Erabutoxin B - 9083-23-2

Erabutoxin B

Catalog Number: EVT-242072
CAS Number: 9083-23-2
Molecular Formula: C286H451N87O94S8
Molecular Weight: 6869 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.

Product Introduction

Description
Erabutoxin B is a potent neurotoxin that is found in the venom of the sea snake, Laticauda semifasciata. It belongs to the family of three-finger toxins and is known for its ability to block the neuromuscular transmission by binding to the nicotinic acetylcholine receptors (nAChRs) in the postsynaptic membrane. Erabutoxin B has been extensively studied for its chemical structure, biological activity, and potential applications in various fields of research.
Applications in Various Fields
Erabutoxin B has potential applications in various fields of research such as medical, environmental, and industrial. In medical research, erabutoxin B has been studied for its role in drug development, particularly in the design of new analgesics and muscle relaxants. Clinical trials have shown promising results in the use of erabutoxin B for the treatment of chronic pain and spasticity. However, its potential side effects such as muscle weakness and respiratory depression need to be carefully monitored. In environmental research, erabutoxin B has been studied for its effects on ecosystems and its role in pollution management. Erabutoxin B has been shown to have a significant impact on the marine food chain, particularly on the fish population. In industrial research, erabutoxin B has been used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations are crucial during the handling and storage of erabutoxin B.

Properties

CAS Number

9083-23-2

Product Name

Erabutoxin B

IUPAC Name

(4S)-4-[[2-[[(2S)-2-[[(2S)-1-[(2R)-2-[[(2S,3R)-2-[[(2S)-6-amino-2-[[(2S,3R)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2R)-2-[[(2S,3S)-2-[[(2S)-2-amino-5-carbamimidamidopentanoyl]amino]-3-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-oxobutanoyl]amino]-5-oxopentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]amino]-3-hydroxybutanoyl]amino]-3-sulfanylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]acetyl]amino]-5-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S,3R)-1-[[(2S,3S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2R)-1-[[2-[[(2R)-1-[(2S)-2-[[(2S,3R)-1-[[(2S)-1-[[(2S)-6-amino-1-[(2S)-2-[[2-[[(2S,3S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-4-amino-1-[[(1S)-3-amino-1-carboxy-3-oxopropyl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]carbamoyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-oxoethyl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-oxoethyl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

