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Insulin (cattle)

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Insulin (cattle) is a polypeptide hormone that regulates glucose metabolism in pancreatic islet B cells.

Category

Peptide Inhibitors

Catalog number

BAT-010509

CAS number

11070-73-8

Molecular Formula

C254H377N65O75S6

Molecular Weight

5733.49

Specification
Reference Reading

IUPAC Name

(4S)-5-[(2S)-1-[2-[(2S)-1-[(2S)-1-[(2S)-1-[(2S,3R)-1-[(2S)-2-[N-[(2S)-6-amino-1-[(1S)-1-carboxyethyl]imino-1-hydroxyhexan-2-yl]-C-hydroxycarbonimidoyl]pyrrolidin-1-yl]-3-hydroxy-1-oxobutan-2-yl]imino-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]imino-1-hydroxy-3-phenylpropan-2-yl]imino-1-hydroxy-3-phenylpropan-2-yl]imino-2-hydroxyethyl]imino-5-carbamimidamido-1-hydroxypentan-2-yl]imino-4-[[2-[[[(1R,6R,12S,15S,18S,21S,24S,27S,30S,33S,36S,39S,42R,47R,50S,53S,56S,59S,62S,65S,68S,71S,74R,77S,80S,83S,88R)-88-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-3-methylpentylidene]amino]-1-hydroxy-3-methylbutylidene]amino]-4-carboxy-1-hydroxybutylidene]amino]-1,5-dihydroxy-5-iminopentylidene]amino]-6-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-1-hydroxy-3-phenylpropylidene]amino]-1-hydroxy-3-methylbutylidene]amino]-1,4-dihydroxy-4-iminobutylidene]amino]-1,5-dihydroxy-5-iminopentylidene]amino]-1-hydroxy-3-(1H-imidazol-5-yl)propylidene]amino]-1-hydroxy-4-methylpentylidene]amino]-24,56-bis(2-carboxyethyl)-47-[N-[(1S)-1-carboxy-3-hydroxy-3-iminopropyl]-C-hydroxycarbonimidoyl]-7,10,13,16,19,22,25,28,31,34,37,40,49,52,55,58,61,64,67,70,73,76,79,82,85,87-hexacosahydroxy-53-(2-hydroxy-2-iminoethyl)-62-(3-hydroxy-3-iminopropyl)-12,71,80-tris(hydroxymethyl)-33,50,65-tris[(4-hydroxyphenyl)methyl]-15-(1H-imidazol-5-ylmethyl)-27,83-dimethyl-18,30,36,59,68-pentakis(2-methylpropyl)-21,39,77-tri(propan-2-yl)-3,4,44,45,90,91-hexathia-8,11,14,17,20,23,26,29,32,35,38,41,48,51,54,57,60,63,66,69,72,75,78,81,84,86-hexacosazabicyclo[72.11.7]dononaconta-7,10,13,16,19,22,25,28,31,34,37,40,48,51,54,57,60,63,66,69,72,75,78,81,84,86-hexacosaen-42-yl]-hydroxymethylidene]amino]-1-hydroxyethylidene]amino]-5-hydroxypentanoic acid

Synonyms

Insulin from bovine pancreas; Phe-Val-Asn-Gln-His-Leu-Cys-Gly-Ser-His-Leu-Val-Glu-Ala-Leu-Tyr-Leu-Val-Cys-Gly-Glu-Arg-Gly-Phe-Phe-Tyr-Thr-Pro-Lys-Ala. Gly-Ile-Val-Glu-Gln-Cys-Cys-Ala-Ser-Val-Cys-Ser-Leu-Tyr-Gln-Leu-Glu-Asn-Tyr-Cys-Asn (Disulfide bridge: Cys7-Cys7', Cys19-Cys20', Cys6'-Cys11')

Appearance

White Lyophilized Powder

Purity

≥97%

Sequence

FVNQHLCGSHLVEALYLVCGERGFFYTPKA. GIVEQCCASVCSLYQLENYCN (Disulfide bridge: Cys7-Cys7', Cys19-Cys20', Cys6'-Cys11')

