cm3 Boiling Point 755.5±60.0 °C at 760 mmHg
Molecular Formula C28H16O5 Melting Point 189ºC (dec.)(lit.)
MSDS Chinese USA Flash Point 266.4±26.4 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Naphthofluorescein


Naphthofluorescein inhibits the interaction between HIF-1 and Mint3.Naphthofluorescein suppresses Mint3-dependent HIF-1 activity and glycolysis in cancer cells and macrophages without cytotoxicity in vitro and adverse effect in vivo[1]. Naphthofluorescein is also a fluorescent pH-sensitive probe that can be used for functional Cerenkov imaging[2].

 Names

Name Naphthofluorescein
Synonym More Synonyms

 Naphthofluorescein Biological Activity

Description Naphthofluorescein inhibits the interaction between HIF-1 and Mint3.Naphthofluorescein suppresses Mint3-dependent HIF-1 activity and glycolysis in cancer cells and macrophages without cytotoxicity in vitro and adverse effect in vivo[1]. Naphthofluorescein is also a fluorescent pH-sensitive probe that can be used for functional Cerenkov imaging[2].
Related Catalog
Target

HIF-1[1]

In Vitro Naphthofluorescein (compound 19) (0-10 μM; 24 hours) suppresses the HIF-1 reporter activity in a concentration-dependent manner[1]. Cell Viability Assay[1] Cell Line: HT1080 cells Concentration: 0-10 μM Incubation Time: 24 hours Result: Significantly suppressed the HIF-1 reporter activity in a concentration-dependent manner.
In Vivo Naphthofluorescein (compound 19) (100 mg/kg; i.p.; once daily for 5 consecutive days followed by 2 days off for 2 weeks)does not show weight loss or apparent histological abnormalities in the lung, liver, and kidney, or cause cause severe adverse effects for at least 2 weeks in mice[1]. Naphthofluorescein (compound 19) (100 mg/kg; i.p.; once daily for 5 consecutive days followed by 2 days off for 2 weeks) strikingly suppresses the tumour growth of subcutaneously injected E0771 cells and significantly attenuates tumour growth of MDA-MB-231 and AsPC-1 cells in immunodeficient mice. In turn, naphthofluorescein does not attenuate tumour growth of FIH-1-depleted MDA-MB-231 cells[1]. Naphthofluorescein (compound 19) (100 mg/kg; i.p.; once daily for 5 consecutive days followed by 2 days off for 2 weeks) suppresses tumour growth in human cancer cells in an FIH-1-dependent manner[1]. Animal Model: Male C57BL/6J mice (8 weeks)[1] Dosage: 100 mg/kg Administration: i.p.; once daily for 5 consecutive days followed by 2 days off for 2 weeks Result: Neither showed weight loss or apparent histological abnormalities in the lung, liver, and kidney, or caused cause severe adverse effects for at least 2 weeks in mice. Animal Model: Female C57BL/6J mice (E0771) and BALB/c nude mice (HT1080, MDA-MB-231, and AsPC-1) (6 weeks)[1] Dosage: 100 mg/kg Administration: i.p.; once daily for 5 consecutive days followed by 2 days off for 2 weeks Result: Strikingly suppressed the tumour growth of subcutaneously injected E0771 cells and significantly attenuated tumour growth of MDA-MB-231 and AsPC-1 cells in immunodeficient mice. In turn, naphthofluorescein did not attenuate tumour growth of FIH-1-depleted MDA-MB-231 cells.
References

[1]. Sakamoto T, et al. Pharmacological inhibition of Mint3 attenuates tumour growth, metastasis, and endotoxic shock. Commun Biol. 2021;4(1):1165. Published 2021 Oct 7.

[2]. Arroyo AD, et al. Development of fluorinated naphthofluoresceins for Cerenkov imaging. J Fluor Chem. 2019;225:27-34.

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 755.5±60.0 °C at 760 mmHg
Melting Point 189ºC (dec.)(lit.)
Molecular Formula C28H16O5
Molecular Weight 432.424
Flash Point 266.4±26.4 °C
Exact Mass 432.099762
PSA 75.99000
LogP 5.09
Vapour Pressure 0.0±2.6 mmHg at 25°C
Index of Refraction 1.861

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi: Irritant;
Risk Phrases R36/37/38
Safety Phrases 26-36
RIDADR NONH for all modes of transport

 Synthetic Route

~78%

Naphthofluorescein Structure

Naphthofluorescein

CAS#:61419-02-1

Literature: Xu, Kehua; Tang, Bo; Huang, Hui; Yang, Guiwen; Chen, Zhenzhen; Li, Ping; An, Liguo Chemical Communications, 2005 , # 48 p. 5974 - 5976

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Naphthofluorescein Structure

Naphthofluorescein

CAS#:61419-02-1

Literature: Fischer,O.; Koenig Chemische Berichte, 1917 , vol. 50, p. 1011

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Naphthofluorescein Structure

Naphthofluorescein

CAS#:61419-02-1

Literature: Fischer,O.; Koenig Chemische Berichte, 1917 , vol. 50, p. 1011

~%

Naphthofluorescein Structure

Naphthofluorescein

CAS#:61419-02-1

Literature: Fischer,O.; Koenig Chemische Berichte, 1917 , vol. 50, p. 1011

~%

Naphthofluorescein Structure

Naphthofluorescein

CAS#:61419-02-1

Literature: Hoechster Farbw. Patent: DE275897 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 217 Full Text Show Details Fischer,O.; Koenig Chemische Berichte, 1914 , vol. 47, p. 1078 Chemische Berichte, 1917 , vol. 50, p. 1011

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Naphthofluorescein Structure

Naphthofluorescein

CAS#:61419-02-1

Literature: Fischer,O.; Koenig Chemische Berichte, 1917 , vol. 50, p. 1011

~%

Naphthofluorescein Structure

Naphthofluorescein

CAS#:61419-02-1

Literature: Fischer,O.; Koenig Chemische Berichte, 1917 , vol. 50, p. 1011

 Articles1

More Articles
O.S. Wolfbeis et al.

Mikrochim. Acta 108 , 133, (1992)

 Synonyms

Spiro[7H-dibenzo[c,h]xanthene-7,1'(3'H)-isobenzofuran]-3'-one, 3,11-dihydroxy-
3',11'-Dihydroxy-3H-spiro[2-benzofuran-1,7'-dibenzo[c,h]xanthen]-3-one
naphthofluorescein
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