Molecular Formula

C286H451N87O94S8

Molecular Weight

6869 g/mol

InChI

InChI=1S/C286H451N87O94S8/c1-20-135(11)218(270(453)329-157(55-33-37-85-288)233(416)334-168(95-132(5)6)242(425)347-185(120-380)257(440)354-190(125-471)263(446)355-188(123-469)259(442)327-163(73-81-212(402)403)238(421)346-180(115-375)252(435)326-165(75-83-214(406)407)240(423)361-216(133(7)8)269(452)356-191(126-472)262(445)342-176(103-204(297)393)250(433)344-178(283(466)467)104-205(298)394)359-209(398)113-315-264(447)195-60-43-91-370(195)279(462)166(57-35-39-87-290)333-268(451)217(134(9)10)362-277(460)226(143(19)386)368-267(450)198-63-46-94-373(198)281(464)193(128-474)320-208(397)111-314-231(414)187(122-468)319-207(396)110-311-228(411)154(58-41-89-308-285(301)302)321-235(418)164(74-82-213(404)405)331-271(454)220(137(13)22-3)364-273(456)221(138(14)23-4)365-276(459)222(139(15)382)360-210(399)112-312-229(412)155(59-42-90-309-286(303)304)322-243(426)169(96-144-47-26-24-27-48-144)335-251(434)177(105-215(408)409)343-254(437)182(117-377)348-246(429)172(99-147-106-310-153-53-31-30-51-151(147)153)338-236(419)160(68-76-199(292)388)324-232(415)156(54-32-36-84-287)323-247(430)173(100-148-107-305-130-316-148)340-244(427)171(98-146-64-66-150(387)67-65-146)337-260(443)189(124-470)353-258(441)186(121-381)351-255(438)183(118-378)345-234(417)159(72-80-211(400)401)318-206(395)109-313-230(413)179(114-374)352-266(449)197-62-45-93-372(197)282(465)194(129-475)358-275(458)223(140(16)383)366-239(422)158(56-34-38-86-289)330-274(457)224(141(17)384)369-278(461)225(142(18)385)367-241(424)162(70-78-201(294)390)328-265(448)196-61-44-92-371(196)280(463)167(71-79-202(295)391)332-253(436)181(116-376)350-256(439)184(119-379)349-248(431)174(101-149-108-306-131-317-149)339-237(420)161(69-77-200(293)389)325-249(432)175(102-203(296)392)341-245(428)170(97-145-49-28-25-29-50-145)336-261(444)192(127-473)357-272(455)219(136(12)21-2)363-227(410)152(291)52-40-88-307-284(299)300/h24-31,47-51,53,64-67,106-108,130-143,152,154-198,216-226,310,374-387,468-475H,20-23,32-46,52,54-63,68-105,109-129,287-291H2,1-19H3,(H2,292,388)(H2,293,389)(H2,294,390)(H2,295,391)(H2,296,392)(H2,297,393)(H2,298,394)(H,305,316)(H,306,317)(H,311,411)(H,312,412)(H,313,413)(H,314,414)(H,315,447)(H,318,395)(H,319,396)(H,320,397)(H,321,418)(H,322,426)(H,323,430)(H,324,415)(H,325,432)(H,326,435)(H,327,442)(H,328,448)(H,329,453)(H,330,457)(H,331,454)(H,332,436)(H,333,451)(H,334,416)(H,335,434)(H,336,444)(H,337,443)(H,338,419)(H,339,420)(H,340,427)(H,341,428)(H,342,445)(H,343,437)(H,344,433)(H,345,417)(H,346,421)(H,347,425)(H,348,429)(H,349,431)(H,350,439)(H,351,438)(H,352,449)(H,353,441)(H,354,440)(H,355,446)(H,356,452)(H,357,455)(H,358,458)(H,359,398)(H,360,399)(H,361,423)(H,362,460)(H,363,410)(H,364,456)(H,365,459)(H,366,422)(H,367,424)(H,368,450)(H,369,461)(H,400,401)(H,402,403)(H,404,405)(H,406,407)(H,408,409)(H,466,467)(H4,299,300,307)(H4,301,302,308)(H4,303,304,309)/t135-,136-,137-,138-,139+,140+,141+,142+,143+,152-,154-,155-,156-,157-,158-,159-,160-,161-,162-,163-,164-,165-,166-,167-,168-,169-,170-,171-,172-,173-,174-,175-,176-,177-,178-,179-,180-,181-,182-,183-,184-,185-,186-,187-,188-,189-,190-,191-,192-,193-,194-,195-,196-,197-,198-,216-,217-,218-,219-,220-,221-,222-,223-,224-,225-,226-/m0/s1

InChI Key

WITZDNDAZYTMTC-MJQGTENLSA-N

SMILES

CCC(C)C(C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(CS)C(=O)NC(CS)C(=O)NC(CCC(=O)O)C(=O)NC(CO)C(=O)NC(CCC(=O)O)C(=O)NC(C(C)C)C(=O)NC(CS)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)N)C(=O)O)NC(=O)CNC(=O)C1CCCN1C(=O)C(CCCCN)NC(=O)C(C(C)C)NC(=O)C(C(C)O)NC(=O)C2CCCN2C(=O)C(CS)NC(=O)CNC(=O)C(CS)NC(=O)CNC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)CC)NC(=O)C(C(C)CC)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(CCCNC(=N)N)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(CC4=CNC5=CC=CC=C54)NC(=O)C(CCC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CC6=CN=CN6)NC(=O)C(CC7=CC=C(C=C7)O)NC(=O)C(CS)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(CCC(=O)O)NC(=O)CNC(=O)C(CO)NC(=O)C8CCCN8C(=O)C(CS)NC(=O)C(C(C)O)NC(=O)C(CCCCN)NC(=O)C(C(C)O)NC(=O)C(C(C)O)NC(=O)C(CCC(=O)N)NC(=O)C9CCCN9C(=O)C(CCC(=O)N)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(CC1=CN=CN1)NC(=O)C(CCC(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(CC1=CC=CC=C1)NC(=O)C(CS)NC(=O)C(C(C)CC)NC(=O)C(CCCNC(=N)N)N

