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2799-07-7

2799-07-7 structure
2799-07-7 structure
  • Name: S-Tritylcysteine
  • Chemical Name: S-Trityl-L-cysteine
  • CAS Number: 2799-07-7
  • Molecular Formula: C22H21NO2S
  • Molecular Weight: 363.47
  • Catalog: Biochemical Amino acids and their derivatives Cysteine derivative
  • Create Date: 2018-07-14 09:42:06
  • Modify Date: 2025-08-25 22:00:10
  • S-Trityl-L-cysteine (NSC 83265) is a selective and allosteric kinesin Eg5 inhibitor with an IC50 of 1 μM for the inhibition of basal ATPase activity and 140 nM for the microtubule-activated ATPase activity. S-Trityl-L-cysteine has antitumor activities[1][2].
Name S-Trityl-L-cysteine
Synonyms S-Triphenylmethyl-L-cysteine
EG5 INHIBITOR II
Cys(Trt)-OH
3-tritylthio-L-alanine
Alanine, 3- (tritylthio)-, D-
L-Cys(trt)-OH
DL-Cysteine, S-(triphenylmethyl)-
L-CYSTEINE, S-(TRIPHENYLMETHYL)-
EINECS 218-195-8
S-Tritylcysteine
(R)-S-Tritylcysteine
(2S)-2-Ammonio-3-(tritylsulfanyl)propanoate
Cysteine, S-(triphenylmethyl)-
D-Cysteine, S- (triphenylmethyl)-
S-Trt-L-Lys-OH
H-Cys(Trt)-OH
L-Cysteine, S- (triphenylmethyl)-
TRITYL-L-CYSTEINE
H-L-Cys(Trt)-OH
MFCD00002611
CYSTEINE(TRT)-OH
Alanine, 3- (tritylthio)-, L-
Tritylthioalanine
Ethanaminium, 1-carboxy-2-[(triphenylmethyl)thio]-, inner salt, (1S)-
Description S-Trityl-L-cysteine (NSC 83265) is a selective and allosteric kinesin Eg5 inhibitor with an IC50 of 1 μM for the inhibition of basal ATPase activity and 140 nM for the microtubule-activated ATPase activity. S-Trityl-L-cysteine has antitumor activities[1][2].
Related Catalog
Target

Eg5

In Vitro S-Trityl-L-cysteine binds to a unique pocket in the Eg5 motor domain formed by secondary structural elements (helix a2/loop L5/helix a3)[1]. S-Trityl-L-cysteine (1-20 µM; for 72 h) could mediate cell apoptosis, as well as cell cycle arrest, in a dose-dependent manner. S-Trityl-L-cysteine-mediated apoptosis and cell cycle arrest were triggered by activation of the mitogen-activated protein kinase and nuclear factor kB signaling pathways[1]. S-Trityl-L-cysteine induces mitotic arrest in HeLa cells (IC50 of 700 nM) with characteristic monoastral spindles[2].
References

[1]. Wei Wu, et al. S-trityl-L-cysteine, a novel Eg5 inhibitor, is a potent chemotherapeutic strategy in neuroblastoma. Oncol Lett. 2018 Jul;16(1):1023-1030.

[2]. Salvatore DeBonis, et al. In vitro screening for inhibitors of the human mitotic kinesin Eg5 with antimitotic and antitumor activities. Mol Cancer Ther. 2004 Sep;3(9):1079-90.
Density 1.2±0.1 g/cm3
Boiling Point 524.7±50.0 °C at 760 mmHg
Melting Point 182-183 °C (dec.)(lit.)
Molecular Formula C22H21NO2S
Molecular Weight 363.47
Flash Point 271.2±30.1 °C
Exact Mass 363.129303
PSA 88.62000
LogP 5.56
Vapour Pressure 0.0±1.4 mmHg at 25°C
Index of Refraction 1.642
Storage condition -20°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AY7710000
CHEMICAL NAME :
Alanine, 3-(tritylthio)-, L-
CAS REGISTRY NUMBER :
2799-07-7
BEILSTEIN REFERENCE NO. :
2339626
LAST UPDATED :
199801
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C22-H21-N-O2-S

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>540 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB81-109993
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
45 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB81-109993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
936 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. (Bethesda, MD 20205) Volume(issue)/page/year: JAN1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
396 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. (Bethesda, MD 20205) Volume(issue)/page/year: JAN1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
59460 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB288-358
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
750 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB81-109993
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB81-109993
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Liver - jaundice, other or unclassified Blood - hemorrhage
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 29,95,1974 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
250 mg/kg/5D-I
TOXIC EFFECTS :
Cardiac - pulse rate Lungs, Thorax, or Respiration - dyspnea Related to Chronic Data - death
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB216-419
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
375 mg/kg/33D-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases Related to Chronic Data - death
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB216-419
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
250 mg/kg/5D-I
TOXIC EFFECTS :
Liver - other changes Kidney, Ureter, Bladder - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB216-419
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful;
Risk Phrases R22
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS AY7710000
HS Code 2930909090
76-84-6 structure

76-84-6

52-89-1 structure

52-89-1

~98%

2799-07-7 structure

2799-07-7

Literature: Silvia, Vertuani; Baldisserotto, Anna; Scalambra, Emanuela; Malisardi, Gemma; Durini, Elisa; Manfredini, Stefano European Journal of Medicinal Chemistry, 2012 , vol. 50, p. 383 - 392
52-89-1 structure

52-89-1

76-83-5 structure

76-83-5

~89%

2799-07-7 structure

2799-07-7

Literature: Marquette University; University of Wisconsin - Milwaukee Patent: US7829709 B1, 2010 ; Location in patent: Page/Page column 19-20 ;
76-84-6 structure

76-84-6

52-90-4 structure

52-90-4

~90%

2799-07-7 structure

2799-07-7

Literature: Jin, Hui-Juan; Lu, Jing; Wu, Xue Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 11 p. 3465 - 3469
103213-32-7 structure

103213-32-7

~83%

2799-07-7 structure

2799-07-7

Literature: Chen, Chun-Chi; Rajagopal, Basker; Liu, Xuan Yu; Chen, Kuan Lin; Tyan, Yu-Chang; Lin, Fui; Lin, Po-Chiao Amino Acids, 2014 , vol. 46, # 2 p. 367 - 374
52-90-4 structure

52-90-4

76-83-5 structure

76-83-5

~%

2799-07-7 structure

2799-07-7

Literature: WO2007/9944 A1, ; Page/Page column 31-32 ;
880762-43-6 structure

880762-43-6

~%

2799-07-7 structure

2799-07-7

Literature: WO2006/102243 A2, ; Page/Page column 63 ; WO 2006/102243 A2
52-89-1 structure

52-89-1

76-83-5 structure

76-83-5

~%

2799-07-7 structure

2799-07-7

27686-50-6 structure

27686-50-6

Literature: Bulletin de la Societe Chimique de France, , p. 698
HS Code 2930909090
Summary 2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%
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