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C254H377N65O75S6/c1-29-131(24)205(312-192(334)103-256)250(389)317-204(130(22)23)246(385)287-158(74-81-199(344)345)216(355)281-155(70-77-188(260)330)220(359)307-183-116-399-400-117-184-242(381)305-177(110-321)238(377)293-161(87-122(6)7)223(362)294-167(94-139-52-60-145(324)61-53-139)226(365)282-153(68-75-186(258)328)217(356)289-160(86-121(4)5)221(360)284-157(73-80-198(342)343)219(358)301-173(100-189(261)331)233(372)297-169(96-141-56-64-147(326)65-57-141)229(368)308-182(241(380)303-175(253(393)394)102-191(263)333)115-398-396-113-180(212(351)270-106-193(335)277-152(71-78-196(338)339)215(354)280-150(50-41-83-268-254(264)265)210(349)269-107-194(336)278-165(92-137-45-35-31-36-46-137)225(364)296-166(93-138-47-37-32-38-48-138)228(367)298-170(97-142-58-66-148(327)67-59-142)236(375)318-206(135(28)323)251(390)319-84-42-51-185(319)244(383)285-151(49-39-40-82-255)213(352)276-134(27)252(391)392)310-248(387)202(128(18)19)315-234(373)163(89-124(10)11)291-227(366)168(95-140-54-62-146(325)63-55-140)295-222(361)159(85-120(2)3)288-207(346)132(25)274-214(353)156(72-79-197(340)341)286-245(384)201(127(16)17)314-235(374)164(90-125(12)13)292-231(370)172(99-144-105-267-119-273-144)300-237(376)176(109-320)279-195(337)108-271-211(350)179(112-395-397-114-181(309-243(183)382)240(379)275-133(26)208(347)304-178(111-322)239(378)316-203(129(20)21)249(388)311-184)306-224(363)162(88-123(8)9)290-230(369)171(98-143-104-266-118-272-143)299-218(357)154(69-76-187(259)329)283-232(371)174(101-190(262)332)302-247(386)200(126(14)15)313-209(348)149(257)91-136-43-33-30-34-44-136/h30-38,43-48,52-67,104-105,118-135,149-185,200-206,320-327H,29,39-42,49-51,68-103,106-117,255-257H2,1-28H3,(H2,258,328)(H2,259,329)(H2,260,330)(H2,261,331)(H2,262,332)(H2,263,333)(H,266,272)(H,267,273)(H,269,349)(H,270,351)(H,271,350)(H,274,353)(H,275,379)(H,276,352)(H,277,335)(H,278,336)(H,279,337)(H,280,354)(H,281,355)(H,282,365)(H,283,371)(H,284,360)(H,285,383)(H,286,384)(H,287,385)(H,288,346)(H,289,356)(H,290,369)(H,291,366)(H,292,370)(H,293,377)(H,294,362)(H,295,361)(H,296,364)(H,297,372)(H,298,367)(H,299,357)(H,300,376)(H,301,358)(H,302,386)(H,303,380)(H,304,347)(H,305,381)(H,306,363)(H,307,359)(H,308,368)(H,309,382)(H,310,387)(H,311,388)(H,312,334)(H,313,348)(H,314,374)(H,315,373)(H,316,378)(H,317,389)(H,318,375)(H,338,339)(H,340,341)(H,342,343)(H,344,345)(H,391,392)(H,393,394)(H4,264,265,268)/t131-,132-,133-,134-,135+,149-,150-,151-,152-,153-,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-,200-,201-,202-,203-,204-,205-,206-/m0/s1