Synonyms

26-L-histidine erabutoxin a
erabutoxin

Canonical SMILES

CCC(C)C(C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(CS)C(=O)NC(CS)C(=O)NC(CCC(=O)O)C(=O)NC(CO)C(=O)NC(CCC(=O)O)C(=O)NC(C(C)C)C(=O)NC(CS)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)N)C(=O)O)NC(=O)CNC(=O)C1CCCN1C(=O)C(CCCCN)NC(=O)C(C(C)C)NC(=O)C(C(C)O)NC(=O)C2CCCN2C(=O)C(CS)NC(=O)CNC(=O)C(CS)NC(=O)CNC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)CC)NC(=O)C(C(C)CC)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(CCCNC(=N)N)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(CC4=CNC5=CC=CC=C54)NC(=O)C(CCC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CC6=CN=CN6)NC(=O)C(CC7=CC=C(C=C7)O)NC(=O)C(CS)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(CCC(=O)O)NC(=O)CNC(=O)C(CO)NC(=O)C8CCCN8C(=O)C(CS)NC(=O)C(C(C)O)NC(=O)C(CCCCN)NC(=O)C(C(C)O)NC(=O)C(C(C)O)NC(=O)C(CCC(=O)N)NC(=O)C9CCCN9C(=O)C(CCC(=O)N)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(CC1=CN=CN1)NC(=O)C(CCC(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(CC1=CC=CC=C1)NC(=O)C(CS)NC(=O)C(C(C)CC)NC(=O)C(CCCNC(=N)N)N

Isomeric SMILES

CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CS)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC(=O)N)C(=O)O)NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H]2CCCN2C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H](CS)NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H]([C@@H](C)O)NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC4=CNC5=CC=CC=C54)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC6=CN=CN6)NC(=O)[C@H](CC7=CC=C(C=C7)O)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@@H]8CCCN8C(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]9CCCN9C(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCCNC(=N)N)N
Method of Synthesis or Extraction
Erabutoxin B is primarily extracted from the venom of Laticauda semifasciata using various chromatographic techniques such as ion-exchange, gel filtration, and reverse-phase chromatography. The yield of erabutoxin B from the venom is relatively low, ranging from 0.1% to 0.5%. Alternatively, erabutoxin B can be synthesized chemically using solid-phase peptide synthesis or recombinant DNA technology. However, the chemical synthesis of erabutoxin B is challenging due to its complex structure and the presence of multiple disulfide bonds. The efficiency and yield of each method depend on various factors such as the purity of the starting material, the type of chromatographic technique used, and the expertise of the researcher. Environmental and safety considerations are crucial during the extraction and synthesis of erabutoxin B, as it is a potent neurotoxin that can cause severe health hazards if mishandled.
Chemical Structure and Biological Activity
Erabutoxin B is a small protein consisting of 62 amino acid residues with a molecular weight of 7 kDa. It contains four disulfide bonds that stabilize its tertiary structure. The three-finger fold of erabutoxin B is similar to that of other snake venom toxins such as α-bungarotoxin and cobratoxin. Erabutoxin B binds specifically to the α-subunit of Erabutoxin B and blocks the ion channel, thereby inhibiting the release of acetylcholine and causing muscle paralysis. Erabutoxin B has been shown to have a high affinity for the Erabutoxin B in the neuromuscular junction and the central nervous system. It also exhibits some degree of selectivity towards the fetal and adult forms of Erabutoxin B.
Biological Effects
Erabutoxin B has been extensively studied for its effects on cell function and signal transduction. It has been shown to inhibit the release of neurotransmitters such as acetylcholine, dopamine, and glutamate. Erabutoxin B also affects the intracellular signaling pathways by modulating the activity of protein kinases and phosphatases. The potential therapeutic and toxic effects of erabutoxin B are still under investigation. Erabutoxin B has been shown to have analgesic, anti-inflammatory, and antitumor properties in preclinical studies. However, its toxicity and potential side effects on human health are still a matter of concern.
Future Perspectives and Challenges
The current limitations in the use and study of erabutoxin B include its low yield, high cost, and potential toxicity. Possible solutions and improvements include the development of more efficient and cost-effective methods for the extraction and synthesis of erabutoxin B. Future trends and prospects in the application of erabutoxin B in scientific research include the development of new drugs and therapies for various diseases, the study of its effects on the nervous system, and the exploration of its potential applications in biotechnology and nanotechnology.
Conclusion:
Erabutoxin B is a potent neurotoxin that has been extensively studied for its chemical structure, biological activity, and potential applications in various fields of research. The method of synthesis or extraction, chemical structure, biological effects, and applications of erabutoxin B have been discussed in detail. The future perspectives and challenges in the use and study of erabutoxin B have also been highlighted. Erabutoxin B has the potential to be a valuable tool in scientific research and drug development, provided that its toxicity and potential side effects are carefully monitored.

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