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CAS No. :	2591-17-5
Formula :	C₁₁H₈N₂O₃S₂
M.W :	280.32
SMILES Code :	O=C([C@@H]1N=C(C2=NC3=CC=C(O)C=C3S2)SC1)O
Synonyms :	Firefly luciferin; Beetle Luciferin; D-(-)-Luciferin
MDL No. :	MFCD00042929
InChI Key :	BJGNCJDXODQBOB-SSDOTTSWSA-N
Pubchem ID :	92934

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

CHO cells	<30 μM	Compared aminoluciferins with D-Luciferin in live cells, finding that most aminoluciferins yield higher flux than D-Luciferin at low concentrations.	PMC4183640
CHO cells	250 μM	At high concentrations, the relative emission from D-Luciferin is still equaled or exceeded by certain aminoluciferins (e.g., CycLuc1, CycLuc10, and CycLuc12).	PMC4183640
L. infantum LLM-2346PpyRE9 promastigotes	250 µM to 0.25 µM	Comparison of different substrates for parasite detection in vitro, CycLuc1 demonstrated a higher luminescent signal than D-luciferin and AkaLumine-HCl.	PMC9781651
L. major JISH118PpyRE9 promastigotes	250 µM to 0.25 µM	Comparison of different substrates for parasite detection in vitro, CycLuc1 demonstrated a higher luminescent signal than D-luciferin and AkaLumine-HCl.	PMC9781651
T. brucei brucei AnTAR1PpyRE9 parasites	250 µM to 0.25 µM	Comparison of different substrates for parasite detection in vitro, CycLuc1 demonstrated a higher luminescent signal than D-luciferin and AkaLumine-HCl.	PMC9781651
L. infantum LLM-2346PpyRE9 promastigotes	250 µM to 2.5 µM	CycLuc1 demonstrated a higher luminescent signal than D-luciferin and AkaLumine-HCl in vitro parasite detection.	PMC9781651
L. major JISH118PpyRE9 promastigotes	250 µM to 2.5 µM	CycLuc1 showed a higher luminescent signal than D-luciferin and AkaLumine-HCl at the highest concentration tested against L. major promastigotes.	PMC9781651
T. brucei brucei AnTAR1.1PpyRE9 parasites	250 µM to 2.5 µM	CycLuc1 showed a higher luminescent signal than D-luciferin and AkaLumine-HCl at the highest concentration tested against T. brucei.	PMC9781651
T. brucei brucei AnTAR1PpyRE9 parasites	250 µM to 2.5 µM	CycLuc1 demonstrated a higher luminescent signal than D-luciferin and AkaLumine-HCl in vitro.	PMC9781651