InChI Key

IXIBAKNTJSCKJM-BUBXBXGNSA-N

Canonical SMILES

CCC(C)C(C(=NC(C(C)C)C(=NC(CCC(=O)O)C(=NC(CCC(=N)O)C(=NC1CSSCC2C(=NC(C(=NC(C(=NC(C(=NC(C(=NC(C(=NC(C(=NC(C(=NC(C(=NC(CSSCC(N=C(C(N=C(C(N=C(C(N=C(C(N=C(C(N=C(C(N=C(C(N=C(C(N=C(C(N=C(C(N=C(CN=C(C(CSSCC(C(=NC(C(=NC(C(=NC(C(=N2)O)C(C)C)O)CO)O)C)O)N=C1O)N=C(C(CC(C)C)N=C(C(CC3=CN=CN3)N=C(C(CCC(=N)O)N=C(C(CC(=N)O)N=C(C(C(C)C)N=C(C(CC4=CC=CC=C4)N)O)O)O)O)O)O)O)O)CO)O)CC5=CN=CN5)O)CC(C)C)O)C(C)C)O)CCC(=O)O)O)C)O)CC(C)C)O)CC6=CC=C(C=C6)O)O)CC(C)C)O)C(C)C)O)C(=NCC(=NC(CCC(=O)O)C(=NC(CCCNC(=N)N)C(=NCC(=NC(CC7=CC=CC=C7)C(=NC(CC8=CC=CC=C8)C(=NC(CC9=CC=C(C=C9)O)C(=NC(C(C)O)C(=O)N1CCCC1C(=NC(CCCCN)C(=NC(C)C(=O)O)O)O)O)O)O)O)O)O)O)O)C(=NC(CC(=N)O)C(=O)O)O)O)CC1=CC=C(C=C1)O)O)CC(=N)O)O)CCC(=O)O)O)CC(C)C)O)CCC(=N)O)O)CC1=CC=C(C=C1)O)O)CC(C)C)O)CO)O)O)O)O)O)N=C(CN)O

1. Growth hormone stimulation of serum insulin concentration in cattle: nutritional dependency and potential mechanisms

H Jiang, F C Gwazdauskas, M Wu, J Feng, Z Gu Domest Anim Endocrinol . 2009 Aug;37(2):84-92. doi: 10.1016/j.domaniend.2009.03.003.

Previous studies on the effect of growth hormone (GH) on serum insulin concentration in cattle had generated seemingly conflicting results, and little was known about the mechanism by which GH affects serum insulin concentration in cattle, if it does. In this study, we determined whether the effect of GH on serum insulin concentration in cattle could be affected by the nutritional levels of the animal and whether GH increased serum insulin concentration in cattle by directly stimulating insulin release or insulin gene expression in the pancreatic islets. Administration of recombinant bovine GH increased serum insulin concentration in nonlactating, nonpregnant beef cows fed a daily concentrate meal in addition to ad libitum hay, but it had no effect in those cows fed hay only. Both GH treatments for 1 and 24h increased insulin concentrations in cultures of pancreatic islets isolated from growing cattle. Growth hormone treatment for 24h increased insulin mRNA expression in cultured bovine pancreatic islets. Growth hormone treatment for 16h increased reporter gene expression directed by a approximately 1,500-bp bovine insulin gene promoter in a rat insulin-producing beta cell line. Taken together, these results suggest that exogenous GH can increase serum insulin concentration in cattle, but this effect depends on the nutritional levels of fed cattle, and that GH increases serum insulin concentration in cattle by stimulating both insulin release and insulin gene expression in the pancreatic islets.

2. Insulin allergy

Mohammad K Ghazavi, Graham A Johnston Clin Dermatol . 2011 May-Jun;29(3):300-5. doi: 10.1016/j.clindermatol.2010.11.009.

Insulin reactions occur rarely but are of tremendous clinical importance. The first was reported in 1922 as a callus reaction at the injection site of insufficiently purified bovine insulin. Porcine insulin was subsequently found to be less allergenic than bovine insulin. Increasingly pure insulins have decreased the risk of adverse reactions, and the production of recombinant insulin with the same amino sequence as human insulin saw a large decrease in adverse reactions. Currently, the prevalence of allergic reactions to insulin products appears to be approximately 2%, and less than one-third of these events have been considered related to the insulin itself. Other reactions occur due to the preservatives added to insulin, including zinc, protamine, and meta-cresol. Allergic reactions can be type I or immunoglobulin E-mediated, type III or Arthus, and type IV or delayed-type hypersensitivity reactions. Type I reactions are the most common and can, rarely, cause anaphylaxis. In contrast, type IV reactions can occur after a delay of several days. Investigations include skin prick testing, patch testing, intradermal testing, and occasionally, skin biopsy.

3. Insulin pharmacology

J S Skyler Med Clin North Am . 1988 Nov;72(6):1337-54. doi: 10.1016/s0025-7125(16)30710-6.

Insulin initially became available for therapy in the 1920s. Over the years, a variety of insulin preparations have been formulated; preparations differ on the basis of purity, species of origin, and time course of action. Currently, highly purified preparations of human insulin are available with a variety of profiles of action.