Mice	BALB/c mice	Intraperitoneal injection	48 mg DTG/kg food	Once daily for 17 weeks	D-Luciferin performs well in vivo imaging but has low uptake in some organs such as the brain.	PMC4026177
Mice	Brain striatum	Intraperitoneal injection	DTG (1.25 mg/kg), FTC (25 mg/kg), TFV (10 mg/kg)	continuous 2 weeks, once daily	Evaluate the performance of mutant luciferases in the brains of live mice, finding significantly reduced signal with D-Luciferin	PMC4972182
Mice	Healthy mice	Intraperitoneal injection	25 mg/kg/day or 50 mg/kg/day	Once daily for 7 days	To measure luciferase activity, results showed that the bioluminescent signal in the colon was 11-fold higher when combined with ultrasound compared to mRNA alone.	PMC5368009
BALB/c and Swiss mice	Natural infection models of leishmaniasis and African trypanosomiasis	Intraperitoneal injection	1 μg/ml	Two immunizations, 10 days apart	Comparison of different substrates for parasite detection in vivo, CycLuc1 showed similar efficacy at a 20-fold lower dose than D-luciferin.	PMC9781651
mice	BALB/c mice, FVB mice, C57BL/6 mice	intraperitoneal injection	20 mg/kg/d	Once daily for 3 days	To evaluate the bioluminescence imaging effect of D-Luciferin in vivo, the results showed that D-Luciferin performs well in vivo, but its uptake in some organs such as the brain is low.	PMC4026177
Mice	Brain striatum	Intraperitoneal injection	20 mg/kg	Daily for three weeks	Evaluate the performance of mutant luciferases in vivo, found that D-Luciferin signal was dramatically reduced	PMC4972182
Mice	Healthy mice	Intraperitoneal injection	150 mg/kg	single injection	Measure luciferase expression	PMC5368009
BALB/c and Swiss mice	Leishmaniasis and African trypanosomiasis models	Intraperitoneal injection	0.2 mL; 10 mg/mL	Single injection	CycLuc1 showed comparable efficacy to D-luciferin at a 20-fold lower dose, suitable for longitudinal follow-up in models of leishmaniasis and African trypanosomiasis.	PMC9781651
Mice	4T1-luc2 breast cancer model, DB7-luc breast cancer model, CMT-64 lung cancer model, L2G85-FVB transgenic mice, AAV9-CMV-luc2 brain striatum model, Dat-Cre+/− Rosa26-luc+/− mice	Intraperitoneal injection	5 mg/kg	Once daily for two weeks	Evaluate the bioluminescence imaging effect of D-Luciferin in various mouse models, results showed that D-Luciferin performed poorly in brain imaging and could not detect luciferase expression in deep brain tissues.	PMC4026177
Mice	Healthy mice and DSS-induced colitis mice	Intraperitoneal injection	3 mg/kg	twice a day for 4 weeks	To evaluate mRNA expression in the colon, results showed that ultrasound-mediated mRNA delivery significantly increased luciferase expression.	PMC5368009
Mice	Brain striatum	Intraperitoneal injection	150 mg/kg	Single injection, imaging duration up to 60 minutes post-injection	To evaluate the performance of these three luciferase mutants in vivo, each codon-optimized mutant was cloned into an adeno-associated viral (AA V) plasmid under the control of a CMV promoter, and packaged into AA V9 vectors. The AA V9-luciferase viruses were then used to transduce FVB mice in the brain striatum. Unlike the use of luciferase-expressing tumor cells, this viral gene delivery method allows luciferase expression in endogenous mouse cells, for the life of the mouse (well over a year). As we have previously described for AA V9 transduction with the WT luciferase, each luciferase-expressing mouse was imaged after i.p. injection with a phosphate-buffered saline (PBS) solution of each luciferin. These experiments were performed in the exact same set of mice, imaged with each substrate on sequential days. For all of the mutant luciferases, brain bioluminescence was dramatically reduced when using D-luciferin compared to CycLuc1 and CycLuc2 (Figure 3). With the L342A luciferase, D-luciferin gave no signal, while both aminoluciferins gave signal that was >50-fold over background. For the R218K luciferase, D- luciferin signal was ~3-fold over background, but CycLuc1 and CycLuc2 were 40–50 fold brighter still. However, combining the R218K and L342A mutations did not yield synergism in vivo. Although no photon flux above background was observed with D-luciferin for the double mutant, the photon flux was also substantially lower for CycLuc1 and CycLuc2 than for the individual point mutants (Figure S4). Thus, at least in the brain, the double mutant was less useful as a selective luciferase for these substrates compared to L342A or R218K alone.	PMC4972182
Mice	Transgenic mice	Intraperitoneal injection	0.2 mL (10 mg/mL)	Single administration	To compare the performance of different luciferase systems in the brain	PMC10229426
BALB/c mice	Dermal and visceral Leishmania infection models	Intraperitoneal injection	13 µmol	Single injection	CycLuc1 showed comparable efficacy at a 20-fold lower dose than D-luciferin, and both substrates can be used to detect parasite levels above 10^6.	PMC9781651

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CAS No.: 2591-17-5

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CAS No.: 2591-17-5

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Preparing Stock Solutions		1mg	5mg	10mg
Preparing Stock Solutions	1 mM 5 mM 10 mM	3.57mL 0.71mL 0.36mL	17.84mL 3.57mL 1.78mL	35.67mL 7.13mL 3.57mL
Dissolving Methods	Animal experiment Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn: in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day; The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound. Protocol 1 Protocol 2

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed